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The title compound, C19H19NO5, is the result of a regioselective nucleophilic epoxide ring-opening performed with methanol on a 1,2,3,4-tetrahydroquinoline 3,4-epoxide bearing a related trans ester functionality. The relative stereochemistry of the resulting diol has shown that the the three adjacent substituents are mutually trans disposed. In the crystal structure, centrosymmetric hydrogen-bonded dimers are observed.
Supporting information
CCDC reference: 239138
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.058
- wR factor = 0.124
- Data-to-parameter ratio = 21.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 19
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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: Collect (Nonius, 1998); cell refinement: COLLECT; data reduction: EVALCCD (Nonius, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: JANA2000 (Petricek & Dusek, 2000); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: JANA2000.
Crystal data top
C19H19NO5 | F(000) = 720 |
Mr = 341.4 | Dx = 1.339 (1) Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 8343 reflections |
a = 13.0672 (4) Å | θ = 2.9–30.0° |
b = 6.7829 (3) Å | µ = 0.10 mm−1 |
c = 19.2623 (8) Å | T = 150 K |
β = 97.381 (3)° | Thick plate, colourless |
V = 1693.14 (12) Å3 | 0.23 × 0.16 × 0.06 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 3228 reflections with I > 2σ(I) |
Horizonally mounted graphite crystal monochromator | Rint = 0.076 |
Detector resolution: 9 pixels mm-1 | θmax = 29.8°, θmin = 6.4° |
φ and ω frames scans | h = −18→18 |
27588 measured reflections | k = −9→9 |
4886 independent reflections | l = −26→26 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F > 3σ(F)] = 0.058 | Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.001936I2] |
wR(F) = 0.124 | (Δ/σ)max = 0.001 |
S = 1.44 | Δρmax = 0.51 e Å−3 |
4886 reflections | Δρmin = −0.44 e Å−3 |
229 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.45544 (7) | 0.28756 (15) | 0.50688 (5) | 0.0243 (3) | |
O2 | 0.16179 (8) | 0.32363 (16) | 0.50236 (6) | 0.0324 (4) | |
O3 | 0.18200 (8) | 0.61612 (16) | 0.55782 (6) | 0.0278 (3) | |
O4 | 0.36320 (8) | 0.81340 (16) | 0.40975 (6) | 0.0275 (3) | |
O5 | 0.08979 (7) | 0.72753 (16) | 0.40556 (6) | 0.0286 (3) | |
N1 | 0.32939 (9) | 0.41095 (18) | 0.42745 (6) | 0.0201 (3) | |
C1 | 0.29682 (10) | 0.5501 (2) | 0.47788 (7) | 0.0205 (4) | |
C2 | 0.27589 (10) | 0.7503 (2) | 0.44125 (8) | 0.0220 (4) | |
