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In the title compound, C23H27NO3, the mol­ecules are held together by inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007367/hg2012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007367/hg2012Isup2.hkl
Contains datablock I

CCDC reference: 605077

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.106
  • Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.20 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 39.00 A   3
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 2428 Count of symmetry unique reflns 2435 Completeness (_total/calc) 99.71% 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 3 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion

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-(3,5-di-tert-butyl-4-hydroxybenzyl)phthalimide top
Crystal data top
C23H27NO3Dx = 1.193 Mg m3
Mr = 365.46Melting point: 439 K
Tetragonal, P43212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4nw 2abwCell parameters from 5012 reflections
a = 17.1925 (16) Åθ = 2.2–24.4°
c = 13.7715 (19) ŵ = 0.08 mm1
V = 4070.6 (8) Å3T = 294 K
Z = 8Block, colorless
F(000) = 15680.26 × 0.22 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2428 independent reflections
Radiation source: fine-focus sealed tube1640 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
φ and ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2117
Tmin = 0.971, Tmax = 0.985k = 1721
23105 measured reflectionsl = 1716
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0391P)2 + 1.0321P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2428 reflectionsΔρmax = 0.14 e Å3
251 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0033 (5)
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
O10.49436 (13)0.85830 (13)0.01311 (19)0.0746 (7)
O20.71347 (13)1.00787 (12)0.00547 (19)0.0673 (6)
O30.82897 (14)0.72522 (14)0.31541 (16)0.0715 (7)
H30.86600.69850.28610.107*
N10.61580 (14)0.91575 (13)0.01022 (17)0.0463 (6)
C10.53491 (17)0.91555 (18)0.0153 (2)0.0481 (7)
C20.51082 (16)0.99845 (18)0.02154 (19)0.0424 (6)
C30.43775 (19)1.0311 (2)0.0266 (2)0.0569 (8)
H3A0.39331.00040.02890.068*
C40.4333 (2)1.1111 (2)0.0283 (2)0.0652 (9)
H40.38481.13490.03180.078*
C50.4993 (2)1.1563 (2)0.0249 (2)0.0639 (9)
H50.49451.21020.02520.077*
C60.57240 (19)1.12367 (17)0.0210 (2)0.0545 (8)
H60.61701.15430.02010.065*
C70.57679 (17)1.04386 (15)0.01855 (19)0.0423 (7)
C80.64551 (18)0.99172 (17)0.0110 (2)0.0473 (7)
