cis-Bis(2,2′-bipyridine)difluoro­chromium(III) perchlorate

In the title compound, cis-[CrF₂(C₁₀H₈N₂)₂]ClO₄, the Cr^III ion is coordinated by the four N atoms [Cr—N = 2.0480 (14)–2.0842 (14) Å] from two 2,2′-bipyridine ligands and two F⁻ ions [Cr—F = 1.8409 (10) and 1.8541 (10) Å] in a distorted octa­hedral arrangement. The crystal packing is stabilized by π–π inter­actions and weak inter­molecular C—H...F and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

cis-Bis(2,2'-bipyridine)difluorochromium(III) perchlorate

Crystal data

[CrF2(C10H8N2)2]ClO4	Z = 2
Mr = 501.82	F(000) = 510
Triclinic, P1	Dx = 1.655 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0017 (4) Å	Cell parameters from 5311 reflections
b = 9.4888 (4) Å	θ = 2.5–27.9°
c = 13.6101 (6) Å	µ = 0.76 mm^−1
α = 95.710 (1)°	T = 173 K
β = 100.7621 (8)°	Plate, black
γ = 93.2530 (9)°	0.52 × 0.51 × 0.32 mm
V = 1007.15 (8) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4766 independent reflections
Radiation source: fine-focus sealed tube	4430 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.366 pixels mm^-1	θmax = 27.9°, θmin = 1.5°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.694, Tmax = 0.794	l = −17→13
7371 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 0.6069P] where P = (Fo^2 + 2Fc^2)/3
4766 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

Special details

Experimental. Elemental analysis (CHN), found: 47.51, 3.18, 7.01%; calculated for C₂₀H₁₆ClCrF₂N₄O₄: 47.87, 3.21, 7.07%.

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.8252 (0.0029) x + 4.8574 (0.0029) y + 10.7255 (0.0036) z = 4.6735 (0.0018)

* -0.0082 (0.0013) N1 * -0.0438 (0.0014) C1 * -0.0380 (0.0016) C2 * 0.0241 (0.0015) C3 * 0.0555 (0.0015) C4 * 0.0218 (0.0014) C5 * 0.0271 (0.0012) N2 * 0.0138 (0.0014) C6 * -0.0239 (0.0015) C7 * -0.0550 (0.0015) C8 * -0.0120 (0.0015) C9 * 0.0386 (0.0014) C10 3.4190 (0.0017) N1_$1 3.3837 (0.0017) N2_$1 3.4546 (0.0019) C1_$1 3.4488 (0.0021) C2_$1 3.3867 (0.0020) C3_$1 3.3553 (0.0019) C4_$1 3.3890 (0.0018) C5_$1 3.3969 (0.0018) C6_$1 3.4347 (0.0019) C7_$1 3.4657 (0.0019) C8_$1

Rms deviation of fitted atoms = 0.0338

- 2.6116 (0.0051) x + 4.7811 (0.0058) y + 10.8703 (0.0058) z = 4.8207 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 1.80 (0.08)

* -0.0130 (0.0010) N2 * 0.0035 (0.0011) C6 * 0.0083 (0.0012) C7 * -0.0109 (0.0013) C8 * 0.0016 (0.0013) C9 * 0.0104 (0.0012) C10

Rms deviation of fitted atoms = 0.0090

- 3.0869 (0.0054) x + 4.8707 (0.0058) y + 10.6093 (0.0061) z = 4.5546 (0.0027)

Angle to previous plane (with approximate e.s.d.) = 3.84 (0.10)

* 0.0073 (0.0011) N1 * 0.0023 (0.0012) C1 * -0.0082 (0.0013) C2 * 0.0048 (0.0013) C3 * 0.0045 (0.0012) C4 * -0.0107 (0.0011) C5

Rms deviation of fitted atoms = 0.0069

7.3473 (0.0024) x + 2.9135 (0.0069) y - 0.6715 (0.0102) z = 3.1986 (0.0020)

Angle to previous plane (with approximate e.s.d.) = 87.26 (0.06)

