Four tri­fluoro­methyl­nitro­benzene analogues

The crystal structures of four tri­fluoro­methyl­nitro­benzene analogues (CF₃)C₆H₃(NO₂)[C₄H₈N₂]R (where C₄H₈N₂ is piperazinyl and R is ethyl carboxyl­ate, CO₂C₂H₅, or phenyl, C₆H₅), have been determined, and their conformations and packing arrangements are compared. The four compounds are ethyl 4-[4-nitro-2-(tri­fluoro­methyl)­phenyl]­piperazine-1-car­boxyl­ate, (I), and ethyl 4-[2-nitro-4-(tri­fluoro­methyl)­phen­yl]piper­azine-1-carboxyl­ate, (II), both C₁₄H₁₆F₃N₃O₄, and 1-­[4-nitro-2-(tri­fluoro­methyl)­phenyl]-4-phenyl­piperazine, (III), and 1-[2-nitro-4-(tri­fluoro­methyl)­phenyl]-4-phenyl­piperazine, (IV), both C₁₇H₁₆F₃N₃O₂. All mol­ecules adopt a rod-like conformation, while the asymmetric units of (II) and (IV) contain two unique mol­ecules that pack as monodirectional pairs. All mol­ecules pack with C—H...O/F close contacts to all but one of the O atoms and to five of the 18 F atoms.

S1. Comment

As part of a continuing series of studies into the conformational and solid-state packing modes of similar compounds, the authors have been investigating chemical isomers based on 3-nitrobenzotrifluoride (CAS No. 98–46-4, trifluoromethylnitrobenzene) where the nitro and trifluoromethyl (CF₃) groups are interchanged in relation to a third substituent on the benzene ring. These studies have the dual purpose of not only comparing structural behaviour in the individual components but also of attempting to prepare cocrystalline adducts with such compounds without the use of strong hydrogen-bonding associations, as achieved by Wheeler and co-workers (Hendi et al., 2001; Fomulu et al., 2002a,b). Both NO₂ and CF₃ groups are known to be weak hydrogen-bond acceptors from strong hydrogen-bond donors (Allen et al., 1997; Brammer et al., 2001), and in the absence of such donors, solid-state packing can only, if at all, be influenced by weaker C—H interactions. Furthermore, choice of the third substituent is based on the use of something flexible, not too bulky, and also lacking in strong hydrogen-bond donors. With this in mind, we prepared a series of analogues of 3-nitrobenzotrifluoride containing 4-substituted piperazines. Previous efforts had concentrated on the use of thiophenol derivatives, which had led to the structural characterization of 1-(4-chlorophenylthio)-2-nitro-4-trifluoromethylbenzene and 1-(4-chlorophenylthio)-4-nitro-2-trifluoromethylbenzene [Lynch & M^cClenaghan, 2003], whose similar conformations did not aid cocrystal formation. Instead it was suggested that the role of the C—H···O interactions in both individual structures promoted phase separation when attempts were made to cocrystallize the two. We report here the singl-crystal structures of 1-(4-carbethoxypiperazinyl)-4-nitro-2-trifluoromethylbenzene, (I), 1-(4-carbethoxypiperazinyl)-2-nitro-4-trifluoromethylbenzene, (II), 4-Nitro-1-(4-phenylpiperazinyl)-2-trifluoromethylbenzene, (III), and 2-Nitro-1-(4-phenylpiperazinyl)-4-trifluoromethylbenzene, (IV), and comment on their structural similarities/differences.

The difficulty in making structural comparisons between chemical isomers is that the structures of both are required. For the thiophenol containing 3-nitrobenzotrifluorides (trifluoromethylnitrobenzene), only one matching pair was characterized. Fortunately, for the 4-substituted piperazines, full structural analyses of two pairs were completed that allowed comparisons not only between (I) and (II), and (III) and (IV), but also between (I) and (III), and (II) and (IV), which share similar nitro (NO₂) and trifluoromethyl (CF₃) positions. The structures of (I)–(IV) are shown, perpendicular to the 3-nitrobenzotrifluoride ring, in Figs. 1–4, respectively, with interactions and contacts listed in Tables 1–4. Compounds (II) and (IV), where the CF₃ group is para to the piperazine ring, each have two unique molecules in their asymmetric units. For ease of comparison, these molecules are both shown as described above (in Figs. 2 and 4) and not as they would appear in the lattice. The numbering of both the N-phenyl and the piperazine rings has also been standardized to aid evaluation. An initial inspection of the molecules of (I)–(IV) shows that each adopts a linear rod-like conformation, as expected. Similarities arise in the rotation of the piperazine rings in (I), (IIA) and (IVB), and (IIB) and (IVA), which can be quantified via the C2—C1—N7—C8 torsion angles, as listed in Table 5. The twists in the N-phenyl rings can be represented by their dihedral angles with the 3-nitrobenzotrifluoride ring, viz. 46.4 (1) (III), and 59.6 (1) and 66.9 (1)° (IV). Both CF₃ groups in (II) are unequally disordered over two rotational occupancies, the major occupancies for both molecules being 85%. The minor occupancies are rotated 30 (3)° (molecule A) and 23 (6)° (molecule B) with respect to the major occupancy sites. The rotational positions of the comparative CF₃ groups in (II) and (IV) are similar; the C3—C4—C41—F43 torsion angles are listed in Table 5. Comparative CF₃ rotational positions in (I) and (III) can be defined by the C1—C2—C21—F22 torsion angle, listed in Table 5. Two torsion angles can be used to define the conformation of the carboxylate groups in (I) and (II), viz. C9—N10—C13—O14 and C13—O14—C15—C16, listed in Table 5, and these angles indicate very different rotational positions with respect to atom C9.