C3 | 0.18771 (10) | 0.7312 (2) | 0.38088 (8) | 0.0216 (4) | |
C4 | 0.13031 (11) | 0.5187 (2) | 0.27692 (8) | 0.0274 (5) | |
C5 | 0.13398 (12) | 0.3512 (2) | 0.23669 (9) | 0.0331 (5) | |
C6 | 0.20378 (12) | 0.2032 (3) | 0.25960 (8) | 0.0306 (5) | |
C7 | 0.26822 (11) | 0.2222 (2) | 0.32214 (8) | 0.0249 (5) | |
C8 | 0.26571 (10) | 0.3941 (2) | 0.36187 (7) | 0.0203 (4) | |
C9 | 0.19599 (10) | 0.5446 (2) | 0.33965 (8) | 0.0208 (4) | |
C10 | 0.20522 (11) | 0.4788 (2) | 0.51258 (7) | 0.0223 (4) | |
C11 | 0.09232 (12) | 0.5790 (3) | 0.59273 (9) | 0.0345 (5) | |
C12 | 0.05746 (13) | 0.9168 (3) | 0.42637 (11) | 0.0426 (6) | |
C13 | 0.42325 (11) | 0.3188 (2) | 0.44449 (8) | 0.0207 (4) | |
C14 | 0.49065 (10) | 0.2792 (2) | 0.38910 (8) | 0.0218 (4) | |
C15 | 0.49675 (12) | 0.4150 (3) | 0.33557 (8) | 0.0288 (5) | |
C16 | 0.56889 (12) | 0.3880 (3) | 0.28915 (9) | 0.0374 (6) | |
C17 | 0.63395 (13) | 0.2273 (3) | 0.29584 (9) | 0.0391 (6) | |
C18 | 0.62855 (12) | 0.0921 (3) | 0.34943 (10) | 0.0356 (5) | |
C19 | 0.55756 (11) | 0.1176 (2) | 0.39635 (8) | 0.0266 (5) | |
Hc1 | 0.354 | 0.5576 | 0.5153 | 0.0246* | |
Hc2 | 0.2633 | 0.8481 | 0.4759 | 0.0265* | |
Hc3 | 0.1887 | 0.8468 | 0.3513 | 0.026* | |
Hc4 | 0.0806 | 0.6203 | 0.2608 | 0.0329* | |
H1o4 | 0.4174 (14) | 0.795 (3) | 0.4392 (10) | 0.033* | |
Hc5 | 0.0883 | 0.3376 | 0.1931 | 0.0397* | |
Hc6 | 0.2076 | 0.0852 | 0.2316 | 0.0367* | |
Hc7 | 0.3149 | 0.1155 | 0.338 | 0.0299* | |
H1c11 | 0.0306 | 0.5858 | 0.559 | 0.0414* | |
H2c11 | 0.0977 | 0.449 | 0.6138 | 0.0414* | |
H3c11 | 0.0885 | 0.6775 | 0.6288 | 0.0414* | |
H1c12 | −0.0113 | 0.9072 | 0.4399 | 0.0511* | |
H2c12 | 0.1049 | 0.9639 | 0.4658 | 0.0511* | |
H3c12 | 0.0568 | 1.0083 | 0.3876 | 0.0511* | |
Hc15 | 0.4509 | 0.528 | 0.3306 | 0.0345* | |
Hc16 | 0.5739 | 0.482 | 0.2518 | 0.0449* | |
Hc17 | 0.6834 | 0.2093 | 0.2629 | 0.0469* | |
Hc18 | 0.6746 | −0.0206 | 0.3541 | 0.0428* | |
Hc19 | 0.5547 | 0.0233 | 0.4339 | 0.0319* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0210 (5) | 0.0287 (5) | 0.0219 (5) | −0.0003 (4) | −0.0021 (4) | 0.0077 (5) |
O2 | 0.0331 (6) | 0.0279 (6) | 0.0377 (7) | −0.0108 (5) | 0.0096 (5) | −0.0018 (5) |
O3 | 0.0252 (6) | 0.0327 (6) | 0.0262 (6) | −0.0060 (5) | 0.0060 (4) | −0.0042 (5) |
O4 | 0.0145 (5) | 0.0311 (6) | 0.0353 (6) | −0.0061 (4) | −0.0030 (4) | 0.0111 (5) |
O5 | 0.0197 (5) | 0.0292 (6) | 0.0370 (6) | 0.0000 (4) | 0.0043 (5) | −0.0061 (5) |
N1 | 0.0173 (6) | 0.0227 (6) | 0.0191 (6) | −0.0004 (5) | −0.0024 (5) | 0.0028 (5) |