* -0.0172 (0.0011) N3 * -0.0027 (0.0012) C11 * 0.0182 (0.0013) C12 * -0.0143 (0.0014) C13 * -0.0053 (0.0013) C14 * 0.0213 (0.0011) C15

Rms deviation of fitted atoms = 0.0148

7.6216 (0.0018) x + 1.8617 (0.0065) y - 0.4983 (0.0096) z = 2.7392 (0.0047)

Angle to previous plane (with approximate e.s.d.) = 6.57 (0.07)

* 0.0061 (0.0011) N4 * 0.0009 (0.0011) C16 * -0.0067 (0.0012) C17 * 0.0058 (0.0013) C18 * 0.0009 (0.0012) C19 * -0.0070 (0.0012) C20

Rms deviation of fitted atoms = 0.0053

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.1357 (2)	0.25919 (19)	0.35002 (13)	0.0281 (3)
H1	0.0234	0.2669	0.3141	0.034*
C2	0.1662 (2)	0.1488 (2)	0.40860 (15)	0.0332 (4)
H2	0.0765	0.0807	0.4123	0.040*
C3	0.3298 (3)	0.1393 (2)	0.46175 (14)	0.0330 (4)
H3	0.3529	0.0653	0.5033	0.040*
C4	0.4595 (2)	0.23816 (19)	0.45409 (13)	0.0276 (3)
H4	0.5723	0.2330	0.4902	0.033*
C5	0.4217 (2)	0.34494 (17)	0.39264 (11)	0.0212 (3)
C6	0.5488 (2)	0.45452 (17)	0.37574 (11)	0.0212 (3)
C7	0.7219 (2)	0.4581 (2)	0.41617 (13)	0.0275 (3)
H7	0.7650	0.3892	0.4583	0.033*
C8	0.8301 (2)	0.5639 (2)	0.39389 (13)	0.0316 (4)
H8	0.9493	0.5669	0.4192	0.038*
C9	0.7640 (2)	0.6652 (2)	0.33460 (14)	0.0307 (4)
H9	0.8367	0.7395	0.3196	0.037*
C10	0.5906 (2)	0.65677 (19)	0.29747 (13)	0.0267 (3)
H10	0.5448	0.7273	0.2576	0.032*
C11	0.3346 (2)	0.28143 (18)	0.12245 (13)	0.0280 (3)
H11	0.3582	0.2340	0.1812	0.034*
C12	0.3564 (3)	0.21276 (19)	0.03209 (14)	0.0322 (4)
H12	0.3975	0.1208	0.0290	0.039*
C13	0.3175 (3)	0.2799 (2)	−0.05376 (14)	0.0340 (4)
H13	0.3266	0.2327	−0.1173	0.041*
C14	0.2652 (2)	0.4165 (2)	−0.04675 (13)	0.0303 (4)
H14	0.2391	0.4648	−0.1050	0.036*
C15	0.2515 (2)	0.48164 (17)	0.04700 (12)	0.0225 (3)
C16	0.20969 (19)	0.63081 (17)	0.06499 (12)	0.0223 (3)
C17	0.1818 (2)	0.72103 (19)	−0.00975 (13)	0.0287 (4)
H17	0.1837	0.6879	−0.0777	0.034*
C18	0.1510 (2)	0.8607 (2)	0.01710 (14)	0.0324 (4)
H18	0.1336	0.9251	−0.0324	0.039*
C19	0.1459 (2)	0.90563 (19)	0.11602 (15)	0.0313 (4)
H19	0.1242	1.0008	0.1353	0.038*
C20	0.1729 (2)	0.80995 (18)	0.18684 (13)	0.0269 (3)
H20	0.1679	0.8403	0.2548	0.032*
Cl1	0.29876 (5)	0.93899 (4)	0.74613 (3)	0.03047 (11)
Cr1	0.22512 (3)	0.52312 (3)	0.259101 (17)	0.01950 (8)
F1	−0.00228 (12)	0.46560 (11)	0.21407 (7)	0.0278 (2)
F2	0.19136 (12)	0.65016 (11)	0.36493 (7)	0.0261 (2)
N1	0.26081 (17)	0.35552 (15)	0.34266 (10)	0.0220 (3)
N2	0.48457 (17)	0.55201 (15)	0.31591 (10)	0.0216 (3)
N3	0.28114 (17)	0.41301 (15)	0.13038 (10)	0.0224 (3)
N4	0.20569 (17)	0.67588 (15)	0.16187 (10)	0.0220 (3)