C90.66315 (19)0.84637 (17)0.0060 (2)0.0560 (8)
H9A0.70120.85780.05600.067*
H9B0.62980.80520.03030.067*
C100.70546 (17)0.81682 (16)0.08289 (19)0.0453 (7)
C110.67911 (17)0.75112 (16)0.13101 (19)0.0453 (7)
H110.63340.72750.11010.054*
C120.71886 (16)0.71914 (16)0.20979 (19)0.0429 (6)
C130.78734 (17)0.75760 (16)0.2392 (2)0.0480 (7)
C140.81384 (16)0.82687 (16)0.1964 (2)0.0467 (7)
C150.77201 (17)0.85358 (16)0.1159 (2)0.0480 (7)
H150.78960.89760.08330.058*
C160.68934 (16)0.64521 (16)0.2601 (2)0.0512 (8)
C170.61318 (19)0.61583 (19)0.2163 (2)0.0649 (9)
H17A0.57420.65560.22160.097*
H17B0.59640.57020.25060.097*
H17C0.62110.60330.14910.097*
C180.74904 (18)0.57915 (18)0.2500 (3)0.0652 (9)
H18A0.75910.56970.18240.098*
H18B0.72880.53270.27940.098*
H18C0.79650.59370.28180.098*
C190.6732 (2)0.6617 (2)0.3683 (2)0.0738 (10)
H19A0.72060.67710.39980.111*
H19B0.65330.61560.39870.111*
H19C0.63560.70280.37390.111*
C200.88475 (18)0.87214 (17)0.2344 (2)0.0573 (8)
C210.8715 (2)0.8959 (2)0.3406 (3)0.0938 (14)
H21A0.86710.85020.38010.141*
H21B0.82450.92590.34540.141*
H21C0.91470.92670.36260.141*
C220.96011 (19)0.8258 (2)0.2255 (3)0.0782 (12)
H22A0.95940.78350.27100.117*
H22B1.00360.85910.23920.117*
H22C0.96470.80560.16080.117*
C230.8965 (3)0.9474 (2)0.1764 (4)0.1039 (16)
H23A0.94030.97530.20190.156*
H23B0.85070.97910.18140.156*
H23C0.90570.93490.10940.156*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0787 (17)0.0501 (14)0.0951 (18)0.0221 (12)0.0143 (15)0.0102 (13)
O20.0460 (13)0.0647 (14)0.0912 (16)0.0062 (11)0.0072 (13)0.0177 (14)
O30.0670 (15)0.0826 (16)0.0649 (14)0.0002 (12)0.0185 (12)0.0211 (13)
N10.0547 (15)0.0401 (13)0.0440 (13)0.0003 (11)0.0044 (12)0.0070 (12)
C10.0559 (19)0.0468 (18)0.0416 (17)0.0093 (15)0.0072 (14)0.0096 (15)
C20.0449 (17)0.0468 (16)0.0356 (14)0.0034 (14)0.0003 (13)0.0060 (13)
C30.053 (2)0.071 (2)0.0470 (19)0.0068 (16)0.0011 (15)0.0019 (16)
C40.060 (2)0.072 (2)0.064 (2)0.0170 (18)0.0074 (18)0.0038 (18)
C50.078 (3)0.0498 (19)0.063 (2)0.0096 (18)0.0106 (19)0.0017 (16)
C60.064 (2)0.0455 (18)0.0542 (19)0.0078 (16)0.0060 (17)0.0003 (15)
C70.0506 (17)0.0421 (16)0.0342 (15)0.0017 (13)0.0006 (14)0.0042 (12)
C80.0500 (18)0.0505 (18)0.0412 (16)0.0041 (14)0.0026 (14)0.0095 (14)
C90.073 (2)0.0481 (18)0.0465 (17)0.0097 (15)0.0048 (17)0.0013 (15)
C100.0543 (18)0.0420 (16)0.0396 (15)0.0106 (14)0.0007 (13)0.0023 (13)
C110.0468 (16)0.0422 (15)0.0468 (15)0.0057 (13)0.0023 (13)0.0052 (12)
C120.0432 (16)0.0437 (16)0.0418 (15)0.0073 (12)0.0036 (12)0.0006 (12)
