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The title compound, C16H13NO2, was synthesized by N-alkyl­ation of 4-methyl­benzyl bromide with phthalimide. The phthalimide ring system is essentially planar and forms a dihedral angle with the tolyl ring of 69.5 (6)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033812/bh2037sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033812/bh2037Isup2.hkl
Contains datablock I

CCDC reference: 620647

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.128
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 656.20 Ang-3 PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.27 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

N-(4-methylbenzyl)phthalimide top
Crystal data top
C16H13NO2Z = 2
Mr = 251.27F(000) = 264
Triclinic, P1Dx = 1.272 Mg m3
Hall symbol: -P 1Melting point = 393.5–394 K
a = 7.107 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.521 (3) ÅCell parameters from 1001 reflections
c = 11.535 (4) Åθ = 2.5–24.6°
α = 102.383 (5)°µ = 0.08 mm1
β = 100.235 (6)°T = 294 K
γ = 99.499 (6)°Rod, colourless
V = 656.2 (4) Å30.26 × 0.22 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2303 independent reflections
Radiation source: fine-focus sealed tube1428 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 68
Tmin = 0.978, Tmax = 0.993k = 1010
3353 measured reflectionsl = 1311
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.0787P]
where P = (Fo2 + 2Fc2)/3
2303 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.15 e Å3
6 restraintsΔρmin = 0.15 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4513 (3)1.1266 (2)0.30478 (17)0.0928 (6)
O20.2237 (2)0.65957 (19)0.00300 (15)0.0707 (5)
N10.3442 (2)0.8694 (2)0.17158 (16)0.0546 (5)
C10.3793 (3)1.0409 (3)0.2030 (2)0.0608 (6)
C20.3130 (3)1.0891 (2)0.0886 (2)0.0520 (5)
C30.3135 (3)1.2426 (3)0.0674 (3)0.0696 (7)
H30.36061.33760.13020.083*
C40.2416 (3)1.2506 (3)0.0507 (3)0.0751 (7)
H40.24061.35260.06730.090*
C50.1715 (3)1.1096 (3)0.1438 (2)0.0707 (7)
H50.12361.11820.22210.085*
C60.1713 (3)0.9554 (3)0.1228 (2)0.0611 (6)
H60.12460.86040.18560.073*
C70.2434 (3)0.9480 (2)0.00452 (19)0.0487 (5)
C80.2644 (3)0.8044 (3)0.0475 (2)0.0519 (5)
C90.3883 (3)0.7702 (3)0.2586 (2)0.0675 (7)
H9A0.50060.83180.32240.081*
H9B0.42270.67090.21700.081*
C100.2177 (3)0.7236 (3)0.3156 (2)0.0571 (6)
C110.0696 (3)0.5879 (3)0.2573 (2)0.0611 (6)
H110.07700.52220.18330.073*
C120.0897 (3)0.5486 (3)0.3076 (2)0.0658 (7)
H120.18800.45720.26610.079*
C130.1062 (4)0.6411 (3)0.4172 (2)0.0677 (7)
C140.0425 (5)0.7763 (3)0.4747 (2)0.0848 (8)
H140.03530.84140.54890.102*
C150.2027 (4)0.8184 (3)0.4253 (2)0.0788 (8)
H150.29990.91070.46640.095*
C160.2792 (4)0.5954 (4)0.4723 (3)0.0954 (9)
H16A0.39350.54570.40850.143*
H16B0.30120.69250.52330.143*
H16C0.25240.51900.52010.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1078 (14)0.0807 (13)0.0680 (12)0.0097 (10)0.0024 (10)0.0025 (10)
O20.0783 (11)0.0503 (10)0.0766 (12)0.0092 (8)0.0117 (9)0.0090 (8)
N10.0504 (11)0.0554 (11)0.0563 (12)0.0103 (8)0.0070 (9)0.0148 (9)
C10.0519 (14)0.0619 (15)0.0606 (15)0.0083 (11)0.0088 (11)0.0044 (12)
C20.0428 (12)0.0502 (13)0.0653 (15)0.0134 (9)0.0156 (10)0.0135 (11)
C30.0620 (15)0.0547 (15)0.092 (2)0.0156 (11)0.0209 (14)0.0139 (14)
C40.0631 (16)0.0707 (18)0.110 (2)0.0265 (13)0.0281 (15)0.0441 (17)