O1	0.3015 (2)	0.79502 (17)	0.76788 (15)	0.0542 (4)
O2	0.4592 (2)	1.01395 (19)	0.79085 (19)	0.0709 (6)
O3	0.1640 (2)	1.0044 (2)	0.78492 (14)	0.0580 (5)
O4	0.2645 (3)	0.9386 (3)	0.63950 (14)	0.0716 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0255 (8)	0.0318 (8)	0.0259 (8)	−0.0025 (6)	0.0022 (6)	0.0054 (7)
C2	0.0339 (9)	0.0306 (9)	0.0355 (9)	−0.0045 (7)	0.0071 (7)	0.0090 (7)
C3	0.0391 (10)	0.0309 (9)	0.0321 (9)	0.0068 (7)	0.0087 (8)	0.0122 (7)
C4	0.0282 (8)	0.0309 (8)	0.0250 (8)	0.0085 (7)	0.0046 (6)	0.0067 (6)
C5	0.0223 (7)	0.0250 (7)	0.0163 (7)	0.0037 (6)	0.0039 (5)	0.0007 (5)
C6	0.0217 (7)	0.0263 (7)	0.0156 (7)	0.0040 (6)	0.0039 (5)	0.0007 (5)
C7	0.0216 (8)	0.0382 (9)	0.0222 (8)	0.0064 (6)	0.0021 (6)	0.0034 (7)
C8	0.0199 (8)	0.0466 (11)	0.0273 (8)	0.0017 (7)	0.0037 (6)	0.0011 (7)
C9	0.0233 (8)	0.0392 (10)	0.0295 (9)	−0.0052 (7)	0.0068 (7)	0.0042 (7)
C10	0.0255 (8)	0.0312 (8)	0.0242 (8)	−0.0002 (6)	0.0057 (6)	0.0066 (6)
C11	0.0321 (9)	0.0266 (8)	0.0255 (8)	0.0056 (7)	0.0041 (7)	0.0047 (6)
C12	0.0385 (10)	0.0259 (8)	0.0326 (9)	0.0055 (7)	0.0085 (7)	−0.0004 (7)
C13	0.0425 (10)	0.0347 (9)	0.0245 (8)	0.0009 (8)	0.0096 (7)	−0.0037 (7)
C14	0.0352 (9)	0.0351 (9)	0.0199 (8)	0.0024 (7)	0.0038 (7)	0.0032 (7)
C15	0.0203 (7)	0.0262 (8)	0.0203 (7)	0.0003 (6)	0.0019 (6)	0.0033 (6)
C16	0.0186 (7)	0.0270 (8)	0.0208 (7)	0.0019 (6)	0.0015 (6)	0.0049 (6)
C17	0.0294 (8)	0.0341 (9)	0.0224 (8)	0.0021 (7)	0.0018 (6)	0.0087 (7)
C18	0.0313 (9)	0.0323 (9)	0.0345 (9)	0.0041 (7)	0.0024 (7)	0.0142 (7)
C19	0.0305 (9)	0.0247 (8)	0.0383 (10)	0.0048 (7)	0.0032 (7)	0.0069 (7)
C20	0.0261 (8)	0.0268 (8)	0.0277 (8)	0.0039 (6)	0.0041 (6)	0.0028 (6)
Cl1	0.0294 (2)	0.0275 (2)	0.0351 (2)	0.00147 (16)	0.00788 (17)	0.00373 (16)
Cr1	0.01803 (13)	0.02384 (14)	0.01612 (13)	0.00153 (9)	0.00131 (9)	0.00363 (9)
F1	0.0198 (5)	0.0351 (5)	0.0264 (5)	0.0000 (4)	−0.0015 (4)	0.0056 (4)
F2	0.0245 (5)	0.0320 (5)	0.0215 (5)	0.0024 (4)	0.0056 (4)	0.0005 (4)
N1	0.0212 (6)	0.0260 (7)	0.0182 (6)	0.0008 (5)	0.0020 (5)	0.0041 (5)
N2	0.0201 (6)	0.0268 (7)	0.0174 (6)	0.0007 (5)	0.0032 (5)	0.0021 (5)
N3	0.0227 (6)	0.0243 (6)	0.0192 (6)	0.0020 (5)	0.0017 (5)	0.0027 (5)
N4	0.0195 (6)	0.0255 (7)	0.0208 (6)	0.0027 (5)	0.0022 (5)	0.0045 (5)
O1	0.0541 (10)	0.0332 (8)	0.0724 (12)	−0.0011 (7)	0.0011 (8)	0.0156 (8)
O2	0.0365 (9)	0.0440 (9)	0.1219 (18)	−0.0096 (7)	−0.0057 (10)	0.0062 (10)
O3	0.0446 (9)	0.0622 (11)	0.0652 (11)	0.0107 (8)	0.0169 (8)	−0.0188 (9)
O4	0.0749 (13)	0.1070 (17)	0.0445 (10)	0.0264 (12)	0.0250 (9)	0.0287 (10)

