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The title compound, C15H11ClF3NO4, a member of the class of nitrophenyl ether herbicides, features an ether O atom that links two substituted aromatic rings, the rings being twisted from each other by 62.5 (1)°. The two ether C-O distances are statistically indistinguishable from each other, despite the different nature of the electron-withdrawing groups in the 4-position (relative to the ether linkage).
Supporting information
CCDC reference: 289882
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.050
- wR factor = 0.157
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for F1'
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C7
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.746 0.941
Tmin(prime) and Tmax expected: 0.895 0.940
RR(prime) = 0.833
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F2
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F3
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F3'
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3'
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4'
| Author Response: The trifluoromethyl group is disordered, but the temperature
factors of the F atoms are merely restrained by an ISOR 0.01 command.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for F1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O3
PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O3 .. 3.11 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O3' .. C6 .. 2.99 Ang.
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
12 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: RAPID AUTO (Rigaku, 1998); cell refinement: RAPID AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2-Chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene
top
Crystal data top
C15H11ClF3NO4 | F(000) = 1472 |
Mr = 361.70 | Dx = 1.521 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 13669 reflections |
a = 29.140 (6) Å | θ = 3.0–27.5° |
b = 7.646 (2) Å | µ = 0.29 mm−1 |
c = 14.511 (3) Å | T = 295 K |
β = 102.19 (3)° | Block, colourless |
V = 3160 (1) Å3 | 0.37 × 0.28 × 0.21 mm |
Z = 8 | |
Data collection top
Rigaku R-AXIS-RAPID IP diffractometer | 3600 independent reflections |
Radiation source: fine-focus sealed tube | 2486 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −33→37 |
Tmin = 0.746, Tmax = 0.941 | k = −8→9 |
14665 measured reflections | l = −18→18 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0871P)2 + 0.6851P] where P = (Fo2 + 2Fc2)/3 |
3600 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 0.36 e Å−3 |
102 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.64492 (3) | 1.07421 (11) | 0.30735 (6) | 0.0771 (3) | |
F1 | 0.78328 (18) | 0.8255 (7) | 0.6609 (5) | 0.112 (3) | 0.50 |
F2 | 0.75215 (15) | 1.0495 (13) | 0.6994 (5) | 0.144 (4) | 0.50 |
F3 | 0.78773 (19) | 1.0528 (12) | 0.5866 (5) | 0.138 (4) | 0.50 |
