A new polymorph of 1,3-bis­(penta­fluoro­phen­yl)urea

Okuno, T.

doi:10.1107/S1600536813007836

organic compounds

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Volume 69| Part 4| April 2013| Page o608

doi:10.1107/S1600536813007836

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A new polymorph of 1,3-bis(pentafluorophenyl)urea

Tsunehisa Okuno ^a ^*

^aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
^*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

(Received 12 March 2013; accepted 21 March 2013; online 28 March 2013)

The title compound, C₁₃H₂F₁₀N₂O, has been previously described in the space group Pbca with Z = 8 [Jai-nhuknan et al. (1997 ). Acta Cryst. C53, 455–457]. The current P2₁2₁2₁ polymorph was obtained from a tetrahydrofuran solution. The pentafluorophenyl rings make dihedral angles of 50.35 (6) and 54.94 (6)° with the urea fragment, in close accord with those reported for the first polymorph. In the crystal, both of the N—H groups donate H atoms to the same carbonyl O atom, forming a one-dimensional molecular array along the a axis. There are close contacts between perfluorophenyl C atoms within the array [3.228 (3) Å] and halogen bonds are also observed between the arrays [F⋯F = 2.709 (2) and 2.7323 (18) Å].

Related literature

For the structure of the first reported ploymorph, see: Jai-nhuknan et al. (1997). For the related structure of 1,3-diphenylurea, see: Dannecker et al. (1979 ). For background to organofluorine chemistry, see: Chambers (2004 ).

Experimental

Crystal data

C₁₃H₂F₁₀N₂O
M_r = 392.16
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.5798 (7) Å
b = 9.5411 (16) Å
c = 29.136 (5) Å
V = 1273.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 93 K
0.15 × 0.15 × 0.03 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ) T_min = 0.978, T_max = 0.993
10307 measured reflections
1993 independent reflections
1941 reflections with F² > 2σ(F²)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.09
1991 reflections
241 parameters
2 restraints
Only H-atom coordinates refined
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.864 (18)	2.057 (18)	2.850 (3)	152 (3)
N2—H2⋯O1ⁱ	0.879 (18)	2.008 (18)	2.825 (3)	154 (3)
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2008 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare, et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007836/ff2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007836/ff2101Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007836/ff2101Isup3.cml

checkCIF report

Comment top

Perfluoro aromatic compounds have attracted interest from the viewpoint of the electronic and structural comparison with the original compounds (Chambers, 2004). The title compound, (I), is a perfluoro compound of 1,3-diphenylurea (Dannecker et al., 1979). Previously, (I) was isolated in an orthorhombic Pbca polymorph with Z = 8 [Jai-nhuknan et al., 1997]. A new orthorhombic P2₁2₁2₁ polymorph was obtained by recrystallization from a tetrahydrofuran solution.

The dihedral angle between the C1—C6/F1—F5 (r.m.s. deviation = 0.0223 Å) and the C7—C12/F6—F10 (r.m.s. deviation = 0.0181 Å) pentafluorophenyl rings is 30.93 (3)°, which is smaller than that of the reported polymorph. The pentafluorophenyl rings make dihedral angles of 50.35 (6)° and 54.94 (6)°, respectively, with the C13/N1/N2/O1 urea fragment (r.m.s. deviation = 0.0011 Å), and this situation is almost accordance with the reported polymorph.

Both of the N—H groups in one molecule donate protons to the same carbonyl O atom, forming a one-dimensional molecular array along the a axis, where the N···O distances were 2.850 (3) Å for N1···O1ⁱ and 2.825 (3) Å for N2···O1ⁱ [Symmetry code: (i) x + 1, y, z] (Figure 2). There are close contacts between perfluorophenyl carbons within the array, where the C2···C5ⁱ distance is 3.228 (3) Å. Halogen-bonds are also recognized between the arrays. The distances of F2···F10ⁱⁱ and F1···F5ⁱⁱⁱ are 2.709 (2) Å and 2.7323 (18) Å, respectively [Symmetry codes: (ii) -x + 1, y + 1/2, -z + 1/2 (iii)-x + 2, y + 1/2, -z + 1/2.] (Figure 2).

Related literature top

For the structure of the first reported ploymorph, see: Jai-nhuknan et al. (1997). For the related structure of 1,3-diphenylurea, see: Dannecker et al. (1979). For background to organofluorine chemistry, see: Chambers (2004).