Packing diagrams for (I)–(IV) are shown in Figs. 5–8, respectively, while C—H···O/F close contacts are listed in Tables 1–4, respectively. The number of these contacts, per molecule, increases for the two carbethoxy-containing analogues as a result of the addition of the two carbethoxy O atoms. All O atoms, except for atom O22B in (II), across all molecules have at least one listed close contact, whereas only five of a possible 18 F atoms have a C—H···F association, none for either molecule in (II). However, in (III), atom F22 lies 3.010 (2) Å from atom N41 (x, 1/2 − y, −1/2 + z). The packing diagrams are typical for rod-shaped molecules, with three of the four being either monoclinic P2₁/c or P2₁/n. It is interesting to note the manner in which the molecules in (II) and (IV) associate asuni-directional pairs in close proximity to one another. The interplanar distance between the two benzene ring centroids in (II) is 3.95 (1) Å and the dihedral angle is 30.9 (4)°. Another feature is the 90° triclinic cell angle in (II). No additional symmetry could be found in this structure and the two molecules display no pseudo-symmetry relationship, thus the cell angle is real. It may eventuate that at 150 K the structure of (II) is near a phase change to a higher crystal system and that one angle had already moved to fit the higher cell, but this remains to be proved. Attempts to cocrystallize all possible combinations of compounds (I)–(IV), by dissolving equimolar amounts of two components in various solvents, with warming, and then allowing evaporation to dryness, led to the recrystallization in each case of the individual compounds. This was identified by distinct differences in crystal morphology as well as infrared analysis of each crystal type. In addition to differing C—H···O/F associations, the role of the paired formation in (II) and (IV) may be responsible for the inability of these compounds to form cocrystalline adducts without the presence of strong complimentary hydrogen-bonding groups. Unfortunately, the existence of pairing in (II) and (IV) adds a new consideration to our use of the 2-nitro-4-trifluoromethylbenzene analogue.

S2. Experimental

All compounds were obtained from Key Organics Ltd. Crystals of (I) were obtained by recrystallization from 313/333 K petroleum ether, crystals of (II) were grown from absolute ethanol solution, while crystals of (III) and (IV) were grown from 5% aqueous ethanol solution.

S3. Refinement

All H atoms were included in the refinement, at calculated positions, in the riding-model approximation, with C—H set to 0.95 (Ar—H), 0.98 (CH₃) and 0.99 Å (CH₂). The isotropic displacement parameters were set equal to 1.25 U_eq of the carrier atom. A high R_int for (II) was the result of weak high-angle data.

Computing details

For all compounds, data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The molecular configuration and atom-numbering scheme for (II), showing 50% probability displacement ellipsoids. For clarity, both molecules have been shown in the direction perpendicular to their benzene rings and their positions, or orientations, cannot be directly compared to one another.
	Fig. 3. The molecular configuration and atom-numbering scheme for (III), showing 50% probability displacement ellipsoids.
	Fig. 4. The molecular configuration and atom-numbering scheme for (IV), showing 50% probability displacement ellipsoids. For clarity, both molecules have been shown in the direction perpendicular to their benzene rings and their positions, or orientations, cannot be directly compared to each other.
	Fig. 5. A packing diagram of (I), viewed along the b axis.
	Fig. 6. A packing diagram of (II), viewed along the a axis. The positions of molecules A and B throughout the unit cell are indicated.
	Fig. 7. A packing diagram of (III), viewed along the a axis.
	Fig. 8. A packing diagram of (IV), viewed along the c axis. The positions of molecules A and B throughout the unit cell are indicated.

(I) 4-[4-nitro-2-(trifluoromethyl)phenyl]piperazine-1-carboxylate

Crystal data

C14H16F3N3O4	F(000) = 720
Mr = 347.30	Dx = 1.529 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5964 reflections
a = 12.555 (3) Å	θ = 2.9–27.5°
b = 7.2688 (15) Å	µ = 0.14 mm^−1
c = 17.366 (4) Å	T = 120 K
β = 107.85 (3)°	Plate, yellow
V = 1508.5 (6) Å^3	0.20 × 0.14 × 0.05 mm
Z = 4

