Insight from electron density and energy framework analysis on the structural features of F_x-TCNQ (x = 0, 2, 4) family of molecules

In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetra­cyano­quinodi­methane (TCNQ) family of molecules, i.e. F_x-TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N[triple bond]C...F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

Computing details

Data collection: Bruker APEX2 for TCNQ, F2'-TCNQ, F2-TCNQ. Cell refinement: Bruker SAINT for TCNQ, F2'-TCNQ, F2-TCNQ. Data reduction: Bruker SAINT for TCNQ, F2'-TCNQ, F2-TCNQ. Program(s) used to solve structure: SHELXS97 (Sheldrick 2008) for TCNQ, F2'-TCNQ, F2-TCNQ. Program(s) used to refine structure: SHELXL2014 (Sheldrick 2014) for TCNQ, F2'-TCNQ, F2-TCNQ; SHELXL2014/7 (Sheldrick, 2014) for F4-TCNQ. Molecular graphics: Bruker SHELXTL for TCNQ, F2'-TCNQ, F2-TCNQ. Software used to prepare material for publication: Bruker SHELXTL for TCNQ, F2'-TCNQ, F2-TCNQ.

(TCNQ)

Crystal data

C12H4N4	F(000) = 416
Mr = 204.19	Dx = 1.362 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.8782 (13) Å	Cell parameters from 4041 reflections
b = 6.9117 (10) Å	θ = 2.5–30.6°
c = 16.398 (2) Å	µ = 0.09 mm^−1
β = 98.288 (6)°	T = 100 K
V = 995.8 (3) Å^3	Block, yellow
Z = 4	0.61 × 0.35 × 0.19 mm

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.103
φ and ω scans	θmax = 30.6°, θmin = 2.5°
11008 measured reflections	h = −11→12
1519 independent reflections	k = −9→9
1097 reflections with I > 2σ(I)	l = −23→23

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.064P)^2 + 0.058P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1519 reflections	Δρmax = 0.31 e Å^−3
81 parameters	Δρmin = −0.26 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
N1	0.80648 (12)	0.74384 (16)	0.23996 (6)	0.0237 (3)
N2	0.47985 (11)	0.93410 (14)	0.40007 (7)	0.0235 (3)
C1	0.78636 (12)	0.80879 (15)	0.30193 (7)	0.0164 (3)
C3	0.76099 (12)	0.88998 (14)	0.37933 (7)	0.0143 (3)
C4	0.87937 (12)	0.94389 (14)	0.43884 (7)	0.0132 (3)
C6	0.84897 (12)	1.02605 (15)	0.51607 (7)	0.0148 (3)
C5	1.03554 (12)	0.92036 (15)	0.42576 (7)	0.0143 (3)
C2	0.60472 (13)	0.91479 (15)	0.39040 (7)	0.0161 (3)
H6	0.7321 (5)	1.0408 (18)	0.5269 (8)	0.023 (3)*
H5	1.0566 (16)	0.8616 (19)	0.3673 (4)	0.031 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0249 (6)	0.0263 (5)	0.0199 (6)	−0.0007 (4)	0.0028 (4)	−0.0035 (4)
N2	0.0191 (5)	0.0287 (6)	0.0223 (6)	0.0000 (4)	0.0020 (4)	0.0005 (4)
C1	0.0136 (5)	0.0171 (5)	0.0182 (6)	−0.0009 (4)	0.0012 (4)	0.0004 (4)
C3	0.0153 (5)	0.0136 (5)	0.0142 (6)	0.0006 (4)	0.0029 (4)	0.0015 (4)
C4	0.0141 (5)	0.0110 (5)	0.0151 (6)	0.0011 (4)	0.0041 (4)	0.0026 (4)
C6	0.0156 (5)	0.0150 (5)	0.0146 (6)	0.0017 (4)	0.0043 (4)	0.0022 (4)
C5	0.0148 (5)	0.0147 (5)	0.0142 (6)	0.0016 (4)	0.0048 (4)	0.0007 (4)
C2	0.0171 (6)	0.0164 (5)	0.0142 (6)	−0.0005 (4)	0.0001 (4)	0.0002 (4)

