N-{2-Chloro-5-[3-methyl-2,6-dioxo-4-(trifluoro­meth­yl)-1,2,3,6-tetra­hydro­pyrimidin­yl]phen­yl}-2,2-bis­(3-fluoro­phen­oxy)acetamide

The title compound, C₂₆H₁₇ClF₅N₃O₅, belongs to a new class of amide compounds having potential biological activity. The pyrimidine ring makes a dihedral angle of 61.66 (2)° with the adjacent benzene ring. The dihedral angle between the other two benzene rings is 73.12 (1)°. There are intra­molecular C—H...O, C—H...F, N—H...O and N—H...Cl hydrogen bonds. One of the fluoro­phenyl groups is disordered over two positions in a ratio of ca. 3:1. The mol­ecules are connected by inter­molecular Cl...O non-bonded inter­actions [Cl...O = 3.054 (2) Å], forming a dimer.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.054
• wR factor = 0.163
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C17    -   C18    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C18    -   C19    ...       1.35 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C19    -   C20    ...       1.36 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C20    -   C21    ...       1.38 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O1      ..       3.05 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C15    = ...          S

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

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

---

S1. Comment

The title compound, (I), is a new class of amide compounds having potential biological activity. Preliminary bioassay showed that the title compound had good herbicidal activity (Huang et al., 2006).

The molecular structure of (I) is shown in Fig. 1. The torsion angle of C9—N3—C14—C15 is 179.1 (2)°. The molecules are connected by two intermolecular Cl···O nonbonded interactions (Bruno et al., 1997) to form a dimer. The distance between atom Cl1 and atom O1 at (2 - x, 1 - y, 2 - z) is 3.0542 (18) Å. The crystal packing is stabilized by van der Waals forces.

Related literature

For the preparation of the title compound, see: Huang et al. (2006). For related literature, see: Bruno et al. (1997).

S2. Experimental

The title compound was synthesized according to the procedure of Huang et al. (2006) in 85% isolated yield. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a DMF and MeOH solution in a ratio of 4:1 at 293 K.

S3. Refinement

One of the fluorophenyl groups was found to be disordered over two orientations. The occupancies refined to 0.751 (5) and 0.249 (5). The N-bound H atom was located in a difference map and the positional parameters were refined, with U_iso(H) = 1.2U_eq(N). The refined N—H distance is 0.85 (4) Å. Other H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined using a riding model, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures

Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius. Only one component of the disordered fluorophenyl group is shown.

N-{2-Chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6- tetrahydropyrimidinyl]phenyl}-2,2-bis(3-fluorophenoxy)acetamide

Crystal data

C26H17ClF5N3O5	F(000) = 1184
Mr = 581.88	Dx = 1.519 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7373 reflections
a = 16.2280 (13) Å	θ = 2.6–26.7°
b = 6.7102 (6) Å	µ = 0.23 mm^−1
c = 23.772 (2) Å	T = 299 K
β = 100.588 (1)°	Block, colorless
V = 2544.5 (4) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area detector diffractometer	5563 independent reflections
Radiation source: fine-focus sealed tube	4336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ϕ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick,1997)	h = −20→20
Tmin = 0.934, Tmax = 0.955	k = −8→8
22744 measured reflections	l = −30→30