Data collection

Nonius KappaCCD area detector diffractometer	3438 independent reflections
Radiation source: Nonius FR591 rotating anode	2583 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −16→15
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −9→9
Tmin = 0.993, Tmax = 0.993	l = −22→22
10705 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0726P)^2 + 0.252P] where P = (Fo^2 + 2Fc^2)/3
3438 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.71754 (12)	0.9337 (2)	0.09555 (9)	0.0188 (3)
C2	0.63996 (13)	0.8756 (2)	0.13577 (9)	0.0185 (3)
C21	0.64564 (13)	0.6951 (2)	0.17898 (10)	0.0221 (4)
F21	0.69701 (8)	0.56039 (13)	0.15254 (6)	0.0287 (3)
F22	0.69744 (9)	0.71006 (15)	0.25949 (6)	0.0316 (3)
F23	0.54197 (8)	0.63119 (15)	0.17232 (6)	0.0332 (3)
C3	0.54820 (13)	0.9847 (2)	0.13308 (9)	0.0200 (4)
H3	0.4976	0.9473	0.1611	0.025*
C4	0.53000 (13)	1.1471 (2)	0.08990 (9)	0.0203 (4)
N41	0.43157 (12)	1.2567 (2)	0.08734 (8)	0.0245 (3)
O41	0.37893 (11)	1.2166 (2)	0.13459 (8)	0.0370 (4)
O42	0.40423 (11)	1.38190 (18)	0.03793 (8)	0.0326 (3)
C5	0.60039 (13)	1.2036 (2)	0.04684 (10)	0.0217 (4)
H5	0.5852	1.3129	0.0154	0.027*
C6	0.69324 (14)	1.0978 (2)	0.05041 (9)	0.0215 (4)
H6	0.7423	1.1370	0.0215	0.027*
N7	0.81138 (11)	0.8303 (2)	0.09724 (8)	0.0208 (3)
C8	0.86425 (14)	0.8638 (3)	0.03380 (10)	0.0241 (4)
H81	0.9148	0.9714	0.0483	0.030*
H82	0.8063	0.8899	−0.0183	0.030*
C9	0.93023 (14)	0.6937 (3)	0.02573 (10)	0.0262 (4)
H91	0.8785	0.5885	0.0077	0.033*
H92	0.9684	0.7156	−0.0156	0.033*
N10	1.01301 (11)	0.6494 (2)	0.10287 (8)	0.0238 (3)
C11	0.96390 (14)	0.6216 (2)	0.16831 (10)	0.0239 (4)
H111	1.0240	0.6018	0.2200	0.030*
H112	0.9155	0.5110	0.1570	0.030*
C12	0.89519 (13)	0.7892 (2)	0.17529 (9)	0.0211 (4)
H121	0.8571	0.7661	0.2165	0.026*
H122	0.9453	0.8964	0.1930	0.026*
C13	1.12257 (14)	0.6888 (2)	0.11464 (10)	0.0229 (4)
O13	1.16077 (10)	0.73633 (19)	0.06119 (7)	0.0313 (3)
O14	1.18508 (9)	0.66508 (17)	0.19241 (7)	0.0263 (3)
C15	1.30424 (14)	0.6955 (3)	0.20817 (12)	0.0337 (5)
H151	1.3178	0.8185	0.1886	0.042*
H152	1.3360	0.6014	0.1802	0.042*
C16	1.35738 (15)	0.6821 (3)	0.29831 (12)	0.0347 (5)
H161	1.3229	0.7722	0.3253	0.043*
H162	1.4377	0.7073	0.3119	0.043*
H163	1.3462	0.5580	0.3165	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0166 (7)	0.0229 (9)	0.0175 (7)	−0.0022 (7)	0.0061 (6)	−0.0029 (6)
C2	0.0171 (7)	0.0221 (9)	0.0161 (7)	−0.0006 (6)	0.0046 (6)	−0.0005 (6)
C21	0.0183 (8)	0.0245 (9)	0.0258 (8)	0.0003 (7)	0.0101 (7)	0.0019 (7)
F21	0.0307 (5)	0.0209 (5)	0.0378 (6)	0.0029 (4)	0.0155 (5)	0.0016 (4)
F22	0.0373 (6)	0.0362 (7)	0.0214 (5)	0.0008 (5)	0.0093 (4)	0.0077 (4)
F23	0.0204 (5)	0.0323 (6)	0.0489 (7)	−0.0031 (4)	0.0137 (5)	0.0113 (5)
C3	0.0186 (8)	0.0246 (9)	0.0186 (7)	−0.0022 (7)	0.0083 (6)	−0.0023 (6)
C4	0.0183 (8)	0.0225 (9)	0.0208 (8)	0.0021 (7)	0.0070 (6)	−0.0029 (6)
N41	0.0231 (7)	0.0282 (8)	0.0210 (7)	0.0033 (6)	0.0051 (6)	−0.0013 (6)
O41	0.0312 (7)	0.0494 (9)	0.0378 (7)	0.0151 (6)	0.0213 (6)	0.0085 (6)
O42	0.0319 (7)	0.0292 (7)	0.0358 (7)	0.0089 (6)	0.0091 (6)	0.0073 (6)
C5	0.0242 (8)	0.0209 (9)	0.0196 (8)	−0.0009 (7)	0.0063 (6)	0.0009 (6)
C6	0.0208 (8)	0.0252 (9)	0.0209 (8)	−0.0023 (7)	0.0102 (6)	0.0008 (7)
N7	0.0175 (7)	0.0297 (8)	0.0172 (7)	0.0032 (6)	0.0080 (5)	0.0022 (5)
C8	0.0226 (8)	0.0325 (10)	0.0203 (8)	0.0031 (7)	0.0113 (7)	0.0028 (7)
C9	0.0242 (8)	0.0353 (10)	0.0213 (8)	0.0047 (8)	0.0105 (7)	−0.0012 (7)
N10	0.0194 (7)	0.0337 (9)	0.0207 (7)	0.0038 (6)	0.0099 (6)	0.0029 (6)
C11	0.0195 (8)	0.0310 (10)	0.0244 (8)	0.0023 (7)	0.0114 (7)	0.0050 (7)
C12	0.0173 (7)	0.0276 (9)	0.0201 (8)	−0.0015 (7)	0.0080 (6)	0.0006 (7)
C13	0.0229 (8)	0.0213 (9)	0.0296 (9)	0.0034 (7)	0.0156 (7)	0.0009 (7)
O13	0.0299 (7)	0.0385 (8)	0.0325 (7)	0.0010 (6)	0.0199 (6)	0.0056 (5)
O14	0.0163 (6)	0.0361 (7)	0.0285 (6)	0.0008 (5)	0.0099 (5)	0.0033 (5)
C15	0.0167 (8)	0.0420 (12)	0.0472 (11)	−0.0020 (8)	0.0171 (8)	−0.0007 (9)
C16	0.0206 (9)	0.0352 (11)	0.0461 (11)	−0.0007 (8)	0.0070 (8)	0.0034 (9)

Geometric parameters (Å, º)