Geometric parameters (Å, º)

N1—C1	1.1482 (15)	C4—C6	1.4484 (16)
N2—C2	1.1501 (14)	C6—C5^i	1.3477 (16)
C1—C3	1.4349 (16)	C6—H6	1.0823 (10)
C3—C4	1.3785 (15)	C5—C6^i	1.3477 (16)
C3—C2	1.4352 (16)	C5—H5	1.0824 (10)
C4—C5	1.4424 (15)
N1—C1—C3	179.92 (14)	C5^i—C6—C4	120.52 (10)
C4—C3—C1	122.08 (10)	C5^i—C6—H6	120.5 (7)
C4—C3—C2	122.03 (10)	C4—C6—H6	118.9 (7)
C1—C3—C2	115.88 (10)	C6^i—C5—C4	120.89 (10)
C3—C4—C5	121.02 (10)	C6^i—C5—H5	121.3 (8)
C3—C4—C6	120.39 (10)	C4—C5—H5	117.8 (8)
C5—C4—C6	118.59 (10)	N2—C2—C3	179.33 (12)
C1—C3—C4—C5	−0.12 (16)	C3—C4—C6—C5^i	−179.72 (10)
C2—C3—C4—C5	−179.00 (10)	C5—C4—C6—C5^i	0.17 (17)
C1—C3—C4—C6	179.76 (10)	C3—C4—C5—C6^i	179.72 (10)
C2—C3—C4—C6	0.88 (15)	C6—C4—C5—C6^i	−0.17 (17)

Symmetry code: (i) −x+2, −y+2, −z+1.

(F2'-TCNQ)

Crystal data

C12H2F2N4	F(000) = 480
Mr = 240.18	Dx = 1.579 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8303 (9) Å	Cell parameters from 7666 reflections
b = 5.4679 (5) Å	θ = 3.3–30.5°
c = 19.2479 (17) Å	µ = 0.13 mm^−1
β = 102.417 (5)°	T = 100 K
V = 1010.39 (16) Å^3	Block, yellow
Z = 4	0.31 × 0.20 × 0.14 mm

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.084
φ and ω scans	θmax = 30.7°, θmin = 2.7°
23312 measured reflections	h = −14→14
3100 independent reflections	k = −7→7
2273 reflections with I > 2σ(I)	l = −27→27