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0929P)^2 + 0.7196P] where P = (Fo^2 + 2Fc^2)/3
5563 reflections	(Δ/σ)max = 0.001
375 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.88345 (19)	0.9362 (5)	0.64714 (12)	0.0825 (8)
C2	0.88883 (14)	0.8305 (3)	0.70435 (9)	0.0552 (5)
C3	0.93968 (15)	0.9015 (3)	0.74941 (9)	0.0588 (5)
H3	0.9698	1.0172	0.7458	0.071*
C4	0.94969 (14)	0.8034 (3)	0.80437 (9)	0.0506 (5)
C5	0.84156 (14)	0.5638 (3)	0.75695 (9)	0.0534 (5)
C6	0.7834 (2)	0.5816 (5)	0.65599 (11)	0.0881 (9)
H6A	0.7297	0.6451	0.6529	0.132*
H6B	0.7772	0.4408	0.6610	0.132*
H6C	0.8053	0.6057	0.6218	0.132*
C7	0.90085 (12)	0.5314 (3)	0.85767 (8)	0.0455 (4)
C8	0.87154 (12)	0.6237 (3)	0.90172 (8)	0.0454 (4)
H8	0.8468	0.7489	0.8964	0.055*
C9	0.87921 (12)	0.5283 (3)	0.95440 (8)	0.0440 (4)
C10	0.91616 (12)	0.3399 (3)	0.96041 (8)	0.0454 (4)
C11	0.94398 (14)	0.2474 (3)	0.91578 (9)	0.0524 (5)
H11	0.9674	0.1207	0.9205	0.063*
C12	0.93680 (14)	0.3443 (3)	0.86379 (9)	0.0519 (5)
H12	0.9559	0.2843	0.8333	0.062*
C14	0.80870 (14)	0.7796 (3)	1.00481 (9)	0.0538 (5)
C15	0.79113 (15)	0.8288 (4)	1.06480 (9)	0.0568 (5)
H15	0.8123	0.9617	1.0770	0.068*
C16	0.65624 (14)	0.9874 (3)	1.05906 (8)	0.0529 (5)
C17	0.57840 (15)	0.9618 (4)	1.07377 (10)	0.0651 (6)
H17	0.5623	0.8388	1.0862	0.078*
C18	0.52584 (16)	1.1224 (5)	1.06957 (12)	0.0747 (7)
H18	0.4729	1.1055	1.0786	0.090*	0.249 (5)
C19	0.5473 (2)	1.3048 (5)	1.05286 (12)	0.0805 (8)
H19	0.5111	1.4128	1.0518	0.097*
C20	0.6237 (2)	1.3247 (4)	1.03773 (13)	0.0836 (8)
H20	0.6391	1.4482	1.0252	0.100*	0.751 (5)
C21	0.67913 (18)	1.1675 (4)	1.04039 (12)	0.0715 (7)
H21	0.7310	1.1842	1.0297	0.086*
C22	0.83759 (15)	0.7165 (4)	1.16139 (9)	0.0615 (6)
C23	0.87687 (17)	0.5641 (5)	1.19444 (10)	0.0733 (7)
H23	0.8940	0.4497	1.1777	0.088*
C24	0.8901 (2)	0.5852 (5)	1.25253 (11)	0.0857 (9)
C25	0.8651 (2)	0.7482 (5)	1.27896 (12)	0.0861 (9)
H25	0.8746	0.7573	1.3187	0.103*
C26	0.82576 (19)	0.8982 (5)	1.24552 (12)	0.0824 (8)
H26	0.8086	1.0118	1.2626	0.099*
