The title compound, C15H12ClNO5, was synthesized by the reaction of ethyl 4-hydroxybenzoate and 1,2-dichloro-4-nitrobenzene in the presence of potassium hydroxide. In the V-shaped molecule, the dihedral angle between the two benzene rings is 72.90 (5)°.
Supporting information
CCDC reference: 605131
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.126
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: WinGX (Farrugia, 1999).
Ethyl 4-(2-chloro-4-nitrophenoxy)benzoate
top
Crystal data top
C15H12ClNO5 | F(000) = 664.00 |
Mr = 321.71 | Dx = 1.439 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 10694 reflections |
a = 12.890 (6) Å | θ = 3.1–27.5° |
b = 8.846 (3) Å | µ = 0.28 mm−1 |
c = 13.967 (5) Å | T = 296 K |
β = 111.230 (16)° | Block, colorless |
V = 1484.5 (10) Å3 | 0.38 × 0.28 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3398 independent reflections |
Radiation source: fine-focus sealed tube | 2406 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
Tmin = 0.891, Tmax = 0.946 | l = −18→18 |
14122 measured reflections | |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.1257P] where P = (Fo2 + 2Fc2)/3 |
3398 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | |
Cl1 | 0.72198 (6) | 0.66363 (6) | 0.97648 (4) | 0.0967 (3) | |
O5 | 0.41489 (11) | 0.18920 (16) | 0.39209 (9) | 0.0727 (4) | |
O3 | 0.53429 (12) | 0.54450 (13) | 0.80786 (8) | 0.0732 (4) | |
O4 | 0.25972 (11) | 0.32380 (17) | 0.35358 (10) | 0.0813 (4) | |
O2 | 0.63498 (12) | 0.04814 (16) | 1.14720 (10) | 0.0795 (4) | |
O1 | 0.74092 (12) | 0.22583 (18) | 1.23393 (9) | 0.0846 (4) | |
C10 | 0.40244 (12) | 0.35672 (17) | 0.51675 (11) | 0.0480 (4) | |
N1 | 0.67267 (13) | 0.17610 (18) | 1.15490 (10) | 0.0611 (4) | |
C1 | 0.63443 (13) | 0.27425 (18) | 1.06446 (11) | 0.0514 (4) | |
C2 | 0.54635 (14) | 0.22717 (19) | 0.97931 (12) | 0.0569 (4) | |
H2 | 0.5107 | 0.1361 | 0.9801 | 0.068* | |
C13 | 0.35030 (13) | 0.29030 (19) | 0.41274 (12) | 0.0526 (4) | |
C11 | 0.34665 (13) | 0.46917 (17) | 0.54669 (12) | 0.0542 (4) | |
H11 | 0.2788 | 0.5039 | 0.5007 | 0.065* | |
C9 | 0.50434 (13) | 0.3070 (2) | 0.58487 (12) | 0.0583 (4) | |
H9 | 0.5433 | 0.2326 | 0.5649 | 0.070* | |
C5 | 0.65416 (14) | 0.49633 (19) | 0.97837 (12) | 0.0569 (4) | |
C4 | 0.56627 (14) | 0.45067 (17) | 0.89119 (11) | 0.0545 (4) | |
C12 | 0.38990 (14) | 0.53095 (18) | 0.64376 (12) | 0.0589 (4) | |
H12 | 0.3520 | 0.6069 | 0.6636 | 0.071* | |
