organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033812/bh2037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033812/bh2037Isup2.hkl |
CCDC reference: 620647
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
C16H13NO2 | Z = 2 |
Mr = 251.27 | F(000) = 264 |
Triclinic, P1 | Dx = 1.272 Mg m−3 |
Hall symbol: -P 1 | Melting point = 393.5–394 K |
a = 7.107 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.521 (3) Å | Cell parameters from 1001 reflections |
c = 11.535 (4) Å | θ = 2.5–24.6° |
α = 102.383 (5)° | µ = 0.08 mm−1 |
β = 100.235 (6)° | T = 294 K |
γ = 99.499 (6)° | Rod, colourless |
V = 656.2 (4) Å3 | 0.26 × 0.22 × 0.08 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2303 independent reflections |
Radiation source: fine-focus sealed tube | 1428 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −6→8 |
Tmin = 0.978, Tmax = 0.993 | k = −10→10 |
3353 measured reflections | l = −13→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-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 parameters | Δρmax = 0.15 e Å−3 |
6 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.4513 (3) | 1.1266 (2) | 0.30478 (17) | 0.0928 (6) | |
O2 | 0.2237 (2) | 0.65957 (19) | −0.00300 (15) | 0.0707 (5) | |
N1 | 0.3442 (2) | 0.8694 (2) | 0.17158 (16) | 0.0546 (5) | |
C1 | 0.3793 (3) | 1.0409 (3) | 0.2030 (2) | 0.0608 (6) | |
C2 | 0.3130 (3) | 1.0891 (2) | 0.0886 (2) | 0.0520 (5) | |
C3 | 0.3135 (3) | 1.2426 (3) | 0.0674 (3) | 0.0696 (7) | |
H3 | 0.3606 | 1.3376 | 0.1302 | 0.083* | |
C4 | 0.2416 (3) | 1.2506 (3) | −0.0507 (3) | 0.0751 (7) | |
H4 | 0.2406 | 1.3526 | −0.0673 | 0.090* | |
C5 | 0.1715 (3) | 1.1096 (3) | −0.1438 (2) | 0.0707 (7) | |
H5 | 0.1236 | 1.1182 | −0.2221 | 0.085* | |
C6 | 0.1713 (3) | 0.9554 (3) | −0.1228 (2) | 0.0611 (6) | |
H6 | 0.1246 | 0.8604 | −0.1856 | 0.073* | |
C7 | 0.2434 (3) | 0.9480 (2) | −0.00452 (19) | 0.0487 (5) | |
C8 | 0.2644 (3) | 0.8044 (3) | 0.0475 (2) | 0.0519 (5) | |
C9 | 0.3883 (3) | 0.7702 (3) | 0.2586 (2) | 0.0675 (7) | |
H9A | 0.5006 | 0.8318 | 0.3224 | 0.081* | |
H9B | 0.4227 | 0.6709 | 0.2170 | 0.081* | |
C10 | 0.2177 (3) | 0.7236 (3) | 0.3156 (2) | 0.0571 (6) | |
C11 | 0.0696 (3) | 0.5879 (3) | 0.2573 (2) | 0.0611 (6) | |
H11 | 0.0770 | 0.5222 | 0.1833 | 0.073* | |
C12 | −0.0897 (3) | 0.5486 (3) | 0.3076 (2) | 0.0658 (7) | |
H12 | −0.1880 | 0.4572 | 0.2661 | 0.079* | |
C13 | −0.1062 (4) | 0.6411 (3) | 0.4172 (2) | 0.0677 (7) | |
C14 | 0.0425 (5) | 0.7763 (3) | 0.4747 (2) | 0.0848 (8) | |
H14 | 0.0353 | 0.8414 | 0.5489 | 0.102* | |
C15 | 0.2027 (4) | 0.8184 (3) | 0.4253 (2) | 0.0788 (8) | |