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	All H-atom parameters refined
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.4801P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3100 reflections	Δρmax = 0.40 e Å^−3
171 parameters	Δρmin = −0.37 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
F2	0.92048 (9)	−0.26958 (17)	0.20358 (5)	0.0224 (2)
F1	0.94270 (9)	0.36736 (17)	0.04012 (5)	0.0222 (2)
N3	0.44424 (15)	0.6836 (3)	0.07372 (7)	0.0250 (3)
N2	1.21929 (13)	0.1565 (2)	0.03203 (7)	0.0202 (3)
N4	0.39781 (13)	0.0763 (3)	0.21822 (7)	0.0205 (3)
N1	1.18901 (15)	−0.4399 (3)	0.16696 (7)	0.0252 (3)
C11	0.48390 (15)	0.5039 (3)	0.10193 (8)	0.0172 (3)
C10	0.54116 (15)	0.2852 (3)	0.13753 (7)	0.0153 (3)
C9	0.67055 (14)	0.2031 (3)	0.13152 (7)	0.0141 (3)
C8	0.74731 (14)	0.3314 (3)	0.08731 (7)	0.0148 (3)
C6	0.87415 (15)	0.2514 (3)	0.08335 (7)	0.0149 (3)
C4	0.94325 (14)	0.0414 (3)	0.12087 (7)	0.0135 (3)
C3	1.07141 (14)	−0.0400 (3)	0.11296 (7)	0.0145 (3)
C2	1.15158 (15)	0.0761 (3)	0.06789 (7)	0.0159 (3)
C12	0.46158 (15)	0.1669 (3)	0.18191 (7)	0.0161 (3)
C1	1.13504 (15)	−0.2612 (3)	0.14495 (7)	0.0172 (3)
C5	0.86132 (15)	−0.0777 (3)	0.16526 (7)	0.0148 (3)
C7	0.73298 (15)	−0.0084 (3)	0.17031 (7)	0.0156 (3)
H7	0.6795 (16)	−0.112 (3)	0.2043 (7)	0.025 (5)*
H8	0.7060 (17)	0.4937 (18)	0.0580 (8)	0.022 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F2	0.0217 (5)	0.0212 (5)	0.0258 (5)	0.0069 (4)	0.0085 (4)	0.0122 (4)
F1	0.0187 (4)	0.0230 (5)	0.0280 (5)	0.0035 (4)	0.0119 (4)	0.0135 (4)
N3	0.0239 (7)	0.0228 (7)	0.0290 (7)	0.0051 (6)	0.0072 (6)	0.0024 (6)
N2	0.0185 (6)	0.0215 (6)	0.0211 (6)	0.0016 (5)	0.0057 (5)	0.0014 (5)
N4	0.0184 (6)	0.0224 (7)	0.0218 (6)	0.0032 (5)	0.0069 (5)	0.0017 (5)
N1	0.0272 (7)	0.0252 (7)	0.0242 (7)	0.0089 (6)	0.0078 (6)	0.0055 (6)
C11	0.0141 (6)	0.0201 (7)	0.0188 (6)	0.0007 (5)	0.0066 (5)	−0.0020 (6)
C10	0.0158 (7)	0.0162 (7)	0.0140 (6)	−0.0002 (5)	0.0030 (5)	−0.0016 (5)
C9	0.0150 (6)	0.0144 (6)	0.0128 (6)	−0.0003 (5)	0.0029 (5)	−0.0022 (5)
C8	0.0163 (7)	0.0139 (6)	0.0144 (6)	0.0013 (5)	0.0036 (5)	0.0019 (5)
C6	0.0163 (7)	0.0148 (7)	0.0147 (6)	−0.0013 (5)	0.0056 (5)	0.0029 (5)
C4	0.0148 (6)	0.0135 (6)	0.0124 (6)	−0.0004 (5)	0.0035 (5)	−0.0002 (5)
C3	0.0154 (6)	0.0141 (6)	0.0136 (6)	0.0003 (5)	0.0026 (5)	0.0011 (5)
C2	0.0139 (6)	0.0180 (7)	0.0151 (6)	0.0036 (5)	0.0018 (5)	0.0003 (5)
C12	0.0144 (6)	0.0170 (7)	0.0168 (6)	0.0032 (5)	0.0028 (5)	−0.0016 (5)
C1	0.0166 (7)	0.0207 (7)	0.0154 (6)	0.0015 (6)	0.0058 (5)	−0.0001 (6)
C5	0.0177 (7)	0.0128 (6)	0.0136 (6)	0.0008 (5)	0.0026 (5)	0.0040 (5)
C7	0.0177 (7)	0.0156 (6)	0.0141 (6)	0.0004 (5)	0.0047 (5)	0.0014 (5)

Geometric parameters (Å, º)