Experimental top

The title compound was commercially purchased and recrystallized from a tetrahydrofuran solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare, et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
	Fig. 2. A view of the intermolecular interactions in the title compound. [Symmetry codes: (i) x + 1, y, z (ii) -x + 1, y + 1/2, -z + 1/2 (iii)-x + 2, y + 1/2, -z + 1/2.]

1,3-Bis(pentafluorophenyl)urea top

Crystal data top

C₁₃H₂F₁₀N₂O	F(000) = 768.00
M_r = 392.16	D_x = 2.046 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4650 reflections
a = 4.5798 (7) Å	θ = 2.3–31.2°
b = 9.5411 (16) Å	µ = 0.23 mm⁻¹
c = 29.136 (5) Å	T = 93 K
V = 1273.1 (4) Å³	Platelet, colorless
Z = 4	0.15 × 0.15 × 0.03 mm

Data collection top

Rigaku Saturn724+ diffractometer	1941 reflections with F² > 2σ(F²)
Detector resolution: 28.445 pixels mm^-1	R_int = 0.023
ω scans	θ_max = 29.0°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −6→5
T_min = 0.978, T_max = 0.993	k = −12→13
10307 measured reflections	l = −39→37
1993 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	Only H-atom coordinates refined
S = 1.09	w = 1/[σ²(F_o²) + (0.0393P)² + 0.6807P] where P = (F_o² + 2F_c²)/3
1991 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.34 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₃H₂F₁₀N₂O	V = 1273.1 (4) Å³
M_r = 392.16	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.5798 (7) Å	µ = 0.23 mm⁻¹
b = 9.5411 (16) Å	T = 93 K
c = 29.136 (5) Å	0.15 × 0.15 × 0.03 mm

Data collection top

Rigaku Saturn724+ diffractometer	1993 independent reflections
Absorption correction: numerical (NUMABS; Rigaku, 1999)	1941 reflections with F² > 2σ(F²)
T_min = 0.978, T_max = 0.993	R_int = 0.023
10307 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.080	Only H-atom coordinates refined
S = 1.09	Δρ_max = 0.34 e Å⁻³
1991 reflections	Δρ_min = −0.20 e Å⁻³
241 parameters

