[3-Meth­oxy-5-(meth­oxy­carbon­yl)isoxazol-4-yl](4-meth­oxy­phen­yl)iodo­nium 2,2,2-tri­fluoro­acetate

A new isoxazole-based iodo­noium salt, C₁₃H₁₃INO₅⁺·C₂F₃O₂⁻, has been synthesized and structurally characterized. In the crystal, ions are linked by short I...O contacts to form a neutral tetra-ion aggregate. These combine with C—H...F and C—H...O inter­actions to form double-layered two-dimensional sheets in the (001) plane.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.060
• wR factor = 0.145
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O12      --C15      .        7.1 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C12      --C13      .        9.7 s.u.
PLAT780_ALERT_1_B Coordinates do not Form a Properly Connected Set     Please Do !

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30 Report
PLAT213_ALERT_2_C Atom C15             has ADP max/min Ratio .....        3.7 prolat
PLAT234_ALERT_4_C Large Hirshfeld Difference O3       --C3       .       0.18 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C11      --C12      .       0.18 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C13      --C14      .       0.18 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT334_ALERT_2_C Small <C-C> Benzene Dist.   C9       -C14      .       1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0156 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.025 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         35 Report

Alert level G
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C16 Check
PLAT335_ALERT_2_G Check Large C6 Ring C-C Range C9       -C14            0.25 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H11      ..F16      .       2.56 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15C     ..O6       .       2.62 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.4 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   3 ALERT level B = A potentially serious problem, consider carefully
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku, 2014); cell refinement: CrystalClear (Rigaku, 2014); data reduction: CrystalClear (Rigaku, 2014); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: CrystalStructure (Rigaku, 2018), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

[3-Methoxy-5-(methoxycarbonyl)isoxazol-4-yl](4-methoxyphenyl)iodonium 2,2,2-trifluoroacetate

Crystal data

C13H13INO5^+·C2F3O2^−	Z = 2
Mr = 503.17	F(000) = 492.00
Triclinic, P1	Dx = 1.842 Mg m^−3
a = 8.436 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.750 (3) Å	Cell parameters from 1722 reflections
c = 11.338 (3) Å	θ = 2.0–25.3°
α = 113.913 (5)°	µ = 1.83 mm^−1
β = 97.392 (4)°	T = 173 K
γ = 98.975 (5)°	Plate, colourless
V = 907.2 (4) Å^3	0.16 × 0.03 × 0.01 mm

