organic compounds
As part of structural studies of 6-ethoxy-2,3,4-tetrahydro-2,2,4-trimethylquinoline derivatives, the crystal structure of the title compound, C14H21NO, has been investigated. The conformation of the tetrahydropyridine ring differs markedly from that of similar compounds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013121/cv6325sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013121/cv6325Isup2.hkl |
CCDC reference: 245279
Computing details top
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
6-ethoxy-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline top
Crystal data top
C14H21NO | F(000) = 480 |
Mr = 219.32 | Dx = 1.099 Mg m−3 |
Monoclinic, P21/c | Melting point = 311–312 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.5418 Å |
a = 13.196 (4) Å | Cell parameters from 25 reflections |
b = 8.865 (6) Å | θ = 30–35° |
c = 11.330 (11) Å | µ = 0.53 mm−1 |
β = 90.77 (6)° | T = 293 K |
V = 1325.3 (16) Å3 | Prism, colourless |
Z = 4 | 0.3 × 0.3 × 0.3 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.058 |
Radiation source: Fine-focus sealed tube | θmax = 74.9°, θmin = 3.4° |
Graphite monochromator | h = −16→16 |
Non–profiled ω/2θ scans | k = −11→11 |
5533 measured reflections | l = 0→14 |
2717 independent reflections | 1 standard reflections every 60 min |
1805 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3 |
2717 reflections | (Δ/σ)max < 0.001 |
153 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.38148 (12) | 0.02040 (16) | 0.17518 (12) | 0.0640 (4) | |
H1 | 0.4348 (16) | 0.063 (3) | 0.1840 (18) | 0.105 (8)* | |
C2 | 0.35815 (13) | −0.10006 (17) | 0.25961 (13) | 0.0619 (4) | |
C21 | 0.40091 (14) | −0.2521 (2) | 0.21842 (19) | 0.0782 (5) | |
H21A | 0.3734 | −0.2762 | 0.1418 | 0.117* | |
H21B | 0.3827 | −0.3295 | 0.2735 | 0.117* | |
H21C | 0.4734 | −0.2457 | 0.2142 | 0.117* | |
C22 | 0.40617 (18) | −0.0575 (3) | 0.37778 (16) | 0.0960 (7) | |
H22A | 0.4779 | −0.0447 | 0.3686 | 0.144* | |
H22B | 0.3939 | −0.1361 | 0.4341 | 0.144* | |
H22C | 0.3771 | 0.0351 | 0.4052 | 0.144* | |
C3 | 0.24376 (13) | −0.1064 (2) | 0.26736 (14) | 0.0693 (4) | |
H3A | 0.2195 | −0.0098 | 0.2958 | 0.083* | |
H3B | 0.2256 | −0.1823 | 0.3250 | 0.083* | |
C4 | 0.18988 (12) | −0.1424 (2) | 0.15114 (14) | 0.0686 (5) | |
H4 | 0.2033 | −0.2487 | 0.1334 | 0.082* | |
C41 | 0.07622 (16) | −0.1249 (4) | 0.1615 (2) | 0.1203 (10) | |
H41A | 0.0603 | −0.0216 | 0.1785 | 0.180* | |
H41B | 0.0523 | −0.1880 | 0.2241 | 0.180* | |
H41C | 0.0440 | −0.1541 | 0.0885 | 0.180* | |
C5 | 0.23523 (11) | −0.04933 (16) | 0.05200 (12) | 0.0544 (3) | |
C6 | 0.18569 (11) | −0.03689 (16) | −0.05646 (13) | 0.0577 (4) | |
H6 | 0.1240 | −0.0860 | −0.0675 | 0.069* | |
