2,4-Bis[2-chloro-4-(trifluoro­meth­yl)phen­oxy]-1-nitro­benzene

Gao, S.; Ng, S.W.

doi:10.1107/S1600536805032769

2,4-Bis[2-chloro-4-(trifluoromethyl)phenoxy]-1-nitrobenzene

The title compound, C₂₀H₉Cl₂F₆NO₄, a member of the class of nitrophenyl ether herbicides, features two ether O atoms that link two trifluoromethyl-substituted aromatic rings to a central aromatic ring. The molecules are linked by an F

F interaction into a linear chain.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032769/sg6036sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032769/sg6036Isup2.hkl Contains datablock I

CCDC reference: 289883

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.051
wR factor = 0.164
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.519     0.928
            Tmin(prime) and Tmax expected:      0.853     0.927
            RR(prime) =      0.608
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.61
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        F1'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         F2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        F3'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O3      ..       3.21 Ang.

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   5 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
   6 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.

Bis-2,4-(2-chloro-4-trifluromethylphenoxy)-1-nitrobenzene top

Crystal data top

C₂₀H₉Cl₂F₆NO₄	F(000) = 1024
M_r = 512.18	D_x = 1.658 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15755 reflections
a = 17.056 (3) Å	θ = 3.1–27.5°
b = 9.074 (2) Å	µ = 0.40 mm⁻¹
c = 13.544 (3) Å	T = 295 K
β = 101.88 (3)°	Prism, colourless
V = 2051.5 (7) Å³	0.39 × 0.25 × 0.19 mm
Z = 4