Geometric parameters (Å, º)

C1—N1	1.341 (2)	C13—C14	1.385 (3)
C1—C2	1.384 (2)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.387 (2)
C2—C3	1.384 (3)	C14—H14	0.9500
C2—H2	0.9500	C15—N3	1.354 (2)
C3—C4	1.385 (3)	C15—C16	1.480 (2)
C3—H3	0.9500	C16—N4	1.352 (2)
C4—C5	1.388 (2)	C16—C17	1.388 (2)
C4—H4	0.9500	C17—C18	1.387 (3)
C5—N1	1.353 (2)	C17—H17	0.9500
C5—C6	1.477 (2)	C18—C19	1.380 (3)
C6—N2	1.353 (2)	C18—H18	0.9500
C6—C7	1.388 (2)	C19—C20	1.385 (2)
C7—C8	1.382 (3)	C19—H19	0.9500
C7—H7	0.9500	C20—N4	1.337 (2)
C8—C9	1.381 (3)	C20—H20	0.9500
C8—H8	0.9500	Cl1—O4	1.4254 (19)
C9—C10	1.380 (2)	Cl1—O1	1.4268 (16)
C9—H9	0.9500	Cl1—O2	1.4295 (17)
C10—N2	1.343 (2)	Cl1—O3	1.4316 (16)
C10—H10	0.9500	Cr1—F1	1.8409 (10)
C11—N3	1.343 (2)	Cr1—F2	1.8541 (10)
C11—C12	1.379 (2)	Cr1—N1	2.0480 (14)
C11—H11	0.9500	Cr1—N4	2.0511 (14)
C12—C13	1.379 (3)	Cr1—N2	2.0680 (13)
C12—H12	0.9500	Cr1—N3	2.0842 (14)
N1—C1—C2	121.63 (16)	C17—C16—C15	123.72 (15)
N1—C1—H1	119.2	C18—C17—C16	118.47 (16)
C2—C1—H1	119.2	C18—C17—H17	120.8
C1—C2—C3	118.84 (17)	C16—C17—H17	120.8
C1—C2—H2	120.6	C19—C18—C17	119.66 (16)
C3—C2—H2	120.6	C19—C18—H18	120.2
C2—C3—C4	119.75 (16)	C17—C18—H18	120.2
C2—C3—H3	120.1	C18—C19—C20	119.06 (17)
C4—C3—H3	120.1	C18—C19—H19	120.5
C3—C4—C5	118.77 (16)	C20—C19—H19	120.5
C3—C4—H4	120.6	N4—C20—C19	121.62 (16)
C5—C4—H4	120.6	N4—C20—H20	119.2
N1—C5—C4	121.19 (15)	C19—C20—H20	119.2
N1—C5—C6	114.58 (14)	O4—Cl1—O1	108.00 (13)
C4—C5—C6	124.23 (15)	O4—Cl1—O2	111.43 (15)
N2—C6—C7	121.61 (15)	O1—Cl1—O2	109.37 (11)
N2—C6—C5	114.89 (13)	O4—Cl1—O3	108.23 (12)
C7—C6—C5	123.49 (15)	O1—Cl1—O3	109.69 (12)
C8—C7—C6	118.71 (16)	O2—Cl1—O3	110.08 (12)
C8—C7—H7	120.6	F1—Cr1—F2	95.43 (5)
C6—C7—H7	120.6	F1—Cr1—N1	91.82 (5)
