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The title compound, C39H38N2O4, possesses crystallographically imposed C2 symmetry, with the twofold axis bis­ecting the central benzene ring. There is an intra­molecular hydrogen bond between the phen­oxy O atom and the amide N atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021537/ww6370sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021537/ww6370Isup2.hkl
Contains datablock I

CCDC reference: 282694

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.054
  • wR factor = 0.151
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C7 PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C6 .. 5.61 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H15A .. H20A .. 1.81 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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.

2,4-Bis[2-(benzylaminocarbonyl)phenoxymethyl]-1,3,5-trimethylbenzene top
Crystal data top
C39H38N2O4F(000) = 1272
Mr = 598.71Dx = 1.204 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 20.5494 (10) Åθ = 2.5–26.1°
b = 12.1369 (10) ŵ = 0.08 mm1
c = 16.3862 (14) ÅT = 293 K
β = 126.097 (10)°Block, colorless
V = 3302.2 (4) Å30.43 × 0.35 × 0.30 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1596 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 26.0°, θmin = 2.1°
ω scansh = 250
Absorption correction: ψ scan
(North et al., 1968)
k = 141
Tmin = 0.905, Tmax = 0.986l = 1620
3668 measured reflections2 standard reflections every 800 reflections
3247 independent reflections intensity decay: none
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)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.055P)2 + 1.5772P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
3247 reflectionsΔρmax = 0.27 e Å3
256 parametersΔρmin = 0.17 e Å3
6 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0045 (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*/UeqOcc. (<1)
O10.24428 (12)0.9937 (2)0.75463 (12)0.1060 (8)
O20.17522 (9)0.98704 (16)0.46259 (10)0.0791 (6)
N10.15951 (15)0.9207 (2)0.60286 (17)0.0967 (9)
C10.0675 (3)0.6983 (5)0.5300 (3)0.1213 (14)
C20.0069 (5)0.6294 (5)0.4544 (5)0.1325 (16)
C30.0703 (4)0.6627 (6)0.4021 (4)0.1303 (17)
C40.0890 (3)0.7611 (6)0.4207 (3)0.1257 (14)
C50.0303 (3)0.8265 (4)0.4942 (3)0.1112 (12)
C60.0478 (3)0.7973 (4)0.5497 (2)0.0987 (11)
C70.1119 (2)0.8702 (4)0.6318 (2)0.1478 (17)
H7A0.08710.92730.64640.177*
H7B0.14680.82710.69280.177*
C80.22227 (15)0.9830 (2)0.66751 (17)0.0723 (7)
C90.26741 (14)1.0357 (2)0.63300 (16)0.0607 (6)
C100.33870 (18)1.0874 (2)0.7070 (2)0.0813 (8)