Data collection top

Rigaku R-AXIS-RAPID IP diffractometer	4666 independent reflections
Radiation source: fine-focus sealed tube	3310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→21
T_min = 0.519, T_max = 0.928	k = −11→11
18242 measured reflections	l = −17→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0873P)² + 0.4142P] where P = (F_o² + 2F_c²)/3
4666 reflections	(Δ/σ)_max = 0.001
354 parameters	Δρ_max = 0.44 e Å⁻³
138 restraints	Δρ_min = −0.39 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.67555 (7)	0.77312 (12)	0.56669 (8)	0.0988 (4)
Cl2	0.20897 (4)	0.37676 (9)	0.66249 (8)	0.0788 (3)
F1	1.0021 (3)	0.4857 (12)	0.7542 (7)	0.134 (4)	0.500 (12)
F2	0.9840 (3)	0.6979 (7)	0.6922 (12)	0.159 (4)	0.500 (12)
F3	0.9905 (3)	0.5165 (16)	0.5989 (6)	0.152 (4)	0.500 (12)
F1'	0.9945 (3)	0.6058 (18)	0.7681 (5)	0.166 (4)	0.500 (12)
F2'	0.9813 (3)	0.6703 (12)	0.6197 (9)	0.152 (4)	0.500 (12)
F3'	0.9990 (3)	0.4465 (8)	0.6567 (12)	0.158 (4)	0.500 (12)
F4	0.1379 (8)	1.0039 (11)	0.5770 (6)	0.153 (5)	0.535 (18)
F5	0.0700 (3)	0.8421 (7)	0.4825 (10)	0.126 (3)	0.535 (18)
F6	0.1572 (4)	0.9596 (9)	0.4309 (6)	0.106 (3)	0.535 (18)
F4'	0.1644 (4)	1.0360 (6)	0.5556 (7)	0.101 (3)	0.465 (18)
F5'	0.0743 (4)	0.8797 (11)	0.5409 (12)	0.121 (4)	0.465 (18)
F6'	0.1359 (7)	0.9192 (12)	0.4203 (5)	0.117 (4)	0.465 (18)
O1	0.62934 (10)	0.4691 (3)	0.60471 (14)	0.0662 (6)
O2	0.46715 (17)	0.6473 (3)	0.95795 (18)	0.0918 (8)
O3	0.36075 (15)	0.5921 (3)	0.84972 (19)	0.0849 (7)
O4	0.37216 (10)	0.4702 (2)	0.67461 (15)	0.0558 (5)
N1	0.43349 (16)	0.6059 (3)	0.87429 (19)	0.0614 (6)
C1	0.71147 (14)	0.4967 (3)	0.62880 (19)	0.0515 (6)
C2	0.74112 (17)	0.6326 (3)	0.6091 (2)	0.0571 (7)
C3	0.82244 (19)	0.6562 (4)	0.6258 (2)	0.0639 (7)
C4	0.87353 (16)	0.5420 (4)	0.6620 (2)	0.0632 (7)
C5	0.84392 (17)	0.4073 (4)	0.6826 (2)	0.0656 (8)
C6	0.76236 (17)	0.3841 (3)	0.6656 (2)	0.0587 (7)
C7	0.9624 (2)	0.5636 (5)	0.6773 (3)	0.1032 (14)
C8	0.58370 (14)	0.5087 (3)	0.67218 (19)	0.0506 (6)
C9	0.50274 (14)	0.4771 (3)	0.64335 (19)	0.0494 (6)
C10	0.45141 (14)	0.5099 (3)	0.70654 (19)	0.0476 (6)
C11	0.48225 (15)	0.5732 (3)	0.80047 (19)	0.0500 (6)
C12	0.56282 (16)	0.6062 (3)	0.8270 (2)	0.0556 (6)
C13	0.61422 (15)	0.5756 (3)	0.7640 (2)	0.0542 (6)
C14	0.31858 (14)	0.5794 (3)	0.63618 (18)	0.0456 (5)
C15	0.23778 (15)	0.5471 (3)	0.6268 (2)	0.0508 (6)
C16	0.18055 (16)	0.6506 (3)	0.5878 (2)	0.0573 (7)
C17	0.20388 (17)	0.7859 (3)	0.5579 (2)	0.0563 (6)
C18	0.28403 (17)	0.8164 (3)	0.5646 (2)	0.0560 (6)
C19	0.34112 (16)	0.7144 (3)	0.6040 (2)	0.0521 (6)
C20	0.1427 (2)	0.9014 (4)	0.5156 (3)	0.0801 (10)
H3	0.8426	0.7478	0.6129	0.077*
H5	0.8790	0.3315	0.7082	0.079*
H6	0.7422	0.2927	0.6791	0.070*
H9	0.4830	0.4335	0.5810	0.059*
H12	0.5827	0.6502	0.8892	0.067*
H13	0.6683	0.5993	0.7825	0.065*
H16	0.1265	0.6291	0.5818	0.069*
H18	0.2994	0.9068	0.5423	0.067*