C27	0.81105 (19)	0.8823 (5)	1.18607 (11)	0.0767 (8)
H27	0.7834	0.9838	1.1634	0.092*
Cl1	0.93109 (4)	0.22525 (8)	1.02710 (2)	0.05918 (19)
F1	0.93072 (17)	1.1027 (4)	0.65464 (9)	0.1384 (9)
F2	0.91365 (15)	0.8294 (4)	0.60997 (7)	0.1204 (8)
F3	0.80970 (13)	0.9976 (4)	0.62507 (9)	0.1256 (8)
F4	0.92954 (19)	0.4374 (4)	1.28489 (8)	0.1533 (11)
F5	0.44825 (14)	1.0954 (5)	1.08063 (13)	0.1160 (12)	0.751 (5)
F5'	0.6391 (6)	1.4752 (10)	1.0068 (3)	0.107 (3)	0.249 (5)
H3A	0.871 (2)	0.556 (6)	1.0340 (17)	0.129*
N1	0.89657 (11)	0.6373 (2)	0.80425 (6)	0.0469 (4)
N2	0.84131 (12)	0.6632 (3)	0.70551 (7)	0.0563 (5)
N3	0.85381 (12)	0.6140 (3)	1.00225 (7)	0.0545 (5)
O1	0.99850 (12)	0.8528 (3)	0.84664 (7)	0.0683 (5)
O2	0.79781 (12)	0.4212 (3)	0.76047 (7)	0.0780 (5)
O3	0.78186 (14)	0.8891 (3)	0.96539 (7)	0.0821 (6)
O4	0.70443 (11)	0.8169 (2)	1.06338 (8)	0.0644 (4)
O5	0.82930 (12)	0.6831 (3)	1.10315 (6)	0.0727 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0791 (18)	0.114 (2)	0.0576 (15)	0.0048 (17)	0.0198 (14)	0.0289 (15)
C2	0.0572 (13)	0.0653 (13)	0.0473 (11)	0.0154 (10)	0.0206 (10)	0.0139 (9)
C3	0.0713 (14)	0.0582 (12)	0.0500 (12)	0.0016 (11)	0.0192 (11)	0.0115 (9)
C4	0.0623 (13)	0.0472 (10)	0.0445 (10)	0.0022 (9)	0.0158 (9)	0.0032 (8)
C5	0.0579 (12)	0.0604 (12)	0.0425 (10)	0.0002 (10)	0.0109 (9)	0.0020 (9)
C6	0.095 (2)	0.111 (2)	0.0495 (13)	−0.0142 (18)	−0.0110 (13)	−0.0026 (14)
C7	0.0502 (11)	0.0483 (10)	0.0380 (9)	−0.0019 (8)	0.0083 (8)	0.0051 (8)
C8	0.0486 (11)	0.0462 (10)	0.0416 (10)	0.0048 (8)	0.0087 (8)	0.0058 (8)
C9	0.0434 (10)	0.0499 (10)	0.0388 (9)	0.0009 (8)	0.0082 (8)	0.0047 (8)
C10	0.0461 (10)	0.0482 (10)	0.0404 (9)	−0.0019 (8)	0.0037 (8)	0.0115 (8)
C11	0.0602 (13)	0.0432 (10)	0.0532 (11)	0.0066 (9)	0.0088 (10)	0.0064 (8)
C12	0.0624 (13)	0.0499 (11)	0.0448 (10)	0.0037 (9)	0.0135 (9)	0.0000 (8)
C14	0.0592 (13)	0.0590 (12)	0.0436 (10)	0.0067 (10)	0.0104 (9)	0.0033 (9)
C15	0.0629 (13)	0.0612 (12)	0.0482 (11)	0.0120 (10)	0.0156 (10)	0.0051 (9)
