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
CCDC reference: 282694
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C39H38N2O4 | F(000) = 1272 |
Mr = 598.71 | Dx = 1.204 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 20.5494 (10) Å | θ = 2.5–26.1° |
b = 12.1369 (10) Å | µ = 0.08 mm−1 |
c = 16.3862 (14) Å | T = 293 K |
β = 126.097 (10)° | Block, colorless |
V = 3302.2 (4) Å3 | 0.43 × 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 tube | Rint = 0.019 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −25→0 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→1 |
Tmin = 0.905, Tmax = 0.986 | l = −16→20 |
3668 measured reflections | 2 standard reflections every 800 reflections |
3247 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H 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 reflections | Δρmax = 0.27 e Å−3 |
256 parameters | Δρmin = −0.17 e Å−3 |
6 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.24428 (12) | 0.9937 (2) | 0.75463 (12) | 0.1060 (8) | |
O2 | 0.17522 (9) | 0.98704 (16) | 0.46259 (10) | 0.0791 (6) | |
N1 | 0.15951 (15) | 0.9207 (2) | 0.60286 (17) | 0.0967 (9) | |
C1 | 0.0675 (3) | 0.6983 (5) | 0.5300 (3) | 0.1213 (14) | |
C2 | 0.0069 (5) | 0.6294 (5) | 0.4544 (5) | 0.1325 (16) | |
C3 | −0.0703 (4) | 0.6627 (6) | 0.4021 (4) | 0.1303 (17) | |
C4 | −0.0890 (3) | 0.7611 (6) | 0.4207 (3) | 0.1257 (14) | |
C5 | −0.0303 (3) | 0.8265 (4) | 0.4942 (3) | 0.1112 (12) | |
C6 | 0.0478 (3) | 0.7973 (4) | 0.5497 (2) | 0.0987 (11) | |
C7 | 0.1119 (2) | 0.8702 (4) | 0.6318 (2) | 0.1478 (17) | |
H7A | 0.0871 | 0.9273 | 0.6464 | 0.177* | |
H7B | 0.1468 | 0.8271 | 0.6928 | 0.177* | |
C8 | 0.22227 (15) | 0.9830 (2) | 0.66751 (17) | 0.0723 (7) | |
C9 | 0.26741 (14) | 1.0357 (2) | 0.63300 (16) | 0.0607 (6) | |
C10 | 0.33870 (18) | 1.0874 (2) | 0.7070 (2) | 0.0813 (8) | |
C11 | 0.3877 (2) | 1.1351 (3) | 0.6872 (3) | 0.1090 (12) | |
C12 | 0.3659 (2) | 1.1339 (3) | 0.5908 (3) | 0.1128 (12) | |
C13 | 0.29611 (18) | 1.0845 (3) | 0.5147 (2) | 0.0907 (10) | |
C14 | 0.24615 (14) | 1.0359 (2) | 0.53503 (16) | 0.0642 (7) | |
C15 | 0.1510 (2) | 0.9776 (4) | 0.36065 (19) | 0.0868 (10) | |
C16 | 0.07260 (15) | 0.9175 (3) | 0.30263 (15) | 0.0647 (7) | |
C17 | 0.07246 (17) | 0.8034 (3) | 0.30329 (17) | 0.0797 (8) | |
C18 | 0.0000 | 0.7499 (5) | 0.2500 | 0.0899 (13) | |
C19 | 0.1494 (2) | 0.7363 (3) | 0.3608 (2) | 0.1340 (15) | |
H19A | 0.1364 | 0.6593 | 0.3508 | 0.201* | |
H19B | 0.1799 | 0.7534 | 0.4315 | 0.201* | |
H19C | 0.1808 | 0.7538 | 0.3365 | 0.201* | |
C20 | 0.0000 | 1.1002 (3) | 0.2500 | 0.0968 (14) | |
H20A | −0.0545 | 1.1266 | 0.2105 | 0.145* | 0.50 |
H20B | 0.0266 | 1.1266 | 0.2215 | 0.145* | 0.50 |
H20C | 0.0279 | 1.1266 | 0.3181 | 0.145* | 0.50 |
C21 | 0.0000 | 0.9755 (3) | 0.2500 | 0.0611 (9) | |
H13 | 0.2812 (12) | 1.0846 (18) | 0.4500 (17) | 0.062 (6)* | |