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections except for two with very negative F². The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
F1	1.1418 (3)	0.61873 (13)	0.20307 (4)	0.0201 (3)
F2	0.9729 (3)	0.60115 (14)	0.11485 (4)	0.0230 (3)
F3	0.5296 (4)	0.42251 (14)	0.09057 (4)	0.0261 (3)
F4	0.2849 (3)	0.25518 (13)	0.15527 (4)	0.0235 (3)
F5	0.4741 (3)	0.26032 (12)	0.24218 (4)	0.0199 (3)
F6	1.1205 (3)	0.65289 (13)	0.41004 (4)	0.0209 (3)
F7	0.9048 (4)	0.66890 (14)	0.49612 (4)	0.0269 (3)
F8	0.4722 (4)	0.49024 (15)	0.52340 (4)	0.0286 (3)
F9	0.2803 (3)	0.28817 (15)	0.46530 (4)	0.0261 (3)
F10	0.5071 (3)	0.26629 (12)	0.38011 (4)	0.0213 (3)
O1	0.4972 (3)	0.46701 (15)	0.30935 (5)	0.0163 (3)
N1	0.9286 (4)	0.4477 (2)	0.27009 (5)	0.0154 (3)
N2	0.9324 (4)	0.45284 (19)	0.34806 (5)	0.0149 (3)
C1	0.8112 (5)	0.4427 (2)	0.22555 (6)	0.0143 (4)
C2	0.9298 (5)	0.5288 (2)	0.19172 (6)	0.0156 (4)
C3	0.8433 (5)	0.5207 (2)	0.14616 (6)	0.0172 (4)
C4	0.6225 (5)	0.4295 (3)	0.13398 (6)	0.0180 (4)
C5	0.4991 (5)	0.3442 (2)	0.16699 (6)	0.0170 (4)
C6	0.5947 (5)	0.3492 (2)	0.21201 (6)	0.0150 (4)
C7	0.8117 (4)	0.4624 (2)	0.39231 (6)	0.0141 (4)
C8	0.9103 (5)	0.5630 (2)	0.42307 (6)	0.0155 (4)
C9	0.8013 (5)	0.5723 (2)	0.46721 (6)	0.0181 (4)
C10	0.5852 (5)	0.4809 (3)	0.48127 (6)	0.0196 (4)
C11	0.4853 (5)	0.3785 (2)	0.45158 (6)	0.0184 (4)
C12	0.6005 (5)	0.3694 (2)	0.40767 (6)	0.0158 (4)
C13	0.7652 (5)	0.4563 (2)	0.30915 (6)	0.0139 (4)
H1	1.117 (4)	0.451 (3)	0.2722 (9)	0.0184*
H2	1.123 (4)	0.459 (3)	0.3452 (9)	0.0179*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0170 (6)	0.0229 (6)	0.0204 (6)	−0.0048 (5)	−0.0003 (5)	−0.0012 (5)
F2	0.0234 (6)	0.0297 (6)	0.0158 (5)	0.0024 (6)	0.0033 (5)	0.0049 (5)
F3	0.0296 (7)	0.0353 (7)	0.0135 (5)	0.0054 (7)	−0.0075 (6)	−0.0045 (5)
F4	0.0220 (6)	0.0210 (6)	0.0276 (6)	−0.0030 (6)	−0.0094 (6)	−0.0061 (5)
F5	0.0200 (6)	0.0195 (6)	0.0202 (6)	−0.0027 (6)	−0.0016 (5)	0.0030 (5)
F6	0.0185 (6)	0.0226 (6)	0.0215 (6)	−0.0072 (6)	−0.0018 (5)	0.0029 (5)
F7	0.0326 (8)	0.0299 (7)	0.0181 (5)	−0.0002 (7)	−0.0049 (6)	−0.0073 (5)
F8	0.0303 (7)	0.0426 (8)	0.0129 (5)	0.0047 (7)	0.0060 (6)	0.0026 (5)
F9	0.0201 (6)	0.0324 (7)	0.0259 (6)	−0.0066 (6)	0.0043 (6)	0.0104 (6)
F10	0.0221 (6)	0.0197 (6)	0.0221 (6)	−0.0056 (6)	−0.0011 (5)	−0.0017 (5)
O1	0.0100 (6)	0.0234 (7)	0.0154 (6)	−0.0001 (6)	−0.0011 (6)	0.0006 (6)
N1	0.0097 (7)	0.0242 (8)	0.0122 (7)	0.0003 (7)	−0.0006 (6)	−0.0007 (6)
N2	0.0094 (7)	0.0237 (8)	0.0117 (7)	0.0000 (7)	−0.0004 (6)	0.0004 (6)
C1	0.0126 (8)	0.0174 (8)	0.0129 (8)	0.0016 (8)	−0.0009 (7)	−0.0011 (7)
C2	0.0134 (8)	0.0178 (8)	0.0155 (8)	0.0009 (7)	−0.0004 (7)	−0.0017 (7)
C3	0.0180 (9)	0.0202 (9)	0.0135 (8)	0.0046 (8)	0.0014 (7)	0.0013 (7)
C4	0.0193 (9)	0.0230 (9)	0.0116 (8)	0.0063 (9)	−0.0036 (8)	−0.0040 (7)
C5	0.0159 (9)	0.0165 (8)	0.0186 (8)	0.0001 (8)	−0.0051 (8)	−0.0043 (7)
C6	0.0136 (8)	0.0163 (8)	0.0152 (8)	0.0015 (8)	−0.0007 (7)	−0.0010 (7)
C7	0.0111 (8)	0.0184 (9)	0.0127 (8)	0.0013 (8)	−0.0003 (7)	0.0026 (7)
C8	0.0134 (8)	0.0180 (8)	0.0151 (8)	−0.0005 (8)	−0.0008 (7)	0.0026 (7)
C9	0.0197 (9)	0.0200 (9)	0.0147 (8)	0.0027 (8)	−0.0029 (8)	−0.0017 (7)
C10	0.0190 (9)	0.0277 (10)	0.0122 (8)	0.0060 (9)	0.0015 (7)	0.0032 (7)
C11	0.0141 (8)	0.0224 (9)	0.0188 (8)	0.0003 (8)	0.0015 (8)	0.0081 (7)
C12	0.0139 (8)	0.0172 (8)	0.0162 (8)	0.0003 (8)	−0.0012 (7)	0.0010 (7)
C13	0.0141 (8)	0.0150 (8)	0.0126 (8)	−0.0006 (7)	−0.0003 (7)	0.0000 (7)