C110.3877 (2)1.1351 (3)0.6872 (3)0.1090 (12)
C120.3659 (2)1.1339 (3)0.5908 (3)0.1128 (12)
C130.29611 (18)1.0845 (3)0.5147 (2)0.0907 (10)
C140.24615 (14)1.0359 (2)0.53503 (16)0.0642 (7)
C150.1510 (2)0.9776 (4)0.36065 (19)0.0868 (10)
C160.07260 (15)0.9175 (3)0.30263 (15)0.0647 (7)
C170.07246 (17)0.8034 (3)0.30329 (17)0.0797 (8)
C180.00000.7499 (5)0.25000.0899 (13)
C190.1494 (2)0.7363 (3)0.3608 (2)0.1340 (15)
H19A0.13640.65930.35080.201*
H19B0.17990.75340.43150.201*
H19C0.18080.75380.33650.201*
C200.00001.1002 (3)0.25000.0968 (14)
H20A0.05451.12660.21050.145*0.50
H20B0.02661.12660.22150.145*0.50
H20C0.02791.12660.31810.145*0.50
C210.00000.9755 (3)0.25000.0611 (9)
H130.2812 (12)1.0846 (18)0.4500 (17)0.062 (6)*
H100.3513 (14)1.086 (2)0.7727 (19)0.085 (8)*
H1N0.1431 (16)0.915 (2)0.539 (2)0.097 (9)*
H120.4033 (18)1.160 (3)0.574 (2)0.120 (10)*
H50.041 (2)0.901 (4)0.514 (3)0.164 (17)*
H110.440 (2)1.169 (3)0.743 (2)0.139 (12)*
H180.00000.675 (4)0.25000.113 (17)*
H10.124 (2)0.685 (3)0.572 (3)0.137 (15)*
H20.027 (2)0.566 (4)0.445 (3)0.16 (2)*
H40.148 (3)0.786 (4)0.382 (3)0.19 (2)*
H15B0.1925 (18)0.940 (3)0.364 (2)0.111 (12)*
H15A0.1472 (18)1.054 (3)0.336 (2)0.118 (12)*
H30.115 (3)0.620 (4)0.348 (4)0.19 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0997 (14)0.171 (2)0.0560 (10)0.0287 (14)0.0506 (10)0.0233 (12)
O20.0698 (11)0.1260 (16)0.0443 (8)0.0299 (11)0.0351 (8)0.0099 (9)
N10.1016 (18)0.145 (2)0.0561 (13)0.0526 (17)0.0536 (14)0.0192 (15)
C10.110 (4)0.171 (5)0.086 (3)0.003 (4)0.059 (3)0.025 (3)
C20.188 (6)0.102 (4)0.133 (4)0.001 (4)0.109 (5)0.012 (3)
C30.152 (5)0.133 (5)0.096 (3)0.054 (4)0.068 (3)0.015 (3)
C40.104 (3)0.160 (5)0.101 (3)0.015 (4)0.053 (3)0.010 (3)
C50.131 (4)0.115 (3)0.098 (3)0.023 (3)0.073 (3)0.002 (2)
C60.111 (3)0.133 (3)0.068 (2)0.044 (3)0.062 (2)0.009 (2)
C70.154 (3)0.230 (4)0.083 (2)0.106 (3)0.083 (2)0.040 (3)
C80.0700 (16)0.098 (2)0.0496 (13)0.0046 (16)0.0359 (13)0.0076 (14)
C90.0628 (14)0.0649 (16)0.0531 (12)0.0016 (13)0.0334 (12)0.0053 (12)
C100.087 (2)0.085 (2)0.0615 (16)0.0166 (17)0.0382 (16)0.0124 (15)
C110.097 (2)0.127 (3)0.086 (2)0.049 (2)0.044 (2)0.019 (2)
C120.093 (2)0.146 (3)0.095 (2)0.051 (2)0.054 (2)0.007 (2)
C130.083 (2)0.125 (3)0.0660 (17)0.0303 (19)0.0450 (16)0.0015 (18)
C140.0587 (14)0.0773 (17)0.0548 (13)0.0089 (14)0.0325 (12)0.0028 (13)
C150.079 (2)0.140 (3)0.0474 (14)0.022 (2)0.0409 (15)0.0077 (17)
C160.0669 (16)0.090 (2)0.0394 (11)0.0061 (16)0.0324 (12)0.0052 (13)
C170.0816 (19)0.091 (2)0.0470 (13)0.0153 (19)0.0273 (13)0.0017 (15)
C180.107 (4)0.068 (3)0.061 (2)0.0000.031 (2)0.000