H19	0.3951	0.7360	0.6091	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1036 (8)	0.0892 (7)	0.0938 (7)	0.0330 (6)	−0.0025 (5)	0.0164 (5)
Cl2	0.0507 (4)	0.0685 (5)	0.1173 (7)	−0.0112 (3)	0.0172 (4)	0.0271 (4)
F1	0.053 (3)	0.168 (7)	0.161 (6)	−0.018 (4)	−0.027 (3)	0.020 (5)
F2	0.079 (4)	0.146 (6)	0.244 (10)	−0.062 (4)	0.012 (5)	−0.037 (6)
F3	0.074 (4)	0.239 (10)	0.160 (6)	−0.040 (5)	0.064 (4)	−0.051 (6)
F1'	0.086 (4)	0.238 (10)	0.151 (6)	−0.062 (6)	−0.032 (4)	−0.014 (7)
F2'	0.080 (4)	0.190 (8)	0.198 (8)	−0.043 (5)	0.061 (4)	0.039 (6)
F3'	0.061 (3)	0.166 (6)	0.257 (11)	0.013 (4)	0.057 (5)	0.002 (7)
F4	0.187 (8)	0.143 (7)	0.124 (5)	0.091 (6)	0.022 (5)	0.000 (5)
F5	0.064 (3)	0.138 (5)	0.162 (7)	0.017 (3)	−0.011 (3)	0.056 (4)
F6	0.092 (4)	0.099 (4)	0.118 (5)	−0.003 (3)	−0.001 (3)	0.057 (4)
F4'	0.102 (4)	0.055 (3)	0.141 (6)	0.020 (3)	0.016 (4)	0.005 (3)
F5'	0.064 (4)	0.105 (5)	0.196 (9)	0.031 (3)	0.034 (4)	0.061 (5)
F6'	0.133 (7)	0.105 (5)	0.092 (5)	0.027 (5)	−0.027 (4)	0.015 (4)
O1	0.0347 (9)	0.1037 (16)	0.0603 (11)	−0.0061 (10)	0.0099 (8)	−0.0311 (11)
O2	0.0961 (18)	0.123 (2)	0.0631 (15)	0.0126 (16)	0.0325 (13)	−0.0168 (14)
O3	0.0681 (15)	0.1020 (19)	0.0949 (17)	0.0064 (13)	0.0410 (12)	−0.0069 (14)
O4	0.0385 (9)	0.0494 (10)	0.0801 (13)	−0.0010 (8)	0.0134 (8)	0.0008 (8)
N1	0.0644 (15)	0.0610 (14)	0.0643 (15)	0.0108 (12)	0.0262 (12)	0.0031 (11)
C1	0.0370 (12)	0.0713 (17)	0.0468 (13)	−0.0042 (12)	0.0103 (9)	−0.0141 (12)
C2	0.0564 (16)	0.0635 (16)	0.0481 (14)	0.0058 (13)	0.0034 (11)	−0.0033 (11)
C3	0.0637 (18)	0.0659 (17)	0.0618 (17)	−0.0175 (15)	0.0119 (13)	−0.0026 (13)
C4	0.0406 (14)	0.081 (2)	0.0672 (17)	−0.0089 (14)	0.0095 (12)	−0.0077 (15)
C5	0.0460 (15)	0.0729 (19)	0.077 (2)	0.0056 (14)	0.0095 (13)	0.0009 (15)
C6	0.0506 (15)	0.0591 (16)	0.0688 (17)	−0.0052 (13)	0.0177 (12)	−0.0018 (13)
C7	0.056 (2)	0.125 (4)	0.127 (4)	−0.019 (2)	0.017 (2)	−0.008 (3)
C8	0.0383 (12)	0.0631 (16)	0.0501 (14)	0.0022 (11)	0.0079 (10)	−0.0082 (11)
C9	0.0395 (12)	0.0555 (14)	0.0519 (13)	−0.0003 (11)	0.0064 (10)	−0.0086 (11)
C10	0.0362 (12)	0.0459 (13)	0.0611 (15)	0.0012 (10)	0.0109 (10)	0.0011 (10)
C11	0.0494 (14)	0.0502 (13)	0.0527 (14)	0.0084 (11)	0.0159 (11)	0.0001 (10)
C12	0.0534 (15)	0.0648 (17)	0.0465 (14)	0.0062 (12)	0.0054 (11)	−0.0084 (11)
C13	0.0387 (12)	0.0693 (17)	0.0522 (14)	−0.0002 (12)	0.0033 (10)	−0.0096 (12)
C14	0.0372 (12)	0.0507 (13)	0.0506 (13)	−0.0013 (10)	0.0127 (9)	−0.0018 (10)
C15	0.0413 (13)	0.0558 (14)	0.0570 (15)	−0.0051 (11)	0.0139 (10)	0.0025 (11)
C16	0.0391 (13)	0.0697 (17)	0.0629 (16)	−0.0007 (12)	0.0103 (11)	0.0087 (13)
C17	0.0513 (15)	0.0611 (16)	0.0549 (15)	0.0042 (12)	0.0069 (11)	0.0065 (12)
C18	0.0574 (16)	0.0545 (15)	0.0554 (15)	−0.0074 (12)	0.0098 (11)	0.0064 (11)
C19	0.0434 (13)	0.0562 (15)	0.0580 (15)	−0.0073 (11)	0.0134 (11)	0.0021 (11)
C20	0.067 (2)	0.083 (2)	0.086 (3)	0.0121 (18)	0.0053 (18)	0.022 (2)