C130.0512 (17)0.0525 (17)0.0404 (15)0.0062 (14)0.0057 (14)0.0007 (14)
C140.0481 (17)0.0408 (16)0.0513 (16)0.0046 (13)0.0016 (14)0.0039 (13)
C150.0543 (18)0.0375 (16)0.0520 (17)0.0037 (13)0.0060 (15)0.0020 (13)
C160.0469 (17)0.0524 (17)0.0543 (17)0.0043 (14)0.0029 (15)0.0080 (15)
C170.057 (2)0.055 (2)0.083 (2)0.0027 (15)0.0008 (18)0.0096 (18)
C180.066 (2)0.0553 (19)0.074 (2)0.0101 (17)0.0044 (18)0.015 (2)
C190.077 (2)0.085 (3)0.059 (2)0.000 (2)0.0180 (18)0.0083 (19)
C200.0509 (18)0.0474 (18)0.074 (2)0.0025 (14)0.0080 (17)0.0083 (17)
C210.086 (3)0.097 (3)0.098 (3)0.005 (2)0.019 (2)0.044 (3)
C220.054 (2)0.068 (2)0.112 (3)0.0015 (18)0.001 (2)0.010 (2)
C230.102 (3)0.058 (2)0.152 (4)0.028 (2)0.040 (3)0.017 (3)
Geometric parameters (Å, º) top
O1—C11.206 (3)C13—C141.404 (4)
O2—C81.203 (3)C14—C151.400 (4)
O3—C131.387 (3)C14—C201.538 (4)
O3—H30.8831C15—H150.9300
N1—C11.393 (4)C16—C171.528 (4)
N1—C81.403 (3)C16—C181.537 (4)
N1—C91.461 (4)C16—C191.543 (4)
C1—C21.487 (4)C17—H17A0.9600
C2—C71.378 (4)C17—H17B0.9600
C2—C31.378 (4)C17—H17C0.9600
C3—C41.377 (4)C18—H18A0.9600
C3—H3A0.9300C18—H18B0.9600
C4—C51.378 (5)C18—H18C0.9600
C4—H40.9300C19—H19A0.9600
C5—C61.377 (4)C19—H19B0.9600
C5—H50.9300C19—H19C0.9600
C6—C71.374 (4)C20—C221.526 (5)
C6—H60.9300C20—C231.534 (5)
C7—C81.487 (4)C20—C211.535 (5)
C9—C101.512 (4)C21—H21A0.9600
C9—H9A0.9700C21—H21B0.9600
C9—H9B0.9700C21—H21C0.9600
C10—C151.384 (4)C22—H22A0.9600
C10—C111.386 (4)C22—H22B0.9600
C11—C121.395 (4)C22—H22C0.9600
C11—H110.9300C23—H23A0.9600
C12—C131.410 (4)C23—H23B0.9600
C12—C161.534 (4)C23—H23C0.9600
C13—O3—H3103.6C10—C15—H15118.8
C1—N1—C8111.4 (2)C14—C15—H15118.8
C1—N1—C9124.2 (3)C17—C16—C12112.3 (2)
C8—N1—C9123.9 (2)C17—C16—C18107.0 (3)
O1—C1—N1125.3 (3)C12—C16—C18110.5 (2)
O1—C1—C2128.5 (3)C17—C16—C19106.8 (3)
N1—C1—C2106.2 (2)C12—C16—C19110.1 (3)
C7—C2—C3121.4 (3)C18—C16—C19110.1 (3)
C7—C2—C1108.2 (3)C16—C17—H17A109.5
C3—C2—C1130.4 (3)C16—C17—H17B109.5
C4—C3—C2117.3 (3)H17A—C17—H17B109.5
C4—C3—H3A121.4C16—C17—H17C109.5
C2—C3—H3A121.4H17A—C17—H17C109.5
C3—C4—C5121.1 (3)H17B—C17—H17C109.5
C3—C4—H4119.4C16—C18—H18A109.5
C5—C4—H4119.4C16—C18—H18B109.5
C6—C5—C4121.5 (3)H18A—C18—H18B109.5
C6—C5—H5119.2C16—C18—H18C109.5
C4—C5—H5119.2H18A—C18—H18C109.5
C7—C6—C5117.3 (3)H18B—C18—H18C109.5
C7—C6—H6121.4C16—C19—H19A109.5
C5—C6—H6121.4C16—C19—H19B109.5
C6—C7—C2121.3 (3)H19A—C19—H19B109.5
C6—C7—C8130.3 (3)C16—C19—H19C109.5
C2—C7—C8108.3 (2)H19A—C19—H19C109.5
O2—C8—N1124.6 (3)H19B—C19—H19C109.5
