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In the title compound, C14H11NO2, the indolizine unit is almost planar. The carboxyl­ate group is oriented almost coplanar with the indolizine unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037494/ez2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037494/ez2034Isup2.hkl
Contains datablock I

CCDC reference: 624211

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.047
  • wR factor = 0.129
  • Data-to-parameter ratio = 36.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C13 .. 5.02 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Methyl pyrrolo[2,1-a]isoquinoline-1-carboxylate top
Crystal data top
C14H11NO2F(000) = 472
Mr = 225.24Dx = 1.402 Mg m3
Monoclinic, P21/cMelting point: 371 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.8733 (1) ÅCell parameters from 5277 reflections
b = 6.9155 (1) Åθ = 2.6–39.9°
c = 15.7532 (2) ŵ = 0.10 mm1
β = 97.283 (1)°T = 100 K
V = 1066.93 (2) Å3Block, colorless
Z = 40.48 × 0.35 × 0.24 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5583 independent reflections
Radiation source: sealed tube4751 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 37.5°, θmin = 2.6°
Absorption correction: multi-scan
(SABADS; Bruker, 2005)
h = 1616
Tmin = 0.956, Tmax = 0.978k = 1111
49755 measured reflectionsl = 2626
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.073P)2 + 0.2336P]
where P = (Fo2 + 2Fc2)/3
5583 reflections(Δ/σ)max = 0.007
155 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.29 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
O10.49284 (6)0.20881 (9)0.22852 (4)0.02168 (12)
O20.29966 (6)0.31610 (10)0.27370 (3)0.02242 (12)
N10.18249 (6)0.20575 (9)0.00328 (4)0.01578 (10)
C10.39414 (7)0.18692 (11)0.06224 (4)0.01830 (12)
H1A0.48820.16940.07270.022*
C20.31617 (7)0.16892 (11)0.01530 (5)0.01868 (12)
H2A0.34740.13760.06690.022*
C30.07229 (8)0.19763 (11)0.06699 (4)0.01856 (12)
H3A0.08570.16780.12290.022*
C40.05402 (8)0.23303 (11)0.04767 (5)0.01928 (13)
H4A0.12820.22540.09020.023*
C50.07546 (7)0.28257 (10)0.03828 (4)0.01621 (11)
C60.20780 (7)0.32327 (11)0.05803 (5)0.02051 (13)
H6A0.28180.31480.01530.025*
C70.22904 (7)0.37543 (12)0.13966 (5)0.02186 (14)
H7A0.31690.40050.15210.026*
C80.11753 (8)0.39052 (12)0.20379 (5)0.02085 (13)
H8A0.13170.42790.25870.025*
C90.01333 (7)0.35045 (11)0.18642 (4)0.01783 (12)
H9A0.08620.36100.22980.021*
C100.03757 (7)0.29376 (9)0.10370 (4)0.01448 (11)
C110.17250 (7)0.25024 (10)0.08184 (4)0.01409 (11)
C120.30685 (7)0.23723 (10)0.12483 (4)0.01522 (11)
C130.35939 (7)0.26053 (10)0.21511 (4)0.01568 (11)
C140.55840 (8)0.22333 (12)0.31513 (5)0.02154 (13)
H14A0.65270.18720.31730.032*
H14B0.51400.13840.35110.032*
H14C0.55230.35400.33480.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0153 (2)0.0315 (3)0.0171 (2)0.00334 (19)0.00209 (17)0.0047 (2)
O20.0177 (2)0.0370 (3)0.0126 (2)0.0007 (2)0.00224 (17)0.0020 (2)
N10.0180 (2)0.0187 (2)0.0106 (2)0.00019 (18)0.00177 (17)0.00039 (17)
C10.0165 (3)0.0236 (3)0.0153 (3)0.0005 (2)0.0041 (2)0.0009 (2)
C20.0197 (3)0.0230 (3)0.0140 (3)0.0010 (2)0.0049 (2)0.0008 (2)