Geometric parameters (Å, º) top

Cl1—C2	1.715 (3)	C3—H3	0.9300
Cl2—C15	1.721 (3)	C4—C5	1.373 (5)
F1—C7	1.323 (6)	C4—C7	1.501 (5)
F2—C7	1.277 (6)	C5—C6	1.379 (4)
F3—C7	1.322 (6)	C5—H5	0.9300
F1'—C7	1.297 (6)	C6—H6	0.9300
F2'—C7	1.324 (6)	C8—C9	1.385 (3)
F3'—C7	1.291 (6)	C8—C13	1.386 (4)
F4—C20	1.262 (6)	C9—C10	1.377 (4)
F5—C20	1.341 (6)	C9—H9	0.9300
F6—C20	1.331 (6)	C10—C11	1.396 (4)
F4'—C20	1.357 (6)	C11—C12	1.380 (4)
F5'—C20	1.298 (6)	C12—C13	1.372 (4)
F6'—C20	1.282 (7)	C12—H12	0.9300
O1—C8	1.365 (3)	C13—H13	0.9300
O1—C1	1.394 (3)	C14—C19	1.381 (4)
O2—N1	1.220 (3)	C14—C15	1.389 (3)
O3—N1	1.223 (3)	C15—C16	1.379 (4)
O4—C14	1.376 (3)	C16—C17	1.377 (4)
O4—C10	1.380 (3)	C16—H16	0.9300
N1—C11	1.457 (3)	C17—C18	1.379 (4)
C1—C6	1.367 (4)	C17—C20	1.506 (4)
C1—C2	1.380 (4)	C18—C19	1.370 (4)
C2—C3	1.375 (4)	C18—H18	0.9300
C3—C4	1.378 (5)	C19—H19	0.9300

C8—O1—C1	118.69 (19)	C9—C10—C11	119.1 (2)
C14—O4—C10	117.54 (19)	O4—C10—C11	123.6 (2)
O2—N1—O3	122.8 (3)	C12—C11—C10	119.7 (2)
O2—N1—C11	118.3 (3)	C12—C11—N1	117.1 (2)
O3—N1—C11	118.9 (3)	C10—C11—N1	123.2 (2)
C6—C1—C2	120.6 (2)	C13—C12—C11	121.6 (2)
C6—C1—O1	118.9 (3)	C13—C12—H12	119.2
C2—C1—O1	120.4 (3)	C11—C12—H12	119.2
C3—C2—C1	120.3 (3)	C12—C13—C8	118.5 (2)
C3—C2—Cl1	120.3 (2)	C12—C13—H13	120.8
C1—C2—Cl1	119.3 (2)	C8—C13—H13	120.8
C2—C3—C4	118.9 (3)	O4—C14—C19	123.5 (2)
C2—C3—H3	120.5	O4—C14—C15	116.9 (2)
C4—C3—H3	120.5	C19—C14—C15	119.6 (2)
C5—C4—C3	120.7 (3)	C16—C15—C14	120.2 (2)
C5—C4—C7	119.4 (3)	C16—C15—Cl2	119.9 (2)
C3—C4—C7	119.9 (3)	C14—C15—Cl2	119.9 (2)
C4—C5—C6	120.2 (3)	C17—C16—C15	119.7 (2)
C4—C5—H5	119.9	C17—C16—H16	120.2
C6—C5—H5	119.9	C15—C16—H16	120.2
C1—C6—C5	119.3 (3)	C16—C17—C18	120.1 (3)
C1—C6—H6	120.3	C16—C17—C20	120.8 (3)
C5—C6—H6	120.3	C18—C17—C20	119.0 (3)
F3'—C7—F1'	108.7 (5)	C19—C18—C17	120.4 (3)
F2—C7—F3	107.2 (5)	C19—C18—H18	119.8
F2—C7—F1	107.5 (5)	C17—C18—H18	119.8
F3—C7—F1	104.4 (5)	C18—C19—C14	120.0 (2)
F3'—C7—F2'	106.7 (5)	C18—C19—H19	120.0
F1'—C7—F2'	103.7 (5)	C14—C19—H19	120.0
F2—C7—C4	113.3 (4)	F6'—C20—F5'	112.6 (5)
F3'—C7—C4	112.5 (4)	F4—C20—F6	108.9 (5)
F1'—C7—C4	112.7 (4)	F4—C20—F5	109.6 (5)
F3—C7—C4	111.6 (4)	F6—C20—F5	101.2 (4)
F1—C7—C4	112.2 (4)	F6'—C20—F4'	104.5 (5)
F2'—C7—C4	112.0 (4)	F5'—C20—F4'	102.5 (5)
O1—C8—C9	115.4 (2)	F4—C20—C17	113.3 (3)
O1—C8—C13	123.8 (2)	F6'—C20—C17	112.5 (3)
C9—C8—C13	120.8 (2)	F5'—C20—C17	112.6 (3)
C10—C9—C8	120.3 (2)	F6—C20—C17	111.5 (3)
C10—C9—H9	119.9	F5—C20—C17	111.6 (3)
C8—C9—H9	119.9	F4'—C20—C17	111.3 (3)
C9—C10—O4	117.1 (2)

