1-(2,6-Difluoro-benzo-yl)-3-(2,3,5-tri-chloro-phen-yl)urea.

The asymmetric unit of the title compound, C(14)H(7)Cl(3)F(2)N(2)O(2), contains two unique molecules. The 2,3,5-trichloro-phenyl ring is almost coplanar with the urea group in both molecules, whereas the 2,6-difluoro-phenyl ring is twisted from the urea plane by 54.83 (10)° in one molecule and 60.58 (10)° in the other. An intra-molecular N-H-O hydrogen bond stabilizes the mol-ecular conformation. The crystal packing is formed by inter-molecular N-H-O hydrogen bonds and F⋯F inter-actions [2.841 (2) Å].

Related literature

For general background, see: Yan et al. (2003 ▶). For synthetic details, see: Lin et al. (2003 ▶, 2005 ▶).

Experimental

Crystal data

C14H7Cl3F2N2O2

M = 379.57

Monoclinic,

a = 7.1669 (4) Å

b = 22.8228 (12) Å

c = 18.2885 (10) Å

β = 94.768 (2)°

V = 2981.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.65 mm−1

T = 113 (2) K

0.24 × 0.14 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2006 ▶) T min = 0.860, T max = 0.927

27779 measured reflections

7091 independent reflections

6011 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.089

S = 1.07

7091 reflections

431 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2006 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032029/jh2065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032029/jh2065Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H7Cl3F2N2O2	Dx = 1.691 Mg m−3
Mr = 379.57	Melting point: 517 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
a = 7.1669 (4) Å	Cell parameters from 6247 reflections
b = 22.8228 (12) Å	θ = 1.8–27.9°
c = 18.2885 (10) Å	µ = 0.65 mm−1
β = 94.768 (2)°	T = 113 K
V = 2981.1 (3) Å3	Prism, colourless
Z = 8	0.24 × 0.14 × 0.12 mm
F(000) = 1520

Rigaku Saturn diffractometer	7091 independent reflections
Radiation source: rotating anode	6011 reflections with I > 2σ(I)
confocal	Rint = 0.050
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 1.8°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2006)	k = −30→30
Tmin = 0.860, Tmax = 0.927	l = −24→24
27779 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.1727P] where P = (Fo2 + 2Fc2)/3
7091 reflections	(Δ/σ)max = 0.001
431 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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

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.