C9—C8—C7	119.68 (16)	F2—Cr1—N1	94.95 (5)
C9—C8—H8	120.2	F1—Cr1—N4	90.05 (5)
C7—C8—H8	120.2	F2—Cr1—N4	92.38 (5)
C10—C9—C8	118.86 (16)	N1—Cr1—N4	172.23 (5)
C10—C9—H9	120.6	F1—Cr1—N2	170.04 (5)
C8—C9—H9	120.6	F2—Cr1—N2	88.59 (5)
N2—C10—C9	122.10 (16)	N1—Cr1—N2	78.72 (5)
N2—C10—H10	118.9	N4—Cr1—N2	98.91 (5)
C9—C10—H10	118.9	F1—Cr1—N3	89.53 (5)
N3—C11—C12	122.35 (16)	F2—Cr1—N3	169.52 (5)
N3—C11—H11	118.8	N1—Cr1—N3	94.11 (5)
C12—C11—H11	118.8	N4—Cr1—N3	78.35 (5)
C11—C12—C13	118.88 (17)	N2—Cr1—N3	88.03 (5)
C11—C12—H12	120.6	C1—N1—C5	119.79 (14)
C13—C12—H12	120.6	C1—N1—Cr1	123.91 (11)
C12—C13—C14	119.54 (17)	C5—N1—Cr1	116.29 (11)
C12—C13—H13	120.2	C10—N2—C6	118.98 (14)
C14—C13—H13	120.2	C10—N2—Cr1	125.55 (11)
C13—C14—C15	118.69 (16)	C6—N2—Cr1	115.47 (10)
C13—C14—H14	120.7	C11—N3—C15	118.68 (14)
C15—C14—H14	120.7	C11—N3—Cr1	126.42 (11)
N3—C15—C14	121.72 (15)	C15—N3—Cr1	114.81 (11)
N3—C15—C16	114.74 (14)	C20—N4—C16	119.66 (14)
C14—C15—C16	123.51 (15)	C20—N4—Cr1	123.95 (11)
N4—C16—C17	121.51 (15)	C16—N4—Cr1	116.03 (11)
N4—C16—C15	114.74 (14)
N1—C1—C2—C3	0.9 (3)	C9—C10—N2—Cr1	−177.00 (13)
C1—C2—C3—C4	−1.1 (3)	C7—C6—N2—C10	−1.7 (2)
C2—C3—C4—C5	−0.1 (3)	C5—C6—N2—C10	179.15 (14)
C3—C4—C5—N1	1.6 (2)	C7—C6—N2—Cr1	177.74 (12)
C3—C4—C5—C6	−178.32 (15)	C5—C6—N2—Cr1	−1.38 (17)
N1—C5—C6—N2	2.3 (2)	F2—Cr1—N2—C10	−85.02 (13)
C4—C5—C6—N2	−177.76 (15)	N1—Cr1—N2—C10	179.65 (14)
N1—C5—C6—C7	−176.80 (15)	N4—Cr1—N2—C10	7.17 (14)
C4—C5—C6—C7	3.1 (2)	N3—Cr1—N2—C10	85.05 (14)
N2—C6—C7—C8	−0.3 (2)	F2—Cr1—N2—C6	95.55 (11)
C5—C6—C7—C8	178.73 (15)	N1—Cr1—N2—C6	0.22 (11)
C6—C7—C8—C9	1.7 (3)	N4—Cr1—N2—C6	−172.26 (11)
C7—C8—C9—C10	−1.1 (3)	N3—Cr1—N2—C6	−94.37 (11)
C8—C9—C10—N2	−1.0 (3)	C12—C11—N3—C15	−1.6 (3)
N3—C11—C12—C13	−1.8 (3)	C12—C11—N3—Cr1	175.03 (14)