H15 | 0.2999 | 0.9107 | 0.4664 | 0.095* | |
C16 | −0.2792 (4) | 0.5954 (4) | 0.4723 (3) | 0.0954 (9) | |
H16A | −0.3935 | 0.5457 | 0.4085 | 0.143* | |
H16B | −0.3012 | 0.6925 | 0.5233 | 0.143* | |
H16C | −0.2524 | 0.5190 | 0.5201 | 0.143* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1078 (14) | 0.0807 (13) | 0.0680 (12) | 0.0097 (10) | −0.0024 (10) | −0.0025 (10) |
O2 | 0.0783 (11) | 0.0503 (10) | 0.0766 (12) | 0.0092 (8) | 0.0117 (9) | 0.0090 (8) |
N1 | 0.0504 (11) | 0.0554 (11) | 0.0563 (12) | 0.0103 (8) | 0.0070 (9) | 0.0148 (9) |
C1 | 0.0519 (14) | 0.0619 (15) | 0.0606 (15) | 0.0083 (11) | 0.0088 (11) | 0.0044 (12) |
C2 | 0.0428 (12) | 0.0502 (13) | 0.0653 (15) | 0.0134 (9) | 0.0156 (10) | 0.0135 (11) |
C3 | 0.0620 (15) | 0.0547 (15) | 0.092 (2) | 0.0156 (11) | 0.0209 (14) | 0.0139 (14) |
C4 | 0.0631 (16) | 0.0707 (18) | 0.110 (2) | 0.0265 (13) | 0.0281 (15) | 0.0441 (17) |
C5 | 0.0590 (15) | 0.0867 (19) | 0.0821 (19) | 0.0264 (13) | 0.0203 (13) | 0.0419 (16) |
C6 | 0.0518 (14) | 0.0715 (16) | 0.0620 (16) | 0.0151 (11) | 0.0143 (11) | 0.0178 (12) |
C7 | 0.0377 (11) | 0.0523 (13) | 0.0585 (14) | 0.0121 (9) | 0.0153 (10) | 0.0132 (11) |
C8 | 0.0402 (12) | 0.0548 (14) | 0.0591 (15) | 0.0098 (10) | 0.0112 (10) | 0.0109 (12) |
C9 | 0.0572 (15) | 0.0753 (16) | 0.0716 (16) | 0.0152 (12) | 0.0036 (12) | 0.0298 (13) |
C10 | 0.0567 (14) | 0.0656 (14) | 0.0506 (14) | 0.0158 (11) | 0.0037 (11) | 0.0224 (12) |
C11 | 0.0664 (15) | 0.0623 (15) | 0.0547 (14) | 0.0175 (12) | 0.0119 (12) | 0.0133 (12) |
C12 | 0.0644 (16) | 0.0668 (15) | 0.0686 (17) | 0.0150 (12) | 0.0131 (13) | 0.0227 (13) |
C13 | 0.0752 (17) | 0.0778 (17) | 0.0644 (17) | 0.0286 (14) | 0.0202 (14) | 0.0348 (14) |
C14 | 0.117 (2) | 0.092 (2) | 0.0483 (15) | 0.0299 (18) | 0.0243 (16) | 0.0140 (15) |
C15 | 0.089 (2) | 0.0800 (18) | 0.0539 (16) | 0.0004 (14) | 0.0045 (14) | 0.0115 (14) |
C16 | 0.095 (2) | 0.127 (2) | 0.097 (2) | 0.0467 (18) | 0.0463 (17) | 0.0602 (19) |
Geometric parameters (Å, º) top
O1—C1 | 1.212 (3) | C9—C10 | 1.516 (3) |
O2—C8 | 1.209 (2) | C9—H9A | 0.9700 |
N1—C8 | 1.394 (3) | C9—H9B | 0.9700 |
N1—C1 | 1.397 (3) | C10—C15 | 1.380 (3) |
N1—C9 | 1.469 (3) | C10—C11 | 1.382 (3) |
C1—C2 | 1.485 (3) | C11—C12 | 1.387 (3) |
C2—C7 | 1.380 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.381 (3) | C12—C13 | 1.375 (3) |
C3—C4 | 1.387 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.381 (3) |
C4—C5 | 1.380 (3) | C13—C16 | 1.514 (3) |
C4—H4 | 0.9300 | C14—C15 | 1.389 (3) |
C5—C6 | 1.386 (3) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—C7 | 1.388 (3) | C16—H16A | 0.9600 |