	x	y	z	Uiso*/Ueq
Cl1	0.03364 (7)	0.50654 (2)	0.15961 (2)	0.02733 (12)
Cl2	−0.07937 (7)	0.40202 (2)	0.05408 (2)	0.03038 (12)
Cl3	−0.17311 (7)	0.26475 (2)	0.28607 (3)	0.03149 (12)
Cl4	0.34943 (7)	0.283841 (19)	0.19434 (2)	0.02671 (11)
Cl5	0.36147 (7)	0.28306 (2)	0.36548 (2)	0.03282 (13)
Cl6	0.54168 (7)	0.51085 (2)	0.37218 (2)	0.02918 (12)
F1	−0.17544 (16)	0.64246 (6)	0.45899 (7)	0.0423 (3)
F2	0.44718 (15)	0.65048 (6)	0.39926 (7)	0.0414 (3)
F3	0.04346 (14)	0.34365 (5)	−0.10568 (6)	0.0303 (3)
F4	0.67828 (15)	0.39222 (5)	−0.10684 (6)	0.0327 (3)
O1	−0.02709 (19)	0.44667 (6)	0.42993 (6)	0.0291 (3)
O2	0.14058 (17)	0.59069 (6)	0.31730 (6)	0.0248 (3)
O3	0.51390 (18)	0.48843 (5)	0.09749 (6)	0.0247 (3)
O4	0.33939 (17)	0.32720 (5)	0.01436 (6)	0.0240 (3)
N1	0.0186 (2)	0.48145 (7)	0.31516 (8)	0.0214 (3)
N2	0.0531 (2)	0.54179 (7)	0.41771 (8)	0.0225 (3)
N3	0.4215 (2)	0.39641 (7)	0.12945 (8)	0.0202 (3)
N4	0.4259 (2)	0.42336 (7)	0.00736 (8)	0.0201 (3)
C1	0.0123 (3)	0.48592 (8)	0.38878 (9)	0.0221 (4)
C2	−0.0276 (2)	0.43225 (8)	0.27132 (9)	0.0197 (4)
C3	−0.0277 (2)	0.43974 (8)	0.19488 (9)	0.0212 (4)
C4	−0.0753 (2)	0.39311 (8)	0.14825 (9)	0.0225 (4)
C5	−0.1203 (2)	0.33913 (8)	0.17552 (10)	0.0246 (4)
H5	−0.1524	0.3073	0.1434	0.029*
C6	−0.1176 (2)	0.33237 (8)	0.25079 (10)	0.0226 (4)
C7	−0.0722 (2)	0.37795 (8)	0.29909 (9)	0.0215 (4)
H7	−0.0717	0.3721	0.3505	0.026*
C8	0.1103 (2)	0.59011 (8)	0.38219 (9)	0.0205 (4)
C9	0.1360 (2)	0.64407 (8)	0.42805 (9)	0.0207 (4)
C10	−0.0058 (3)	0.66965 (9)	0.46427 (10)	0.0270 (4)
C11	0.0158 (3)	0.72142 (9)	0.50213 (11)	0.0331 (5)
H11	−0.0859	0.7382	0.5250	0.040*
C12	0.1879 (3)	0.74862 (9)	0.50626 (10)	0.0314 (5)
H12	0.2058	0.7840	0.5334	0.038*
C13	0.3350 (3)	0.72521 (8)	0.47147 (10)	0.0291 (4)
H13	0.4537	0.7440	0.4742	0.035*
C14	0.3047 (3)	0.67426 (8)	0.43304 (10)	0.0252 (4)
C15	0.4574 (2)	0.43923 (8)	0.08133 (9)	0.0193 (4)
C16	0.4364 (2)	0.39918 (8)	0.20631 (9)	0.0193 (4)
C17	0.4017 (2)	0.34714 (8)	0.24369 (9)	0.0205 (4)
C18	0.4090 (3)	0.34667 (8)	0.31982 (9)	0.0227 (4)
C19	0.4524 (2)	0.39688 (8)	0.36001 (9)	0.0241 (4)