C1—N7	1.390 (2)	C13—O13	1.218 (2)
C1—C2	1.426 (2)	C13—O14	1.349 (2)
C1—C6	1.408 (2)	O14—C15	1.453 (2)
C2—C3	1.387 (2)	C15—C16	1.505 (3)
C2—C21	1.503 (2)	C3—H3	0.95
C21—F21	1.3294 (19)	C5—H5	0.95
C21—F22	1.3535 (19)	C6—H6	0.95
C21—F23	1.3530 (18)	C8—H81	0.99
C3—C4	1.380 (2)	C8—H82	0.99
C4—C5	1.383 (2)	C9—H91	0.99
C4—N41	1.459 (2)	C9—H92	0.99
N41—O41	1.2359 (19)	C11—H111	0.99
N41—O42	1.2253 (19)	C11—H112	0.99
C5—C6	1.382 (2)	C12—H121	0.99
N7—C12	1.469 (2)	C12—H122	0.99
N7—C8	1.470 (2)	C15—H151	0.99
C8—C9	1.518 (2)	C15—H152	0.99
C9—N10	1.457 (2)	C16—H161	0.98
N10—C13	1.358 (2)	C16—H162	0.98
N10—C11	1.464 (2)	C16—H163	0.98
C11—C12	1.519 (2)
N7—C1—C6	120.49 (14)	N10—C9—H91	109.6
N7—C1—C2	122.10 (15)	C8—C9—H91	109.5
C6—C1—C2	117.36 (15)	N10—C9—H92	109.5
C3—C2—C1	119.96 (15)	C8—C9—H92	109.5
C3—C2—C21	115.31 (14)	H91—C9—H92	108.1
C1—C2—C21	124.65 (14)	C13—N10—C9	119.74 (14)
F21—C21—F23	105.86 (13)	C13—N10—C11	124.11 (14)
F21—C21—F22	106.60 (13)	C9—N10—C11	113.12 (13)
F23—C21—F22	105.13 (13)	N10—C11—C12	109.61 (14)
F21—C21—C2	115.12 (13)	N10—C11—H111	109.7
F23—C21—C2	111.10 (13)	C12—C11—H111	109.7
F22—C21—C2	112.33 (14)	N10—C11—H112	109.7
C4—C3—C2	120.31 (15)	C12—C11—H112	109.7
C4—C3—H3	119.8	H111—C11—H112	108.2
C2—C3—H3	119.8	N7—C12—C11	110.68 (13)
C3—C4—C5	121.38 (15)	N7—C12—H121	109.5
C3—C4—N41	118.76 (14)	C11—C12—H121	109.5
C5—C4—N41	119.81 (15)	N7—C12—H122	109.5
O42—N41—O41	123.23 (15)	C11—C12—H122	109.5
O42—N41—C4	118.65 (14)	H121—C12—H122	108.1
O41—N41—C4	118.12 (14)	O13—C13—O14	123.71 (15)
C6—C5—C4	118.73 (15)	O13—C13—N10	124.23 (16)
C6—C5—H5	120.6	O14—C13—N10	112.05 (14)
C4—C5—H5	120.6	C13—O14—C15	114.74 (13)
C5—C6—C1	122.15 (15)	O14—C15—C16	106.77 (15)
C5—C6—H6	118.9	O14—C15—H151	110.4
C1—C6—H6	118.9	C16—C15—H151	110.4
C1—N7—C12	119.48 (12)	O14—C15—H152	110.4
C1—N7—C8	117.97 (13)	C16—C15—H152	110.4
C12—N7—C8	111.39 (12)	H151—C15—H152	108.6
N7—C8—C9	108.59 (14)	C15—C16—H161	109.5
N7—C8—H81	110.0	C15—C16—H162	109.5
C9—C8—H81	110.0	H161—C16—H162	109.5
N7—C8—H82	110.0	C15—C16—H163	109.5
C9—C8—H82	110.0	H161—C16—H163	109.5
H81—C8—H82	108.4	H162—C16—H163	109.5
N10—C9—C8	110.50 (14)
N7—C1—C2—C3	179.29 (14)	C2—C1—C6—C5	2.2 (2)
C6—C1—C2—C3	−3.4 (2)	C6—C1—N7—C12	122.93 (16)
N7—C1—C2—C21	−4.2 (2)	C2—C1—N7—C12	−59.9 (2)
C6—C1—C2—C21	173.11 (14)	C6—C1—N7—C8	−17.8 (2)
C3—C2—C21—F21	150.65 (14)	C2—C1—N7—C8	159.36 (15)
C1—C2—C21—F21	−26.0 (2)	C1—N7—C8—C9	−157.18 (14)
C3—C2—C21—F23	30.35 (19)	C12—N7—C8—C9	59.08 (17)
C1—C2—C21—F23	−146.35 (15)	N7—C8—C9—N10	−57.40 (18)
C3—C2—C21—F22	−87.09 (17)	C8—C9—N10—C13	−104.02 (18)
C1—C2—C21—F22	96.21 (18)	C8—C9—N10—C11	57.08 (19)
C1—C2—C3—C4	1.6 (2)	C13—N10—C11—C12	105.21 (18)
C21—C2—C3—C4	−175.23 (14)	C9—N10—C11—C12	−54.93 (19)
C2—C3—C4—C5	1.6 (2)	C1—N7—C12—C11	158.28 (14)
C2—C3—C4—N41	179.00 (14)	C8—N7—C12—C11	−58.60 (18)
C3—C4—N41—O42	−166.98 (15)	N10—C11—C12—N7	54.65 (18)
C5—C4—N41—O42	10.5 (2)	C9—N10—C13—O13	−10.7 (3)
C3—C4—N41—O41	12.0 (2)	C11—N10—C13—O13	−169.65 (17)
C5—C4—N41—O41	−170.50 (16)	C9—N10—C13—O14	170.69 (14)
C3—C4—C5—C6	−2.8 (2)	C11—N10—C13—O14	11.8 (2)
N41—C4—C5—C6	179.80 (14)	O13—C13—O14—C15	−1.7 (2)
C4—C5—C6—C1	0.8 (2)	N10—C13—O14—C15	176.85 (15)
N7—C1—C6—C5	179.56 (14)	C13—O14—C15—C16	174.27 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O42^i	0.95	2.42	3.346 (2)	164
C6—H6···O13^ii	0.95	2.34	3.278 (2)	171
C9—H92···O13	0.99	2.38	2.786 (2)	104
C11—H111···O14	0.99	2.26	2.697 (2)	105
C11—H111···O41^iii	0.99	2.58	3.456 (2)	147
C12—H121···F21	0.99	2.48	2.917 (2)	106
C12—H121···F22	0.99	2.38	3.295 (2)	154

Symmetry codes: (i) −x+1, −y+3, −z; (ii) −x+2, −y+2, −z; (iii) −x+3/2, y−1/2, −z+1/2.

(II) 4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine-1-carboxylate

Crystal data

C14H16F3N3O4	Z = 4
Mr = 347.30	F(000) = 720
Triclinic, P1	Dx = 1.454 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8211 (18) Å	Cell parameters from 3808 reflections
b = 11.717 (2) Å	θ = 1.0–27.5°
c = 15.528 (3) Å	µ = 0.13 mm^−1
α = 86.55 (3)°	T = 150 K
β = 81.97 (3)°	Prism, yellow
γ = 90.00 (3)°	0.42 × 0.24 × 0.10 mm
V = 1586.3 (5) Å^3