C50.0590 (15)0.0867 (19)0.0821 (19)0.0264 (13)0.0203 (13)0.0419 (16)
C60.0518 (14)0.0715 (16)0.0620 (16)0.0151 (11)0.0143 (11)0.0178 (12)
C70.0377 (11)0.0523 (13)0.0585 (14)0.0121 (9)0.0153 (10)0.0132 (11)
C80.0402 (12)0.0548 (14)0.0591 (15)0.0098 (10)0.0112 (10)0.0109 (12)
C90.0572 (15)0.0753 (16)0.0716 (16)0.0152 (12)0.0036 (12)0.0298 (13)
C100.0567 (14)0.0656 (14)0.0506 (14)0.0158 (11)0.0037 (11)0.0224 (12)
C110.0664 (15)0.0623 (15)0.0547 (14)0.0175 (12)0.0119 (12)0.0133 (12)
C120.0644 (16)0.0668 (15)0.0686 (17)0.0150 (12)0.0131 (13)0.0227 (13)
C130.0752 (17)0.0778 (17)0.0644 (17)0.0286 (14)0.0202 (14)0.0348 (14)
C140.117 (2)0.092 (2)0.0483 (15)0.0299 (18)0.0243 (16)0.0140 (15)
C150.089 (2)0.0800 (18)0.0539 (16)0.0004 (14)0.0045 (14)0.0115 (14)
C160.095 (2)0.127 (2)0.097 (2)0.0467 (18)0.0463 (17)0.0602 (19)
Geometric parameters (Å, º) top
O1—C11.212 (3)C9—C101.516 (3)
O2—C81.209 (2)C9—H9A0.9700
N1—C81.394 (3)C9—H9B0.9700
N1—C11.397 (3)C10—C151.380 (3)
N1—C91.469 (3)C10—C111.382 (3)
C1—C21.485 (3)C11—C121.387 (3)
C2—C71.380 (3)C11—H110.9300
C2—C31.381 (3)C12—C131.375 (3)
C3—C41.387 (3)C12—H120.9300
C3—H30.9300C13—C141.381 (3)
C4—C51.380 (3)C13—C161.514 (3)
C4—H40.9300C14—C151.389 (3)
C5—C61.386 (3)C14—H140.9300
C5—H50.9300C15—H150.9300
C6—C71.388 (3)C16—H16A0.9600
C6—H60.9300C16—H16B0.9600
C7—C81.491 (3)C16—H16C0.9600
C8—N1—C1111.62 (18)C10—C9—H9A109.1
C8—N1—C9124.37 (18)N1—C9—H9B109.1
C1—N1—C9124.01 (19)C10—C9—H9B109.1
O1—C1—N1124.4 (2)H9A—C9—H9B107.8
O1—C1—C2129.6 (2)C15—C10—C11118.1 (2)
N1—C1—C2106.00 (18)C15—C10—C9120.9 (2)
C7—C2—C3121.2 (2)C11—C10—C9120.9 (2)
C7—C2—C1108.36 (19)C10—C11—C12120.8 (2)
C3—C2—C1130.5 (2)C10—C11—H11119.6
C2—C3—C4117.9 (2)C12—C11—H11119.6
C2—C3—H3121.1C13—C12—C11121.7 (2)
C4—C3—H3121.1C13—C12—H12119.1
C5—C4—C3121.0 (2)C11—C12—H12119.1
C5—C4—H4119.5C12—C13—C14116.9 (2)
C3—C4—H4119.5C12—C13—C16121.3 (2)
C4—C5—C6121.2 (2)C14—C13—C16121.8 (3)
C4—C5—H5119.4C13—C14—C15122.2 (2)
C6—C5—H5119.4C13—C14—H14118.9
C5—C6—C7117.5 (2)C15—C14—H14118.9
C5—C6—H6121.2C10—C15—C14120.1 (2)
C7—C6—H6121.2C10—C15—H15119.9
C2—C7—C6121.2 (2)C14—C15—H15119.9
C2—C7—C8108.01 (19)C13—C16—H16A109.5
C6—C7—C8130.8 (2)C13—C16—H16B109.5
O2—C8—N1124.7 (2)H16A—C16—H16B109.5
O2—C8—C7129.3 (2)C13—C16—H16C109.5
N1—C8—C7106.00 (18)H16A—C16—H16C109.5
N1—C9—C10112.50 (17)H16B—C16—H16C109.5
N1—C9—H9A109.1
C8—N1—C1—O1178.6 (2)C1—N1—C8—C71.1 (2)
C9—N1—C1—O10.7 (3)C9—N1—C8—C7179.56 (17)
C8—N1—C1—C20.9 (2)C2—C7—C8—O2178.9 (2)
C9—N1—C1—C2179.77 (17)C6—C7—C8—O20.6 (4)
O1—C1—C2—C7179.2 (2)C2—C7—C8—N10.9 (2)
N1—C1—C2—C70.3 (2)C6—C7—C8—N1179.61 (19)
O1—C1—C2—C30.6 (4)C8—N1—C9—C1090.4 (2)
N1—C1—C2—C3179.9 (2)C1—N1—C9—C1090.4 (2)
C7—C2—C3—C40.1 (3)N1—C9—C10—C1593.6 (3)
C1—C2—C3—C4179.9 (2)N1—C9—C10—C1184.2 (3)
C2—C3—C4—C50.1 (3)C15—C10—C11—C120.1 (3)
C3—C4—C5—C60.3 (3)C9—C10—C11—C12177.77 (19)
C4—C5—C6—C70.3 (3)C10—C11—C12—C130.6 (3)
C3—C2—C7—C60.1 (3)C11—C12—C13—C140.6 (3)
C1—C2—C7—C6179.92 (17)C11—C12—C13—C16178.9 (2)
C3—C2—C7—C8179.49 (18)C12—C13—C14—C150.1 (4)
C1—C2—C7—C80.4 (2)C16—C13—C14—C15179.4 (2)
C5—C6—C7—C20.1 (3)C11—C10—C15—C140.3 (4)
C5—C6—C7—C8179.53 (19)C9—C10—C15—C14178.2 (2)
C1—N1—C8—O2178.72 (19)C13—C14—C15—C100.3 (4)
C9—N1—C8—O20.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.593.437 (3)152
Symmetry code: (i) x, y+1, z.
 

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