H19	0.4574	0.3966	0.4121	0.029*
C20	0.4882 (2)	0.44752 (8)	0.32218 (9)	0.0219 (4)
C21	0.4809 (2)	0.44985 (8)	0.24629 (9)	0.0208 (4)
H21	0.5058	0.4854	0.2220	0.025*
C22	0.3743 (2)	0.37040 (7)	−0.02176 (9)	0.0181 (4)
C23	0.3613 (2)	0.36860 (7)	−0.10363 (9)	0.0185 (4)
C24	0.1951 (3)	0.35418 (8)	−0.14347 (9)	0.0219 (4)
C25	0.1753 (3)	0.35137 (8)	−0.21846 (10)	0.0265 (4)
H25	0.0583	0.3416	−0.2438	0.032*
C26	0.3300 (3)	0.36319 (8)	−0.25635 (10)	0.0290 (4)
H26	0.3189	0.3617	−0.3084	0.035*
C27	0.5015 (3)	0.37721 (8)	−0.21950 (10)	0.0281 (4)
H27	0.6082	0.3848	−0.2456	0.034*
C28	0.5121 (2)	0.37969 (8)	−0.14440 (10)	0.0224 (4)
H1	0.050 (3)	0.5150 (9)	0.2941 (11)	0.033 (6)*
H2	0.053 (3)	0.5433 (10)	0.4626 (12)	0.039 (6)*
H3	0.392 (3)	0.3651 (9)	0.1119 (12)	0.036 (7)*
H4	0.441 (3)	0.4529 (10)	−0.0251 (12)	0.045 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0356 (3)	0.0278 (3)	0.0190 (2)	−0.0018 (2)	0.00479 (18)	−0.00021 (17)
Cl2	0.0346 (3)	0.0393 (3)	0.0171 (2)	0.0015 (2)	0.00166 (18)	−0.00678 (18)
Cl3	0.0359 (3)	0.0224 (3)	0.0360 (3)	−0.0003 (2)	0.0023 (2)	−0.00089 (19)
Cl4	0.0352 (3)	0.0200 (2)	0.0249 (2)	−0.00355 (19)	0.00249 (19)	0.00437 (17)
Cl5	0.0422 (3)	0.0311 (3)	0.0256 (2)	−0.0054 (2)	0.0058 (2)	0.01259 (19)
Cl6	0.0362 (3)	0.0271 (3)	0.0243 (2)	0.0022 (2)	0.00324 (19)	−0.00380 (18)
F1	0.0232 (6)	0.0534 (9)	0.0519 (8)	−0.0052 (6)	0.0122 (5)	−0.0179 (6)
F2	0.0237 (6)	0.0504 (8)	0.0518 (8)	−0.0071 (6)	0.0141 (5)	−0.0213 (6)
F3	0.0211 (6)	0.0405 (7)	0.0298 (6)	−0.0052 (5)	0.0058 (5)	0.0026 (5)
F4	0.0204 (6)	0.0436 (7)	0.0345 (6)	−0.0041 (5)	0.0055 (5)	−0.0001 (5)
O1	0.0437 (8)	0.0258 (7)	0.0185 (6)	−0.0046 (6)	0.0073 (6)	−0.0011 (5)
O2	0.0277 (7)	0.0292 (7)	0.0178 (6)	−0.0046 (6)	0.0037 (5)	−0.0016 (5)
O3	0.0349 (8)	0.0192 (7)	0.0204 (6)	−0.0058 (6)	0.0052 (5)	0.0014 (5)
O4	0.0319 (7)	0.0177 (7)	0.0229 (6)	−0.0010 (5)	0.0050 (5)	0.0041 (5)
N1	0.0256 (9)	0.0223 (9)	0.0166 (7)	−0.0023 (7)	0.0035 (6)	−0.0022 (6)
N2	0.0290 (9)	0.0241 (9)	0.0149 (7)	−0.0038 (7)	0.0048 (6)	−0.0033 (6)
N3	0.0258 (8)	0.0179 (8)	0.0172 (7)	−0.0012 (7)	0.0031 (6)	0.0026 (6)