Data collection

Nonius KappaCCD area detector diffractometer	5256 independent reflections
Radiation source: Nonius FR591 rotating anode	3744 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 1.3°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
Tmin = 0.987, Tmax = 0.987	l = −18→18
17250 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1213P)^2] where P = (Fo^2 + 2Fc^2)/3
5256 reflections	(Δ/σ)max < 0.001
489 parameters	Δρmax = 0.42 e Å^−3
54 restraints	Δρmin = −0.44 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	−0.0004 (3)	0.7705 (2)	0.71272 (17)	0.0293 (6)
C2A	−0.0916 (3)	0.8425 (2)	0.76890 (18)	0.0312 (6)
N21A	−0.1383 (3)	0.9576 (2)	0.74027 (16)	0.0358 (6)
O21A	−0.1011 (3)	0.99384 (18)	0.66507 (14)	0.0475 (6)
O22A	−0.2212 (3)	1.01174 (18)	0.79394 (15)	0.0546 (6)
C3A	−0.1564 (3)	0.8042 (3)	0.85229 (19)	0.0372 (7)
H3A	−0.2127	0.8556	0.8894	0.046*
C4A	−0.1396 (3)	0.6927 (3)	0.88137 (19)	0.0395 (7)
C41A	−0.2110 (4)	0.6503 (3)	0.9705 (2)	0.0543 (9)
F41A	−0.1140 (5)	0.5949 (4)	1.0149 (2)	0.0988 (15)	0.85
F42A	−0.2675 (5)	0.7337 (3)	1.01961 (19)	0.0805 (11)	0.85
F43A	−0.3282 (5)	0.5798 (4)	0.9682 (2)	0.1041 (14)	0.85
F44A	−0.112 (2)	0.6489 (17)	1.0255 (13)	0.077 (7)	0.15
F45A	−0.3336 (19)	0.7067 (19)	1.0006 (14)	0.086 (8)	0.15
F46A	−0.2531 (19)	0.5447 (11)	0.9730 (11)	0.052 (4)	0.15
C5A	−0.0582 (3)	0.6179 (2)	0.82630 (19)	0.0385 (7)
H5A	−0.0488	0.5400	0.8454	0.048*
C6A	0.0089 (3)	0.6562 (2)	0.74437 (18)	0.0348 (7)
H6A	0.0635	0.6035	0.7078	0.043*
N7A	0.0713 (3)	0.80572 (18)	0.62962 (14)	0.0305 (5)
C8A	0.1203 (3)	0.7161 (2)	0.56942 (17)	0.0302 (6)
H81A	0.0406	0.6557	0.5746	0.038*
H82A	0.2161	0.6809	0.5842	0.038*
C9A	0.1461 (3)	0.7694 (2)	0.47731 (17)	0.0310 (6)
H91A	0.1782	0.7100	0.4360	0.039*
H92A	0.0496	0.8033	0.4623	0.039*
N10A	0.2637 (2)	0.85752 (17)	0.47029 (14)	0.0293 (5)
C11A	0.2287 (3)	0.9471 (2)	0.53104 (17)	0.0300 (6)
H11A	0.1407	0.9922	0.5152	0.037*
H12A	0.3178	0.9994	0.5275	0.037*
C12A	0.1906 (3)	0.8949 (2)	0.62313 (17)	0.0297 (6)
H13A	0.2843	0.8613	0.6423	0.037*
H14A	0.1551	0.9557	0.6626	0.037*
C13A	0.3686 (3)	0.8775 (2)	0.39867 (17)	0.0294 (6)
O13A	0.4581 (2)	0.95722 (16)	0.38758 (13)	0.0374 (5)
O14A	0.3661 (2)	0.79405 (15)	0.34261 (12)	0.0332 (5)
C15A	0.4822 (3)	0.8003 (3)	0.26623 (18)	0.0402 (7)
H15A	0.5802	0.7692	0.2812	0.050*
H16A	0.4992	0.8806	0.2433	0.050*
C16A	0.4241 (4)	0.7305 (3)	0.1997 (2)	0.0484 (8)
H17A	0.4024	0.6523	0.2244	0.060*
H18A	0.5018	0.7290	0.1481	0.060*
H19A	0.3301	0.7646	0.1831	0.060*
C1B	0.5027 (3)	0.7006 (2)	0.70923 (17)	0.0298 (6)
C2B	0.4109 (3)	0.6217 (2)	0.76624 (18)	0.0335 (7)
N21B	0.3630 (3)	0.5104 (2)	0.73993 (17)	0.0369 (6)
O21B	0.3995 (3)	0.48387 (18)	0.66438 (14)	0.0483 (6)
O22B	0.2822 (3)	0.44873 (19)	0.79370 (16)	0.0566 (6)
C3B	0.3449 (3)	0.6495 (3)	0.84903 (19)	0.0395 (7)
H3B	0.2875	0.5936	0.8870	0.049*
C4B	0.3626 (4)	0.7578 (3)	0.87592 (19)	0.0421 (8)
C41B	0.2857 (5)	0.7914 (3)	0.9624 (2)	0.0612 (10)
F41B	0.1540 (4)	0.8462 (4)	0.9562 (2)	0.0951 (14)	0.85
F42B	0.2505 (5)	0.7010 (3)	1.01912 (17)	0.0838 (11)	0.85
F43B	0.3708 (7)	0.8613 (5)	1.0003 (4)	0.0763 (16)	0.85
F44B	0.206 (2)	0.8889 (14)	0.9543 (15)	0.072 (7)	0.15
F45B	0.180 (2)	0.7196 (19)	0.9970 (15)	0.100 (9)	0.15
F46B	0.386 (3)	0.827 (2)	1.0105 (19)	0.054 (7)	0.15
C5B	0.4463 (3)	0.8389 (3)	0.82036 (19)	0.0392 (7)
H5B	0.4566	0.9142	0.8384	0.049*
C6B	0.5153 (3)	0.8109 (2)	0.73866 (19)	0.0353 (7)
H6B	0.5725	0.8678	0.7016	0.044*
N7B	0.5741 (3)	0.67630 (18)	0.62615 (15)	0.0316 (5)
C8B	0.6934 (3)	0.5871 (2)	0.62052 (18)	0.0331 (7)
H81B	0.6570	0.5205	0.6603	0.041*
H82B	0.7870	0.6175	0.6397	0.041*
C9B	0.7316 (3)	0.5490 (2)	0.52915 (18)	0.0327 (6)
H91B	0.8205	0.4972	0.5261	0.041*
H92B	0.6435	0.5062	0.5136	0.041*
N10B	0.7671 (3)	0.64690 (18)	0.46730 (15)	0.0299 (5)
C11B	0.6496 (3)	0.7344 (2)	0.47362 (18)	0.0317 (6)
H11B	0.5531	0.7029	0.4587	0.040*
H12B	0.6822	0.7999	0.4319	0.040*
C12B	0.6237 (3)	0.7740 (2)	0.56532 (17)	0.0317 (6)
H13B	0.7196	0.8069	0.5799	0.040*
H14B	0.5444	0.8340	0.5699	0.040*
C13B	0.8716 (3)	0.6368 (2)	0.39527 (18)	0.0303 (6)
O13B	0.9603 (2)	0.55761 (16)	0.38438 (13)	0.0384 (5)
O14B	0.8677 (2)	0.72722 (15)	0.33808 (12)	0.0348 (5)
C15B	0.9831 (4)	0.7308 (3)	0.26090 (19)	0.0426 (8)
H15B	0.9980	0.6536	0.2387	0.053*
H16B	1.0822	0.7586	0.2750	0.053*