F2—C5	1.3410 (16)	C9—C7	1.440 (2)
F1—C6	1.3377 (16)	C8—C6	1.339 (2)
N3—C11	1.149 (2)	C8—H8	1.0827 (10)
N2—C2	1.1446 (19)	C6—C4	1.4461 (19)
N4—C12	1.1469 (19)	C4—C3	1.3750 (19)
N1—C1	1.149 (2)	C4—C5	1.4488 (19)
C11—C10	1.432 (2)	C3—C1	1.438 (2)
C10—C9	1.377 (2)	C3—C2	1.439 (2)
C10—C12	1.431 (2)	C5—C7	1.341 (2)
C9—C8	1.436 (2)	C7—H7	1.0827 (10)
N3—C11—C10	176.76 (16)	C3—C4—C5	123.95 (13)
C9—C10—C12	122.41 (13)	C6—C4—C5	112.99 (12)
C9—C10—C11	120.49 (13)	C4—C3—C1	123.34 (13)
C12—C10—C11	117.01 (13)	C4—C3—C2	123.87 (13)
C10—C9—C8	120.19 (13)	C1—C3—C2	112.65 (12)
C10—C9—C7	121.11 (13)	N2—C2—C3	176.18 (15)
C8—C9—C7	118.68 (13)	N4—C12—C10	178.64 (16)
C6—C8—C9	119.25 (13)	N1—C1—C3	175.94 (15)
C6—C8—H8	119.2 (9)	F2—C5—C7	119.00 (12)
C9—C8—H8	121.6 (9)	F2—C5—C4	116.47 (12)
F1—C6—C8	118.72 (12)	C7—C5—C4	124.53 (13)
F1—C6—C4	116.21 (12)	C5—C7—C9	119.48 (13)
C8—C6—C4	125.04 (13)	C5—C7—H7	118.9 (9)
C3—C4—C6	123.03 (12)	C9—C7—H7	121.7 (10)
C12—C10—C9—C8	−178.77 (13)	C6—C4—C3—C1	−174.12 (13)
C11—C10—C9—C8	−2.3 (2)	C5—C4—C3—C1	3.6 (2)
C12—C10—C9—C7	−0.2 (2)	C6—C4—C3—C2	1.2 (2)
C11—C10—C9—C7	176.33 (13)	C5—C4—C3—C2	178.89 (13)
C10—C9—C8—C6	178.64 (13)	C3—C4—C5—F2	4.2 (2)
C7—C9—C8—C6	0.0 (2)	C6—C4—C5—F2	−177.90 (11)
C9—C8—C6—F1	177.74 (12)	C3—C4—C5—C7	−176.06 (14)
C9—C8—C6—C4	−0.2 (2)	C6—C4—C5—C7	1.9 (2)
F1—C6—C4—C3	−0.7 (2)	F2—C5—C7—C9	177.61 (12)
C8—C6—C4—C3	177.30 (14)	C4—C5—C7—C9	−2.1 (2)
F1—C6—C4—C5	−178.62 (12)	C10—C9—C7—C5	−177.50 (14)
C8—C6—C4—C5	−0.6 (2)	C8—C9—C7—C5	1.1 (2)

(F2-TCNQ)

Crystal data

C12H2F2N4	F(000) = 240
Mr = 240.18	Dx = 1.579 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 10.1713 (19) Å	Cell parameters from 3976 reflections
b = 5.8670 (12) Å	θ = 2.4–30.4°
c = 8.8512 (17) Å	µ = 0.13 mm^−1
β = 106.969 (7)°	T = 100 K
V = 505.20 (17) Å^3	Block, yellow
Z = 2	0.23 × 0.18 × 0.13 mm

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.059
φ and ω scans	θmax = 30.6°, θmin = 2.4°
8822 measured reflections	h = −11→14
849 independent reflections	k = −8→8
688 reflections with I > 2σ(I)	l = −12→12

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0384P)^2 + 0.6736P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.109	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.45 e Å^−3
849 reflections	Δρmin = −0.28 e Å^−3
59 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.027 (5)

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.