Data collection

Rigaku XtaLAB P200 diffractometer	3270 independent reflections
Radiation source: Rotating Anode, Rigaku FR-X	2423 reflections with F^2 > 2.0σ(F^2)
Rigaku Osmic Confocal Optical System monochromator	Rint = 0.053
Detector resolution: 5.814 pixels mm^-1	θmax = 25.4°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2014)	k = −12→12
Tmin = 0.862, Tmax = 0.982	l = −13→13
11079 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 4.1326P] where P = (Fo^2 + 2Fc^2)/3
3270 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 1.49 e Å^−3
0 restraints	Δρmin = −0.65 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Carbon-bound H atoms were included in calculated positions (C—H = 0.95–0.98 Å) and refined as riding atoms with U_iso(H) = 1.2U_eq (sp²) or U_iso(H) = 1.5U_eq (sp³).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I4	0.20970 (6)	0.42981 (5)	0.12013 (5)	0.0509 (2)
F16	0.2459 (9)	0.9270 (9)	0.2807 (8)	0.152 (4)
F17	0.0378 (8)	0.9854 (6)	0.3427 (6)	0.111 (3)
F18	0.1490 (12)	0.8548 (8)	0.4008 (6)	0.136 (3)
O1	0.4332 (8)	0.6834 (6)	0.5238 (5)	0.0632 (16)
O3	0.5054 (8)	0.7371 (7)	0.2570 (7)	0.0717 (18)
O6	0.1162 (9)	0.3812 (7)	0.3838 (7)	0.0777 (19)
O7	0.2682 (9)	0.4996 (8)	0.5853 (7)	0.081 (2)
O12	0.7116 (10)	0.0695 (8)	0.1381 (8)	0.094 (2)
O17	−0.0913 (8)	0.7775 (6)	0.1053 (6)	0.076 (2)
O18	0.0342 (9)	0.6423 (7)	0.1656 (7)	0.086 (2)
N2	0.5171 (10)	0.7647 (9)	0.4715 (8)	0.074 (2)
C3	0.4577 (11)	0.6993 (9)	0.3442 (9)	0.061 (3)
C4	0.3342 (10)	0.5742 (9)	0.3109 (8)	0.057 (2)
C5	0.3256 (11)	0.5714 (10)	0.4265 (9)	0.064 (2)
C6	0.2232 (12)	0.4716 (11)	0.4574 (9)	0.064 (3)
C7	0.1665 (14)	0.4074 (13)	0.6255 (13)	0.095 (4)
H7A	0.165550	0.309983	0.568918	0.143*
H7B	0.054106	0.421058	0.616962	0.143*
H7C	0.211381	0.429339	0.717581	0.143*
C8	0.6252 (12)	0.8788 (11)	0.3162 (11)	0.084 (3)
H8A	0.723922	0.876368	0.370487	0.126*
H8B	0.573436	0.950570	0.371279	0.126*
H8C	0.655593	0.900916	0.245180	0.126*
C9	0.3799 (11)	0.3064 (9)	0.1113 (8)	0.055 (2)
C10	0.3599 (15)	0.2162 (11)	0.1705 (9)	0.080 (3)
H10	0.267985	0.210169	0.209962	0.096*
C11	0.4686 (15)	0.1368 (12)	0.1732 (10)	0.083 (3)
H11	0.447999	0.068052	0.205282	0.099*
C12	0.5986 (13)	0.1563 (11)	0.1318 (11)	0.070 (3)
