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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007871/su6092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007871/su6092Isup2.hkl
Contains datablock I

CCDC reference: 239138

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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.

(I) top
Crystal data top
C19H19NO5F(000) = 720
Mr = 341.4Dx = 1.339 (1) Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 8343 reflections
a = 13.0672 (4) Åθ = 2.9–30.0°
b = 6.7829 (3) ŵ = 0.10 mm1
c = 19.2623 (8) ÅT = 150 K
β = 97.381 (3)°Thick plate, colourless
V = 1693.14 (12) Å30.23 × 0.16 × 0.06 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3228 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.076
Detector resolution: 9 pixels mm-1θmax = 29.8°, θmin = 6.4°
φ and ω frames scansh = 1818
27588 measured reflectionsk = 99
4886 independent reflectionsl = 2626
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.058Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.001936I2]
wR(F) = 0.124(Δ/σ)max = 0.001
S = 1.44Δρmax = 0.51 e Å3
4886 reflectionsΔρmin = 0.44 e Å3
229 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.45544 (7)0.28756 (15)0.50688 (5)0.0243 (3)
O20.16179 (8)0.32363 (16)0.50236 (6)0.0324 (4)
O30.18200 (8)0.61612 (16)0.55782 (6)0.0278 (3)
O40.36320 (8)0.81340 (16)0.40975 (6)0.0275 (3)
O50.08979 (7)0.72753 (16)0.40556 (6)0.0286 (3)
N10.32939 (9)0.41095 (18)0.42745 (6)0.0201 (3)
C10.29682 (10)0.5501 (2)0.47788 (7)0.0205 (4)
C20.27589 (10)0.7503 (2)0.44125 (8)0.0220 (4)
C30.18771 (10)0.7312 (2)0.38088 (8)0.0216 (4)
C40.13031 (11)0.5187 (2)0.27692 (8)0.0274 (5)
C50.13398 (12)0.3512 (2)0.23669 (9)0.0331 (5)
C60.20378 (12)0.2032 (3)0.25960 (8)0.0306 (5)
C70.26822 (11)0.2222 (2)0.32214 (8)0.0249 (5)
C80.26571 (10)0.3941 (2)0.36187 (7)0.0203 (4)
C90.19599 (10)0.5446 (2)0.33965 (8)0.0208 (4)
C100.20522 (11)0.4788 (2)0.51258 (7)0.0223 (4)
C110.09232 (12)0.5790 (3)0.59273 (9)0.0345 (5)
C120.05746 (13)0.9168 (3)0.42637 (11)0.0426 (6)
C130.42325 (11)0.3188 (2)0.44449 (8)0.0207 (4)
C140.49065 (10)0.2792 (2)0.38910 (8)0.0218 (4)
C150.49675 (12)0.4150 (3)0.33557 (8)0.0288 (5)
C160.56889 (12)0.3880 (3)0.28915 (9)0.0374 (6)
C170.63395 (13)0.2273 (3)0.29584 (9)0.0391 (6)
C180.62855 (12)0.0921 (3)0.34943 (10)0.0356 (5)
C190.55756 (11)0.1176 (2)0.39635 (8)0.0266 (5)
Hc10.3540.55760.51530.0246*