F1' | 0.7671 (3) | 0.8694 (12) | 0.7003 (6) | 0.181 (5) | 0.50 |
F2' | 0.75769 (18) | 1.1307 (7) | 0.6598 (5) | 0.108 (2) | 0.50 |
F3' | 0.79424 (14) | 0.9734 (13) | 0.5872 (5) | 0.128 (4) | 0.50 |
O1 | 0.58735 (7) | 0.8267 (3) | 0.37727 (16) | 0.0751 (7) | |
O2 | 0.44010 (6) | 0.5641 (2) | 0.38038 (15) | 0.0561 (5) | |
O3 | 0.43689 (17) | 0.2329 (9) | 0.3414 (4) | 0.0613 (14) | 0.50 |
O4 | 0.49759 (18) | 0.1042 (4) | 0.4211 (4) | 0.0807 (14) | 0.50 |
O3' | 0.4434 (3) | 0.2105 (11) | 0.3872 (6) | 0.098 (3) | 0.50 |
O4' | 0.4925 (2) | 0.1079 (6) | 0.3109 (5) | 0.1046 (18) | 0.50 |
N1 | 0.47862 (10) | 0.2287 (3) | 0.3690 (2) | 0.0731 (8) | |
C1 | 0.62936 (9) | 0.8487 (3) | 0.4400 (2) | 0.0535 (6) | |
C2 | 0.65997 (9) | 0.9693 (3) | 0.4148 (2) | 0.0542 (7) | |
C3 | 0.70220 (9) | 1.0042 (4) | 0.4751 (2) | 0.0605 (7) | |
H3 | 0.7230 | 1.0839 | 0.4578 | 0.073* | |
C4 | 0.71363 (10) | 0.9216 (4) | 0.5608 (2) | 0.0609 (7) | |
C5 | 0.68310 (11) | 0.8020 (4) | 0.5866 (2) | 0.0622 (7) | |
H5 | 0.6910 | 0.7461 | 0.6447 | 0.075* | |
C6 | 0.64083 (10) | 0.7656 (4) | 0.5259 (2) | 0.0593 (7) | |
H6 | 0.6202 | 0.6852 | 0.5431 | 0.071* | |
C7 | 0.75842 (12) | 0.9658 (5) | 0.6272 (3) | 0.0834 (11) | |
C8 | 0.56162 (9) | 0.6745 (4) | 0.37919 (19) | 0.0538 (6) | |
C9 | 0.51513 (9) | 0.6967 (3) | 0.38072 (18) | 0.0490 (6) | |
H9 | 0.5032 | 0.8088 | 0.3839 | 0.059* | |
C10 | 0.48578 (8) | 0.5525 (3) | 0.37762 (17) | 0.0435 (5) | |
C11 | 0.50609 (9) | 0.3881 (3) | 0.37285 (18) | 0.0496 (6) | |
C12 | 0.55282 (10) | 0.3691 (4) | 0.3701 (2) | 0.0614 (7) | |
H12 | 0.5651 | 0.2577 | 0.3661 | 0.074* | |
C13 | 0.58138 (10) | 0.5121 (4) | 0.3731 (2) | 0.0619 (7) | |
H13 | 0.6129 | 0.5001 | 0.3710 | 0.074* | |
C14 | 0.41922 (10) | 0.7349 (4) | 0.3780 (2) | 0.0613 (7) | |
H14a | 0.4232 | 0.7978 | 0.3221 | 0.074* | |
H14b | 0.4339 | 0.8017 | 0.4331 | 0.074* | |
C15 | 0.36816 (12) | 0.7089 (5) | 0.3765 (3) | 0.0886 (11) | |
H15a | 0.3530 | 0.8207 | 0.3749 | 0.133* | |
H15b | 0.3647 | 0.6465 | 0.4320 | 0.133* | |
H15c | 0.3540 | 0.6430 | 0.3215 | 0.133* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0783 (6) | 0.0752 (5) | 0.0755 (6) | −0.0178 (4) | 0.0109 (4) | 0.0161 (4) |
F1 | 0.074 (3) | 0.112 (4) | 0.123 (5) | 0.029 (3) | −0.038 (3) | −0.026 (4) |
F2 | 0.089 (4) | 0.186 (8) | 0.142 (6) | 0.012 (4) | −0.012 (4) | −0.110 (6) |
F3 | 0.070 (4) | 0.138 (6) | 0.181 (8) | −0.034 (4) | −0.026 (4) | 0.016 (5) |
F1' | 0.151 (7) | 0.197 (9) | 0.147 (7) | −0.075 (6) | −0.079 (5) | 0.072 (6) |
F2' | 0.091 (4) | 0.096 (4) | 0.127 (5) | −0.028 (3) | −0.002 (3) | −0.051 (3) |
F3' | 0.042 (3) | 0.184 (8) | 0.154 (6) | 0.010 (3) | 0.008 (3) | −0.067 (6) |
O1 | 0.0510 (11) | 0.0743 (14) | 0.0894 (16) | −0.0214 (9) | −0.0091 (10) | 0.0263 (11) |
O2 | 0.0410 (10) | 0.0514 (10) | 0.0744 (13) | 0.0006 (7) | 0.0088 (8) | 0.0030 (8) |