C7 | 0.22513 (11) | 0.04636 (17) | −0.14911 (12) | 0.0571 (4) | |
O7 | 0.16833 (9) | 0.04510 (14) | −0.25191 (9) | 0.0731 (4) | |
C71 | 0.20138 (15) | 0.1343 (2) | −0.34731 (14) | 0.0798 (5) | |
H71A | 0.2673 | 0.1001 | −0.3732 | 0.096* | |
H71B | 0.2073 | 0.2389 | −0.3230 | 0.096* | |
C72 | 0.12574 (18) | 0.1203 (3) | −0.44545 (16) | 0.1035 (8) | |
H72A | 0.1213 | 0.0168 | −0.4700 | 0.155* | |
H72B | 0.1465 | 0.1814 | −0.5108 | 0.155* | |
H72C | 0.0607 | 0.1535 | −0.4189 | 0.155* | |
C8 | 0.31598 (12) | 0.12003 (17) | −0.13336 (13) | 0.0602 (4) | |
H8 | 0.3427 | 0.1779 | −0.1939 | 0.072* | |
C9 | 0.36729 (12) | 0.10722 (17) | −0.02630 (13) | 0.0593 (4) | |
H9 | 0.4292 | 0.1561 | −0.0164 | 0.071* | |
C10 | 0.32872 (11) | 0.02296 (15) | 0.06727 (12) | 0.0521 (3) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0703 (9) | 0.0581 (7) | 0.0634 (7) | −0.0115 (7) | −0.0095 (7) | 0.0061 (6) |
C2 | 0.0685 (10) | 0.0568 (8) | 0.0601 (8) | −0.0027 (8) | −0.0062 (7) | 0.0093 (7) |
C21 | 0.0686 (11) | 0.0634 (10) | 0.1025 (13) | 0.0053 (8) | 0.0005 (10) | 0.0123 (9) |
C22 | 0.1199 (18) | 0.0993 (15) | 0.0682 (10) | −0.0184 (13) | −0.0228 (11) | 0.0164 (10) |
C3 | 0.0726 (11) | 0.0688 (10) | 0.0666 (8) | 0.0034 (9) | 0.0105 (8) | 0.0130 (8) |
C4 | 0.0561 (9) | 0.0752 (10) | 0.0747 (9) | −0.0060 (8) | 0.0049 (8) | 0.0195 (8) |
C41 | 0.0619 (12) | 0.190 (3) | 0.1099 (15) | −0.0093 (15) | 0.0148 (11) | 0.0584 (18) |
C5 | 0.0488 (8) | 0.0514 (7) | 0.0630 (8) | 0.0007 (6) | 0.0036 (6) | 0.0033 (6) |
C6 | 0.0469 (7) | 0.0572 (8) | 0.0689 (8) | −0.0033 (7) | −0.0004 (6) | 0.0028 (7) |
C7 | 0.0543 (8) | 0.0578 (8) | 0.0591 (8) | 0.0029 (7) | −0.0022 (6) | 0.0009 (7) |
O7 | 0.0719 (8) | 0.0841 (8) | 0.0630 (6) | −0.0124 (6) | −0.0086 (6) | 0.0120 (6) |
C71 | 0.0949 (14) | 0.0805 (12) | 0.0639 (9) | −0.0057 (10) | −0.0053 (9) | 0.0151 (8) |
C72 | 0.1145 (18) | 0.1261 (19) | 0.0696 (11) | −0.0077 (15) | −0.0147 (11) | 0.0216 (12) |
C8 | 0.0637 (9) | 0.0569 (8) | 0.0599 (8) | −0.0051 (7) | 0.0035 (7) | 0.0060 (7) |
C9 | 0.0569 (9) | 0.0557 (8) | 0.0654 (8) | −0.0122 (7) | 0.0003 (7) | 0.0038 (7) |
C10 | 0.0529 (8) | 0.0461 (7) | 0.0571 (7) | −0.0026 (6) | −0.0004 (6) | 0.0015 (6) |
Geometric parameters (Å, º) top
N1—C10 | 1.399 (2) | C41—H41B | 0.9600 |
N1—C2 | 1.469 (2) | C41—H41C | 0.9600 |
N1—H1 | 0.80 (2) | C5—C6 | 1.388 (2) |
C2—C3 | 1.514 (2) | C5—C10 | 1.399 (2) |
C2—C22 | 1.521 (3) | C6—C7 | 1.390 (2) |
C2—C21 | 1.537 (2) | C6—H6 | 0.9300 |
C21—H21A | 0.9600 | C7—C8 | 1.375 (2) |
C21—H21B | 0.9600 | C7—O7 | 1.377 (2) |
C21—H21C | 0.9600 | O7—C71 | 1.413 (2) |
C22—H22A | 0.9600 | C71—C72 | 1.489 (3) |
C22—H22B | 0.9600 | C71—H71A | 0.9700 |
C22—H22C | 0.9600 | C71—H71B | 0.9700 |