C16B	0.9257 (4)	0.8107 (3)	0.1942 (2)	0.0492 (8)
H17B	0.8333	0.7783	0.1764	0.062*
H18B	1.0047	0.8217	0.1433	0.062*
H19B	0.9015	0.8845	0.2191	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0296 (14)	0.0330 (15)	0.0256 (15)	0.0006 (12)	−0.0028 (12)	−0.0059 (12)
C2A	0.0306 (15)	0.0318 (15)	0.0317 (16)	0.0031 (12)	−0.0042 (12)	−0.0062 (12)
N21A	0.0322 (13)	0.0360 (13)	0.0398 (16)	0.0038 (11)	−0.0043 (11)	−0.0090 (11)
O21A	0.0612 (14)	0.0465 (13)	0.0322 (13)	0.0171 (11)	0.0002 (10)	0.0037 (10)
O22A	0.0664 (15)	0.0414 (12)	0.0509 (14)	0.0154 (11)	0.0128 (12)	−0.0096 (11)
C3A	0.0353 (16)	0.0440 (17)	0.0314 (16)	0.0052 (13)	0.0008 (13)	−0.0093 (13)
C4A	0.0426 (17)	0.0445 (18)	0.0299 (16)	0.0033 (14)	0.0003 (13)	−0.0020 (13)
C41A	0.062 (2)	0.058 (2)	0.039 (2)	0.008 (2)	0.0090 (17)	−0.0005 (17)
F41A	0.115 (3)	0.127 (4)	0.0400 (18)	0.058 (3)	0.0186 (16)	0.038 (2)
F42A	0.115 (3)	0.078 (2)	0.0356 (16)	0.019 (2)	0.0313 (18)	0.0030 (14)
F43A	0.101 (3)	0.138 (4)	0.064 (2)	−0.049 (3)	0.013 (2)	0.021 (2)
F44A	0.081 (8)	0.084 (9)	0.068 (8)	−0.005 (5)	−0.016 (5)	−0.002 (5)
F45A	0.086 (9)	0.084 (9)	0.084 (9)	0.006 (5)	−0.002 (5)	−0.005 (5)
F46A	0.058 (6)	0.049 (6)	0.046 (6)	−0.012 (4)	−0.003 (4)	0.006 (4)
C5A	0.0454 (18)	0.0351 (16)	0.0337 (17)	0.0011 (14)	−0.0022 (14)	0.0010 (13)
C6A	0.0395 (16)	0.0322 (15)	0.0332 (17)	0.0048 (13)	−0.0053 (13)	−0.0065 (12)
N7A	0.0353 (13)	0.0279 (12)	0.0277 (13)	−0.0026 (10)	0.0001 (10)	−0.0078 (10)
C8A	0.0354 (15)	0.0243 (14)	0.0298 (15)	−0.0017 (12)	0.0021 (12)	−0.0072 (11)
C9A	0.0352 (15)	0.0302 (14)	0.0276 (15)	−0.0040 (12)	−0.0020 (12)	−0.0080 (11)
N10A	0.0364 (13)	0.0221 (11)	0.0289 (13)	−0.0019 (10)	−0.0012 (10)	−0.0048 (9)
C11A	0.0339 (15)	0.0240 (13)	0.0316 (15)	−0.0004 (11)	−0.0012 (12)	−0.0065 (11)
C12A	0.0327 (15)	0.0279 (14)	0.0293 (15)	−0.0013 (12)	−0.0041 (12)	−0.0078 (11)
C13A	0.0329 (15)	0.0270 (14)	0.0284 (15)	0.0038 (13)	−0.0050 (12)	0.0000 (12)
O13A	0.0402 (11)	0.0332 (11)	0.0370 (12)	−0.0069 (10)	0.0011 (9)	−0.0029 (9)
O14A	0.0397 (11)	0.0315 (10)	0.0271 (10)	0.0016 (8)	0.0016 (8)	−0.0049 (8)
C15A	0.0395 (17)	0.0486 (18)	0.0292 (16)	0.0032 (14)	0.0064 (13)	−0.0023 (13)
C16A	0.052 (2)	0.061 (2)	0.0297 (17)	0.0107 (16)	0.0024 (14)	−0.0055 (15)
C1B	0.0305 (15)	0.0331 (15)	0.0254 (15)	0.0019 (12)	−0.0041 (11)	0.0012 (12)
C2B	0.0341 (15)	0.0341 (15)	0.0324 (16)	−0.0024 (12)	−0.0055 (12)	−0.0016 (12)
N21B	0.0335 (13)	0.0359 (13)	0.0404 (16)	−0.0030 (11)	−0.0039 (11)	0.0018 (12)
O21B	0.0580 (14)	0.0503 (13)	0.0362 (13)	−0.0184 (11)	−0.0042 (10)	−0.0063 (10)
O22B	0.0648 (15)	0.0407 (13)	0.0564 (15)	−0.0145 (11)	0.0173 (12)	0.0012 (11)
C3B	0.0393 (17)	0.0493 (19)	0.0285 (16)	−0.0011 (14)	−0.0023 (13)	0.0029 (14)
C4B	0.0474 (18)	0.053 (2)	0.0267 (16)	−0.0016 (15)	−0.0049 (14)	−0.0069 (14)
C41B	0.073 (3)	0.068 (3)	0.040 (2)	−0.004 (2)	0.0022 (19)	−0.0088 (19)
F41B	0.070 (2)	0.153 (4)	0.062 (2)	0.029 (3)	0.0049 (18)	−0.045 (2)
F42B	0.128 (3)	0.086 (2)	0.0286 (15)	−0.026 (2)	0.0192 (17)	−0.0072 (13)
F43B	0.116 (3)	0.076 (3)	0.037 (2)	−0.017 (3)	−0.0031 (18)	−0.019 (2)
F44B	0.073 (8)	0.071 (8)	0.070 (8)	0.010 (5)	−0.001 (5)	−0.010 (5)
F45B	0.098 (10)	0.103 (10)	0.095 (10)	0.001 (5)	−0.002 (5)	−0.011 (5)
F46B	0.075 (10)	0.064 (11)	0.023 (8)	0.000 (8)	−0.008 (6)	−0.007 (7)
C5B	0.0455 (18)	0.0405 (17)	0.0323 (17)	0.0000 (14)	−0.0052 (14)	−0.0086 (13)
C6B	0.0365 (16)	0.0361 (16)	0.0333 (16)	−0.0026 (13)	−0.0046 (13)	−0.0024 (13)
N7B	0.0367 (13)	0.0274 (12)	0.0293 (13)	0.0028 (10)	−0.0002 (10)	0.0000 (10)
C8B	0.0382 (16)	0.0292 (14)	0.0319 (16)	0.0016 (12)	−0.0054 (12)	−0.0008 (12)
C9B	0.0367 (16)	0.0246 (14)	0.0364 (17)	0.0013 (12)	−0.0040 (13)	−0.0017 (12)
N10B	0.0353 (13)	0.0234 (11)	0.0301 (13)	0.0044 (10)	−0.0013 (10)	−0.0017 (9)
C11B	0.0367 (15)	0.0273 (14)	0.0304 (16)	0.0034 (12)	−0.0024 (12)	0.0004 (11)
C12B	0.0373 (15)	0.0253 (14)	0.0310 (16)	0.0036 (12)	−0.0003 (12)	−0.0001 (11)
C13B	0.0339 (15)	0.0281 (14)	0.0298 (16)	−0.0017 (12)	−0.0051 (12)	−0.0069 (12)
O13B	0.0407 (11)	0.0323 (11)	0.0415 (12)	0.0062 (9)	−0.0009 (9)	−0.0089 (9)
O14B	0.0400 (11)	0.0317 (10)	0.0306 (11)	0.0024 (8)	0.0039 (9)	−0.0042 (8)
C15B	0.0436 (18)	0.0452 (18)	0.0347 (17)	−0.0021 (14)	0.0100 (14)	−0.0042 (14)
C16B	0.054 (2)	0.055 (2)	0.0359 (19)	−0.0066 (16)	0.0040 (15)	−0.0035 (15)