C16	0.0584 (12)	0.0557 (12)	0.0454 (10)	0.0053 (10)	0.0119 (9)	−0.0046 (9)
C17	0.0677 (15)	0.0713 (15)	0.0595 (13)	−0.0063 (12)	0.0201 (11)	−0.0160 (11)
C18	0.0584 (15)	0.101 (2)	0.0655 (15)	0.0096 (14)	0.0146 (12)	−0.0249 (14)
C19	0.086 (2)	0.088 (2)	0.0665 (16)	0.0330 (16)	0.0116 (14)	−0.0071 (14)
C20	0.104 (2)	0.0643 (16)	0.0851 (19)	0.0186 (15)	0.0228 (17)	0.0117 (14)
C21	0.0702 (16)	0.0648 (14)	0.0845 (17)	0.0095 (12)	0.0273 (14)	0.0109 (13)
C22	0.0621 (14)	0.0810 (15)	0.0451 (11)	0.0121 (12)	0.0194 (10)	0.0060 (10)
C23	0.0777 (17)	0.0929 (18)	0.0534 (13)	0.0225 (15)	0.0226 (12)	0.0106 (12)
C24	0.0880 (19)	0.117 (2)	0.0524 (14)	0.0277 (18)	0.0141 (13)	0.0201 (15)
C25	0.086 (2)	0.125 (3)	0.0460 (13)	0.0088 (18)	0.0090 (13)	0.0008 (15)
C26	0.090 (2)	0.102 (2)	0.0570 (14)	0.0049 (17)	0.0183 (14)	−0.0113 (14)
C27	0.093 (2)	0.0870 (18)	0.0519 (13)	0.0207 (15)	0.0182 (13)	0.0032 (12)
Cl1	0.0670 (4)	0.0602 (3)	0.0492 (3)	0.0042 (2)	0.0075 (2)	0.0205 (2)
F1	0.168 (2)	0.155 (2)	0.0876 (13)	−0.0499 (18)	0.0122 (13)	0.0612 (14)
F2	0.1407 (18)	0.177 (2)	0.0551 (9)	0.0265 (15)	0.0492 (11)	0.0164 (11)
F3	0.0993 (13)	0.177 (2)	0.0969 (13)	0.0403 (14)	0.0087 (11)	0.0773 (14)
F4	0.210 (3)	0.177 (2)	0.0691 (11)	0.096 (2)	0.0160 (14)	0.0350 (13)
F5	0.0706 (16)	0.134 (2)	0.152 (3)	0.0061 (14)	0.0437 (16)	−0.0359 (19)
F5'	0.156 (8)	0.066 (4)	0.093 (5)	0.022 (4)	0.007 (5)	0.001 (4)
N1	0.0576 (10)	0.0485 (9)	0.0354 (8)	0.0017 (7)	0.0106 (7)	0.0029 (6)
N2	0.0582 (11)	0.0739 (12)	0.0360 (8)	0.0076 (9)	0.0061 (7)	0.0006 (8)
N3	0.0632 (11)	0.0629 (11)	0.0395 (9)	0.0129 (9)	0.0152 (8)	0.0097 (7)
O1	0.0873 (12)	0.0661 (10)	0.0489 (9)	−0.0207 (9)	0.0056 (8)	−0.0010 (7)
O2	0.0875 (12)	0.0848 (12)	0.0570 (10)	−0.0268 (11)	0.0004 (9)	0.0027 (8)
O3	0.1186 (15)	0.0829 (12)	0.0449 (8)	0.0448 (11)	0.0155 (9)	0.0115 (8)
O4	0.0674 (10)	0.0515 (8)	0.0794 (11)	0.0045 (7)	0.0274 (8)	0.0028 (8)
O5	0.0974 (13)	0.0815 (11)	0.0427 (8)	0.0353 (10)	0.0218 (8)	0.0094 (8)