H10 | 0.3513 (14) | 1.086 (2) | 0.7727 (19) | 0.085 (8)* | |
H1N | 0.1431 (16) | 0.915 (2) | 0.539 (2) | 0.097 (9)* | |
H12 | 0.4033 (18) | 1.160 (3) | 0.574 (2) | 0.120 (10)* | |
H5 | −0.041 (2) | 0.901 (4) | 0.514 (3) | 0.164 (17)* | |
H11 | 0.440 (2) | 1.169 (3) | 0.743 (2) | 0.139 (12)* | |
H18 | 0.0000 | 0.675 (4) | 0.2500 | 0.113 (17)* | |
H1 | 0.124 (2) | 0.685 (3) | 0.572 (3) | 0.137 (15)* | |
H2 | 0.027 (2) | 0.566 (4) | 0.445 (3) | 0.16 (2)* | |
H4 | −0.148 (3) | 0.786 (4) | 0.382 (3) | 0.19 (2)* | |
H15B | 0.1925 (18) | 0.940 (3) | 0.364 (2) | 0.111 (12)* | |
H15A | 0.1472 (18) | 1.054 (3) | 0.336 (2) | 0.118 (12)* | |
H3 | −0.115 (3) | 0.620 (4) | 0.348 (4) | 0.19 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0997 (14) | 0.171 (2) | 0.0560 (10) | −0.0287 (14) | 0.0506 (10) | −0.0233 (12) |
O2 | 0.0698 (11) | 0.1260 (16) | 0.0443 (8) | −0.0299 (11) | 0.0351 (8) | −0.0099 (9) |
N1 | 0.1016 (18) | 0.145 (2) | 0.0561 (13) | −0.0526 (17) | 0.0536 (14) | −0.0192 (15) |
C1 | 0.110 (4) | 0.171 (5) | 0.086 (3) | −0.003 (4) | 0.059 (3) | 0.025 (3) |
C2 | 0.188 (6) | 0.102 (4) | 0.133 (4) | 0.001 (4) | 0.109 (5) | 0.012 (3) |
C3 | 0.152 (5) | 0.133 (5) | 0.096 (3) | −0.054 (4) | 0.068 (3) | −0.015 (3) |
C4 | 0.104 (3) | 0.160 (5) | 0.101 (3) | −0.015 (4) | 0.053 (3) | 0.010 (3) |
C5 | 0.131 (4) | 0.115 (3) | 0.098 (3) | −0.023 (3) | 0.073 (3) | −0.002 (2) |
C6 | 0.111 (3) | 0.133 (3) | 0.068 (2) | −0.044 (3) | 0.062 (2) | −0.009 (2) |
C7 | 0.154 (3) | 0.230 (4) | 0.083 (2) | −0.106 (3) | 0.083 (2) | −0.040 (3) |
C8 | 0.0700 (16) | 0.098 (2) | 0.0496 (13) | −0.0046 (16) | 0.0359 (13) | −0.0076 (14) |
C9 | 0.0628 (14) | 0.0649 (16) | 0.0531 (12) | −0.0016 (13) | 0.0334 (12) | −0.0053 (12) |
C10 | 0.087 (2) | 0.085 (2) | 0.0615 (16) | −0.0166 (17) | 0.0382 (16) | −0.0124 (15) |
C11 | 0.097 (2) | 0.127 (3) | 0.086 (2) | −0.049 (2) | 0.044 (2) | −0.019 (2) |
C12 | 0.093 (2) | 0.146 (3) | 0.095 (2) | −0.051 (2) | 0.054 (2) | −0.007 (2) |
C13 | 0.083 (2) | 0.125 (3) | 0.0660 (17) | −0.0303 (19) | 0.0450 (16) | −0.0015 (18) |
C14 | 0.0587 (14) | 0.0773 (17) | 0.0548 (13) | −0.0089 (14) | 0.0325 (12) | −0.0028 (13) |
C15 | 0.079 (2) | 0.140 (3) | 0.0474 (14) | −0.022 (2) | 0.0409 (15) | −0.0077 (17) |
C16 | 0.0669 (16) | 0.090 (2) | 0.0394 (11) | −0.0061 (16) | 0.0324 (12) | −0.0052 (13) |
C17 | 0.0816 (19) | 0.091 (2) | 0.0470 (13) | 0.0153 (19) | 0.0273 (13) | 0.0017 (15) |
C18 | 0.107 (4) | 0.068 (3) | 0.061 (2) | 0.000 | 0.031 (2) | 0.000 |
C19 | 0.112 (3) | 0.152 (3) | 0.088 (2) | 0.060 (3) | 0.032 (2) | 0.014 (2) |
C20 | 0.141 (4) | 0.073 (3) | 0.105 (3) | 0.000 | 0.088 (3) | 0.000 |
C21 | 0.080 (2) | 0.071 (3) | 0.0449 (16) | 0.000 | 0.0441 (18) | 0.000 |
Geometric parameters (Å, º) top
O1—C8 | 1.224 (3) | C10—H10 | 0.95 (2) |
O2—C14 | 1.359 (3) | C11—C12 | 1.365 (4) |
O2—C15 | 1.439 (3) | C11—H11 | 1.01 (3) |