O3 | 0.061 (3) | 0.062 (3) | 0.064 (3) | −0.023 (2) | 0.020 (2) | −0.008 (3) |
O4 | 0.099 (3) | 0.0303 (18) | 0.100 (3) | −0.0005 (19) | −0.008 (3) | 0.0037 (19) |
O3' | 0.124 (6) | 0.076 (4) | 0.113 (6) | −0.038 (4) | 0.071 (5) | −0.026 (4) |
O4' | 0.116 (4) | 0.055 (3) | 0.150 (5) | 0.003 (3) | 0.044 (4) | −0.014 (3) |
N1 | 0.0663 (18) | 0.0424 (13) | 0.102 (2) | −0.0043 (11) | −0.0018 (16) | 0.0004 (13) |
C1 | 0.0387 (13) | 0.0578 (15) | 0.0625 (16) | −0.0065 (11) | 0.0074 (11) | −0.0003 (12) |
C2 | 0.0488 (15) | 0.0525 (14) | 0.0623 (17) | −0.0043 (11) | 0.0140 (12) | −0.0023 (11) |
C3 | 0.0467 (15) | 0.0558 (15) | 0.079 (2) | −0.0108 (12) | 0.0133 (14) | −0.0084 (14) |
C4 | 0.0483 (15) | 0.0607 (16) | 0.0704 (19) | −0.0010 (12) | 0.0048 (13) | −0.0148 (14) |
C5 | 0.0623 (17) | 0.0632 (16) | 0.0573 (17) | 0.0000 (13) | 0.0043 (13) | −0.0038 (13) |
C6 | 0.0495 (15) | 0.0654 (16) | 0.0631 (17) | −0.0080 (12) | 0.0124 (13) | 0.0045 (13) |
C7 | 0.061 (2) | 0.083 (2) | 0.096 (3) | −0.0119 (18) | −0.0060 (19) | −0.020 (2) |
C8 | 0.0454 (14) | 0.0600 (15) | 0.0510 (15) | −0.0114 (11) | −0.0012 (11) | 0.0084 (11) |
C9 | 0.0471 (14) | 0.0442 (12) | 0.0517 (14) | −0.0034 (10) | 0.0014 (11) | 0.0015 (10) |
C10 | 0.0406 (12) | 0.0463 (12) | 0.0407 (12) | −0.0021 (9) | 0.0018 (9) | 0.0013 (9) |
C11 | 0.0493 (14) | 0.0438 (12) | 0.0511 (14) | −0.0033 (10) | 0.0003 (11) | −0.0017 (10) |
C12 | 0.0516 (16) | 0.0570 (15) | 0.0702 (19) | 0.0097 (13) | 0.0009 (13) | −0.0064 (13) |
C13 | 0.0400 (14) | 0.0788 (19) | 0.0646 (18) | 0.0028 (13) | 0.0061 (12) | 0.0005 (14) |
C14 | 0.0524 (16) | 0.0588 (16) | 0.0706 (18) | 0.0116 (12) | 0.0077 (13) | 0.0059 (13) |
C15 | 0.0539 (19) | 0.092 (2) | 0.119 (3) | 0.0197 (17) | 0.0171 (19) | 0.018 (2) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.726 (3) | C4—C5 | 1.381 (4) |
F1—C7 | 1.328 (6) | C4—C7 | 1.488 (4) |
F2—C7 | 1.274 (6) | C5—C6 | 1.382 (4) |
F3—C7 | 1.315 (7) | C5—H5 | 0.9300 |
F1'—C7 | 1.272 (6) | C6—H6 | 0.9300 |
F2'—C7 | 1.348 (6) | C8—C9 | 1.370 (4) |
F3'—C7 | 1.298 (6) | C8—C13 | 1.380 (4) |
O1—C1 | 1.373 (3) | C9—C10 | 1.390 (3) |
O1—C8 | 1.388 (3) | C9—H9 | 0.9300 |
O2—C10 | 1.343 (3) | C10—C11 | 1.398 (3) |
O2—C14 | 1.438 (3) | C11—C12 | 1.378 (4) |
O3—N1 | 1.197 (5) | C12—C13 | 1.369 (4) |
O4—N1 | 1.267 (4) | C12—H12 | 0.9300 |
O3'—N1 | 1.120 (6) | C13—H13 | 0.9300 |
O4'—N1 | 1.368 (5) | C14—C15 | 1.497 (4) |
N1—C11 | 1.453 (3) | C14—H14a | 0.9700 |
C1—C6 | 1.375 (4) | C14—H14b | 0.9700 |
C1—C2 | 1.385 (4) | C15—H15a | 0.9600 |
C2—C3 | 1.378 (4) | C15—H15b | 0.9600 |
C3—C4 | 1.372 (4) | C15—H15c | 0.9600 |
C3—H3 | 0.9300 | | |
| | | |
C1—O1—C8 | 119.9 (2) | F3'—C7—C4 | 113.6 (3) |
C10—O2—C14 | 118.44 (19) | F3—C7—C4 | 112.9 (4) |
O3—N1—O4 | 120.3 (4) | F1—C7—C4 | 113.0 (3) |
O3'—N1—O4' | 117.9 (5) | F2'—C7—C4 | 111.3 (3) |
O3'—N1—C11 | 128.3 (5) | C9—C8—C13 | 122.7 (2) |
