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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032757/sg6035sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032757/sg6035Isup2.hkl
Contains datablock I

CCDC reference: 289882

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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
C15H11ClF3NO4F(000) = 1472
Mr = 361.70Dx = 1.521 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 13669 reflections
a = 29.140 (6) Åθ = 3.0–27.5°
b = 7.646 (2) ŵ = 0.29 mm1
c = 14.511 (3) ÅT = 295 K
β = 102.19 (3)°Block, colourless
V = 3160 (1) Å30.37 × 0.28 × 0.21 mm
Z = 8
Data collection top
Rigaku R-AXIS-RAPID IP
diffractometer
3600 independent reflections
Radiation source: fine-focus sealed tube2486 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 3337
Tmin = 0.746, Tmax = 0.941k = 89
14665 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-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 parametersΔρmax = 0.36 e Å3
102 restraintsΔρmin = 0.31 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.64492 (3)1.07421 (11)0.30735 (6)0.0771 (3)
F10.78328 (18)0.8255 (7)0.6609 (5)0.112 (3)0.50
F20.75215 (15)1.0495 (13)0.6994 (5)0.144 (4)0.50
F30.78773 (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
O10.58735 (7)0.8267 (3)0.37727 (16)0.0751 (7)
O20.44010 (6)0.5641 (2)0.38038 (15)0.0561 (5)
O30.43689 (17)0.2329 (9)0.3414 (4)0.0613 (14)0.50
O40.49759 (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
N10.47862 (10)0.2287 (3)0.3690 (2)0.0731 (8)
C10.62936 (9)0.8487 (3)0.4400 (2)0.0535 (6)
C20.65997 (9)0.9693 (3)0.4148 (2)0.0542 (7)
C30.70220 (9)1.0042 (4)0.4751 (2)0.0605 (7)
H30.72301.08390.45780.073*
C40.71363 (10)0.9216 (4)0.5608 (2)0.0609 (7)
C50.68310 (11)0.8020 (4)0.5866 (2)0.0622 (7)
H50.69100.74610.64470.075*
C60.64083 (10)0.7656 (4)0.5259 (2)0.0593 (7)
H60.62020.68520.54310.071*
C70.75842 (12)0.9658 (5)0.6272 (3)0.0834 (11)
C80.56162 (9)0.6745 (4)0.37919 (19)0.0538 (6)
C90.51513 (9)0.6967 (3)0.38072 (18)0.0490 (6)
H90.50320.80880.38390.059*
C100.48578 (8)0.5525 (3)0.37762 (17)0.0435 (5)
C110.50609 (9)0.3881 (3)0.37285 (18)0.0496 (6)
C120.55282 (10)0.3691 (4)0.3701 (2)0.0614 (7)
H120.56510.25770.36610.074*
C130.58138 (10)0.5121 (4)0.3731 (2)0.0619 (7)
H130.61290.50010.37100.074*
C140.41922 (10)0.7349 (4)0.3780 (2)0.0613 (7)
H14a0.42320.79780.32210.074*
H14b0.43390.80170.43310.074*