C3—C4 | 1.522 (3) | C72—H72A | 0.9600 |
C3—H3A | 0.9700 | C72—H72B | 0.9600 |
C3—H3B | 0.9700 | C72—H72C | 0.9600 |
C4—C41 | 1.514 (3) | C8—C9 | 1.386 (2) |
C4—C5 | 1.523 (2) | C8—H8 | 0.9300 |
C4—H4 | 0.9800 | C9—C10 | 1.398 (2) |
C41—H41A | 0.9600 | C9—H9 | 0.9300 |
C10—N1—C2 | 118.34 (14) | H41A—C41—H41B | 109.5 |
C10—N1—H1 | 121.7 (15) | C4—C41—H41C | 109.5 |
C2—N1—H1 | 116.8 (16) | H41A—C41—H41C | 109.5 |
N1—C2—C3 | 106.40 (14) | H41B—C41—H41C | 109.5 |
N1—C2—C22 | 107.72 (15) | C6—C5—C10 | 118.49 (14) |
C3—C2—C22 | 111.22 (16) | C6—C5—C4 | 120.72 (14) |
N1—C2—C21 | 111.04 (15) | C10—C5—C4 | 120.78 (14) |
C3—C2—C21 | 110.84 (14) | C5—C6—C7 | 122.27 (14) |
C22—C2—C21 | 109.55 (16) | C5—C6—H6 | 118.9 |
C2—C21—H21A | 109.5 | C7—C6—H6 | 118.9 |
C2—C21—H21B | 109.5 | C8—C7—O7 | 125.28 (14) |
H21A—C21—H21B | 109.5 | C8—C7—C6 | 119.27 (14) |
C2—C21—H21C | 109.5 | O7—C7—C6 | 115.44 (14) |
H21A—C21—H21C | 109.5 | C7—O7—C71 | 118.20 (14) |
H21B—C21—H21C | 109.5 | O7—C71—C72 | 108.27 (17) |
C2—C22—H22A | 109.5 | O7—C71—H71A | 110.0 |
C2—C22—H22B | 109.5 | C72—C71—H71A | 110.0 |
H22A—C22—H22B | 109.5 | O7—C71—H71B | 110.0 |
C2—C22—H22C | 109.5 | C72—C71—H71B | 110.0 |
H22A—C22—H22C | 109.5 | H71A—C71—H71B | 108.4 |
H22B—C22—H22C | 109.5 | C71—C72—H72A | 109.5 |
C2—C3—C4 | 114.33 (14) | C71—C72—H72B | 109.5 |
C2—C3—H3A | 108.7 | H72A—C72—H72B | 109.5 |
C4—C3—H3A | 108.7 | C71—C72—H72C | 109.5 |
C2—C3—H3B | 108.7 | H72A—C72—H72C | 109.5 |
C4—C3—H3B | 108.7 | H72B—C72—H72C | 109.5 |
H3A—C3—H3B | 107.6 | C7—C8—C9 | 119.32 (14) |
C41—C4—C3 | 111.30 (17) | C7—C8—H8 | 120.3 |
C41—C4—C5 | 113.67 (15) | C9—C8—H8 | 120.3 |
C3—C4—C5 | 109.93 (14) | C8—C9—C10 | 121.93 (14) |
C41—C4—H4 | 107.2 | C8—C9—H9 | 119.0 |
C3—C4—H4 | 107.2 | C10—C9—H9 | 119.0 |
C5—C4—H4 | 107.2 | C9—C10—N1 | 119.30 (14) |
C4—C41—H41A | 109.5 | C9—C10—C5 | 118.71 (14) |
C4—C41—H41B | 109.5 | N1—C10—C5 | 121.89 (14) |
C10—N1—C2—C3 | −47.77 (19) | C5—C6—C7—O7 | 178.57 (13) |
C10—N1—C2—C22 | −167.12 (16) | C8—C7—O7—C71 | −4.6 (2) |
C10—N1—C2—C21 | 72.9 (2) | C6—C7—O7—C71 | 176.52 (15) |
N1—C2—C3—C4 | 60.71 (18) | C7—O7—C71—C72 | −177.32 (17) |
C22—C2—C3—C4 | 177.74 (16) | O7—C7—C8—C9 | −177.56 (15) |
C21—C2—C3—C4 | −60.12 (18) | C6—C7—C8—C9 | 1.3 (2) |
C2—C3—C4—C41 | −171.89 (17) | C7—C8—C9—C10 | −0.9 (2) |
C2—C3—C4—C5 | −45.04 (19) | C8—C9—C10—N1 | −176.81 (14) |
C41—C4—C5—C6 | −40.4 (2) | C8—C9—C10—C5 | −0.5 (2) |
C3—C4—C5—C6 | −165.90 (14) | C2—N1—C10—C9 | −162.32 (14) |
C41—C4—C5—C10 | 140.95 (19) | C2—N1—C10—C5 | 21.5 (2) |
C3—C4—C5—C10 | 15.4 (2) | C6—C5—C10—C9 | 1.4 (2) |
C10—C5—C6—C7 | −0.9 (2) | C4—C5—C10—C9 | −179.96 (14) |
C4—C5—C6—C7 | −179.63 (14) | C6—C5—C10—N1 | 177.59 (14) |
C5—C6—C7—C8 | −0.4 (2) | C4—C5—C10—N1 | −3.7 (2) |