Download citation
Download citation
link to html
The title compound [systematic name: (2S)-1-(2-hydroxy-1-naphthyl­meth­yl)pyrrolidinio-2-carboxyl­ate], C16H17NO3, a derivative of L-proline, was synthesized via the Mannich reaction. The X-ray crystal analysis reveals that the pyrrolidine ring adopts an envelope conformation, with the flap C atom deviating by 0.631 (9) Å from the plane defined by the other four atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006859/ww6352sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006859/ww6352Isup2.hkl
Contains datablock I

CCDC reference: 270576

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.039
  • wR factor = 0.113
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.16 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 6.36 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat O3 -H3 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat O3 -H3 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.73(3), Rep 1.731(12) ...... 2.50 su-Rat H3 -O2 1.555 3.656
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.97 From the CIF: _reflns_number_total 1980 Count of symmetry unique reflns 1980 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(2S)-1-(2-Hydroxy-1-naphthylmethyl)pyrrolidinio-2-carboxylate top
Crystal data top
C16H17NO3F(000) = 576
Mr = 271.31Dx = 1.278 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1714 reflections
a = 5.8037 (7) Åθ = 2.6–22.2°
b = 12.0508 (15) ŵ = 0.09 mm1
c = 20.160 (3) ÅT = 293 K
V = 1410.0 (3) Å3Block, colourless
Z = 40.24 × 0.16 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1980 independent reflections
Radiation source: fine-focus sealed tube1329 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 77
Tmin = 0.964, Tmax = 0.988k = 1515
9621 measured reflectionsl = 2619
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1866P]
where P = (Fo2 + 2Fc2)/3
1980 reflections(Δ/σ)max = 0.001
188 parametersΔρmax = 0.18 e Å3
14 restraintsΔρmin = 0.15 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0132 (3)0.23124 (15)0.70192 (11)0.0504 (5)
H10.159 (2)0.2567 (18)0.7068 (12)0.053 (7)*
O10.4361 (3)0.16119 (16)0.69549 (13)0.0833 (7)
O20.3504 (4)0.01668 (17)0.68613 (17)0.1076 (10)
O30.2728 (3)0.37754 (15)0.78763 (11)0.0686 (5)
H30.393 (4)0.416 (3)0.7972 (18)0.103*
C10.3025 (4)0.0831 (2)0.69123 (15)0.0608 (7)
C20.0445 (4)0.10908 (18)0.68787 (12)0.0474 (6)
H20.04010.06450.72050.057*
C30.0552 (5)0.0922 (2)0.61914 (14)0.0648 (7)
H3A0.21510.06900.62140.078*
H3B0.03200.03720.59450.078*
