The molecule of the title compound, C
22H
20N
2O
4, is centrosymmetric. Intermolecular N—H
O hydrogen bonds link the molecules, forming a ribbon structure.
Supporting information
CCDC reference: 618146
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.117
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit C -2yc
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C22 H20 N2 O4
Atom count from _chemical_formula_moiety:C11 H10 N1 O2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
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.
1,4-phenylenebis(methylene) bis(phenylcarbamate)
top
Crystal data top
C11H10NO2 | F(000) = 396 |
Mr = 376.40 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/c | Melting point: 459(2) K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.973 (5) Å | Cell parameters from 1587 reflections |
b = 5.0236 (14) Å | θ = 4.1–26.1° |
c = 9.915 (3) Å | µ = 0.09 mm−1 |
β = 95.944 (5)° | T = 294 K |
V = 939.9 (5) Å3 | Block, colourless |
Z = 2 | 0.30 × 0.26 × 0.18 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 1911 independent reflections |
Radiation source: fine-focus sealed tube | 1210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 26.3°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→21 |
Tmin = 0.973, Tmax = 0.984 | k = −6→6 |
4948 measured reflections | l = −12→10 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1435P] where P = (Fo2 + 2Fc2)/3 |
1911 reflections | (Δ/σ)max < 0.001 |
131 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Special details top
Experimental. 1H NMR (d6-DMSO, δ, p.p.m.): 9.729 (s, 2 H), 6.595–7.457 (m, 14 H), 5.144
(s, 4 H). |
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 >
2σ(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 | |
O1 | 0.22067 (7) | 0.1055 (2) | 0.34455 (15) | 0.0677 (4) | |
O2 | 0.15509 (6) | 0.4343 (2) | 0.24220 (13) | 0.0590 (4) | |
N1 | 0.24491 (8) | 0.5403 (3) | 0.39117 (16) | 0.0516 (4) | |
H1 | 0.2313 (10) | 0.697 (4) | 0.370 (2) | 0.071 (6)* | |
C1 | 0.31840 (10) | 0.6901 (4) | 0.5879 (2) | 0.0608 (5) | |
H1A | 0.2843 | 0.8178 | 0.6010 | 0.073* | |
C2 | 0.37962 (12) | 0.6793 (5) | 0.6744 (2) | 0.0723 (6) | |
H2 | 0.3867 | 0.7992 | 0.7459 | 0.087* | |
C3 | 0.43019 (11) | 0.4935 (5) | 0.6560 (2) | 0.0737 (6) | |
H3 | 0.4718 | 0.4869 | 0.7144 | 0.088* | |
C4 | 0.41927 (10) | 0.3176 (4) | 0.5512 (3) | 0.0769 (7) | |
H4 | 0.4535 | 0.1899 | 0.5389 | 0.092* | |
C5 | 0.35802 (10) | 0.3264 (4) | 0.4630 (2) | 0.0626 (5) | |
H5 | 0.3512 | 0.2067 | 0.3913 | 0.075* | |
C6 | 0.30719 (8) | 0.5139 (3) | 0.48222 (17) | 0.0452 (4) | |
C7 | 0.20869 (9) | 0.3396 (3) | 0.32753 (18) | 0.0476 (4) | |
C8 | 0.11519 (10) | 0.2373 (4) | 0.1611 (2) | 0.0622 (5) | |
H8A | 0.0967 | 0.1044 | 0.2191 | 0.075* | |
H8B | 0.1454 | 0.1488 | 0.1019 | 0.075* | |
C9 | 0.05577 (9) | 0.3754 (3) | 0.07905 (17) | 0.0498 (5) | |
C10 | −0.01323 (10) | 0.2962 (4) | 0.0853 (2) | 0.0589 (5) | |
H10 | −0.0229 | 0.1580 | 0.1430 | 0.071* | |
C11 | −0.06825 (10) | 0.4183 (4) | 0.00748 (19) | 0.0594 (5) | |
H11 | −0.1145 | 0.3611 | 0.0132 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0705 (8) | 0.0270 (7) | 0.1009 (11) | 0.0029 (6) | −0.0145 (7) | 0.0044 (7) |