C1 | 0.0160 (7) | 0.0231 (7) | 0.0212 (7) | −0.0019 (6) | −0.0019 (6) | 0.0012 (6) |
C2 | 0.0170 (7) | 0.0208 (7) | 0.0276 (8) | −0.0034 (6) | −0.0004 (6) | 0.0023 (6) |
C3 | 0.0148 (7) | 0.0204 (7) | 0.0289 (8) | −0.0018 (6) | −0.0002 (6) | 0.0033 (6) |
C4 | 0.0222 (8) | 0.0303 (8) | 0.0279 (8) | 0.0031 (6) | −0.0040 (6) | 0.0039 (7) |
C5 | 0.0300 (9) | 0.0400 (10) | 0.0259 (8) | 0.0027 (7) | −0.0091 (7) | −0.0024 (8) |
C6 | 0.0293 (8) | 0.0312 (9) | 0.0293 (9) | −0.0002 (7) | −0.0034 (7) | −0.0060 (7) |
C7 | 0.0200 (7) | 0.0246 (8) | 0.0292 (8) | −0.0009 (6) | −0.0003 (6) | 0.0019 (7) |
C8 | 0.0163 (7) | 0.0241 (7) | 0.0198 (7) | −0.0045 (6) | −0.0002 (6) | 0.0031 (6) |
C9 | 0.0151 (6) | 0.0244 (8) | 0.0223 (7) | −0.0027 (6) | 0.0003 (6) | 0.0030 (6) |
C10 | 0.0198 (7) | 0.0258 (8) | 0.0199 (7) | −0.0017 (6) | −0.0025 (6) | 0.0020 (6) |
C11 | 0.0297 (9) | 0.0469 (11) | 0.0282 (9) | −0.0037 (8) | 0.0088 (7) | 0.0002 (8) |
C12 | 0.0289 (9) | 0.0415 (10) | 0.0566 (12) | 0.0050 (8) | 0.0024 (9) | −0.0212 (10) |
C13 | 0.0179 (7) | 0.0177 (7) | 0.0255 (8) | −0.0040 (6) | −0.0015 (6) | 0.0047 (6) |
C14 | 0.0157 (7) | 0.0258 (7) | 0.0229 (8) | −0.0041 (6) | −0.0014 (6) | 0.0014 (6) |
C15 | 0.0219 (8) | 0.0359 (9) | 0.0279 (8) | −0.0015 (7) | 0.0008 (6) | 0.0073 (7) |
C16 | 0.0296 (9) | 0.0555 (12) | 0.0281 (9) | −0.0062 (8) | 0.0071 (7) | 0.0067 (9) |
C17 | 0.0260 (8) | 0.0598 (12) | 0.0326 (9) | −0.0066 (8) | 0.0076 (7) | −0.0127 (9) |
C18 | 0.0255 (8) | 0.0360 (9) | 0.0445 (10) | 0.0004 (7) | 0.0010 (7) | −0.0132 (9) |
C19 | 0.0214 (7) | 0.0248 (8) | 0.0320 (9) | −0.0034 (6) | −0.0026 (6) | −0.0013 (7) |
Geometric parameters (Å, º) top
O1—C13 | 1.2396 (17) | C6—C7 | 1.384 (2) |
O2—C10 | 1.1997 (18) | C6—Hc6 | 0.97 |
O3—C10 | 1.3369 (19) | C7—C8 | 1.398 (2) |
O3—C11 | 1.446 (2) | C7—Hc7 | 0.97 |
O4—C2 | 1.4252 (18) | C8—C9 | 1.3983 (19) |
O4—H1o4 | 0.858 (18) | C11—H1c11 | 0.97 |
O5—C3 | 1.4214 (17) | C11—H2c11 | 0.97 |
O5—C12 | 1.425 (2) | C11—H3c11 | 0.97 |
N1—C1 | 1.4567 (19) | C12—H1c12 | 0.97 |
N1—C8 | 1.4251 (17) | C12—H2c12 | 0.97 |
N1—C13 | 1.3782 (18) | C12—H3c12 | 0.97 |
C1—C2 | 1.538 (2) | C13—C14 | 1.492 (2) |
C1—C10 | 1.523 (2) | C14—C15 | 1.392 (2) |
C1—Hc1 | 0.97 | C14—C19 | 1.398 (2) |
C2—C3 | 1.5337 (19) | C15—C16 | 1.392 (2) |
C2—Hc2 | 0.97 | C15—Hc15 | 0.97 |
C3—C9 | 1.506 (2) | C16—C17 | 1.378 (3) |
C3—Hc3 | 0.97 | C16—Hc16 | 0.97 |
C4—C5 | 1.380 (2) | C17—C18 | 1.389 (3) |
C4—C9 | 1.400 (2) | C17—Hc17 | 0.97 |