N4	0.0257 (8)	0.0174 (8)	0.0176 (7)	−0.0017 (6)	0.0039 (6)	0.0034 (6)
C1	0.0236 (10)	0.0244 (10)	0.0184 (8)	−0.0008 (8)	0.0027 (7)	−0.0035 (7)
C2	0.0163 (9)	0.0248 (10)	0.0182 (8)	0.0019 (7)	0.0023 (7)	−0.0053 (7)
C3	0.0180 (9)	0.0248 (10)	0.0212 (8)	0.0025 (7)	0.0032 (7)	−0.0002 (7)
C4	0.0177 (9)	0.0317 (11)	0.0178 (8)	0.0041 (8)	0.0007 (7)	−0.0059 (7)
C5	0.0216 (10)	0.0263 (10)	0.0259 (9)	0.0025 (8)	0.0026 (7)	−0.0067 (7)
C6	0.0179 (9)	0.0216 (10)	0.0286 (9)	0.0031 (7)	0.0031 (7)	−0.0017 (7)
C7	0.0182 (9)	0.0265 (10)	0.0198 (8)	0.0029 (7)	0.0015 (7)	−0.0006 (7)
C8	0.0155 (9)	0.0257 (10)	0.0203 (8)	0.0000 (7)	0.0017 (7)	0.0000 (7)
C9	0.0220 (9)	0.0226 (10)	0.0173 (8)	0.0009 (7)	0.0005 (7)	0.0004 (7)
C10	0.0212 (10)	0.0313 (11)	0.0287 (10)	0.0002 (8)	0.0040 (8)	−0.0021 (8)
C11	0.0374 (12)	0.0305 (12)	0.0325 (11)	0.0085 (9)	0.0101 (9)	−0.0058 (8)
C12	0.0482 (13)	0.0213 (10)	0.0249 (9)	0.0001 (9)	0.0043 (9)	−0.0016 (8)
C13	0.0349 (12)	0.0274 (11)	0.0251 (9)	−0.0068 (9)	0.0028 (8)	0.0001 (8)
C14	0.0235 (10)	0.0278 (11)	0.0250 (9)	−0.0001 (8)	0.0052 (7)	−0.0012 (7)
C15	0.0188 (9)	0.0206 (10)	0.0190 (8)	0.0016 (7)	0.0039 (7)	0.0029 (7)
C16	0.0171 (9)	0.0221 (9)	0.0190 (8)	0.0025 (7)	0.0027 (7)	0.0039 (7)
C17	0.0175 (9)	0.0213 (10)	0.0231 (9)	0.0011 (7)	0.0034 (7)	0.0036 (7)
C18	0.0219 (9)	0.0244 (10)	0.0221 (9)	0.0023 (8)	0.0047 (7)	0.0090 (7)
C19	0.0227 (10)	0.0316 (11)	0.0185 (8)	0.0034 (8)	0.0049 (7)	0.0044 (7)
C20	0.0184 (9)	0.0243 (10)	0.0232 (9)	0.0040 (7)	0.0027 (7)	−0.0003 (7)
C21	0.0199 (9)	0.0206 (9)	0.0223 (9)	0.0028 (7)	0.0039 (7)	0.0047 (7)
C22	0.0156 (9)	0.0177 (9)	0.0214 (8)	0.0036 (7)	0.0032 (7)	−0.0001 (7)
C23	0.0217 (9)	0.0147 (9)	0.0197 (8)	0.0030 (7)	0.0049 (7)	0.0013 (6)
C24	0.0237 (10)	0.0179 (9)	0.0250 (9)	−0.0003 (7)	0.0075 (7)	0.0028 (7)
C25	0.0301 (11)	0.0239 (10)	0.0249 (9)	−0.0028 (8)	−0.0017 (8)	0.0020 (7)
C26	0.0461 (13)	0.0223 (10)	0.0192 (9)	−0.0019 (9)	0.0056 (8)	−0.0004 (7)
C27	0.0328 (11)	0.0251 (11)	0.0283 (10)	−0.0008 (8)	0.0142 (8)	0.0011 (8)
C28	0.0209 (9)	0.0203 (10)	0.0265 (9)	0.0010 (7)	0.0040 (7)	−0.0014 (7)