C40.0333 (7)0.2066 (3)0.58757 (16)0.0861 (10)
H4A0.12340.22080.57320.103*
H4B0.13660.21450.55000.103*
C50.1011 (6)0.2820 (2)0.64328 (15)0.0716 (9)
H5A0.04580.35690.63570.086*
H5B0.26710.28380.64880.086*
C60.1087 (4)0.2593 (2)0.76545 (13)0.0592 (7)
H6A0.14760.33760.76550.071*
H6B0.25110.21740.76800.071*
C70.0349 (5)0.2340 (2)0.82431 (13)0.0558 (6)
C80.2267 (5)0.2995 (2)0.83358 (15)0.0602 (7)
C90.3704 (7)0.2858 (3)0.88968 (19)0.0868 (11)
H90.49940.33050.89550.104*
C100.3175 (10)0.2068 (4)0.93467 (19)0.1061 (15)
H100.41040.19910.97200.127*
C110.1295 (9)0.1366 (3)0.92729 (17)0.0960 (14)
C120.0173 (6)0.1493 (2)0.87105 (16)0.0733 (9)
C130.2108 (7)0.0785 (3)0.8648 (2)0.0992 (13)
H130.30740.08470.82820.119*
C140.2566 (11)0.0004 (4)0.9135 (4)0.137 (2)
H140.38570.04580.90990.164*
C150.1118 (14)0.0114 (5)0.9668 (3)0.150 (3)
H150.14380.06560.99830.180*
C160.0740 (13)0.0530 (4)0.9752 (2)0.141 (2)
H160.16730.04341.01230.169*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0374 (9)0.0417 (9)0.0720 (13)0.0060 (8)0.0070 (11)0.0037 (9)
O10.0394 (9)0.0697 (12)0.141 (2)0.0114 (9)0.0017 (12)0.0181 (13)
O20.0498 (10)0.0566 (11)0.216 (3)0.0081 (10)0.0158 (16)0.0136 (15)
O30.0487 (10)0.0552 (10)0.1020 (15)0.0087 (9)0.0097 (11)0.0106 (11)
C10.0373 (12)0.0529 (14)0.092 (2)0.0004 (11)0.0058 (14)0.0053 (14)
C20.0380 (11)0.0399 (11)0.0643 (15)0.0073 (9)0.0042 (11)0.0021 (11)
C30.0602 (17)0.0639 (16)0.0705 (17)0.0014 (14)0.0103 (15)0.0056 (13)
C40.092 (2)0.092 (2)0.074 (2)0.013 (2)0.017 (2)0.0204 (18)
C50.0700 (19)0.0546 (15)0.090 (2)0.0071 (15)0.0170 (17)0.0217 (15)
C60.0366 (12)0.0527 (14)0.088 (2)0.0007 (12)0.0019 (13)0.0123 (14)
C70.0496 (13)0.0491 (12)0.0688 (16)0.0077 (12)0.0067 (13)0.0095 (12)
C80.0563 (15)0.0502 (14)0.0743 (17)0.0093 (12)0.0031 (15)0.0180 (13)
C90.092 (2)0.080 (2)0.088 (2)0.025 (2)0.032 (2)0.0338 (19)
C100.157 (4)0.095 (3)0.066 (2)0.050 (3)0.029 (3)0.030 (2)
C110.158 (4)0.074 (2)0.057 (2)0.044 (3)0.021 (2)0.0084 (18)
C120.083 (2)0.0533 (15)0.084 (2)0.0153 (16)0.0335 (19)0.0103 (14)
C130.093 (3)0.0634 (17)0.141 (3)0.0041 (18)0.066 (3)0.000 (2)
C140.146 (4)0.071 (2)0.193 (5)0.013 (3)0.104 (5)0.004 (3)
C150.221 (7)0.104 (4)0.126 (4)0.030 (5)0.098 (5)0.000 (3)
C160.257 (8)0.097 (3)0.070 (2)0.065 (4)0.048 (4)0.004 (2)
Geometric parameters (Å, º) top
N1—C51.487 (3)C6—H6A0.97
N1—C61.502 (3)C6—H6B0.97
N1—C21.510 (3)C7—C81.378 (4)
N1—H10.90 (1)C7—C121.421 (4)
O1—C11.222 (3)C8—C91.415 (4)
O2—C11.239 (3)C9—C101.351 (5)
O3—C81.347 (3)C9—H90.93
O3—H30.86 (1)C10—C111.389 (6)
C1—C21.531 (3)C10—H100.93
C2—C31.515 (4)C11—C121.427 (5)