C11—C12—C13—C14	2.9 (3)	C14—C15—N3—C11	3.9 (2)
C12—C13—C14—C15	−0.7 (3)	C16—C15—N3—C11	−174.25 (14)
C13—C14—C15—N3	−2.8 (3)	C14—C15—N3—Cr1	−173.08 (13)
C13—C14—C15—C16	175.20 (16)	C16—C15—N3—Cr1	8.78 (17)
N3—C15—C16—N4	−0.6 (2)	F1—Cr1—N3—C11	−96.58 (14)
C14—C15—C16—N4	−178.69 (15)	F2—Cr1—N3—C11	145.0 (2)
N3—C15—C16—C17	177.35 (15)	N1—Cr1—N3—C11	−4.78 (15)
C14—C15—C16—C17	−0.8 (3)	N4—Cr1—N3—C11	173.28 (15)
N4—C16—C17—C18	0.7 (2)	N2—Cr1—N3—C11	73.76 (14)
C15—C16—C17—C18	−177.11 (16)	F1—Cr1—N3—C15	80.13 (11)
C16—C17—C18—C19	−1.2 (3)	F2—Cr1—N3—C15	−38.2 (3)
C17—C18—C19—C20	0.5 (3)	N1—Cr1—N3—C15	171.92 (11)
C18—C19—C20—N4	0.8 (3)	N4—Cr1—N3—C15	−10.02 (11)
C2—C1—N1—C5	0.6 (3)	N2—Cr1—N3—C15	−109.53 (11)
C2—C1—N1—Cr1	−179.17 (14)	C19—C20—N4—C16	−1.3 (2)
C4—C5—N1—C1	−1.9 (2)	C19—C20—N4—Cr1	−174.12 (13)
C6—C5—N1—C1	178.05 (14)	C17—C16—N4—C20	0.5 (2)
C4—C5—N1—Cr1	177.93 (12)	C15—C16—N4—C20	178.53 (14)
C6—C5—N1—Cr1	−2.13 (17)	C17—C16—N4—Cr1	173.91 (12)
F1—Cr1—N1—C1	−2.27 (14)	C15—C16—N4—Cr1	−8.10 (17)
F2—Cr1—N1—C1	93.34 (14)	F1—Cr1—N4—C20	93.33 (13)
N2—Cr1—N1—C1	−179.09 (14)	F2—Cr1—N4—C20	−2.10 (13)
N3—Cr1—N1—C1	−91.93 (14)	N2—Cr1—N4—C20	−91.05 (13)
F1—Cr1—N1—C5	177.92 (11)	N3—Cr1—N4—C20	−177.16 (14)
F2—Cr1—N1—C5	−86.47 (11)	F1—Cr1—N4—C16	−79.72 (11)
N2—Cr1—N1—C5	1.10 (11)	F2—Cr1—N4—C16	−175.15 (11)
N3—Cr1—N1—C5	88.26 (12)	N2—Cr1—N4—C16	95.90 (11)
C9—C10—N2—C6	2.4 (2)	N3—Cr1—N4—C16	9.79 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F1^i	0.95	2.43	3.189 (2)	137
C14—H14···F1^i	0.95	2.35	3.138 (2)	140
C8—H8···F2^ii	0.95	2.32	3.067 (2)	135
C7—H7···F2^iii	0.95	2.43	3.214 (2)	139
C3—H3···O4^iv	0.95	2.49	3.321 (3)	146
C13—H13···O3^v	0.95	2.57	3.264 (2)	130

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