C8—O1—C1—C6	99.5 (3)	O4—C10—C11—N1	−0.9 (4)
C8—O1—C1—C2	−85.0 (3)	O2—N1—C11—C12	−6.6 (4)
C6—C1—C2—C3	0.3 (4)	O3—N1—C11—C12	172.7 (3)
O1—C1—C2—C3	−175.1 (2)	O2—N1—C11—C10	172.7 (3)
C6—C1—C2—Cl1	−177.9 (2)	O3—N1—C11—C10	−8.0 (4)
O1—C1—C2—Cl1	6.7 (3)	C10—C11—C12—C13	−1.3 (4)
C1—C2—C3—C4	0.3 (4)	N1—C11—C12—C13	178.1 (3)
Cl1—C2—C3—C4	178.6 (2)	C11—C12—C13—C8	−0.7 (4)
C2—C3—C4—C5	−1.1 (5)	O1—C8—C13—C12	−178.0 (3)
C2—C3—C4—C7	177.8 (3)	C9—C8—C13—C12	1.8 (4)
C3—C4—C5—C6	1.1 (5)	C10—O4—C14—C19	17.2 (3)
C7—C4—C5—C6	−177.7 (3)	C10—O4—C14—C15	−165.1 (2)
C2—C1—C6—C5	−0.2 (4)	O4—C14—C15—C16	−179.3 (2)
O1—C1—C6—C5	175.2 (2)	C19—C14—C15—C16	−1.6 (4)
C4—C5—C6—C1	−0.5 (4)	O4—C14—C15—Cl2	0.0 (3)
C5—C4—C7—F2	−155.7 (8)	C19—C14—C15—Cl2	177.7 (2)
C3—C4—C7—F2	25.4 (9)	C14—C15—C16—C17	0.3 (4)
C5—C4—C7—F3'	34.6 (9)	Cl2—C15—C16—C17	−179.0 (2)
C3—C4—C7—F3'	−144.2 (8)	C15—C16—C17—C18	1.5 (4)
C5—C4—C7—F1'	−88.6 (9)	C15—C16—C17—C20	−179.7 (3)
C3—C4—C7—F1'	92.5 (9)	C16—C17—C18—C19	−2.0 (4)
C5—C4—C7—F3	83.2 (8)	C20—C17—C18—C19	179.1 (3)
C3—C4—C7—F3	−95.7 (8)	C17—C18—C19—C14	0.7 (4)
C5—C4—C7—F1	−33.7 (8)	O4—C14—C19—C18	178.6 (2)
C3—C4—C7—F1	147.5 (7)	C15—C14—C19—C18	1.1 (4)
C5—C4—C7—F2'	154.8 (7)	C16—C17—C20—F4	104.6 (9)
C3—C4—C7—F2'	−24.1 (8)	C18—C17—C20—F4	−76.6 (10)
C1—O1—C8—C9	−179.6 (3)	C16—C17—C20—F6'	−107.7 (8)
C1—O1—C8—C13	0.2 (4)	C18—C17—C20—F6'	71.2 (9)
O1—C8—C9—C10	178.8 (2)	C16—C17—C20—F5'	21.0 (9)
C13—C8—C9—C10	−1.0 (4)	C18—C17—C20—F5'	−160.2 (9)
C8—C9—C10—O4	−177.6 (2)	C16—C17—C20—F6	−132.1 (6)
C8—C9—C10—C11	−1.0 (4)	C18—C17—C20—F6	46.7 (7)
C14—O4—C10—C9	−102.3 (3)	C16—C17—C20—F5	−19.7 (8)
C14—O4—C10—C11	81.3 (3)	C18—C17—C20—F5	159.1 (7)
C9—C10—C11—C12	2.1 (4)	C16—C17—C20—F4'	135.5 (6)
O4—C10—C11—C12	178.4 (2)	C18—C17—C20—F4'	−45.7 (7)
C9—C10—C11—N1	−177.2 (2)

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2,4-Bis[2-chloro-4-(trifluoro­meth­yl)phen­oxy]-1-nitro­benzene

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2,4-Bis[2-chloro-4-(trifluoromethyl)phenoxy]-1-nitrobenzene