O2 | 0.0670 (8) | 0.0330 (6) | 0.0716 (8) | 0.0042 (6) | −0.0181 (7) | −0.0024 (6) |
N1 | 0.0590 (9) | 0.0270 (8) | 0.0657 (10) | 0.0064 (7) | −0.0089 (8) | 0.0004 (7) |
C1 | 0.0621 (12) | 0.0518 (11) | 0.0669 (13) | 0.0066 (9) | −0.0003 (10) | −0.0075 (9) |
C2 | 0.0771 (14) | 0.0723 (14) | 0.0647 (13) | −0.0055 (12) | −0.0064 (11) | −0.0076 (11) |
C3 | 0.0613 (12) | 0.0657 (14) | 0.0893 (16) | −0.0048 (11) | −0.0153 (11) | 0.0117 (12) |
C4 | 0.0550 (12) | 0.0586 (13) | 0.1148 (19) | 0.0133 (10) | −0.0021 (13) | 0.0010 (13) |
C5 | 0.0584 (11) | 0.0475 (11) | 0.0808 (14) | 0.0086 (9) | 0.0015 (10) | −0.0079 (10) |
C6 | 0.0479 (9) | 0.0322 (8) | 0.0551 (10) | −0.0005 (7) | 0.0025 (8) | 0.0070 (7) |
C7 | 0.0508 (10) | 0.0327 (9) | 0.0585 (11) | 0.0046 (8) | 0.0015 (8) | 0.0036 (8) |
C8 | 0.0703 (12) | 0.0416 (10) | 0.0704 (13) | −0.0007 (9) | −0.0123 (10) | −0.0078 (9) |
C9 | 0.0589 (11) | 0.0381 (9) | 0.0506 (10) | −0.0009 (8) | −0.0026 (8) | −0.0060 (8) |
C10 | 0.0696 (12) | 0.0486 (11) | 0.0576 (11) | −0.0068 (9) | 0.0024 (10) | 0.0093 (9) |
C11 | 0.0543 (10) | 0.0557 (11) | 0.0677 (12) | −0.0079 (9) | 0.0049 (10) | 0.0033 (10) |
Geometric parameters (Å, º) top
O1—C7 | 1.2064 (19) | C4—C5 | 1.381 (3) |
O2—C7 | 1.341 (2) | C4—H4 | 0.930 |
O2—C8 | 1.440 (2) | C5—C6 | 1.375 (2) |
N1—C7 | 1.341 (2) | C5—H5 | 0.930 |
N1—C6 | 1.417 (2) | C8—C9 | 1.491 (2) |
N1—H1 | 0.85 (2) | C8—H8A | 0.970 |
C1—C6 | 1.371 (3) | C8—H8B | 0.970 |
C1—C2 | 1.372 (3) | C9—C10 | 1.376 (2) |
C1—H1A | 0.930 | C9—C11i | 1.381 (3) |
C2—C3 | 1.364 (3) | C10—C11 | 1.376 (2) |
C2—H2 | 0.930 | C10—H10 | 0.930 |
C3—C4 | 1.363 (3) | C11—C9i | 1.381 (3) |
C3—H3 | 0.930 | C11—H11 | 0.930 |
| | | |
C7—O2—C8 | 115.41 (13) | C1—C6—N1 | 118.65 (15) |
C7—N1—C6 | 125.62 (15) | C5—C6—N1 | 121.76 (16) |
C7—N1—H1 | 117.0 (14) | O1—C7—N1 | 125.97 (17) |
C6—N1—H1 | 117.1 (14) | O1—C7—O2 | 123.62 (16) |
C6—C1—C2 | 120.42 (18) | N1—C7—O2 | 110.39 (14) |
C6—C1—H1A | 119.8 | O2—C8—C9 | 108.00 (14) |
C2—C1—H1A | 119.8 | O2—C8—H8A | 110.1 |
C3—C2—C1 | 120.4 (2) | C9—C8—H8A | 110.1 |
C3—C2—H2 | 119.8 | O2—C8—H8B | 110.1 |
C1—C2—H2 | 119.8 | C9—C8—H8B | 110.1 |
C4—C3—C2 | 119.47 (19) | H8A—C8—H8B | 108.4 |
C4—C3—H3 | 120.3 | C10—C9—C11i | 118.03 (16) |
C2—C3—H3 | 120.3 | C10—C9—C8 | 120.68 (17) |
C3—C4—C5 | 120.86 (19) | C11i—C9—C8 | 121.27 (17) |
C3—C4—H4 | 119.6 | C9—C10—C11 | 121.08 (17) |
C5—C4—H4 | 119.6 | C9—C10—H10 | 119.5 |
C6—C5—C4 | 119.40 (19) | C11—C10—H10 | 119.5 |
C6—C5—H5 | 120.3 | C10—C11—C9i | 120.90 (17) |
C4—C5—H5 | 120.3 | C10—C11—H11 | 119.6 |
C1—C6—C5 | 119.50 (16) | C9i—C11—H11 | 119.6 |
| | | |
C6—C1—C2—C3 | 0.2 (3) | C6—N1—C7—O1 | 5.2 (3) |
C1—C2—C3—C4 | −0.3 (3) | C6—N1—C7—O2 | −176.07 (15) |
C2—C3—C4—C5 | 0.5 (4) | C8—O2—C7—O1 | −5.3 (3) |
C3—C4—C5—C6 | −0.6 (3) | C8—O2—C7—N1 | 175.97 (15) |
C2—C1—C6—C5 | −0.3 (3) | C7—O2—C8—C9 | 176.76 (15) |
C2—C1—C6—N1 | −176.85 (17) | O2—C8—C9—C10 | −124.53 (19) |
C4—C5—C6—C1 | 0.5 (3) | O2—C8—C9—C11i | 56.9 (2) |
C4—C5—C6—N1 | 176.92 (18) | C11i—C9—C10—C11 | 0.2 (3) |
C7—N1—C6—C1 | −146.85 (18) | C8—C9—C10—C11 | −178.42 (17) |
C7—N1—C6—C5 | 36.7 (3) | C9—C10—C11—C9i | −0.2 (3) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.85 (2) | 2.07 (2) | 2.906 (2) | 166.4 (19) |
Symmetry code: (ii) x, y+1, z. |