C13	0.6360 (12)	0.2401 (12)	0.0699 (11)	0.090 (4)
H13	0.733464	0.245200	0.036741	0.108*
C14	0.5113 (13)	0.3240 (11)	0.0579 (10)	0.077 (3)
H14	0.524458	0.384409	0.015910	0.093*
C15	0.8561 (13)	0.1021 (16)	0.1053 (14)	0.137 (7)
H15A	0.925082	0.038937	0.112025	0.206*
H15B	0.835017	0.092238	0.014517	0.206*
H15C	0.912545	0.198818	0.165580	0.206*
C16	0.1083 (10)	0.8821 (9)	0.3002 (8)	0.056 (2)
C17	0.0083 (9)	0.7542 (9)	0.1774 (8)	0.049 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I4	0.0529 (4)	0.0449 (3)	0.0430 (3)	0.0166 (2)	−0.0062 (2)	0.0102 (2)
F16	0.085 (5)	0.135 (7)	0.130 (7)	−0.041 (5)	0.028 (5)	−0.023 (5)
F17	0.099 (5)	0.068 (4)	0.098 (5)	0.038 (4)	−0.031 (4)	−0.021 (3)
F18	0.212 (9)	0.098 (5)	0.057 (4)	0.025 (5)	−0.042 (5)	0.017 (4)
O1	0.067 (4)	0.062 (4)	0.040 (3)	0.014 (3)	−0.004 (3)	0.007 (3)
O3	0.069 (4)	0.068 (4)	0.077 (5)	0.009 (3)	0.009 (4)	0.035 (4)
O6	0.075 (5)	0.071 (5)	0.073 (4)	−0.005 (4)	0.003 (4)	0.029 (4)
O7	0.080 (5)	0.101 (5)	0.063 (4)	0.023 (4)	0.009 (4)	0.037 (4)
O12	0.105 (6)	0.095 (6)	0.093 (5)	0.038 (5)	0.019 (5)	0.047 (5)
O17	0.089 (5)	0.054 (4)	0.060 (4)	0.020 (3)	−0.024 (3)	0.011 (3)
O18	0.096 (5)	0.057 (4)	0.083 (5)	0.032 (4)	−0.019 (4)	0.013 (4)
N2	0.070 (5)	0.067 (5)	0.068 (5)	0.006 (4)	−0.002 (4)	0.019 (5)
C3	0.052 (5)	0.046 (5)	0.054 (5)	0.012 (4)	−0.015 (4)	−0.002 (4)
C4	0.057 (5)	0.060 (6)	0.045 (5)	0.027 (5)	0.000 (4)	0.011 (4)
C5	0.056 (5)	0.065 (6)	0.055 (5)	0.019 (5)	0.002 (4)	0.013 (5)
C6	0.058 (6)	0.069 (7)	0.057 (6)	0.027 (5)	−0.002 (5)	0.021 (5)
C7	0.078 (8)	0.118 (10)	0.118 (10)	0.029 (7)	0.036 (7)	0.073 (9)
C8	0.065 (6)	0.067 (7)	0.091 (8)	−0.002 (5)	−0.010 (5)	0.020 (6)
C9	0.059 (5)	0.051 (5)	0.043 (4)	0.023 (4)	−0.006 (4)	0.010 (4)
C10	0.115 (9)	0.073 (7)	0.051 (5)	0.054 (6)	0.009 (5)	0.016 (5)
C11	0.099 (9)	0.090 (8)	0.062 (6)	0.044 (7)	0.016 (6)	0.028 (6)
C12	0.057 (6)	0.083 (7)	0.079 (7)	0.012 (5)	0.002 (5)	0.051 (6)
C13	0.055 (6)	0.083 (8)	0.078 (7)	0.000 (6)	0.025 (5)	−0.015 (6)
C14	0.074 (7)	0.060 (6)	0.079 (7)	0.014 (5)	0.025 (6)	0.010 (5)
C15	0.042 (6)	0.154 (13)	0.122 (11)	−0.036 (7)	0.039 (7)	−0.018 (9)
C16	0.043 (5)	0.057 (6)	0.051 (5)	0.008 (4)	−0.003 (4)	0.013 (4)
C17	0.043 (4)	0.048 (5)	0.047 (5)	0.018 (4)	0.005 (4)	0.012 (4)