C7 | 0.49012 (14) | 0.47804 (18) | 0.71052 (11) | 0.0563 (4) | |
C6 | 0.68845 (14) | 0.40878 (19) | 1.06586 (12) | 0.0578 (4) | |
H6 | 0.7467 | 0.4399 | 1.1245 | 0.069* | |
C8 | 0.54819 (15) | 0.3677 (2) | 0.68232 (13) | 0.0644 (5) | |
H8 | 0.6164 | 0.3341 | 0.7284 | 0.077* | |
C3 | 0.51213 (14) | 0.31683 (18) | 0.89322 (13) | 0.0594 (4) | |
H3 | 0.4519 | 0.2871 | 0.8358 | 0.071* | |
C14 | 0.37253 (19) | 0.1138 (3) | 0.29342 (15) | 0.0841 (6) | |
H14A | 0.3291 | 0.1840 | 0.2408 | 0.101* | |
H14B | 0.3248 | 0.0303 | 0.2959 | 0.101* | |
C15 | 0.4673 (2) | 0.0580 (3) | 0.2695 (2) | 0.0959 (7) | |
H15A | 0.5112 | 0.1419 | 0.2626 | 0.144* | |
H15B | 0.4406 | 0.0021 | 0.2063 | 0.144* | |
H15C | 0.5121 | −0.0067 | 0.3239 | 0.144* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1182 (5) | 0.0769 (4) | 0.0769 (4) | −0.0505 (3) | 0.0135 (3) | −0.0059 (3) |
O5 | 0.0686 (8) | 0.0828 (9) | 0.0586 (7) | 0.0104 (7) | 0.0135 (6) | −0.0138 (6) |
O3 | 0.1020 (10) | 0.0491 (6) | 0.0491 (6) | −0.0103 (6) | 0.0043 (6) | 0.0002 (5) |
O4 | 0.0650 (8) | 0.0905 (10) | 0.0635 (7) | 0.0114 (7) | −0.0065 (6) | −0.0136 (7) |
O2 | 0.0890 (10) | 0.0712 (8) | 0.0756 (9) | −0.0006 (7) | 0.0267 (7) | 0.0182 (7) |
O1 | 0.0922 (10) | 0.0941 (10) | 0.0479 (7) | 0.0119 (8) | 0.0016 (6) | −0.0012 (7) |
C10 | 0.0452 (8) | 0.0485 (8) | 0.0461 (7) | −0.0037 (6) | 0.0114 (6) | 0.0075 (6) |
N1 | 0.0637 (9) | 0.0694 (9) | 0.0494 (8) | 0.0118 (7) | 0.0193 (6) | 0.0016 (7) |
C1 | 0.0520 (8) | 0.0548 (8) | 0.0445 (8) | 0.0046 (7) | 0.0142 (6) | −0.0025 (7) |
C2 | 0.0592 (9) | 0.0482 (8) | 0.0562 (9) | −0.0072 (7) | 0.0122 (7) | −0.0022 (7) |
C13 | 0.0511 (9) | 0.0537 (8) | 0.0481 (8) | −0.0039 (7) | 0.0122 (7) | 0.0036 (7) |
C11 | 0.0499 (8) | 0.0500 (8) | 0.0524 (8) | 0.0039 (7) | 0.0063 (7) | 0.0052 (7) |
C9 | 0.0505 (9) | 0.0648 (10) | 0.0532 (9) | 0.0090 (7) | 0.0110 (7) | 0.0032 (8) |
C5 | 0.0627 (10) | 0.0506 (8) | 0.0512 (8) | −0.0125 (7) | 0.0135 (7) | −0.0094 (7) |
C4 | 0.0637 (10) | 0.0479 (8) | 0.0441 (8) | −0.0018 (7) | 0.0102 (7) | −0.0041 (7) |
C12 | 0.0649 (10) | 0.0475 (8) | 0.0593 (9) | 0.0042 (7) | 0.0166 (8) | 0.0028 (7) |
C7 | 0.0659 (10) | 0.0481 (8) | 0.0449 (8) | −0.0098 (7) | 0.0081 (7) | 0.0024 (7) |
C6 | 0.0565 (9) | 0.0641 (10) | 0.0439 (8) | −0.0068 (8) | 0.0073 (7) | −0.0107 (7) |
C8 | 0.0528 (9) | 0.0727 (11) | 0.0523 (9) | 0.0059 (8) | 0.0005 (7) | 0.0061 (8) |
C3 | 0.0584 (9) | 0.0528 (9) | 0.0513 (8) | −0.0090 (7) | 0.0012 (7) | −0.0045 (7) |