Geometric parameters (Å, º) top

F1—C2	1.337 (3)	C1—C2	1.393 (3)
F2—C3	1.332 (3)	C1—C6	1.391 (3)
F3—C4	1.336 (3)	C2—C3	1.387 (3)
F4—C5	1.342 (3)	C3—C4	1.380 (3)
F5—C6	1.340 (3)	C4—C5	1.381 (3)
F6—C8	1.344 (3)	C5—C6	1.384 (3)
F7—C9	1.336 (3)	C7—C8	1.389 (3)
F8—C10	1.335 (3)	C7—C12	1.387 (3)
F9—C11	1.336 (3)	C8—C9	1.382 (3)
F10—C12	1.340 (3)	C9—C10	1.381 (3)
O1—C13	1.232 (3)	C10—C11	1.383 (3)
N1—C1	1.405 (3)	C11—C12	1.387 (3)
N1—C13	1.364 (3)	N1—H1	0.864 (18)
N2—C7	1.406 (3)	N2—H2	0.879 (18)
N2—C13	1.368 (3)

F1···F2	2.6895 (18)	F9···C11^xiv	3.197 (3)
F1···N1	2.725 (2)	F10···F1^vi	3.2313 (18)
F2···F3	2.744 (2)	F10···F2^viii	2.709 (2)
F3···F4	2.7126 (18)	F10···F2^vi	2.859 (2)
F4···F5	2.6767 (18)	F10···F3^viii	3.3936 (19)
F5···O1	2.7803 (19)	F10···N2^v	3.312 (3)
F5···N1	2.862 (3)	F10···C3^viii	2.942 (3)
F5···C13	3.014 (3)	F10···C4^viii	3.293 (3)
F6···F7	2.6999 (18)	O1···F4ⁱ	3.101 (2)
F6···N2	2.765 (2)	O1···F5ⁱ	3.1785 (19)
F7···F8	2.732 (2)	O1···N1^v	2.850 (3)
F8···F9	2.712 (2)	O1···N2^v	2.825 (3)
F9···F10	2.6989 (18)	O1···C13^v	3.354 (3)
F10···O1	2.8143 (19)	N1···F1^vi	3.251 (3)
F10···N2	2.799 (3)	N1···F5ⁱⁱⁱ	3.178 (3)
F10···C13	2.993 (3)	N1···F5ⁱ	3.525 (3)
O1···C1	2.843 (3)	N1···O1ⁱⁱⁱ	2.850 (3)
O1···C6	3.083 (3)	N2···F1^vi	3.535 (3)
O1···C7	2.814 (3)	N2···F2^vi	3.552 (3)
O1···C12	3.049 (3)	N2···F4ⁱ	3.053 (3)
C1···C4	2.807 (3)	N2···F10ⁱⁱⁱ	3.312 (3)
C2···C5	2.741 (3)	N2···O1ⁱⁱⁱ	2.825 (3)
C2···C13	3.571 (3)	C1···F1^v	3.557 (3)
C3···C6	2.767 (3)	C1···F4ⁱⁱⁱ	3.478 (3)
C6···C13	3.109 (3)	C1···F5ⁱⁱⁱ	3.532 (3)
C7···C10	2.797 (3)	C1···F5ⁱ	3.432 (3)
C8···C11	2.753 (3)	C2···F4ⁱⁱⁱ	3.254 (3)
C8···C13	3.535 (3)	C2···F5ⁱ	3.466 (3)
C9···C12	2.757 (3)	C2···C5ⁱⁱⁱ	3.228 (3)
C12···C13	3.082 (3)	C2···C6ⁱⁱⁱ	3.544 (3)
F1···F5ⁱ	3.5106 (18)	C3···F4ⁱⁱⁱ	3.252 (3)
F1···F5ⁱⁱ	2.7323 (18)	C3···F10ⁱ	2.942 (3)
F1···F10ⁱⁱ	3.2313 (18)	C3···C5ⁱⁱⁱ	3.496 (3)
F1···N1ⁱⁱ	3.251 (3)	C4···F1^v	3.487 (3)
F1···N2ⁱⁱ	3.535 (3)	C4···F2^v	3.441 (3)
F1···C1ⁱⁱⁱ	3.557 (3)	C4···F4ⁱⁱⁱ	3.515 (3)
F1···C4ⁱⁱⁱ	3.487 (3)	C4···F6^vi	3.162 (3)
F1···C5ⁱⁱⁱ	3.263 (3)	C4···F10ⁱ	3.293 (3)
F1···C6ⁱⁱⁱ	3.315 (3)	C5···F1^v	3.263 (3)
F1···C6ⁱⁱ	3.523 (3)	C5···F6^vi	3.377 (3)
F1···C13ⁱⁱ	3.269 (3)	C5···C2^v	3.228 (3)
F2···F3ⁱⁱⁱ	3.147 (2)	C5···C3^v	3.496 (3)
F2···F8^iv	2.8148 (18)	C6···F1^v	3.315 (3)
F2···F9ⁱ	3.1594 (19)	C6···F1^vi	3.523 (3)
F2···F10ⁱ	2.709 (2)	C6···C2^v	3.544 (3)
F2···F10ⁱⁱ	2.859 (2)	C7···F2^vi	3.591 (3)
F2···N2ⁱⁱ	3.552 (3)	C7···F4ⁱ	3.150 (3)
F2···C4ⁱⁱⁱ	3.441 (3)	C7···F9ⁱⁱⁱ	3.448 (3)