Geometric parameters (Å, º)

C1—F3	1.283 (3)	C14—C15	1.541 (3)
C1—F2	1.302 (4)	C15—O5	1.401 (3)
C1—F1	1.348 (4)	C15—O4	1.403 (3)
C1—C2	1.522 (3)	C15—H15	0.9800
C2—C3	1.315 (3)	C16—C21	1.362 (3)
C2—N2	1.365 (3)	C16—O4	1.379 (3)
C3—C4	1.445 (3)	C16—C17	1.382 (3)
C3—H3	0.9300	C17—C18	1.366 (4)
C4—O1	1.206 (3)	C17—H17	0.9300
C4—N1	1.408 (3)	C18—F5	1.345 (4)
C5—O2	1.204 (3)	C18—C19	1.352 (4)
C5—N1	1.391 (3)	C18—H18	0.9300
C5—N2	1.392 (3)	C19—C20	1.360 (4)
C6—N2	1.471 (3)	C19—H19	0.9300
C6—H6A	0.9600	C20—F5'	1.299 (8)
C6—H6B	0.9600	C20—C21	1.380 (4)
C6—H6C	0.9600	C20—H20	0.9300
C7—C8	1.375 (3)	C21—H21	0.9300
C7—C12	1.380 (3)	C22—C27	1.364 (4)
C7—N1	1.446 (2)	C22—C23	1.373 (3)
C8—C9	1.392 (2)	C22—O5	1.384 (3)
C8—H8	0.9300	C23—C24	1.366 (4)
C9—C10	1.395 (3)	C23—H23	0.9300
C9—N3	1.402 (2)	C24—F4	1.343 (3)
C10—C11	1.375 (3)	C24—C25	1.360 (4)
C10—Cl1	1.7387 (18)	C25—C26	1.366 (4)
C11—C12	1.382 (3)	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.394 (4)
C12—H12	0.9300	C26—H26	0.9300
C14—O3	1.208 (3)	C27—H27	0.9300
C14—N3	1.338 (3)	N3—H3A	0.85 (4)
F3—C1—F2	109.8 (3)	C21—C16—O4	125.1 (2)
F3—C1—F1	104.7 (3)	C21—C16—C17	120.6 (2)
F2—C1—F1	105.7 (3)	O4—C16—C17	114.2 (2)
F3—C1—C2	114.3 (2)	C18—C17—C16	118.1 (3)
F2—C1—C2	112.5 (3)	C18—C17—H17	121.0
F1—C1—C2	109.3 (2)	C16—C17—H17	121.0
C3—C2—N2	123.61 (19)	F5—C18—C19	118.7 (3)
C3—C2—C1	118.9 (2)	F5—C18—C17	118.3 (3)
N2—C2—C1	117.5 (2)	C19—C18—C17	123.0 (3)
C2—C3—C4	121.4 (2)	C19—C18—H18	118.5
C2—C3—H3	119.3	C17—C18—H18	118.5
C4—C3—H3	119.3	C18—C19—C20	117.6 (3)
O1—C4—N1	121.80 (18)	C18—C19—H19	121.2
O1—C4—C3	125.2 (2)	C20—C19—H19	121.2
N1—C4—C3	113.04 (19)	F5'—C20—C19	120.4 (5)
O2—C5—N1	121.66 (19)	F5'—C20—C21	115.4 (5)
O2—C5—N2	122.4 (2)	C19—C20—C21	122.1 (3)
N1—C5—N2	115.97 (19)	C19—C20—H20	119.0
N2—C6—H6A	109.5	C21—C20—H20	119.0
N2—C6—H6B	109.5	C16—C21—C20	118.6 (3)
H6A—C6—H6B	109.5	C16—C21—H21	120.7
N2—C6—H6C	109.5	C20—C21—H21	120.7
H6A—C6—H6C	109.5	C27—C22—C23	120.8 (2)
H6B—C6—H6C	109.5	C27—C22—O5	125.6 (2)
C8—C7—C12	121.87 (17)	C23—C22—O5	113.7 (2)
C8—C7—N1	118.68 (17)	C24—C23—C22	118.1 (3)
C12—C7—N1	119.40 (17)	C24—C23—H23	120.9
C7—C8—C9	119.47 (18)	C22—C23—H23	120.9
C7—C8—H8	120.3	F4—C24—C25	118.7 (3)
C9—C8—H8	120.3	F4—C24—C23	118.2 (3)
C8—C9—C10	118.33 (17)	C25—C24—C23	123.1 (3)
C8—C9—N3	123.38 (18)	C24—C25—C26	118.1 (3)
C10—C9—N3	118.27 (16)	C24—C25—H25	120.9
C11—C10—C9	121.73 (17)	C26—C25—H25	120.9
C11—C10—Cl1	119.57 (15)	C25—C26—C27	120.6 (3)
C9—C10—Cl1	118.64 (15)	C25—C26—H26	119.7
C10—C11—C12	119.46 (18)	C27—C26—H26	119.7
C10—C11—H11	120.3	C22—C27—C26	119.3 (3)
C12—C11—H11	120.3	C22—C27—H27	120.3