O2—C8—C7129.6 (3)C22—C20—C23106.7 (3)
N1—C8—C7105.8 (2)C22—C20—C21110.0 (3)
N1—C9—C10114.8 (2)C23—C20—C21106.9 (3)
N1—C9—H9A108.6C22—C20—C14112.4 (2)
C10—C9—H9A108.6C23—C20—C14110.7 (3)
N1—C9—H9B108.6C21—C20—C14110.0 (3)
C10—C9—H9B108.6C20—C21—H21A109.5
H9A—C9—H9B107.6C20—C21—H21B109.5
C15—C10—C11119.0 (3)H21A—C21—H21B109.5
C15—C10—C9120.7 (3)C20—C21—H21C109.5
C11—C10—C9120.3 (3)H21A—C21—H21C109.5
C10—C11—C12122.2 (3)H21B—C21—H21C109.5
C10—C11—H11118.9C20—C22—H22A109.5
C12—C11—H11118.9C20—C22—H22B109.5
C11—C12—C13116.6 (3)H22A—C22—H22B109.5
C11—C12—C16121.0 (3)C20—C22—H22C109.5
C13—C12—C16122.4 (3)H22A—C22—H22C109.5
O3—C13—C14119.4 (3)H22B—C22—H22C109.5
O3—C13—C12117.4 (3)C20—C23—H23A109.5
C14—C13—C12123.2 (3)C20—C23—H23B109.5
C15—C14—C13116.3 (3)H23A—C23—H23B109.5
C15—C14—C20120.7 (3)C20—C23—H23C109.5
C13—C14—C20122.9 (3)H23A—C23—H23C109.5
C10—C15—C14122.4 (3)H23B—C23—H23C109.5
C8—N1—C1—O1177.8 (3)N1—C9—C10—C11104.7 (3)
C9—N1—C1—O14.9 (5)C15—C10—C11—C122.2 (4)
C8—N1—C1—C21.0 (3)C9—C10—C11—C12176.1 (3)
C9—N1—C1—C2173.9 (2)C10—C11—C12—C130.7 (4)
O1—C1—C2—C7177.9 (3)C10—C11—C12—C16178.5 (3)
N1—C1—C2—C70.9 (3)C11—C12—C13—O3178.0 (2)
O1—C1—C2—C30.2 (5)C16—C12—C13—O31.2 (4)
N1—C1—C2—C3179.0 (3)C11—C12—C13—C143.2 (4)
C7—C2—C3—C40.2 (5)C16—C12—C13—C14177.6 (3)
C1—C2—C3—C4177.7 (3)O3—C13—C14—C15175.9 (2)
C2—C3—C4—C50.1 (5)C12—C13—C14—C155.3 (4)
C3—C4—C5—C60.9 (5)O3—C13—C14—C204.0 (4)
C4—C5—C6—C71.4 (5)C12—C13—C14—C20174.7 (3)
C5—C6—C7—C21.1 (5)C11—C10—C15—C140.1 (4)
C5—C6—C7—C8177.7 (3)C9—C10—C15—C14178.4 (3)
C3—C2—C7—C60.3 (4)C13—C14—C15—C103.7 (4)
C1—C2—C7—C6178.7 (3)C20—C14—C15—C10176.3 (3)
C3—C2—C7—C8178.7 (3)C11—C12—C16—C172.2 (4)
C1—C2—C7—C80.4 (3)C13—C12—C16—C17178.7 (3)
C1—N1—C8—O2178.6 (3)C11—C12—C16—C18117.2 (3)
C9—N1—C8—O25.7 (5)C13—C12—C16—C1861.9 (4)
C1—N1—C8—C70.8 (3)C11—C12—C16—C19121.0 (3)
C9—N1—C8—C7173.7 (2)C13—C12—C16—C1959.9 (4)
C6—C7—C8—O20.2 (6)C15—C14—C20—C22116.1 (3)
C2—C7—C8—O2179.1 (3)C13—C14—C20—C2263.9 (4)
C6—C7—C8—N1179.1 (3)C15—C14—C20—C233.1 (4)
C2—C7—C8—N10.2 (3)C13—C14—C20—C23176.9 (3)
C1—N1—C9—C10105.7 (3)C15—C14—C20—C21121.1 (3)
C8—N1—C9—C1082.2 (3)C13—C14—C20—C2159.0 (4)
N1—C9—C10—C1577.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.882.513.364 (3)164
C9—H9B···O10.972.572.921 (4)101
C15—H15···O20.932.543.219 (4)130
C17—H17A···O2ii0.962.573.490 (4)161
C22—H22A···O1i0.962.553.223 (4)127
Symmetry codes: (i) x+1/2, y+3/2, z+1/4; (ii) y1/2, x+3/2, z+1/4.
 

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