Cl1—C3	1.7265 (18)	C5—H5	0.9500
Cl2—C4	1.7320 (18)	C6—C7	1.386 (2)
Cl3—C6	1.7317 (19)	C7—H7	0.9500
Cl4—C17	1.7280 (18)	C8—C9	1.493 (2)
Cl5—C18	1.7228 (18)	C9—C10	1.387 (2)
Cl6—C20	1.7362 (19)	C9—C14	1.388 (3)
F1—C10	1.361 (2)	C10—C11	1.372 (3)
F2—C14	1.350 (2)	C11—C12	1.377 (3)
F3—C24	1.357 (2)	C11—H11	0.9500
F4—C28	1.355 (2)	C12—C13	1.383 (3)
O1—C1	1.218 (2)	C12—H12	0.9500
O2—C8	1.224 (2)	C13—C14	1.367 (3)
O3—C15	1.222 (2)	C13—H13	0.9500
O4—C22	1.224 (2)	C16—C21	1.391 (2)
N1—C1	1.355 (2)	C16—C17	1.403 (2)
N1—C2	1.403 (2)	C17—C18	1.389 (2)
N1—H1	0.89 (2)	C18—C19	1.383 (3)
N2—C8	1.360 (2)	C19—C20	1.382 (2)
N2—C1	1.402 (2)	C19—H19	0.9500
N2—H2	0.82 (2)	C20—C21	1.386 (2)
N3—C15	1.354 (2)	C21—H21	0.9500
N3—C16	1.402 (2)	C22—C23	1.493 (2)
N3—H3	0.80 (2)	C23—C24	1.383 (2)
N4—C22	1.360 (2)	C23—C28	1.386 (2)
N4—C15	1.401 (2)	C24—C25	1.369 (2)
N4—H4	0.91 (2)	C25—C26	1.382 (3)
C2—C7	1.387 (2)	C25—H25	0.9500
C2—C3	1.408 (2)	C26—C27	1.389 (3)
C3—C4	1.388 (2)	C26—H26	0.9500
C4—C5	1.377 (3)	C27—C28	1.370 (2)
C5—C6	1.384 (2)	C27—H27	0.9500
C1—N1—C2	127.03 (16)	C14—C13—C12	118.06 (19)
C1—N1—H1	113.2 (13)	C14—C13—H13	121.0
C2—N1—H1	119.6 (13)	C12—C13—H13	121.0
C8—N2—C1	128.23 (15)	F2—C14—C13	118.90 (17)
C8—N2—H2	117.9 (15)	F2—C14—C9	117.26 (16)
C1—N2—H2	113.4 (15)	C13—C14—C9	123.81 (18)
C15—N3—C16	128.03 (16)	O3—C15—N3	125.68 (16)
C15—N3—H3	116.0 (16)	O3—C15—N4	119.67 (15)
C16—N3—H3	115.9 (16)	N3—C15—N4	114.65 (15)
C22—N4—C15	128.67 (14)	C21—C16—N3	124.02 (15)
C22—N4—H4	116.5 (14)	C21—C16—C17	119.34 (16)
C15—N4—H4	114.8 (14)	N3—C16—C17	116.64 (15)
O1—C1—N1	125.96 (17)	C18—C17—C16	120.11 (16)
O1—C1—N2	119.17 (15)	C18—C17—Cl4	120.36 (14)
N1—C1—N2	114.85 (15)	C16—C17—Cl4	119.53 (13)
C7—C2—N1	123.82 (15)	C19—C18—C17	120.96 (16)
C7—C2—C3	119.40 (16)	C19—C18—Cl5	119.04 (13)
N1—C2—C3	116.79 (16)	C17—C18—Cl5	120.00 (14)
C4—C3—C2	119.77 (17)	C20—C19—C18	118.02 (16)
C4—C3—Cl1	120.30 (14)	C20—C19—H19	121.0
C2—C3—Cl1	119.93 (14)	C18—C19—H19	121.0
C5—C4—C3	121.06 (16)	C19—C20—C21	122.72 (17)
C5—C4—Cl2	118.68 (14)	C19—C20—Cl6	118.33 (13)
C3—C4—Cl2	120.25 (15)	C21—C20—Cl6	118.94 (14)
C4—C5—C6	118.41 (17)	C20—C21—C16	118.84 (16)
C4—C5—H5	120.8	C20—C21—H21	120.6
C6—C5—H5	120.8	C16—C21—H21	120.6
C5—C6—C7	122.24 (17)	O4—C22—N4	124.46 (16)
C5—C6—Cl3	119.04 (14)	O4—C22—C23	121.38 (15)
C7—C6—Cl3	118.72 (14)	N4—C22—C23	114.16 (14)
C6—C7—C2	119.11 (16)	C24—C23—C28	115.82 (16)
C6—C7—H7	120.4	C24—C23—C22	120.91 (15)
C2—C7—H7	120.4	C28—C23—C22	123.25 (16)
O2—C8—N2	123.81 (17)	F3—C24—C25	118.75 (16)
O2—C8—C9	120.80 (16)	F3—C24—C23	117.71 (15)
N2—C8—C9	115.39 (15)	C25—C24—C23	123.53 (17)
C10—C9—C14	115.37 (17)	C24—C25—C26	118.19 (17)
C10—C9—C8	123.65 (16)	C24—C25—H25	120.9
C14—C9—C8	120.86 (16)	C26—C25—H25	120.9
F1—C10—C11	119.38 (17)	C25—C26—C27	121.07 (17)
F1—C10—C9	117.38 (17)	C25—C26—H26	119.5
C11—C10—C9	123.19 (18)	C27—C26—H26	119.5
C10—C11—C12	118.59 (19)	C28—C27—C26	117.96 (17)
C10—C11—H11	120.7	C28—C27—H27	121.0