C2—H20.98C11—C161.432 (6)
C3—C41.524 (4)C12—C131.416 (5)
C3—H3A0.97C13—C141.393 (6)
C3—H3B0.97C13—H130.93
C4—C51.498 (4)C14—C151.370 (8)
C4—H4A0.97C14—H140.93
C4—H4B0.97C15—C161.339 (8)
C5—H5A0.97C15—H150.93
C5—H5B0.97C16—H160.93
C6—C71.482 (4)
C5—N1—C6112.1 (2)C7—C6—H6A109.3
C5—N1—C2107.8 (2)N1—C6—H6A109.3
C6—N1—C2115.84 (19)C7—C6—H6B109.3
C5—N1—H1111.3 (16)N1—C6—H6B109.3
C6—N1—H1105.7 (16)H6A—C6—H6B107.9
C2—N1—H1103.8 (15)C8—C7—C12119.6 (3)
C8—O3—H3112 (2)C8—C7—C6116.4 (2)
O1—C1—O2127.6 (3)C12—C7—C6124.0 (3)
O1—C1—C2117.8 (2)O3—C8—C7117.9 (3)
O2—C1—C2114.5 (2)O3—C8—C9121.0 (3)
N1—C2—C3104.87 (19)C7—C8—C9121.2 (3)
N1—C2—C1107.96 (18)C10—C9—C8119.0 (4)
C3—C2—C1112.7 (2)C10—C9—H9120.5
N1—C2—H2110.4C8—C9—H9120.5
C3—C2—H2110.4C9—C10—C11122.4 (4)
C1—C2—H2110.4C9—C10—H10118.8
C2—C3—C4103.2 (2)C11—C10—H10118.8
C2—C3—H3A111.1C10—C11—C12119.3 (3)
C4—C3—H3A111.1C10—C11—C16122.2 (5)
C2—C3—H3B111.1C12—C11—C16118.5 (5)
C4—C3—H3B111.1C13—C12—C7122.9 (3)
H3A—C3—H3B109.1C13—C12—C11118.6 (4)
C5—C4—C3102.4 (2)C7—C12—C11118.5 (3)
C5—C4—H4A111.3C14—C13—C12120.0 (5)
C3—C4—H4A111.3C14—C13—H13120.0
C5—C4—H4B111.3C12—C13—H13120.0
C3—C4—H4B111.3C15—C14—C13120.1 (6)
H4A—C4—H4B109.2C15—C14—H14119.9
N1—C5—C4103.3 (2)C13—C14—H14119.9
N1—C5—H5A111.1C16—C15—C14122.5 (6)
C4—C5—H5A111.1C16—C15—H15118.7
N1—C5—H5B111.1C14—C15—H15118.7
C4—C5—H5B111.1C15—C16—C11120.2 (6)
H5A—C5—H5B109.1C15—C16—H16119.9
C7—C6—N1111.8 (2)C11—C16—H16119.9
C5—N1—C2—C30.2 (3)C6—C7—C8—C9177.2 (2)
C6—N1—C2—C3126.6 (2)O3—C8—C9—C10179.8 (3)
C5—N1—C2—C1120.6 (2)C7—C8—C9—C100.1 (4)
C6—N1—C2—C1113.0 (2)C8—C9—C10—C111.4 (5)
O1—C1—C2—N19.0 (4)C9—C10—C11—C121.5 (5)
O2—C1—C2—N1174.2 (3)C9—C10—C11—C16179.9 (4)
O1—C1—C2—C3106.4 (3)C8—C7—C12—C13179.8 (2)
O2—C1—C2—C370.5 (3)C6—C7—C12—C131.7 (4)
N1—C2—C3—C425.1 (3)C8—C7—C12—C111.3 (4)
C1—C2—C3—C492.1 (3)C6—C7—C12—C11177.2 (2)
C2—C3—C4—C541.2 (3)C10—C11—C12—C13178.9 (3)
C6—N1—C5—C4154.4 (2)C16—C11—C12—C130.4 (4)
C2—N1—C5—C425.8 (3)C10—C11—C12—C70.1 (4)
C3—C4—C5—N141.1 (3)C16—C11—C12—C7178.6 (3)
C5—N1—C6—C7165.4 (2)C7—C12—C13—C14177.9 (3)
C2—N1—C6—C770.4 (3)C11—C12—C13—C141.0 (4)
N1—C6—C7—C868.8 (3)C12—C13—C14—C151.5 (6)
N1—C6—C7—C12112.7 (3)C13—C14—C15—C161.3 (8)
C12—C7—C8—O3178.9 (2)C14—C15—C16—C110.6 (8)
C6—C7—C8—O32.5 (3)C10—C11—C16—C15178.6 (4)
C12—C7—C8—C91.4 (4)C12—C11—C16—C150.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.90 (1)1.99 (2)2.599 (3)123 (2)
N1—H1···O30.90 (1)2.28 (2)2.892 (3)124 (2)
O3—H3···O2i0.86 (1)1.73 (1)2.586 (3)175 (4)
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds