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The title compound, C20H17NO, adopts a gauche conformation and the pyrrolizine ring system is planar. An inter­molecular C—H...O inter­action is found in the mol­ecular packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056571/sj2202sup1.cif
Contains datablocks 1, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056571/sj2202Isup2.hkl
Contains datablock I

CCDC reference: 644024

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.108
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C2
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.45 From the CIF: _reflns_number_total 1817 Count of symmetry unique reflns 1824 Completeness (_total/calc) 99.62% 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 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

7-phenyl-6-benzoyl-2,3-dihydro-1H-pyrrolizine top
Crystal data top
C20H17NOF(000) = 608
Mr = 287.35Dx = 1.246 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1193 reflections
a = 8.302 (2) Åθ = 2.2–20.1°
b = 11.452 (4) ŵ = 0.08 mm1
c = 16.106 (5) ÅT = 294 K
V = 1531.3 (8) Å3Block, colorless
Z = 40.12 × 0.10 × 0.06 mm
Data collection top
Bruker CCD area detector
diffractometer
1817 independent reflections
Radiation source: fine-focus sealed tube1008 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
φ and ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 610
Tmin = 0.983, Tmax = 0.992k = 1414
8692 measured reflectionsl = 1920
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0428P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1817 reflectionsΔρmax = 0.16 e Å3
200 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0071 (16)
Special details top

Experimental. 1H NMR (CDCl3): 7.03–7.81 (m, C6H5, 10H), 5.82 (s, pyrooline-H, 2H), 3.65 (m, CH2, 2H), 2.41 (m, CH2, 2H), 1.92 (m, CH2, 2H); Ms(M + 1): 288.4.

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
O10.8831 (3)0.4706 (2)0.30633 (15)0.0701 (9)
N10.7618 (3)0.6181 (3)0.55621 (14)0.0450 (7)
C10.7555 (5)0.6678 (3)0.63994 (19)0.0601 (11)
H1A0.86260.67650.66320.072*
H1B0.69100.61980.67680.072*
C20.6785 (6)0.7835 (4)0.6256 (2)0.0940 (17)
H2A0.74390.84450.65030.113*
H2B0.57330.78520.65180.113*
C30.6608 (5)0.8057 (3)0.5348 (2)0.0622 (11)
H3A0.55000.82400.52080.075*
H3B0.72940.86970.51720.075*
C40.7122 (4)0.6939 (3)0.49572 (19)0.0423 (9)
C50.7257 (4)0.6392 (3)0.42013 (18)0.0425 (9)
C60.7858 (4)0.5240 (3)0.43708 (19)0.0438 (9)
C70.8062 (4)0.5160 (3)0.5229 (2)0.0488 (9)
H70.84390.45120.55180.059*
C80.8427 (4)0.4382 (3)0.3763 (2)0.0495 (10)
C90.8571 (4)0.3126 (3)0.3979 (2)0.0450 (9)
C100.9604 (5)0.2440 (3)0.3515 (2)0.0529 (10)
H101.01810.27770.30820.063*
C110.9799 (5)0.1263 (4)0.3681 (3)0.0664 (12)
H111.05050.08150.33650.080*
C120.8937 (5)0.0763 (3)0.4316 (2)0.0656 (12)
H120.90800.00230.44400.079*
C130.7866 (5)0.1417 (3)0.4770 (2)0.0615 (11)
H130.72680.10690.51910.074*
C140.7675 (5)0.2585 (3)0.4604 (2)0.0508 (10)
H140.69410.30200.49110.061*
C150.6772 (4)0.6908 (3)0.33977 (19)0.0438 (9)
C160.7170 (5)0.8047 (3)0.3206 (2)0.0573 (10)
H160.77880.84780.35780.069*
C170.6670 (5)0.8560 (4)0.2473 (3)0.0745 (14)
H170.69570.93280.23580.089*
C180.5763 (6)0.7950 (5)0.1921 (3)0.0812 (15)
H180.54250.83010.14300.097*
C190.5346 (5)0.6814 (5)0.2089 (2)0.0747 (13)
H190.47220.63930.17140.090*
C200.5863 (5)0.6294 (3)0.2824 (2)0.0583 (11)
H200.55920.55210.29320.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.100 (2)0.0652 (17)0.0454 (16)0.0117 (16)0.0176 (15)0.0055 (14)
N10.0532 (19)0.0509 (17)0.0310 (15)0.0068 (17)0.0012 (14)0.0036 (14)
C10.080 (3)0.064 (3)0.036 (2)0.016 (2)0.002 (2)0.0095 (18)
C20.109 (4)0.111 (4)0.061 (3)0.047 (3)0.023 (3)0.032 (3)
C30.074 (3)0.055 (2)0.057 (2)0.001 (2)0.008 (2)0.001 (2)
C40.043 (2)0.043 (2)0.040 (2)0.0026 (18)0.0023 (16)0.0025 (19)
C50.046 (2)0.043 (2)0.0385 (19)0.0030 (18)0.0002 (18)0.0028 (16)
C60.052 (2)0.044 (2)0.0359 (19)0.0013 (18)0.0003 (18)0.0001 (17)
C70.060 (2)0.046 (2)0.0403 (19)0.0053 (19)0.0016 (19)0.0017 (18)
C80.052 (2)0.053 (3)0.043 (2)0.0024 (19)0.0014 (19)0.0012 (19)
C90.052 (2)0.045 (2)0.038 (2)0.003 (2)0.0034 (18)0.0054 (18)
C100.059 (3)0.056 (3)0.044 (2)0.006 (2)0.0004 (19)0.003 (2)
C110.068 (3)0.069 (3)0.062 (3)0.016 (2)0.008 (2)0.013 (2)
C120.085 (3)0.044 (2)0.068 (3)0.001 (2)0.007 (3)0.003 (2)
C130.081 (3)0.049 (3)0.054 (2)0.010 (2)0.001 (2)0.004 (2)
C140.058 (3)0.046 (2)0.048 (2)0.002 (2)0.001 (2)0.0050 (18)
C150.042 (2)0.050 (2)0.0395 (19)0.0031 (19)0.0010 (17)0.0007 (18)
C160.058 (3)0.057 (2)0.057 (2)0.002 (2)0.002 (2)0.010 (2)
C170.059 (3)0.088 (3)0.077 (3)0.013 (3)0.010 (3)0.041 (3)
C180.069 (3)0.132 (5)0.043 (2)0.039 (3)0.004 (2)0.019 (3)
C190.073 (3)0.103 (4)0.049 (3)0.022 (3)0.015 (2)0.011 (3)
C200.065 (3)0.063 (3)0.047 (2)0.009 (2)0.011 (2)0.006 (2)
Geometric parameters (Å, º) top
O1—C81.232 (4)C9—C141.397 (5)
N1—C71.339 (4)C10—C111.384 (5)