C6—H6 | 0.9300 | C16—H16B | 0.9600 |
C7—C8 | 1.491 (3) | C16—H16C | 0.9600 |
C8—N1—C1 | 111.62 (18) | C10—C9—H9A | 109.1 |
C8—N1—C9 | 124.37 (18) | N1—C9—H9B | 109.1 |
C1—N1—C9 | 124.01 (19) | C10—C9—H9B | 109.1 |
O1—C1—N1 | 124.4 (2) | H9A—C9—H9B | 107.8 |
O1—C1—C2 | 129.6 (2) | C15—C10—C11 | 118.1 (2) |
N1—C1—C2 | 106.00 (18) | C15—C10—C9 | 120.9 (2) |
C7—C2—C3 | 121.2 (2) | C11—C10—C9 | 120.9 (2) |
C7—C2—C1 | 108.36 (19) | C10—C11—C12 | 120.8 (2) |
C3—C2—C1 | 130.5 (2) | C10—C11—H11 | 119.6 |
C2—C3—C4 | 117.9 (2) | C12—C11—H11 | 119.6 |
C2—C3—H3 | 121.1 | C13—C12—C11 | 121.7 (2) |
C4—C3—H3 | 121.1 | C13—C12—H12 | 119.1 |
C5—C4—C3 | 121.0 (2) | C11—C12—H12 | 119.1 |
C5—C4—H4 | 119.5 | C12—C13—C14 | 116.9 (2) |
C3—C4—H4 | 119.5 | C12—C13—C16 | 121.3 (2) |
C4—C5—C6 | 121.2 (2) | C14—C13—C16 | 121.8 (3) |
C4—C5—H5 | 119.4 | C13—C14—C15 | 122.2 (2) |
C6—C5—H5 | 119.4 | C13—C14—H14 | 118.9 |
C5—C6—C7 | 117.5 (2) | C15—C14—H14 | 118.9 |
C5—C6—H6 | 121.2 | C10—C15—C14 | 120.1 (2) |
C7—C6—H6 | 121.2 | C10—C15—H15 | 119.9 |
C2—C7—C6 | 121.2 (2) | C14—C15—H15 | 119.9 |
C2—C7—C8 | 108.01 (19) | C13—C16—H16A | 109.5 |
C6—C7—C8 | 130.8 (2) | C13—C16—H16B | 109.5 |
O2—C8—N1 | 124.7 (2) | H16A—C16—H16B | 109.5 |
O2—C8—C7 | 129.3 (2) | C13—C16—H16C | 109.5 |
N1—C8—C7 | 106.00 (18) | H16A—C16—H16C | 109.5 |
N1—C9—C10 | 112.50 (17) | H16B—C16—H16C | 109.5 |
N1—C9—H9A | 109.1 | ||
C8—N1—C1—O1 | −178.6 (2) | C1—N1—C8—C7 | −1.1 (2) |
C9—N1—C1—O1 | 0.7 (3) | C9—N1—C8—C7 | 179.56 (17) |
C8—N1—C1—C2 | 0.9 (2) | C2—C7—C8—O2 | −178.9 (2) |
C9—N1—C1—C2 | −179.77 (17) | C6—C7—C8—O2 | 0.6 (4) |
O1—C1—C2—C7 | 179.2 (2) | C2—C7—C8—N1 | 0.9 (2) |
N1—C1—C2—C7 | −0.3 (2) | C6—C7—C8—N1 | −179.61 (19) |
O1—C1—C2—C3 | −0.6 (4) | C8—N1—C9—C10 | −90.4 (2) |
N1—C1—C2—C3 | 179.9 (2) | C1—N1—C9—C10 | 90.4 (2) |
C7—C2—C3—C4 | 0.1 (3) | N1—C9—C10—C15 | −93.6 (3) |
C1—C2—C3—C4 | 179.9 (2) | N1—C9—C10—C11 | 84.2 (3) |
C2—C3—C4—C5 | 0.1 (3) | C15—C10—C11—C12 | 0.1 (3) |
C3—C4—C5—C6 | −0.3 (3) | C9—C10—C11—C12 | −177.77 (19) |
C4—C5—C6—C7 | 0.3 (3) | C10—C11—C12—C13 | −0.6 (3) |
C3—C2—C7—C6 | −0.1 (3) | C11—C12—C13—C14 | 0.6 (3) |
C1—C2—C7—C6 | −179.92 (17) | C11—C12—C13—C16 | −178.9 (2) |
C3—C2—C7—C8 | 179.49 (18) | C12—C13—C14—C15 | −0.1 (4) |
C1—C2—C7—C8 | −0.4 (2) | C16—C13—C14—C15 | 179.4 (2) |
C5—C6—C7—C2 | −0.1 (3) | C11—C10—C15—C14 | 0.3 (4) |
C5—C6—C7—C8 | −179.53 (19) | C9—C10—C15—C14 | 178.2 (2) |
C1—N1—C8—O2 | 178.72 (19) | C13—C14—C15—C10 | −0.3 (4) |
C9—N1—C8—O2 | −0.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.59 | 3.437 (3) | 152 |
Symmetry code: (i) x, y+1, z. |