Geometric parameters (Å, º)

I4—C9	2.087 (8)	C7—H7A	0.9800
I4—C4	2.092 (8)	C7—H7B	0.9800
F16—C16	1.268 (11)	C7—H7C	0.9800
F17—C16	1.290 (10)	C8—H8A	0.9800
F18—C16	1.307 (11)	C8—H8B	0.9800
O1—C5	1.347 (10)	C8—H8C	0.9800
O1—N2	1.397 (10)	C9—C14	1.353 (13)
O3—C3	1.297 (12)	C9—C10	1.388 (14)
O3—C8	1.520 (11)	C10—C11	1.353 (14)
O6—C6	1.154 (11)	C10—H10	0.9500
O7—C6	1.344 (11)	C11—C12	1.268 (15)
O7—C7	1.459 (13)	C11—H11	0.9500
O12—C15	1.355 (12)	C12—C13	1.374 (15)
O12—C12	1.449 (12)	C13—C14	1.515 (16)
O17—C17	1.221 (9)	C13—H13	0.9500
O18—C17	1.214 (10)	C14—H14	0.9500
N2—C3	1.308 (12)	C15—H15A	0.9800
C3—C4	1.445 (13)	C15—H15B	0.9800
C4—C5	1.334 (13)	C15—H15C	0.9800
C5—C6	1.453 (14)	C16—C17	1.524 (11)
C9—I4—C4	90.8 (3)	C10—C9—I4	117.9 (7)
C5—O1—N2	110.3 (7)	C11—C10—C9	121.3 (11)
C3—O3—C8	113.8 (8)	C11—C10—H10	119.3
C6—O7—C7	114.1 (9)	C9—C10—H10	119.3
C15—O12—C12	114.6 (11)	C12—C11—C10	118.4 (12)
C3—N2—O1	104.8 (8)	C12—C11—H11	120.8
O3—C3—N2	125.4 (9)	C10—C11—H11	120.8
O3—C3—C4	123.4 (8)	C11—C12—C13	127.0 (11)
N2—C3—C4	111.1 (10)	C11—C12—O12	116.1 (10)
C5—C4—C3	104.5 (8)	C13—C12—O12	116.5 (10)
C5—C4—I4	129.6 (8)	C12—C13—C14	115.5 (9)
C3—C4—I4	125.8 (7)	C12—C13—H13	122.2
C4—C5—O1	109.2 (9)	C14—C13—H13	122.2
C4—C5—C6	130.6 (9)	C9—C14—C13	115.1 (10)
O1—C5—C6	120.2 (9)	C9—C14—H14	122.5
O6—C6—O7	123.9 (10)	C13—C14—H14	122.5
O6—C6—C5	125.4 (9)	O12—C15—H15A	109.5
O7—C6—C5	110.8 (9)	O12—C15—H15B	109.5
O7—C7—H7A	109.5	H15A—C15—H15B	109.5
O7—C7—H7B	109.5	O12—C15—H15C	109.5
H7A—C7—H7B	109.5	H15A—C15—H15C	109.5
O7—C7—H7C	109.5	H15B—C15—H15C	109.5
H7A—C7—H7C	109.5	F16—C16—F17	107.8 (9)
H7B—C7—H7C	109.5	F16—C16—F18	103.2 (9)
O3—C8—H8A	109.5	F17—C16—F18	105.7 (8)
O3—C8—H8B	109.5	F16—C16—C17	110.8 (8)
H8A—C8—H8B	109.5	F17—C16—C17	115.2 (7)
O3—C8—H8C	109.5	F18—C16—C17	113.2 (8)
H8A—C8—H8C	109.5	O18—C17—O17	128.3 (8)
H8B—C8—H8C	109.5	O18—C17—C16	116.1 (7)
C14—C9—C10	122.3 (9)	O17—C17—C16	115.6 (7)
C14—C9—I4	119.7 (7)
C5—O1—N2—C3	0.0 (9)	O1—C5—C6—O7	−7.7 (11)
C8—O3—C3—N2	−7.7 (13)	C14—C9—C10—C11	−2.6 (15)
C8—O3—C3—C4	174.8 (8)	I4—C9—C10—C11	−177.5 (8)
O1—N2—C3—O3	−177.8 (8)	C9—C10—C11—C12	6.9 (16)
O1—N2—C3—C4	−0.1 (10)	C10—C11—C12—C13	−7.7 (18)
O3—C3—C4—C5	177.9 (8)	C10—C11—C12—O12	179.4 (9)
N2—C3—C4—C5	0.1 (10)	C15—O12—C12—C11	−173.9 (10)
O3—C3—C4—I4	0.4 (12)	C15—O12—C12—C13	12.4 (14)
N2—C3—C4—I4	−177.4 (6)	C11—C12—C13—C14	3.9 (17)
C3—C4—C5—O1	−0.1 (10)	O12—C12—C13—C14	176.8 (8)
I4—C4—C5—O1	177.3 (5)	C10—C9—C14—C13	−1.1 (13)
C3—C4—C5—C6	179.6 (9)	I4—C9—C14—C13	173.7 (6)
I4—C4—C5—C6	−3.0 (15)	C12—C13—C14—C9	0.7 (13)
N2—O1—C5—C4	0.1 (10)	F16—C16—C17—O18	86.1 (11)
N2—O1—C5—C6	−179.7 (8)	F17—C16—C17—O18	−151.2 (9)
C7—O7—C6—O6	−1.6 (14)	F18—C16—C17—O18	−29.4 (12)
C7—O7—C6—C5	177.5 (8)	F16—C16—C17—O17	−96.1 (11)
C4—C5—C6—O6	−8.3 (16)	F17—C16—C17—O17	26.7 (12)
O1—C5—C6—O6	171.4 (9)	F18—C16—C17—O17	148.5 (9)
C4—C5—C6—O7	172.5 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O12^i	0.98	2.58	3.475 (14)	152
C11—H11···F16^ii	0.95	2.56	3.405 (17)	148
C15—H15C···O6^iii	0.98	2.62	3.503 (14)	151

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) x+1, y, z.