C30.0225 (3)0.0212 (3)0.0112 (2)0.0010 (2)0.0009 (2)0.0007 (2)
C40.0208 (3)0.0212 (3)0.0146 (3)0.0011 (2)0.0025 (2)0.0010 (2)
C50.0162 (3)0.0165 (3)0.0152 (3)0.00018 (19)0.0006 (2)0.0005 (2)
C60.0156 (3)0.0225 (3)0.0227 (3)0.0004 (2)0.0001 (2)0.0003 (2)
C70.0162 (3)0.0256 (3)0.0242 (3)0.0020 (2)0.0040 (2)0.0009 (3)
C80.0188 (3)0.0271 (3)0.0173 (3)0.0034 (2)0.0049 (2)0.0013 (2)
C90.0168 (3)0.0236 (3)0.0133 (2)0.0024 (2)0.0026 (2)0.0005 (2)
C100.0151 (2)0.0154 (3)0.0129 (2)0.00035 (18)0.00174 (19)0.00107 (18)
C110.0159 (2)0.0159 (3)0.0105 (2)0.00032 (19)0.00191 (18)0.00056 (18)
C120.0147 (2)0.0188 (3)0.0122 (2)0.00010 (19)0.00197 (19)0.00011 (19)
C130.0153 (2)0.0178 (3)0.0138 (2)0.00131 (19)0.00116 (19)0.0009 (2)
C140.0191 (3)0.0250 (3)0.0187 (3)0.0004 (2)0.0047 (2)0.0013 (2)
Geometric parameters (Å, º) top
O1—C131.3558 (9)C5—C101.4220 (9)
O1—C141.4375 (9)C6—C71.3770 (11)
O2—C131.2187 (9)C6—H6A0.9300
N1—C21.3806 (9)C7—C81.4005 (11)
N1—C31.3847 (9)C7—H7A0.9300
N1—C111.3915 (8)C8—C91.3822 (10)
C1—C21.3645 (10)C8—H8A0.9300
C1—C121.4323 (9)C9—C101.4101 (9)
C1—H1A0.9300C9—H9A0.9300
C2—H2A0.9300C10—C111.4492 (9)
C3—C41.3432 (11)C11—C121.4137 (9)
C3—H3A0.9300C12—C131.4596 (9)
C4—C51.4381 (10)C14—H14A0.9600
C4—H4A0.9300C14—H14B0.9600
C5—C61.4094 (10)C14—H14C0.9600
C13—O1—C14116.18 (6)C9—C8—C7120.75 (7)
C2—N1—C3124.76 (6)C9—C8—H8A119.6
C2—N1—C11111.02 (6)C7—C8—H8A119.6
C3—N1—C11124.21 (6)C8—C9—C10120.74 (7)
C2—C1—C12108.54 (6)C8—C9—H9A119.6
C2—C1—H1A125.7C10—C9—H9A119.6
C12—C1—H1A125.7C9—C10—C5118.38 (6)
C1—C2—N1107.52 (6)C9—C10—C11123.11 (6)
C1—C2—H2A126.2C5—C10—C11118.50 (6)
N1—C2—H2A126.2N1—C11—C12105.71 (6)
C4—C3—N1119.68 (6)N1—C11—C10117.03 (6)
C4—C3—H3A120.2C12—C11—C10137.26 (6)
N1—C3—H3A120.2C11—C12—C1107.20 (6)
C3—C4—C5120.57 (7)C11—C12—C13130.97 (6)
C3—C4—H4A119.7C1—C12—C13121.81 (6)
C5—C4—H4A119.7O2—C13—O1121.27 (6)
C6—C5—C10119.57 (6)O2—C13—C12128.79 (7)
C6—C5—C4120.45 (6)O1—C13—C12109.94 (6)
C10—C5—C4119.98 (6)O1—C14—H14A109.5
C7—C6—C5120.91 (7)O1—C14—H14B109.5
C7—C6—H6A119.5H14A—C14—H14B109.5
C5—C6—H6A119.5O1—C14—H14C109.5
C6—C7—C8119.62 (7)H14A—C14—H14C109.5
C6—C7—H7A120.2H14B—C14—H14C109.5
C8—C7—H7A120.2
C12—C1—C2—N10.20 (9)C3—N1—C11—C12178.40 (6)
C3—N1—C2—C1178.61 (7)C2—N1—C11—C10179.55 (6)
C11—N1—C2—C10.71 (9)C3—N1—C11—C101.13 (10)
C2—N1—C3—C4178.83 (7)C9—C10—C11—N1176.78 (6)
C11—N1—C3—C40.41 (11)C5—C10—C11—N11.93 (9)
N1—C3—C4—C51.09 (12)C9—C10—C11—C123.89 (13)
C3—C4—C5—C6178.78 (7)C5—C10—C11—C12177.40 (8)
C3—C4—C5—C100.22 (11)N1—C11—C12—C10.77 (8)
C10—C5—C6—C70.59 (11)C10—C11—C12—C1179.85 (8)
C4—C5—C6—C7178.41 (7)N1—C11—C12—C13177.28 (7)
C5—C6—C7—C80.76 (12)C10—C11—C12—C132.10 (14)
C6—C7—C8—C91.11 (12)C2—C1—C12—C110.37 (8)
C7—C8—C9—C100.11 (12)C2—C1—C12—C13177.90 (7)
C8—C9—C10—C51.22 (11)C14—O1—C13—O20.07 (11)
C8—C9—C10—C11179.92 (7)C14—O1—C13—C12179.66 (6)
C6—C5—C10—C91.56 (10)C11—C12—C13—O28.08 (13)
C4—C5—C10—C9177.45 (7)C1—C12—C13—O2174.11 (8)
C6—C5—C10—C11179.68 (6)C11—C12—C13—O1171.62 (7)
C4—C5—C10—C111.32 (10)C1—C12—C13—O16.19 (10)
C2—N1—C11—C120.92 (8)
 

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