Geometric parameters (Å, º)

C1A—N7A	1.394 (4)	C1B—N7B	1.400 (3)
C1A—C6A	1.404 (4)	C1B—C6B	1.407 (4)
C1A—C2A	1.419 (4)	C1B—C2B	1.412 (4)
C2A—C3A	1.388 (4)	C2B—C3B	1.393 (4)
C2A—N21A	1.472 (4)	C2B—N21B	1.469 (4)
N21A—O21A	1.218 (3)	N21B—O22B	1.220 (3)
N21A—O22A	1.235 (3)	N21B—O21B	1.231 (3)
C3A—C4A	1.371 (4)	C3B—C4B	1.375 (4)
C3A—H3A	0.95	C4B—C5B	1.384 (4)
C4A—C5A	1.391 (4)	C4B—C41B	1.493 (5)
C4A—C41A	1.494 (4)	C41B—F45B	1.295 (15)
C41A—F41A	1.319 (5)	C41B—F43B	1.327 (6)
C41A—F46A	1.289 (12)	C41B—F42B	1.343 (5)
C41A—F42A	1.330 (4)	C41B—F46B	1.320 (17)
C41A—F43A	1.329 (5)	C41B—F41B	1.339 (5)
C41A—F44A	1.306 (15)	C41B—F44B	1.349 (15)
C41A—F45A	1.312 (14)	C5B—C6B	1.386 (4)
C5A—C6A	1.375 (4)	N7B—C12B	1.466 (3)
N7A—C8A	1.472 (3)	N7B—C8B	1.480 (3)
N7A—C12A	1.473 (3)	C8B—C9B	1.506 (4)
C8A—C9A	1.513 (4)	C9B—N10B	1.456 (4)
C9A—N10A	1.452 (3)	N10B—C13B	1.357 (4)
N10A—C13A	1.352 (3)	N10B—C11B	1.455 (3)
N10A—C11A	1.458 (3)	C11B—C12B	1.512 (4)
C11A—C12A	1.514 (4)	C13B—O13B	1.218 (3)
C13A—O13A	1.212 (3)	C13B—O14B	1.345 (3)
C13A—O14A	1.350 (3)	O14B—C15B	1.459 (3)
O14A—C15A	1.453 (3)	C15B—C16B	1.495 (4)
C15A—C16A	1.499 (4)	C3B—H3B	0.95
C5A—H5A	0.95	C5B—H5B	0.95
C6A—H6A	0.95	C6B—H6B	0.95
C8A—H81A	0.99	C8B—H81B	0.99
C8A—H82A	0.99	C8B—H82B	0.99
C9A—H91A	0.99	C9B—H91B	0.99
C9A—H92A	0.99	C9B—H92B	0.99
C11A—H11A	0.99	C11B—H11B	0.99
C11A—H12A	0.99	C11B—H12B	0.99
C12A—H13A	0.99	C12B—H13B	0.99
C12A—H14A	0.99	C12B—H14B	0.99
C15A—H15A	0.99	C15B—H15B	0.99
C15A—H16A	0.99	C15B—H16B	0.99
C16A—H17A	0.98	C16B—H17B	0.98
C16A—H18A	0.98	C16B—H18B	0.98
C16A—H19A	0.98	C16B—H19B	0.98
N7A—C1A—C6A	120.4 (2)	C15A—C16A—H19A	109.5
N7A—C1A—C2A	124.1 (2)	H17A—C16A—H19A	109.5
C6A—C1A—C2A	115.5 (2)	H18A—C16A—H19A	109.5
C3A—C2A—C1A	121.8 (3)	N7B—C1B—C6B	119.7 (2)
C3A—C2A—N21A	115.1 (2)	N7B—C1B—C2B	124.1 (2)
C1A—C2A—N21A	122.8 (2)	C6B—C1B—C2B	116.1 (2)
O21A—N21A—O22A	122.6 (2)	C3B—C2B—C1B	121.8 (3)
O21A—N21A—C2A	120.0 (2)	C3B—C2B—N21B	114.7 (2)
O22A—N21A—C2A	117.3 (3)	C1B—C2B—N21B	123.1 (2)
C4A—C3A—C2A	120.4 (3)	O22B—N21B—O21B	121.9 (3)
C4A—C3A—H3A	119.8	O22B—N21B—C2B	118.2 (3)
C2A—C3A—H3A	119.8	O21B—N21B—C2B	119.8 (2)
C3A—C4A—C5A	119.4 (3)	C4B—C3B—C2B	120.1 (3)
C3A—C4A—C41A	120.8 (3)	C4B—C3B—H3B	120.0
C5A—C4A—C41A	119.8 (3)	C2B—C3B—H3B	120.0
F41A—C41A—F42A	106.0 (4)	C3B—C4B—C5B	119.7 (3)
F41A—C41A—F43A	106.9 (4)	C3B—C4B—C41B	121.0 (3)
F42A—C41A—F43A	105.3 (4)	C5B—C4B—C41B	119.3 (3)