Hc20.26330.84810.47590.0265*
Hc30.18870.84680.35130.026*
Hc40.08060.62030.26080.0329*
H1o40.4174 (14)0.795 (3)0.4392 (10)0.033*
Hc50.08830.33760.19310.0397*
Hc60.20760.08520.23160.0367*
Hc70.31490.11550.3380.0299*
H1c110.03060.58580.5590.0414*
H2c110.09770.4490.61380.0414*
H3c110.08850.67750.62880.0414*
H1c120.01130.90720.43990.0511*
H2c120.10490.96390.46580.0511*
H3c120.05681.00830.38760.0511*
Hc150.45090.5280.33060.0345*
Hc160.57390.4820.25180.0449*
Hc170.68340.20930.26290.0469*
Hc180.67460.02060.35410.0428*
Hc190.55470.02330.43390.0319*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0210 (5)0.0287 (5)0.0219 (5)0.0003 (4)0.0021 (4)0.0077 (5)
O20.0331 (6)0.0279 (6)0.0377 (7)0.0108 (5)0.0096 (5)0.0018 (5)
O30.0252 (6)0.0327 (6)0.0262 (6)0.0060 (5)0.0060 (4)0.0042 (5)
O40.0145 (5)0.0311 (6)0.0353 (6)0.0061 (4)0.0030 (4)0.0111 (5)
O50.0197 (5)0.0292 (6)0.0370 (6)0.0000 (4)0.0043 (5)0.0061 (5)
N10.0173 (6)0.0227 (6)0.0191 (6)0.0004 (5)0.0024 (5)0.0028 (5)
C10.0160 (7)0.0231 (7)0.0212 (7)0.0019 (6)0.0019 (6)0.0012 (6)
C20.0170 (7)0.0208 (7)0.0276 (8)0.0034 (6)0.0004 (6)0.0023 (6)
C30.0148 (7)0.0204 (7)0.0289 (8)0.0018 (6)0.0002 (6)0.0033 (6)
C40.0222 (8)0.0303 (8)0.0279 (8)0.0031 (6)0.0040 (6)0.0039 (7)
C50.0300 (9)0.0400 (10)0.0259 (8)0.0027 (7)0.0091 (7)0.0024 (8)
C60.0293 (8)0.0312 (9)0.0293 (9)0.0002 (7)0.0034 (7)0.0060 (7)
C70.0200 (7)0.0246 (8)0.0292 (8)0.0009 (6)0.0003 (6)0.0019 (7)
C80.0163 (7)0.0241 (7)0.0198 (7)0.0045 (6)0.0002 (6)0.0031 (6)
C90.0151 (6)0.0244 (8)0.0223 (7)0.0027 (6)0.0003 (6)0.0030 (6)
C100.0198 (7)0.0258 (8)0.0199 (7)0.0017 (6)0.0025 (6)0.0020 (6)
C110.0297 (9)0.0469 (11)0.0282 (9)0.0037 (8)0.0088 (7)0.0002 (8)
C120.0289 (9)0.0415 (10)0.0566 (12)0.0050 (8)0.0024 (9)0.0212 (10)
C130.0179 (7)0.0177 (7)0.0255 (8)0.0040 (6)0.0015 (6)0.0047 (6)
C140.0157 (7)0.0258 (7)0.0229 (8)0.0041 (6)0.0014 (6)0.0014 (6)
C150.0219 (8)0.0359 (9)0.0279 (8)0.0015 (7)0.0008 (6)0.0073 (7)
C160.0296 (9)0.0555 (12)0.0281 (9)0.0062 (8)0.0071 (7)0.0067 (9)
C170.0260 (8)0.0598 (12)0.0326 (9)0.0066 (8)0.0076 (7)0.0127 (9)
C180.0255 (8)0.0360 (9)0.0445 (10)0.0004 (7)0.0010 (7)0.0132 (9)
C190.0214 (7)0.0248 (8)0.0320 (9)0.0034 (6)0.0026 (6)0.0013 (7)
Geometric parameters (Å, º) top
O1—C131.2396 (17)C6—C71.384 (2)
O2—C101.1997 (18)C6—Hc60.97
O3—C101.3369 (19)C7—C81.398 (2)
O3—C111.446 (2)C7—Hc70.97
O4—C21.4252 (18)C8—C91.3983 (19)