C190.112 (3)0.152 (3)0.088 (2)0.060 (3)0.032 (2)0.014 (2)
C200.141 (4)0.073 (3)0.105 (3)0.0000.088 (3)0.000
C210.080 (2)0.071 (3)0.0449 (16)0.0000.0441 (18)0.000
Geometric parameters (Å, º) top
O1—C81.224 (3)C10—H100.95 (2)
O2—C141.359 (3)C11—C121.365 (4)
O2—C151.439 (3)C11—H111.01 (3)
N1—C81.322 (3)C12—C131.365 (4)
N1—C71.451 (3)C12—H121.01 (3)
N1—H1N0.90 (3)C13—C141.384 (3)
C1—C61.367 (6)C13—H130.91 (2)
C1—C21.402 (7)C15—C161.492 (4)
C1—H10.95 (4)C15—H15B0.94 (3)
C2—C31.347 (7)C15—H15A1.00 (3)
C2—H20.93 (4)C16—C171.384 (4)
C3—C41.343 (6)C16—C211.396 (3)
C3—H30.97 (5)C17—C181.368 (4)
C4—C51.350 (6)C17—C191.516 (4)
C4—H41.03 (5)C18—C17i1.368 (4)
C5—C61.345 (5)C18—H180.91 (5)
C5—H51.03 (4)C19—H19A0.9600
C6—C71.497 (4)C19—H19B0.9600
C7—H7A0.9700C19—H19C0.9600
C7—H7B0.9700C20—C211.513 (5)
C8—C91.486 (3)C20—H20A0.9600
C9—C101.385 (3)C20—H20B0.9600
C9—C141.393 (3)C20—H20C0.9600
C10—C111.356 (4)C21—C16i1.396 (3)
C14—O2—C15120.55 (19)C11—C12—C13120.9 (3)
C8—N1—C7120.5 (2)C11—C12—H12121.9 (17)
C8—N1—H1N120.1 (18)C13—C12—H12116.8 (17)
C7—N1—H1N119.2 (18)C12—C13—C14119.8 (3)
C6—C1—C2120.0 (5)C12—C13—H13120.8 (14)
C6—C1—H1112 (2)C14—C13—H13119.4 (14)
C2—C1—H1128 (2)O2—C14—C13122.8 (2)
C3—C2—C1118.9 (5)O2—C14—C9116.9 (2)
C3—C2—H2128 (3)C13—C14—C9120.3 (2)
C1—C2—H2113 (3)O2—C15—C16106.5 (2)
C4—C3—C2120.6 (5)O2—C15—H15B106.9 (18)
C4—C3—H3116 (3)C16—C15—H15B113.7 (19)
C2—C3—H3123 (3)O2—C15—H15A107.0 (19)
C3—C4—C5120.0 (5)C16—C15—H15A113.5 (18)
C3—C4—H4121 (3)H15B—C15—H15A109 (3)
C5—C4—H4119 (3)C17—C16—C21120.2 (3)
C6—C5—C4122.1 (5)C17—C16—C15119.4 (3)
C6—C5—H5114 (2)C21—C16—C15120.4 (3)
C4—C5—H5124 (2)C18—C17—C16118.5 (3)
C5—C6—C1118.3 (4)C18—C17—C19119.1 (3)
C5—C6—C7121.3 (5)C16—C17—C19122.4 (3)
C1—C6—C7120.4 (5)C17—C18—C17i123.2 (5)
N1—C7—C6111.2 (2)C17—C18—H18118.4 (2)
N1—C7—H7A109.4C17i—C18—H18118.4 (2)
C6—C7—H7A109.4C17—C19—H19A109.5
N1—C7—H7B109.4C17—C19—H19B109.5
C6—C7—H7B109.4H19A—C19—H19B109.5
H7A—C7—H7B108.0C17—C19—H19C109.5
O1—C8—N1120.7 (2)H19A—C19—H19C109.5
O1—C8—C9120.9 (2)H19B—C19—H19C109.5
N1—C8—C9118.3 (2)C21—C20—H20A109.5
C10—C9—C14117.4 (2)C21—C20—H20B109.5
C10—C9—C8115.9 (2)H20A—C20—H20B109.5
C14—C9—C8126.7 (2)C21—C20—H20C109.5
C11—C10—C9122.3 (3)H20A—C20—H20C109.5
C11—C10—H10122.5 (15)H20B—C20—H20C109.5
C9—C10—H10115.2 (15)C16i—C21—C16119.4 (3)
C10—C11—C12119.3 (3)C16i—C21—C20120.30 (17)
C10—C11—H11120.1 (19)C16—C21—C20120.30 (17)
C12—C11—H11121 (2)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.90 (3)1.93 (3)2.628 (3)133 (3)
 

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