C14 | 0.0870 (14) | 0.0957 (15) | 0.0652 (11) | −0.0038 (12) | 0.0222 (10) | −0.0257 (11) |
C15 | 0.1112 (18) | 0.0835 (14) | 0.1110 (17) | −0.0159 (13) | 0.0619 (15) | −0.0295 (13) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.7239 (18) | C9—C8 | 1.379 (2) |
O5—C13 | 1.323 (2) | C9—H9 | 0.9300 |
O5—C14 | 1.448 (2) | C5—C6 | 1.377 (2) |
O3—C4 | 1.3661 (19) | C5—C4 | 1.389 (2) |
O3—C7 | 1.3991 (18) | C4—C3 | 1.380 (2) |
O4—C13 | 1.1980 (19) | C12—C7 | 1.373 (2) |
O2—N1 | 1.221 (2) | C12—H12 | 0.9300 |
O1—N1 | 1.2176 (18) | C7—C8 | 1.372 (3) |
C10—C11 | 1.378 (2) | C6—H6 | 0.9300 |
C10—C9 | 1.385 (2) | C8—H8 | 0.9300 |
C10—C13 | 1.483 (2) | C3—H3 | 0.9300 |
N1—C1 | 1.463 (2) | C14—C15 | 1.464 (3) |
C1—C6 | 1.375 (2) | C14—H14A | 0.9700 |
C1—C2 | 1.378 (2) | C14—H14B | 0.9700 |
C2—C3 | 1.373 (2) | C15—H15A | 0.9600 |
C2—H2 | 0.9300 | C15—H15B | 0.9600 |
C11—C12 | 1.378 (2) | C15—H15C | 0.9600 |
C11—H11 | 0.9300 | | |
| | | |
C13—O5—C14 | 117.94 (14) | C3—C4—C5 | 119.30 (15) |
C4—O3—C7 | 117.63 (12) | C7—C12—C11 | 118.61 (16) |
C11—C10—C9 | 119.32 (15) | C7—C12—H12 | 120.7 |
C11—C10—C13 | 118.82 (13) | C11—C12—H12 | 120.7 |
C9—C10—C13 | 121.85 (15) | C8—C7—C12 | 121.64 (15) |
O1—N1—O2 | 123.27 (16) | C8—C7—O3 | 120.37 (15) |
O1—N1—C1 | 118.36 (16) | C12—C7—O3 | 117.93 (16) |
O2—N1—C1 | 118.37 (14) | C1—C6—C5 | 118.41 (14) |
C6—C1—C2 | 121.90 (15) | C1—C6—H6 | 120.8 |
C6—C1—N1 | 119.38 (13) | C5—C6—H6 | 120.8 |
C2—C1—N1 | 118.71 (15) | C7—C8—C9 | 119.27 (15) |
C3—C2—C1 | 118.96 (15) | C7—C8—H8 | 120.4 |
C3—C2—H2 | 120.5 | C9—C8—H8 | 120.4 |
C1—C2—H2 | 120.5 | C2—C3—C4 | 120.61 (14) |
O4—C13—O5 | 123.36 (16) | C2—C3—H3 | 119.7 |
O4—C13—C10 | 124.08 (16) | C4—C3—H3 | 119.7 |
O5—C13—C10 | 112.56 (13) | O5—C14—C15 | 108.32 (18) |
C10—C11—C12 | 121.00 (14) | O5—C14—H14A | 110.0 |
C10—C11—H11 | 119.5 | C15—C14—H14A | 110.0 |
C12—C11—H11 | 119.5 | O5—C14—H14B | 110.0 |
C8—C9—C10 | 120.15 (17) | C15—C14—H14B | 110.0 |
C8—C9—H9 | 119.9 | H14A—C14—H14B | 108.4 |
C10—C9—H9 | 119.9 | C14—C15—H15A | 109.5 |
C6—C5—C4 | 120.79 (15) | C14—C15—H15B | 109.5 |
C6—C5—Cl1 | 119.65 (12) | H15A—C15—H15B | 109.5 |
C4—C5—Cl1 | 119.56 (13) | C14—C15—H15C | 109.5 |
O3—C4—C3 | 122.69 (13) | H15A—C15—H15C | 109.5 |
O3—C4—C5 | 117.95 (14) | H15B—C15—H15C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.58 | 3.418 (3) | 151 |
C8—H8···O4ii | 0.93 | 2.47 | 3.362 (3) | 162 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2. |