C4—Hc4 | 0.97 | C18—C19 | 1.387 (2) |
C5—C6 | 1.389 (2) | C18—Hc18 | 0.97 |
C5—Hc5 | 0.97 | C19—Hc19 | 0.97 |
| | | |
C10—O3—C11 | 116.57 (12) | C10—C1—Hc1 | 105.29 |
C3—O5—C12 | 112.96 (12) | O4—C2—Hc2 | 107.64 |
C1—N1—C8 | 117.11 (11) | C1—C2—Hc2 | 108.90 |
C1—N1—C13 | 117.54 (11) | C1—C2—H1o4 | 92.0 (5) |
C8—N1—C13 | 125.11 (12) | C3—C2—Hc2 | 113.70 |
N1—C1—C2 | 108.43 (12) | C3—C2—H1o4 | 130.0 (6) |
N1—C1—C10 | 113.58 (11) | Hc2—C2—H1o4 | 99.1 |
C2—C1—C10 | 112.24 (11) | O5—C3—Hc3 | 106.93 |
O4—C2—C1 | 110.83 (11) | C2—C3—Hc3 | 108.17 |
O4—C2—C3 | 105.48 (12) | C9—C3—Hc3 | 111.25 |
C1—C2—C3 | 110.22 (11) | C5—C4—Hc4 | 118.37 |
O5—C3—C2 | 111.64 (12) | C9—C4—Hc4 | 119.89 |
O5—C3—C9 | 106.88 (11) | C4—C5—Hc5 | 120.15 |
C2—C3—C9 | 111.88 (11) | C6—C5—Hc5 | 120.81 |
C5—C4—C9 | 121.74 (14) | C5—C6—Hc6 | 119.84 |
C4—C5—C6 | 119.04 (14) | C7—C6—Hc6 | 119.47 |
C5—C6—C7 | 120.69 (15) | C6—C7—Hc7 | 119.54 |
C6—C7—C8 | 119.97 (14) | C8—C7—Hc7 | 120.49 |
N1—C8—C7 | 120.01 (12) | O3—C11—H1c11 | 109.47 |
N1—C8—C9 | 119.73 (13) | O3—C11—H2c11 | 109.47 |
C7—C8—C9 | 120.12 (12) | O3—C11—H3c11 | 109.47 |
C3—C9—C4 | 118.87 (12) | H1c11—C11—H2c11 | 109.47 |
C3—C9—C8 | 122.72 (12) | H1c11—C11—H3c11 | 109.47 |
C4—C9—C8 | 118.40 (13) | H2c11—C11—H3c11 | 109.47 |
O2—C10—O3 | 125.17 (14) | O5—C12—H1c12 | 109.47 |
O2—C10—C1 | 126.06 (14) | O5—C12—H2c12 | 109.47 |
O3—C10—C1 | 108.76 (12) | O5—C12—H3c12 | 109.47 |
O1—C13—N1 | 119.29 (13) | H1c12—C12—H2c12 | 109.5 |
O1—C13—C14 | 120.29 (12) | H1c12—C12—H3c12 | 109.47 |
N1—C13—C14 | 120.02 (12) | H2c12—C12—H3c12 | 109.47 |
C13—C14—C15 | 120.37 (13) | C14—C15—Hc15 | 120.12 |
C13—C14—C19 | 119.25 (13) | C16—C15—Hc15 | 120.12 |
C15—C14—C19 | 119.86 (14) | C15—C16—Hc16 | 120.36 |
C14—C15—C16 | 119.77 (15) | C17—C16—Hc16 | 119.33 |
C15—C16—C17 | 120.30 (17) | C16—C17—Hc17 | 119.55 |
C16—C17—C18 | 120.12 (17) | C18—C17—Hc17 | 120.34 |
C17—C18—C19 | 120.27 (16) | C17—C18—Hc18 | 119.95 |
C14—C19—C18 | 119.68 (15) | C19—C18—Hc18 | 119.77 |
C2—O4—H1o4 | 108.2 (13) | C14—C19—Hc19 | 120.56 |
N1—C1—Hc1 | 105.44 | C18—C19—Hc19 | 119.76 |
C2—C1—Hc1 | 111.67 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H1O4···O1i | 0.86 (2) | 1.93 (2) | 2.7724 (14) | 169 (2) |
C1—HC1···O1 | 0.97 | 2.28 | 2.7353 (17) | 108 |
C7—HC7···O4ii | 0.97 | 2.51 | 3.3969 (18) | 153 |
C19—HC19···O1iii | 0.97 | 2.41 | 3.3372 (17) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+1, −y, −z+1. |
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