C12—C11—H11	120.7	C26—C27—H27	121.0
C11—C12—C13	120.94 (19)	F4—C28—C27	119.34 (16)
C11—C12—H12	119.5	F4—C28—C23	117.21 (15)
C13—C12—H12	119.5	C27—C28—C23	123.43 (17)
C2—N1—C1—O1	3.5 (3)	C16—N3—C15—O3	1.6 (3)
C2—N1—C1—N2	−175.52 (16)	C16—N3—C15—N4	−178.88 (16)
C8—N2—C1—O1	175.84 (18)	C22—N4—C15—O3	175.83 (17)
C8—N2—C1—N1	−5.1 (3)	C22—N4—C15—N3	−3.8 (3)
C1—N1—C2—C7	−6.0 (3)	C15—N3—C16—C21	4.5 (3)
C1—N1—C2—C3	173.97 (17)	C15—N3—C16—C17	−176.16 (17)
C7—C2—C3—C4	1.1 (3)	C21—C16—C17—C18	1.0 (3)
N1—C2—C3—C4	−178.90 (16)	N3—C16—C17—C18	−178.33 (16)
C7—C2—C3—Cl1	−178.25 (13)	C21—C16—C17—Cl4	−179.16 (13)
N1—C2—C3—Cl1	1.8 (2)	N3—C16—C17—Cl4	1.5 (2)
C2—C3—C4—C5	−0.9 (3)	C16—C17—C18—C19	−0.8 (3)
Cl1—C3—C4—C5	178.44 (14)	Cl4—C17—C18—C19	179.40 (14)
C2—C3—C4—Cl2	179.03 (13)	C16—C17—C18—Cl5	178.62 (14)
Cl1—C3—C4—Cl2	−1.7 (2)	Cl4—C17—C18—Cl5	−1.2 (2)
C3—C4—C5—C6	0.2 (3)	C17—C18—C19—C20	0.0 (3)
Cl2—C4—C5—C6	−179.71 (13)	Cl5—C18—C19—C20	−179.39 (13)
C4—C5—C6—C7	0.3 (3)	C18—C19—C20—C21	0.5 (3)
C4—C5—C6—Cl3	−179.82 (13)	C18—C19—C20—Cl6	179.69 (14)
C5—C6—C7—C2	−0.1 (3)	C19—C20—C21—C16	−0.3 (3)
Cl3—C6—C7—C2	−179.98 (13)	Cl6—C20—C21—C16	−179.44 (13)
N1—C2—C7—C6	179.38 (16)	N3—C16—C21—C20	178.79 (16)
C3—C2—C7—C6	−0.6 (3)	C17—C16—C21—C20	−0.5 (3)
C1—N2—C8—O2	−2.4 (3)	C15—N4—C22—O4	2.9 (3)
C1—N2—C8—C9	177.94 (17)	C15—N4—C22—C23	−177.49 (16)
O2—C8—C9—C10	121.2 (2)	O4—C22—C23—C24	58.7 (2)
N2—C8—C9—C10	−59.1 (2)	N4—C22—C23—C24	−120.91 (18)
O2—C8—C9—C14	−54.5 (2)	O4—C22—C23—C28	−119.8 (2)
N2—C8—C9—C14	125.14 (18)	N4—C22—C23—C28	60.5 (2)
C14—C9—C10—F1	178.06 (16)	C28—C23—C24—F3	−179.26 (15)
C8—C9—C10—F1	2.1 (3)	C22—C23—C24—F3	2.1 (2)
C14—C9—C10—C11	0.6 (3)	C28—C23—C24—C25	−0.8 (3)
C8—C9—C10—C11	−175.38 (18)	C22—C23—C24—C25	−179.46 (17)
F1—C10—C11—C12	−179.34 (17)	F3—C24—C25—C26	178.90 (16)
C9—C10—C11—C12	−1.9 (3)	C23—C24—C25—C26	0.5 (3)
C10—C11—C12—C13	1.7 (3)	C24—C25—C26—C27	0.4 (3)
C11—C12—C13—C14	−0.1 (3)	C25—C26—C27—C28	−0.8 (3)
C12—C13—C14—F2	−179.42 (17)	C26—C27—C28—F4	178.83 (16)
C12—C13—C14—C9	−1.3 (3)	C26—C27—C28—C23	0.4 (3)
C10—C9—C14—F2	179.24 (16)	C24—C23—C28—F4	−178.09 (15)
C8—C9—C14—F2	−4.7 (3)	C22—C23—C28—F4	0.5 (3)
C10—C9—C14—C13	1.1 (3)	C24—C23—C28—C27	0.4 (3)
C8—C9—C14—C13	177.14 (17)	C22—C23—C28—C27	178.97 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.89 (2)	2.46 (2)	2.9126 (15)	111.8 (16)
N1—H1···O2	0.89 (2)	1.88 (2)	2.641 (2)	141.5 (19)
N2—H2···O1i	0.82 (2)	2.00 (2)	2.8205 (19)	173 (2)
N3—H3···Cl4	0.80 (2)	2.43 (2)	2.8944 (16)	118.2 (19)
N3—H3···O4	0.80 (2)	1.99 (2)	2.658 (2)	140 (2)
N4—H4···O3ii	0.91 (2)	1.93 (2)	2.8378 (18)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.89 (2)	2.46 (2)	2.9126 (15)	111.8 (16)
N1—H1⋯O2	0.89 (2)	1.88 (2)	2.641 (2)	141.5 (19)
N2—H2⋯O1i	0.82 (2)	2.00 (2)	2.8205 (19)	173 (2)
N3—H3⋯Cl4	0.80 (2)	2.43 (2)	2.8944 (16)	118.2 (19)
N3—H3⋯O4	0.80 (2)	1.99 (2)	2.658 (2)	140 (2)
N4—H4⋯O3ii	0.91 (2)	1.93 (2)	2.8378 (18)	176 (2)

Symmetry codes: (i) ; (ii) .