C150.36816 (12)0.7089 (5)0.3765 (3)0.0886 (11)
H15a0.35300.82070.37490.133*
H15b0.36470.64650.43200.133*
H15c0.35400.64300.32150.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0783 (6)0.0752 (5)0.0755 (6)0.0178 (4)0.0109 (4)0.0161 (4)
F10.074 (3)0.112 (4)0.123 (5)0.029 (3)0.038 (3)0.026 (4)
F20.089 (4)0.186 (8)0.142 (6)0.012 (4)0.012 (4)0.110 (6)
F30.070 (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)
O10.0510 (11)0.0743 (14)0.0894 (16)0.0214 (9)0.0091 (10)0.0263 (11)
O20.0410 (10)0.0514 (10)0.0744 (13)0.0006 (7)0.0088 (8)0.0030 (8)
O30.061 (3)0.062 (3)0.064 (3)0.023 (2)0.020 (2)0.008 (3)
O40.099 (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)
N10.0663 (18)0.0424 (13)0.102 (2)0.0043 (11)0.0018 (16)0.0004 (13)
C10.0387 (13)0.0578 (15)0.0625 (16)0.0065 (11)0.0074 (11)0.0003 (12)
C20.0488 (15)0.0525 (14)0.0623 (17)0.0043 (11)0.0140 (12)0.0023 (11)
C30.0467 (15)0.0558 (15)0.079 (2)0.0108 (12)0.0133 (14)0.0084 (14)
C40.0483 (15)0.0607 (16)0.0704 (19)0.0010 (12)0.0048 (13)0.0148 (14)
C50.0623 (17)0.0632 (16)0.0573 (17)0.0000 (13)0.0043 (13)0.0038 (13)
C60.0495 (15)0.0654 (16)0.0631 (17)0.0080 (12)0.0124 (13)0.0045 (13)
C70.061 (2)0.083 (2)0.096 (3)0.0119 (18)0.0060 (19)0.020 (2)
C80.0454 (14)0.0600 (15)0.0510 (15)0.0114 (11)0.0012 (11)0.0084 (11)
C90.0471 (14)0.0442 (12)0.0517 (14)0.0034 (10)0.0014 (11)0.0015 (10)
C100.0406 (12)0.0463 (12)0.0407 (12)0.0021 (9)0.0018 (9)0.0013 (9)
C110.0493 (14)0.0438 (12)0.0511 (14)0.0033 (10)0.0003 (11)0.0017 (10)
C120.0516 (16)0.0570 (15)0.0702 (19)0.0097 (13)0.0009 (13)0.0064 (13)
C130.0400 (14)0.0788 (19)0.0646 (18)0.0028 (13)0.0061 (12)0.0005 (14)
C140.0524 (16)0.0588 (16)0.0706 (18)0.0116 (12)0.0077 (13)0.0059 (13)
C150.0539 (19)0.092 (2)0.119 (3)0.0197 (17)0.0171 (19)0.018 (2)
Geometric parameters (Å, º) top
Cl1—C21.726 (3)C4—C51.381 (4)
F1—C71.328 (6)C4—C71.488 (4)
F2—C71.274 (6)C5—C61.382 (4)
F3—C71.315 (7)C5—H50.9300
F1'—C71.272 (6)C6—H60.9300
F2'—C71.348 (6)C8—C91.370 (4)
F3'—C71.298 (6)C8—C131.380 (4)
O1—C11.373 (3)C9—C101.390 (3)
O1—C81.388 (3)C9—H90.9300
O2—C101.343 (3)C10—C111.398 (3)
O2—C141.438 (3)C11—C121.378 (4)
O3—N11.197 (5)C12—C131.369 (4)
O4—N11.267 (4)C12—H120.9300
O3'—N11.120 (6)C13—H130.9300
O4'—N11.368 (5)C14—C151.497 (4)
N1—C111.453 (3)C14—H14a0.9700
C1—C61.375 (4)C14—H14b0.9700
C1—C21.385 (4)C15—H15a0.9600
C2—C31.378 (4)C15—H15b0.9600
C3—C41.372 (4)C15—H15c0.9600
C3—H30.9300