O4—H1o40.858 (18)C11—H1c110.97
O5—C31.4214 (17)C11—H2c110.97
O5—C121.425 (2)C11—H3c110.97
N1—C11.4567 (19)C12—H1c120.97
N1—C81.4251 (17)C12—H2c120.97
N1—C131.3782 (18)C12—H3c120.97
C1—C21.538 (2)C13—C141.492 (2)
C1—C101.523 (2)C14—C151.392 (2)
C1—Hc10.97C14—C191.398 (2)
C2—C31.5337 (19)C15—C161.392 (2)
C2—Hc20.97C15—Hc150.97
C3—C91.506 (2)C16—C171.378 (3)
C3—Hc30.97C16—Hc160.97
C4—C51.380 (2)C17—C181.389 (3)
C4—C91.400 (2)C17—Hc170.97
C4—Hc40.97C18—C191.387 (2)
C5—C61.389 (2)C18—Hc180.97
C5—Hc50.97C19—Hc190.97
C10—O3—C11116.57 (12)C10—C1—Hc1105.29
C3—O5—C12112.96 (12)O4—C2—Hc2107.64
C1—N1—C8117.11 (11)C1—C2—Hc2108.90
C1—N1—C13117.54 (11)C1—C2—H1o492.0 (5)
C8—N1—C13125.11 (12)C3—C2—Hc2113.70
N1—C1—C2108.43 (12)C3—C2—H1o4130.0 (6)
N1—C1—C10113.58 (11)Hc2—C2—H1o499.1
C2—C1—C10112.24 (11)O5—C3—Hc3106.93
O4—C2—C1110.83 (11)C2—C3—Hc3108.17
O4—C2—C3105.48 (12)C9—C3—Hc3111.25
C1—C2—C3110.22 (11)C5—C4—Hc4118.37
O5—C3—C2111.64 (12)C9—C4—Hc4119.89
O5—C3—C9106.88 (11)C4—C5—Hc5120.15
C2—C3—C9111.88 (11)C6—C5—Hc5120.81
C5—C4—C9121.74 (14)C5—C6—Hc6119.84
C4—C5—C6119.04 (14)C7—C6—Hc6119.47
C5—C6—C7120.69 (15)C6—C7—Hc7119.54
C6—C7—C8119.97 (14)C8—C7—Hc7120.49
N1—C8—C7120.01 (12)O3—C11—H1c11109.47
N1—C8—C9119.73 (13)O3—C11—H2c11109.47
C7—C8—C9120.12 (12)O3—C11—H3c11109.47
C3—C9—C4118.87 (12)H1c11—C11—H2c11109.47
C3—C9—C8122.72 (12)H1c11—C11—H3c11109.47
C4—C9—C8118.40 (13)H2c11—C11—H3c11109.47
O2—C10—O3125.17 (14)O5—C12—H1c12109.47
O2—C10—C1126.06 (14)O5—C12—H2c12109.47
O3—C10—C1108.76 (12)O5—C12—H3c12109.47
O1—C13—N1119.29 (13)H1c12—C12—H2c12109.5
O1—C13—C14120.29 (12)H1c12—C12—H3c12109.47
N1—C13—C14120.02 (12)H2c12—C12—H3c12109.47
C13—C14—C15120.37 (13)C14—C15—Hc15120.12
C13—C14—C19119.25 (13)C16—C15—Hc15120.12
C15—C14—C19119.86 (14)C15—C16—Hc16120.36
C14—C15—C16119.77 (15)C17—C16—Hc16119.33
C15—C16—C17120.30 (17)C16—C17—Hc17119.55
C16—C17—C18120.12 (17)C18—C17—Hc17120.34
C17—C18—C19120.27 (16)C17—C18—Hc18119.95
C14—C19—C18119.68 (15)C19—C18—Hc18119.77
C2—O4—H1o4108.2 (13)C14—C19—Hc19120.56
N1—C1—Hc1105.44C18—C19—Hc19119.76
C2—C1—Hc1111.67
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1O4···O1i0.86 (2)1.93 (2)2.7724 (14)169 (2)
C1—HC1···O10.972.282.7353 (17)108
C7—HC7···O4ii0.972.513.3969 (18)153
C19—HC19···O1iii0.972.413.3372 (17)160
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x+1, y, z+1.
 

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