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

	x	y	z	Uiso*/Ueq
F1	0.76125 (11)	0.5000	0.97938 (13)	0.0191 (3)
N1	0.33218 (17)	0.5000	0.44923 (19)	0.0196 (4)
N2	0.02227 (18)	0.5000	0.6963 (2)	0.0235 (4)
C5	0.52791 (19)	0.5000	0.8524 (2)	0.0143 (4)
C6	0.63140 (17)	0.5000	0.9873 (2)	0.0138 (4)
C2	0.13778 (19)	0.5000	0.7091 (2)	0.0163 (4)
C4	0.38735 (18)	0.5000	0.8568 (2)	0.0135 (4)
C1	0.30968 (19)	0.5000	0.5689 (2)	0.0155 (4)
C3	0.28096 (19)	0.5000	0.7187 (2)	0.0148 (4)
H5	0.549 (2)	0.5000	0.7394 (12)	0.017 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0144 (5)	0.0297 (6)	0.0156 (5)	0.000	0.0083 (4)	0.000
N1	0.0196 (8)	0.0248 (8)	0.0153 (8)	0.000	0.0066 (6)	0.000
N2	0.0209 (8)	0.0297 (9)	0.0193 (8)	0.000	0.0048 (6)	0.000
C5	0.0176 (8)	0.0151 (8)	0.0121 (8)	0.000	0.0073 (6)	0.000
C6	0.0142 (8)	0.0153 (8)	0.0137 (8)	0.000	0.0072 (6)	0.000
C2	0.0197 (9)	0.0185 (9)	0.0114 (8)	0.000	0.0058 (6)	0.000
C4	0.0174 (8)	0.0116 (8)	0.0125 (8)	0.000	0.0060 (6)	0.000
C1	0.0152 (8)	0.0177 (8)	0.0128 (8)	0.000	0.0028 (6)	0.000
C3	0.0176 (8)	0.0146 (8)	0.0136 (8)	0.000	0.0066 (6)	0.000

Geometric parameters (Å, º)

F1—C6	1.3430 (19)	C6—C4^i	1.447 (2)
N1—C1	1.147 (2)	C2—C3	1.434 (3)
N2—C2	1.147 (3)	C4—C3	1.376 (3)
C5—C6	1.342 (2)	C4—C6^i	1.447 (2)
C5—C4	1.442 (2)	C1—C3	1.439 (3)
C5—H5	1.0828 (11)
C6—C5—C4	120.14 (15)	C3—C4—C5	120.32 (16)
C6—C5—H5	120.4 (11)	C3—C4—C6^i	123.97 (16)
C4—C5—H5	119.4 (11)	C5—C4—C6^i	115.71 (16)
C5—C6—F1	118.77 (15)	N1—C1—C3	179.8 (2)
C5—C6—C4^i	124.14 (16)	C4—C3—C2	125.10 (16)
F1—C6—C4^i	117.08 (15)	C4—C3—C1	120.01 (16)
N2—C2—C3	177.9 (2)	C2—C3—C1	114.89 (16)

Symmetry code: (i) −x+1, −y+1, −z+2.

(F4-TCNQ)

Crystal data

C12F4N4	Dx = 1.701 Mg m^−3
Mr = 276.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4348 reflections
a = 9.1905 (18) Å	θ = 2.8–29.8°
b = 8.0558 (17) Å	µ = 0.16 mm^−1
c = 14.564 (3) Å	T = 100 K
V = 1078.3 (4) Å^3	Block, yellow
Z = 4	0.33 × 0.12 × 0.11 mm
F(000) = 544

Data collection

Bruker APEX-II CCD diffractometer	Rint = 0.182
φ and ω scans	θmax = 30.6°, θmin = 2.8°
24791 measured reflections	h = −13→13
1658 independent reflections	k = −11→11
1024 reflections with I > 2σ(I)	l = −20→20