F2···C7ⁱⁱ	3.591 (3)	C8···F4ⁱ	3.061 (3)
F2···C12ⁱⁱ	3.286 (3)	C8···F9ⁱⁱⁱ	3.356 (3)
F3···F2^v	3.147 (2)	C8···C11ⁱⁱⁱ	3.275 (3)
F3···F6^vi	3.0309 (19)	C9···F7^xi	3.246 (3)
F3···F7^iv	2.9024 (18)	C9···F8ⁱⁱⁱ	3.568 (3)
F3···F8^vii	3.131 (2)	C9···F9ⁱⁱⁱ	3.487 (3)
F3···F8^iv	3.119 (2)	C10···F6^v	3.395 (3)
F3···F10ⁱ	3.3936 (19)	C10···F7^xi	3.504 (3)
F4···F6^viii	2.8319 (18)	C10···F9^xiii	3.133 (3)
F4···F6^vi	3.4627 (19)	C11···F6^v	3.333 (3)
F4···O1^viii	3.101 (2)	C11···F9^xiii	3.197 (3)
F4···N2^viii	3.053 (3)	C11···C8^v	3.275 (3)
F4···C1^v	3.478 (3)	C12···F2^vi	3.286 (3)
F4···C2^v	3.254 (3)	C12···F6^v	3.486 (3)
F4···C3^v	3.252 (3)	C13···F1^vi	3.269 (3)
F4···C4^v	3.515 (3)	C13···F4ⁱ	3.043 (3)
F4···C7^viii	3.150 (3)	C13···F5ⁱ	3.442 (3)
F4···C8^viii	3.061 (3)	C13···O1ⁱⁱⁱ	3.354 (3)
F4···C13^viii	3.043 (3)	F1···H1	2.58 (3)
F5···F1^viii	3.5106 (18)	F5···H1	3.57 (2)
F5···F1^vi	2.7323 (18)	F6···H2	2.64 (3)
F5···O1^viii	3.1785 (19)	F10···H2	3.52 (3)
F5···N1^v	3.178 (3)	O1···H1	3.040 (19)
F5···N1^viii	3.525 (3)	O1···H2	3.052 (19)
F5···C1^v	3.532 (3)	N1···H2	2.37 (3)
F5···C1^viii	3.432 (3)	N2···H1	2.37 (3)
F5···C2^viii	3.466 (3)	C2···H1	2.61 (3)
F5···C13^viii	3.442 (3)	C6···H1	3.12 (3)
F6···F3ⁱⁱ	3.0309 (19)	C8···H2	2.66 (3)
F6···F4ⁱ	2.8319 (18)	C12···H2	3.13 (3)
F6···F4ⁱⁱ	3.4627 (19)	H1···H2	2.13 (4)
F6···F7^ix	3.4730 (18)	F1···H1ⁱⁱ	3.46 (3)
F6···C4ⁱⁱ	3.162 (3)	F4···H2^viii	3.39 (3)
F6···C5ⁱⁱ	3.377 (3)	F5···H1^v	2.60 (3)
F6···C10ⁱⁱⁱ	3.395 (3)	F5···H1^vi	3.52 (3)
F6···C11ⁱⁱⁱ	3.333 (3)	F10···H2^v	2.74 (3)
F6···C12ⁱⁱⁱ	3.486 (3)	O1···H1^v	2.06 (2)
F7···F3^x	2.9024 (18)	O1···H2^v	2.01 (2)
F7···F6^xi	3.4730 (18)	C1···H1^v	3.460 (19)
F7···F7^xi	2.773 (2)	C6···H1^v	2.97 (3)
F7···F7^ix	2.773 (2)	C7···H2^v	3.44 (2)
F7···F8ⁱⁱⁱ	3.208 (3)	C11···H2^v	3.60 (3)
F7···F8^ix	3.316 (2)	C12···H2^v	2.97 (3)
F7···C9^ix	3.246 (3)	C13···H1^v	3.160 (19)
F7···C10^ix	3.504 (3)	C13···H2^v	3.123 (19)
F8···F2^x	2.8148 (18)	H1···F1^vi	3.46 (3)
F8···F3^xii	3.131 (2)	H1···F5ⁱⁱⁱ	2.60 (3)
F8···F3^x	3.119 (2)	H1···F5ⁱⁱ	3.52 (3)
F8···F7^v	3.208 (3)	H1···O1ⁱⁱⁱ	2.06 (2)
F8···F7^xi	3.316 (2)	H1···C1ⁱⁱⁱ	3.460 (19)
F8···F9^xiii	3.026 (2)	H1···C6ⁱⁱⁱ	2.97 (3)
F8···C9^v	3.568 (3)	H1···C13ⁱⁱⁱ	3.160 (19)
F9···F2^viii	3.1594 (19)	H2···F4ⁱ	3.39 (3)
F9···F8^xiv	3.026 (2)	H2···F10ⁱⁱⁱ	2.74 (3)
F9···F9^xiv	3.1405 (19)	H2···O1ⁱⁱⁱ	2.01 (2)
F9···F9^xiii	3.1405 (19)	H2···C7ⁱⁱⁱ	3.44 (2)
F9···C7^v	3.448 (3)	H2···C11ⁱⁱⁱ	3.60 (3)
F9···C8^v	3.356 (3)	H2···C12ⁱⁱⁱ	2.97 (3)
F9···C9^v	3.487 (3)	H2···C13ⁱⁱⁱ	3.123 (19)
F9···C10^xiv	3.133 (3)