N1—C8 | 1.322 (3) | C12—C13 | 1.365 (4) |
N1—C7 | 1.451 (3) | C12—H12 | 1.01 (3) |
N1—H1N | 0.90 (3) | C13—C14 | 1.384 (3) |
C1—C6 | 1.367 (6) | C13—H13 | 0.91 (2) |
C1—C2 | 1.402 (7) | C15—C16 | 1.492 (4) |
C1—H1 | 0.95 (4) | C15—H15B | 0.94 (3) |
C2—C3 | 1.347 (7) | C15—H15A | 1.00 (3) |
C2—H2 | 0.93 (4) | C16—C17 | 1.384 (4) |
C3—C4 | 1.343 (6) | C16—C21 | 1.396 (3) |
C3—H3 | 0.97 (5) | C17—C18 | 1.368 (4) |
C4—C5 | 1.350 (6) | C17—C19 | 1.516 (4) |
C4—H4 | 1.03 (5) | C18—C17i | 1.368 (4) |
C5—C6 | 1.345 (5) | C18—H18 | 0.91 (5) |
C5—H5 | 1.03 (4) | C19—H19A | 0.9600 |
C6—C7 | 1.497 (4) | C19—H19B | 0.9600 |
C7—H7A | 0.9700 | C19—H19C | 0.9600 |
C7—H7B | 0.9700 | C20—C21 | 1.513 (5) |
C8—C9 | 1.486 (3) | C20—H20A | 0.9600 |
C9—C10 | 1.385 (3) | C20—H20B | 0.9600 |
C9—C14 | 1.393 (3) | C20—H20C | 0.9600 |
C10—C11 | 1.356 (4) | C21—C16i | 1.396 (3) |
| | | |
C14—O2—C15 | 120.55 (19) | C11—C12—C13 | 120.9 (3) |
C8—N1—C7 | 120.5 (2) | C11—C12—H12 | 121.9 (17) |
C8—N1—H1N | 120.1 (18) | C13—C12—H12 | 116.8 (17) |
C7—N1—H1N | 119.2 (18) | C12—C13—C14 | 119.8 (3) |
C6—C1—C2 | 120.0 (5) | C12—C13—H13 | 120.8 (14) |
C6—C1—H1 | 112 (2) | C14—C13—H13 | 119.4 (14) |
C2—C1—H1 | 128 (2) | O2—C14—C13 | 122.8 (2) |
C3—C2—C1 | 118.9 (5) | O2—C14—C9 | 116.9 (2) |
C3—C2—H2 | 128 (3) | C13—C14—C9 | 120.3 (2) |
C1—C2—H2 | 113 (3) | O2—C15—C16 | 106.5 (2) |
C4—C3—C2 | 120.6 (5) | O2—C15—H15B | 106.9 (18) |
C4—C3—H3 | 116 (3) | C16—C15—H15B | 113.7 (19) |
C2—C3—H3 | 123 (3) | O2—C15—H15A | 107.0 (19) |
C3—C4—C5 | 120.0 (5) | C16—C15—H15A | 113.5 (18) |
C3—C4—H4 | 121 (3) | H15B—C15—H15A | 109 (3) |
C5—C4—H4 | 119 (3) | C17—C16—C21 | 120.2 (3) |
C6—C5—C4 | 122.1 (5) | C17—C16—C15 | 119.4 (3) |
C6—C5—H5 | 114 (2) | C21—C16—C15 | 120.4 (3) |
C4—C5—H5 | 124 (2) | C18—C17—C16 | 118.5 (3) |
C5—C6—C1 | 118.3 (4) | C18—C17—C19 | 119.1 (3) |
C5—C6—C7 | 121.3 (5) | C16—C17—C19 | 122.4 (3) |
C1—C6—C7 | 120.4 (5) | C17—C18—C17i | 123.2 (5) |
N1—C7—C6 | 111.2 (2) | C17—C18—H18 | 118.4 (2) |
N1—C7—H7A | 109.4 | C17i—C18—H18 | 118.4 (2) |
C6—C7—H7A | 109.4 | C17—C19—H19A | 109.5 |
N1—C7—H7B | 109.4 | C17—C19—H19B | 109.5 |
C6—C7—H7B | 109.4 | H19A—C19—H19B | 109.5 |
H7A—C7—H7B | 108.0 | C17—C19—H19C | 109.5 |
O1—C8—N1 | 120.7 (2) | H19A—C19—H19C | 109.5 |
O1—C8—C9 | 120.9 (2) | H19B—C19—H19C | 109.5 |
N1—C8—C9 | 118.3 (2) | C21—C20—H20A | 109.5 |
C10—C9—C14 | 117.4 (2) | C21—C20—H20B | 109.5 |
C10—C9—C8 | 115.9 (2) | H20A—C20—H20B | 109.5 |
C14—C9—C8 | 126.7 (2) | C21—C20—H20C | 109.5 |
C11—C10—C9 | 122.3 (3) | H20A—C20—H20C | 109.5 |
C11—C10—H10 | 122.5 (15) | H20B—C20—H20C | 109.5 |
C9—C10—H10 | 115.2 (15) | C16i—C21—C16 | 119.4 (3) |
C10—C11—C12 | 119.3 (3) | C16i—C21—C20 | 120.30 (17) |
C10—C11—H11 | 120.1 (19) | C16—C21—C20 | 120.30 (17) |
C12—C11—H11 | 121 (2) | | |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.90 (3) | 1.93 (3) | 2.628 (3) | 133 (3) |