N1—C41.368 (4)C10—H100.9300
N1—C11.465 (4)C11—C121.374 (5)
C1—C21.490 (5)C11—H110.9300
C1—H1A0.9700C12—C131.374 (5)
C1—H1B0.9700C12—H120.9300
C2—C31.491 (5)C13—C141.373 (5)
C2—H2A0.9700C13—H130.9300
C2—H2B0.9700C14—H140.9300
C3—C41.489 (4)C15—C161.380 (5)
C3—H3A0.9700C15—C201.384 (4)
C3—H3B0.9700C16—C171.383 (5)
C4—C51.374 (4)C16—H160.9300
C5—C61.437 (4)C17—C181.359 (6)
C5—C151.478 (4)C17—H170.9300
C6—C71.395 (4)C18—C191.374 (6)
C6—C81.466 (5)C18—H180.9300
C7—H70.9300C19—C201.392 (5)
C8—C91.484 (5)C19—H190.9300
C9—C101.383 (4)C20—H200.9300
C7—N1—C4110.6 (2)C10—C9—C14117.9 (3)
C7—N1—C1135.9 (3)C10—C9—C8118.3 (3)
C4—N1—C1113.5 (3)C14—C9—C8123.8 (3)
N1—C1—C2102.6 (3)C9—C10—C11121.5 (4)
N1—C1—H1A111.2C9—C10—H10119.3
C2—C1—H1A111.2C11—C10—H10119.3
N1—C1—H1B111.2C12—C11—C10119.3 (4)
C2—C1—H1B111.2C12—C11—H11120.4
H1A—C1—H1B109.2C10—C11—H11120.4
C1—C2—C3110.2 (3)C13—C12—C11120.4 (4)
C1—C2—H2A109.6C13—C12—H12119.8
C3—C2—H2A109.6C11—C12—H12119.8
C1—C2—H2B109.6C14—C13—C12120.1 (4)
C3—C2—H2B109.6C14—C13—H13119.9
H2A—C2—H2B108.1C12—C13—H13119.9
C4—C3—C2103.9 (3)C13—C14—C9120.8 (4)
C4—C3—H3A111.0C13—C14—H14119.6
C2—C3—H3A111.0C9—C14—H14119.6
C4—C3—H3B111.0C16—C15—C20117.5 (3)
C2—C3—H3B111.0C16—C15—C5120.5 (3)
H3A—C3—H3B109.0C20—C15—C5122.0 (3)
N1—C4—C5108.5 (3)C15—C16—C17121.4 (4)
N1—C4—C3109.3 (3)C15—C16—H16119.3
C5—C4—C3142.2 (3)C17—C16—H16119.3
C4—C5—C6106.2 (3)C18—C17—C16120.5 (4)
C4—C5—C15124.9 (3)C18—C17—H17119.8
C6—C5—C15128.9 (3)C16—C17—H17119.8
C7—C6—C5106.9 (3)C17—C18—C19119.8 (4)
C7—C6—C8125.3 (3)C17—C18—H18120.1
C5—C6—C8126.9 (3)C19—C18—H18120.1
N1—C7—C6107.8 (3)C18—C19—C20119.7 (4)
N1—C7—H7126.1C18—C19—H19120.2
C6—C7—H7126.1C20—C19—H19120.2
O1—C8—C6119.8 (3)C15—C20—C19121.2 (4)
O1—C8—C9119.0 (3)C15—C20—H20119.4
C6—C8—C9121.2 (3)C19—C20—H20119.4
C7—N1—C1—C2175.5 (4)C5—C6—C8—C9162.1 (3)
C4—N1—C1—C25.5 (4)O1—C8—C9—C1020.6 (5)
N1—C1—C2—C37.2 (5)C6—C8—C9—C10157.7 (3)
C1—C2—C3—C46.4 (5)O1—C8—C9—C14156.7 (3)
C7—N1—C4—C50.4 (4)C6—C8—C9—C1425.1 (5)
C1—N1—C4—C5179.0 (3)C14—C9—C10—C112.5 (5)
C7—N1—C4—C3179.0 (3)C8—C9—C10—C11179.9 (3)
C1—N1—C4—C31.7 (4)C9—C10—C11—C120.5 (6)
C2—C3—C4—N12.9 (5)C10—C11—C12—C131.5 (6)
C2—C3—C4—C5176.1 (5)C11—C12—C13—C141.5 (6)
N1—C4—C5—C60.4 (4)C12—C13—C14—C90.5 (6)
C3—C4—C5—C6178.6 (5)C10—C9—C14—C132.5 (5)
N1—C4—C5—C15177.3 (3)C8—C9—C14—C13179.8 (3)
C3—C4—C5—C151.7 (7)C4—C5—C15—C1644.6 (5)
C4—C5—C6—C70.3 (4)C6—C5—C15—C16139.2 (4)
C15—C5—C6—C7177.0 (3)C4—C5—C15—C20133.1 (4)
C4—C5—C6—C8170.4 (3)C6—C5—C15—C2043.1 (6)
C15—C5—C6—C812.9 (6)C20—C15—C16—C170.6 (5)
C4—N1—C7—C60.2 (4)C5—C15—C16—C17177.2 (3)
C1—N1—C7—C6178.9 (4)C15—C16—C17—C180.2 (6)
C5—C6—C7—N10.1 (4)C16—C17—C18—C190.3 (6)
C8—C6—C7—N1170.4 (3)C17—C18—C19—C200.2 (7)
C7—C6—C8—O1148.7 (4)C16—C15—C20—C191.1 (5)
C5—C6—C8—O119.6 (6)C5—C15—C20—C19176.6 (3)
C7—C6—C8—C929.6 (6)C18—C19—C20—C151.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1i0.972.413.319 (4)156
Symmetry code: (i) x+3/2, y+1, z+1/2.
 

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