C1—N1—C13	124.23 (17)	F6—C8—C7	119.45 (16)
C7—N2—C13	122.57 (16)	F6—C8—C9	118.75 (17)
N1—C1—C2	118.94 (18)	C7—C8—C9	121.79 (19)
N1—C1—C6	123.82 (17)	F7—C9—C8	120.16 (19)
C2—C1—C6	117.09 (17)	F7—C9—C10	120.19 (17)
F1—C2—C1	119.10 (16)	C8—C9—C10	119.65 (18)
F1—C2—C3	118.66 (17)	F8—C10—C9	120.58 (18)
C1—C2—C3	122.19 (18)	F8—C10—C11	119.58 (19)
F2—C3—C2	119.74 (18)	C9—C10—C11	119.84 (17)
F2—C3—C4	120.90 (16)	F9—C11—C10	120.09 (17)
C2—C3—C4	119.36 (18)	F9—C11—C12	120.21 (17)
F3—C4—C3	120.55 (18)	C10—C11—C12	119.70 (19)
F3—C4—C5	119.96 (19)	F10—C12—C7	119.93 (16)
C3—C4—C5	119.49 (17)	F10—C12—C11	118.52 (18)
F4—C5—C4	119.68 (17)	C7—C12—C11	121.54 (18)
F4—C5—C6	119.63 (17)	O1—C13—N1	123.73 (17)
C4—C5—C6	120.70 (19)	O1—C13—N2	123.75 (17)
F5—C6—C1	120.90 (16)	N1—C13—N2	112.52 (17)
F5—C6—C5	118.00 (17)	C1—N1—H1	116.7 (17)
C1—C6—C5	121.09 (18)	C13—N1—H1	119.0 (17)
N2—C7—C8	120.58 (17)	C7—N2—H2	118.2 (17)
N2—C7—C12	121.92 (17)	C13—N2—H2	118.4 (17)
C8—C7—C12	117.45 (17)