Refinement

Refinement on F^2	91 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.071	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.8314P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.36 e Å^−3
1658 reflections	Δρmin = −0.37 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
F2	0.34968 (13)	0.99415 (17)	0.33988 (8)	0.0213 (3)
F1	0.34137 (13)	1.26315 (16)	0.44053 (9)	0.0204 (3)
N1	0.3887 (2)	0.6728 (3)	0.23144 (14)	0.0282 (5)
N2	0.6559 (2)	0.4467 (3)	0.42763 (14)	0.0238 (5)
C1	0.4446 (2)	0.6989 (3)	0.30024 (16)	0.0190 (5)
C3	0.5166 (2)	0.7150 (3)	0.38750 (15)	0.0159 (5)
C4	0.5081 (2)	0.8521 (3)	0.44267 (14)	0.0150 (5)
C6	0.4200 (2)	1.1343 (3)	0.47016 (15)	0.0158 (5)
C5	0.4255 (2)	0.9975 (3)	0.41807 (14)	0.0147 (5)
C2	0.5975 (2)	0.5685 (3)	0.41154 (15)	0.0180 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F2	0.0203 (6)	0.0229 (7)	0.0205 (7)	−0.0010 (6)	−0.0101 (5)	0.0038 (6)
F1	0.0191 (7)	0.0171 (7)	0.0251 (7)	0.0051 (6)	−0.0058 (6)	0.0045 (6)
N1	0.0291 (11)	0.0327 (13)	0.0229 (11)	0.0025 (10)	−0.0016 (9)	−0.0005 (10)
N2	0.0203 (10)	0.0250 (11)	0.0261 (11)	0.0017 (9)	−0.0004 (9)	−0.0027 (9)
C1	0.0183 (11)	0.0186 (12)	0.0200 (12)	0.0005 (10)	0.0043 (9)	0.0007 (10)
C3	0.0110 (9)	0.0188 (12)	0.0179 (11)	−0.0014 (9)	0.0019 (8)	0.0033 (9)
C4	0.0099 (9)	0.0190 (12)	0.0160 (11)	−0.0012 (9)	0.0021 (8)	0.0047 (9)
C6	0.0098 (10)	0.0179 (12)	0.0198 (11)	−0.0002 (9)	−0.0005 (8)	0.0076 (9)
C5	0.0107 (9)	0.0197 (12)	0.0137 (10)	−0.0022 (9)	−0.0028 (8)	0.0037 (9)
C2	0.0138 (10)	0.0214 (13)	0.0187 (11)	−0.0015 (10)	0.0031 (9)	−0.0025 (10)

Geometric parameters (Å, º)

F2—C5	1.335 (2)	C3—C2	1.438 (3)
F1—C6	1.337 (2)	C4—C6^i	1.436 (3)
N1—C1	1.146 (3)	C4—C5	1.441 (3)
N2—C2	1.143 (3)	C6—C5	1.338 (3)
C1—C3	1.439 (3)	C6—C4^i	1.436 (3)
C3—C4	1.368 (3)
N1—C1—C3	174.6 (3)	F1—C6—C5	118.47 (19)
C4—C3—C2	123.3 (2)	F1—C6—C4^i	118.4 (2)
C4—C3—C1	124.4 (2)	C5—C6—C4^i	123.2 (2)
C2—C3—C1	112.3 (2)	F2—C5—C6	118.7 (2)
C3—C4—C6^i	123.7 (2)	F2—C5—C4	118.1 (2)
C3—C4—C5	122.71 (19)	C6—C5—C4	123.21 (19)
C6^i—C4—C5	113.60 (19)	N2—C2—C3	175.9 (2)
C2—C3—C4—C6^i	0.7 (3)	F1—C6—C5—C4	179.24 (18)
C1—C3—C4—C6^i	179.6 (2)	C4^i—C6—C5—C4	−2.2 (4)
C2—C3—C4—C5	−179.41 (19)	C3—C4—C5—F2	2.8 (3)
C1—C3—C4—C5	−0.5 (3)	C6^i—C4—C5—F2	−177.26 (18)
F1—C6—C5—F2	−1.5 (3)	C3—C4—C5—C6	−177.9 (2)
C4^i—C6—C5—F2	177.06 (19)	C6^i—C4—C5—C6	2.0 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.