C1—O1—C8119.9 (2)F3'—C7—C4113.6 (3)
C10—O2—C14118.44 (19)F3—C7—C4112.9 (4)
O3—N1—O4120.3 (4)F1—C7—C4113.0 (3)
O3'—N1—O4'117.9 (5)F2'—C7—C4111.3 (3)
O3'—N1—C11128.3 (5)C9—C8—C13122.7 (2)
O3—N1—C11120.2 (4)C9—C8—O1115.9 (2)
O4—N1—C11116.1 (3)C13—C8—O1121.3 (2)
O4'—N1—C11110.9 (3)C8—C9—C10120.3 (2)
O1—C1—C6123.8 (2)C8—C9—H9119.8
O1—C1—C2116.1 (2)C10—C9—H9119.8
C6—C1—C2120.0 (3)O2—C10—C9123.6 (2)
C3—C2—C1120.0 (3)O2—C10—C11119.6 (2)
C3—C2—Cl1120.5 (2)C9—C10—C11116.8 (2)
C1—C2—Cl1119.6 (2)C12—C11—C10121.8 (2)
C4—C3—C2120.0 (3)C12—C11—N1116.8 (2)
C4—C3—H3120.0C10—C11—N1121.4 (2)
C2—C3—H3120.0C13—C12—C11120.8 (3)
C3—C4—C5120.2 (3)C13—C12—H12119.6
C3—C4—C7119.6 (3)C11—C12—H12119.6
C5—C4—C7120.2 (3)C12—C13—C8117.5 (3)
C4—C5—C6120.0 (3)C12—C13—H13121.3
C4—C5—H5120.0C8—C13—H13121.3
C6—C5—H5120.0O2—C14—C15107.1 (3)
C1—C6—C5119.8 (3)O2—C14—H14a110.3
C1—C6—H6120.1C15—C14—H14a110.3
C5—C6—H6120.1O2—C14—H14b110.3
F1'—C7—F3'111.1 (5)C15—C14—H14b110.3
F1'—C7—F3129.2 (5)H14a—C14—H14b108.5
F2—C7—F3109.5 (5)C14—C15—H15a109.5
F2—C7—F1105.3 (5)C14—C15—H15b109.5
F3—C7—F1102.6 (5)H15a—C15—H15b109.5
F1'—C7—F2'105.3 (5)C14—C15—H15c109.5
F3'—C7—F2'100.9 (4)H15a—C15—H15c109.5
F1'—C7—C4113.7 (3)H15B—C15—H15c109.5
F2—C7—C4112.8 (3)
C8—O1—C1—C624.7 (4)C1—O1—C8—C9130.1 (3)
C8—O1—C1—C2158.7 (3)C1—O1—C8—C1354.4 (4)
O1—C1—C2—C3177.7 (3)C13—C8—C9—C101.1 (4)
C6—C1—C2—C30.9 (4)O1—C8—C9—C10176.6 (2)
O1—C1—C2—Cl12.6 (4)C14—O2—C10—C95.8 (4)
C6—C1—C2—Cl1179.4 (2)C14—O2—C10—C11175.3 (2)
C1—C2—C3—C41.0 (4)C8—C9—C10—O2178.9 (2)
Cl1—C2—C3—C4179.3 (2)C8—C9—C10—C110.1 (4)
C2—C3—C4—C50.6 (4)O2—C10—C11—C12179.9 (2)
C2—C3—C4—C7177.4 (3)C9—C10—C11—C120.8 (4)
C3—C4—C5—C60.1 (4)O2—C10—C11—N11.2 (4)
C7—C4—C5—C6177.9 (3)C9—C10—C11—N1179.8 (2)
O1—C1—C6—C5176.9 (3)O3'—N1—C11—C12164.0 (7)
C2—C1—C6—C50.4 (4)O3—N1—C11—C12156.2 (4)
C4—C5—C6—C10.0 (4)O4—N1—C11—C1244.8 (5)
C3—C4—C7—F1'173.9 (7)O4'—N1—C11—C1236.2 (4)
C5—C4—C7—F1'8.1 (8)O3'—N1—C11—C1017.0 (8)
C3—C4—C7—F2109.9 (7)O3—N1—C11—C1022.8 (5)
C5—C4—C7—F268.1 (7)O4—N1—C11—C10136.2 (4)
C3—C4—C7—F3'45.5 (6)O4'—N1—C11—C10142.8 (4)
C5—C4—C7—F3'136.5 (6)C10—C11—C12—C130.8 (4)
C3—C4—C7—F314.8 (6)N1—C11—C12—C13179.8 (3)
C5—C4—C7—F3167.1 (6)C11—C12—C13—C80.2 (4)
C3—C4—C7—F1130.7 (5)C9—C8—C13—C121.1 (4)
C5—C4—C7—F151.3 (6)O1—C8—C13—C12176.4 (3)
C3—C4—C7—F2'67.4 (5)C10—O2—C14—C15176.9 (3)
C5—C4—C7—F2'110.6 (5)
 

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