C7—C12—C11	119.11 (19)	C26—C27—H27	120.3
C7—C12—H12	120.4	C5—N1—C4	125.71 (17)
C11—C12—H12	120.4	C5—N1—C7	117.09 (17)
O3—C14—N3	126.3 (2)	C4—N1—C7	117.18 (16)
O3—C14—C15	119.10 (19)	C2—N2—C5	120.07 (18)
N3—C14—C15	114.58 (18)	C2—N2—C6	124.8 (2)
O5—C15—O4	107.31 (18)	C5—N2—C6	115.0 (2)
O5—C15—C14	108.54 (17)	C14—N3—C9	128.49 (17)
O4—C15—C14	108.71 (19)	C14—N3—H3A	115 (3)
O5—C15—H15	110.7	C9—N3—H3A	116 (3)
O4—C15—H15	110.7	C16—O4—C15	120.45 (18)
C14—C15—H15	110.7	C22—O5—C15	119.20 (18)
F3—C1—C2—C3	−121.5 (3)	C22—C23—C24—F4	−179.1 (3)
F2—C1—C2—C3	112.5 (3)	C22—C23—C24—C25	1.1 (5)
F1—C1—C2—C3	−4.6 (4)	F4—C24—C25—C26	179.4 (3)
F3—C1—C2—N2	59.9 (4)	C23—C24—C25—C26	−0.7 (5)
F2—C1—C2—N2	−66.1 (3)	C24—C25—C26—C27	0.7 (5)
F1—C1—C2—N2	176.8 (2)	C23—C22—C27—C26	1.4 (4)
N2—C2—C3—C4	0.8 (4)	O5—C22—C27—C26	−178.2 (3)
C1—C2—C3—C4	−177.7 (2)	C25—C26—C27—C22	−1.0 (5)
C2—C3—C4—O1	175.5 (2)	O2—C5—N1—C4	−179.6 (2)
C2—C3—C4—N1	−3.6 (3)	N2—C5—N1—C4	1.3 (3)
C12—C7—C8—C9	1.0 (3)	O2—C5—N1—C7	1.8 (3)
N1—C7—C8—C9	−176.61 (18)	N2—C5—N1—C7	−177.28 (17)
C7—C8—C9—C10	−0.5 (3)	O1—C4—N1—C5	−176.6 (2)
C7—C8—C9—N3	177.68 (19)	C3—C4—N1—C5	2.6 (3)
C8—C9—C10—C11	−0.6 (3)	O1—C4—N1—C7	2.0 (3)
N3—C9—C10—C11	−178.9 (2)	C3—C4—N1—C7	−178.86 (17)
C8—C9—C10—Cl1	176.62 (15)	C8—C7—N1—C5	−112.3 (2)
N3—C9—C10—Cl1	−1.7 (3)	C12—C7—N1—C5	70.0 (3)
C9—C10—C11—C12	1.3 (3)	C8—C7—N1—C4	69.0 (2)
Cl1—C10—C11—C12	−175.96 (17)	C12—C7—N1—C4	−108.7 (2)
C8—C7—C12—C11	−0.4 (3)	C3—C2—N2—C5	3.5 (3)
N1—C7—C12—C11	177.22 (19)	C1—C2—N2—C5	−177.9 (2)
C10—C11—C12—C7	−0.7 (3)	C3—C2—N2—C6	179.4 (3)
O3—C14—C15—O5	−179.1 (2)	C1—C2—N2—C6	−2.1 (3)
N3—C14—C15—O5	0.8 (3)	O2—C5—N2—C2	176.6 (2)
O3—C14—C15—O4	64.4 (3)	N1—C5—N2—C2	−4.4 (3)
N3—C14—C15—O4	−115.6 (2)	O2—C5—N2—C6	0.3 (3)
C21—C16—C17—C18	−0.6 (4)	N1—C5—N2—C6	179.4 (2)
O4—C16—C17—C18	−178.7 (2)	O3—C14—N3—C9	−0.9 (4)
C16—C17—C18—F5	176.2 (3)	C15—C14—N3—C9	179.1 (2)
C16—C17—C18—C19	−1.4 (4)	C8—C9—N3—C14	10.5 (4)
F5—C18—C19—C20	−175.1 (3)	C10—C9—N3—C14	−171.3 (2)
C17—C18—C19—C20	2.5 (4)	C21—C16—O4—C15	19.0 (3)
C18—C19—C20—F5'	160.7 (5)	C17—C16—O4—C15	−163.0 (2)
C18—C19—C20—C21	−1.6 (5)	O5—C15—O4—C16	142.56 (19)
O4—C16—C21—C20	179.2 (2)	C14—C15—O4—C16	−100.2 (2)
C17—C16—C21—C20	1.4 (4)	C27—C22—O5—C15	0.3 (4)
F5'—C20—C21—C16	−163.5 (5)	C23—C22—O5—C15	−179.3 (2)
C19—C20—C21—C16	−0.3 (5)	O4—C15—O5—C22	−76.2 (3)
C27—C22—C23—C24	−1.4 (4)	C14—C15—O5—C22	166.5 (2)
O5—C22—C23—C24	178.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	0.93	2.31	2.896 (3)	121
C6—H6C···F2	0.96	2.37	3.046 (4)	127
N3—H3A···O5	0.85 (4)	2.07 (4)	2.545 (2)	115 (3)
N3—H3A···Cl1	0.85 (4)	2.44 (4)	2.9074 (19)	115 (3)