C1—N1—C13—O1	−3.5 (3)	F4—C5—C6—F5	2.1 (3)
C1—N1—C13—N2	177.01 (17)	F4—C5—C6—C1	−178.37 (15)
C13—N1—C1—C2	133.29 (19)	C4—C5—C6—F5	−177.65 (17)
C13—N1—C1—C6	−51.4 (3)	C4—C5—C6—C1	1.8 (3)
C7—N2—C13—O1	−0.5 (3)	N2—C7—C8—F6	0.8 (3)
C7—N2—C13—N1	179.00 (16)	N2—C7—C8—C9	−178.16 (16)
C13—N2—C7—C8	−125.94 (19)	N2—C7—C12—F10	0.4 (3)
C13—N2—C7—C12	56.8 (3)	N2—C7—C12—C11	179.16 (16)
N1—C1—C2—F1	−3.3 (3)	C8—C7—C12—F10	−176.99 (16)
N1—C1—C2—C3	174.14 (16)	C8—C7—C12—C11	1.8 (3)
N1—C1—C6—F5	3.0 (3)	C12—C7—C8—F6	178.23 (16)
N1—C1—C6—C5	−176.48 (16)	C12—C7—C8—C9	−0.8 (3)
C2—C1—C6—F5	178.43 (16)	F6—C8—C9—F7	−0.1 (3)
C2—C1—C6—C5	−1.1 (3)	F6—C8—C9—C10	179.98 (15)
C6—C1—C2—F1	−178.95 (16)	C7—C8—C9—F7	178.88 (17)
C6—C1—C2—C3	−1.5 (3)	C7—C8—C9—C10	−1.0 (3)
F1—C2—C3—F2	0.4 (3)	F7—C9—C10—F8	1.7 (3)
F1—C2—C3—C4	−179.26 (15)	F7—C9—C10—C11	−178.09 (17)
C1—C2—C3—F2	−177.03 (17)	C8—C9—C10—F8	−178.41 (18)
C1—C2—C3—C4	3.3 (3)	C8—C9—C10—C11	1.8 (3)
F2—C3—C4—F3	−1.5 (3)	F8—C10—C11—F9	−1.1 (3)
F2—C3—C4—C5	177.88 (16)	F8—C10—C11—C12	179.42 (16)
C2—C3—C4—F3	178.15 (17)	C9—C10—C11—F9	178.72 (18)
C2—C3—C4—C5	−2.5 (3)	C9—C10—C11—C12	−0.8 (3)
F3—C4—C5—F4	−0.4 (3)	F9—C11—C12—F10	−1.8 (3)
F3—C4—C5—C6	179.35 (16)	F9—C11—C12—C7	179.43 (16)
C3—C4—C5—F4	−179.83 (18)	C10—C11—C12—F10	177.76 (17)
C3—C4—C5—C6	−0.0 (3)	C10—C11—C12—C7	−1.0 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+3/2, −y+1, z−1/2; (v) x−1, y, z; (vi) −x+2, y−1/2, −z+1/2; (vii) −x+1/2, −y+1, z−1/2; (viii) −x+1, y−1/2, −z+1/2; (ix) x+1/2, −y+3/2, −z+1; (x) −x+3/2, −y+1, z+1/2; (xi) x−1/2, −y+3/2, −z+1; (xii) −x+1/2, −y+1, z+1/2; (xiii) x+1/2, −y+1/2, −z+1; (xiv) x−1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱⁱ	0.864 (18)	2.057 (18)	2.850 (3)	152 (3)
N2—H2···O1ⁱⁱⁱ	0.879 (18)	2.008 (18)	2.825 (3)	154 (3)

Symmetry code: (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₂F₁₀N₂O
M_r	392.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	93
a, b, c (Å)	4.5798 (7), 9.5411 (16), 29.136 (5)
V (Å³)	1273.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.15 × 0.15 × 0.03

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	Numerical (NUMABS; Rigaku, 1999)
T_min, T_max	0.978, 0.993
No. of measured, independent and observed [F² > 2σ(F²)] reflections	10307, 1993, 1941
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.09
No. of reflections	1991
No. of parameters	241
No. of restraints	2
H-atom treatment	Only H-atom coordinates refined
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.20

Computer programs: CrystalClear (Rigaku, 2008), SIR92 (Altomare, et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.864 (18)	2.057 (18)	2.850 (3)	152 (3)
N2—H2···O1ⁱ	0.879 (18)	2.008 (18)	2.825 (3)	154 (3)

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by `Research for Promoting Technological Seeds' of the Japan Science and Technology Agency (JST).

References

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