O3—N1—C11 | 120.2 (4) | C9—C8—O1 | 115.9 (2) |
O4—N1—C11 | 116.1 (3) | C13—C8—O1 | 121.3 (2) |
O4'—N1—C11 | 110.9 (3) | C8—C9—C10 | 120.3 (2) |
O1—C1—C6 | 123.8 (2) | C8—C9—H9 | 119.8 |
O1—C1—C2 | 116.1 (2) | C10—C9—H9 | 119.8 |
C6—C1—C2 | 120.0 (3) | O2—C10—C9 | 123.6 (2) |
C3—C2—C1 | 120.0 (3) | O2—C10—C11 | 119.6 (2) |
C3—C2—Cl1 | 120.5 (2) | C9—C10—C11 | 116.8 (2) |
C1—C2—Cl1 | 119.6 (2) | C12—C11—C10 | 121.8 (2) |
C4—C3—C2 | 120.0 (3) | C12—C11—N1 | 116.8 (2) |
C4—C3—H3 | 120.0 | C10—C11—N1 | 121.4 (2) |
C2—C3—H3 | 120.0 | C13—C12—C11 | 120.8 (3) |
C3—C4—C5 | 120.2 (3) | C13—C12—H12 | 119.6 |
C3—C4—C7 | 119.6 (3) | C11—C12—H12 | 119.6 |
C5—C4—C7 | 120.2 (3) | C12—C13—C8 | 117.5 (3) |
C4—C5—C6 | 120.0 (3) | C12—C13—H13 | 121.3 |
C4—C5—H5 | 120.0 | C8—C13—H13 | 121.3 |
C6—C5—H5 | 120.0 | O2—C14—C15 | 107.1 (3) |
C1—C6—C5 | 119.8 (3) | O2—C14—H14a | 110.3 |
C1—C6—H6 | 120.1 | C15—C14—H14a | 110.3 |
C5—C6—H6 | 120.1 | O2—C14—H14b | 110.3 |
F1'—C7—F3' | 111.1 (5) | C15—C14—H14b | 110.3 |
F1'—C7—F3 | 129.2 (5) | H14a—C14—H14b | 108.5 |
F2—C7—F3 | 109.5 (5) | C14—C15—H15a | 109.5 |
F2—C7—F1 | 105.3 (5) | C14—C15—H15b | 109.5 |
F3—C7—F1 | 102.6 (5) | H15a—C15—H15b | 109.5 |
F1'—C7—F2' | 105.3 (5) | C14—C15—H15c | 109.5 |
F3'—C7—F2' | 100.9 (4) | H15a—C15—H15c | 109.5 |
F1'—C7—C4 | 113.7 (3) | H15B—C15—H15c | 109.5 |
F2—C7—C4 | 112.8 (3) | | |
| | | |
C8—O1—C1—C6 | −24.7 (4) | C1—O1—C8—C9 | 130.1 (3) |
C8—O1—C1—C2 | 158.7 (3) | C1—O1—C8—C13 | −54.4 (4) |
O1—C1—C2—C3 | 177.7 (3) | C13—C8—C9—C10 | 1.1 (4) |
C6—C1—C2—C3 | 0.9 (4) | O1—C8—C9—C10 | 176.6 (2) |
O1—C1—C2—Cl1 | −2.6 (4) | C14—O2—C10—C9 | 5.8 (4) |
C6—C1—C2—Cl1 | −179.4 (2) | C14—O2—C10—C11 | −175.3 (2) |
C1—C2—C3—C4 | −1.0 (4) | C8—C9—C10—O2 | 178.9 (2) |
Cl1—C2—C3—C4 | 179.3 (2) | C8—C9—C10—C11 | −0.1 (4) |
C2—C3—C4—C5 | 0.6 (4) | O2—C10—C11—C12 | −179.9 (2) |
C2—C3—C4—C7 | −177.4 (3) | C9—C10—C11—C12 | −0.8 (4) |
C3—C4—C5—C6 | −0.1 (4) | O2—C10—C11—N1 | 1.2 (4) |
C7—C4—C5—C6 | 177.9 (3) | C9—C10—C11—N1 | −179.8 (2) |
O1—C1—C6—C5 | −176.9 (3) | O3'—N1—C11—C12 | 164.0 (7) |
C2—C1—C6—C5 | −0.4 (4) | O3—N1—C11—C12 | −156.2 (4) |
C4—C5—C6—C1 | 0.0 (4) | O4—N1—C11—C12 | 44.8 (5) |
C3—C4—C7—F1' | −173.9 (7) | O4'—N1—C11—C12 | −36.2 (4) |
C5—C4—C7—F1' | 8.1 (8) | O3'—N1—C11—C10 | −17.0 (8) |
C3—C4—C7—F2 | 109.9 (7) | O3—N1—C11—C10 | 22.8 (5) |
C5—C4—C7—F2 | −68.1 (7) | O4—N1—C11—C10 | −136.2 (4) |
C3—C4—C7—F3' | −45.5 (6) | O4'—N1—C11—C10 | 142.8 (4) |
C5—C4—C7—F3' | 136.5 (6) | C10—C11—C12—C13 | 0.8 (4) |
C3—C4—C7—F3 | −14.8 (6) | N1—C11—C12—C13 | 179.8 (3) |
C5—C4—C7—F3 | 167.1 (6) | C11—C12—C13—C8 | 0.2 (4) |
C3—C4—C7—F1 | −130.7 (5) | C9—C8—C13—C12 | −1.1 (4) |
C5—C4—C7—F1 | 51.3 (6) | O1—C8—C13—C12 | −176.4 (3) |
C3—C4—C7—F2' | 67.4 (5) | C10—O2—C14—C15 | 176.9 (3) |
C5—C4—C7—F2' | −110.6 (5) | | |
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