F46A—C41A—F44A	102.9 (11)	F43B—C41B—F41B	106.0 (5)
F44A—C41A—F45A	110.5 (13)	F42B—C41B—F41B	106.2 (4)
F46A—C41A—F45A	105.8 (12)	F43B—C41B—F42B	106.7 (4)
F41A—C41A—C4A	112.9 (3)	F45B—C41B—F44B	102.2 (13)
F42A—C41A—C4A	113.1 (3)	F45B—C41B—F46B	119.3 (17)
F43A—C41A—C4A	112.1 (3)	F46B—C41B—F44B	99.0 (14)
F44A—C41A—C4A	111.2 (11)	C4B—C5B—C6B	120.5 (3)
F45A—C41A—C4A	113.8 (10)	C4B—C5B—H5B	119.8
F46A—C41A—C4A	112.0 (8)	C6B—C5B—H5B	119.8
C6A—C5A—C4A	120.3 (3)	C5B—C6B—C1B	121.7 (3)
C6A—C5A—H5A	119.8	C5B—C6B—H6B	119.2
C4A—C5A—H5A	119.8	C1B—C6B—H6B	119.2
C5A—C6A—C1A	122.4 (3)	C1B—N7B—C12B	117.0 (2)
C5A—C6A—H6A	118.8	C1B—N7B—C8B	117.6 (2)
C1A—C6A—H6A	118.8	C12B—N7B—C8B	110.1 (2)
C1A—N7A—C8A	117.4 (2)	N7B—C8B—C9B	111.7 (2)
C1A—N7A—C12A	117.4 (2)	N7B—C8B—H81B	109.3
C8A—N7A—C12A	110.1 (2)	C9B—C8B—H81B	109.3
N7A—C8A—C9A	108.8 (2)	N7B—C8B—H82B	109.3
N7A—C8A—H81A	109.9	C9B—C8B—H82B	109.3
C9A—C8A—H81A	109.9	H81B—C8B—H82B	107.9
N7A—C8A—H82A	109.9	N10B—C9B—C8B	110.7 (2)
C9A—C8A—H82A	109.9	N10B—C9B—H91B	109.5
H81A—C8A—H82A	108.3	C8B—C9B—H91B	109.5
N10A—C9A—C8A	109.5 (2)	N10B—C9B—H92B	109.5
N10A—C9A—H91A	109.8	C8B—C9B—H92B	109.5
C8A—C9A—H91A	109.8	H91B—C9B—H92B	108.1
N10A—C9A—H92A	109.8	C13B—N10B—C11B	123.2 (2)
C8A—C9A—H92A	109.8	C13B—N10B—C9B	119.9 (2)
H91A—C9A—H92A	108.2	C11B—N10B—C9B	113.6 (2)
C13A—N10A—C9A	123.3 (2)	N10B—C11B—C12B	109.5 (2)
C13A—N10A—C11A	119.7 (2)	N10B—C11B—H11B	109.8
C9A—N10A—C11A	113.7 (2)	C12B—C11B—H11B	109.8
N10A—C11A—C12A	110.2 (2)	N10B—C11B—H12B	109.8
N10A—C11A—H11A	109.6	C12B—C11B—H12B	109.8
C12A—C11A—H11A	109.6	H11B—C11B—H12B	108.2
N10A—C11A—H12A	109.6	N7B—C12B—C11B	109.1 (2)
C12A—C11A—H12A	109.6	N7B—C12B—H13B	109.9
H11A—C11A—H12A	108.1	C11B—C12B—H13B	109.9
N7A—C12A—C11A	111.8 (2)	N7B—C12B—H14B	109.9
N7A—C12A—H13A	109.3	C11B—C12B—H14B	109.9
C11A—C12A—H13A	109.3	H13B—C12B—H14B	108.3
N7A—C12A—H14A	109.3	O13B—C13B—O14B	124.1 (3)
C11A—C12A—H14A	109.3	O13B—C13B—N10B	124.7 (3)
H13A—C12A—H14A	107.9	O14B—C13B—N10B	111.3 (2)
O13A—C13A—O14A	124.0 (2)	C13B—O14B—C15B	116.5 (2)
O13A—C13A—N10A	124.6 (2)	O14B—C15B—C16B	106.9 (2)
O14A—C13A—N10A	111.3 (2)	O14B—C15B—H15B	110.3
C13A—O14A—C15A	116.8 (2)	C16B—C15B—H15B	110.3
O14A—C15A—C16A	106.9 (2)	O14B—C15B—H16B	110.3
O14A—C15A—H15A	110.3	C16B—C15B—H16B	110.3
C16A—C15A—H15A	110.3	H15B—C15B—H16B	108.6
O14A—C15A—H16A	110.3	C15B—C16B—H17B	109.5
C16A—C15A—H16A	110.3	C15B—C16B—H18B	109.5
H15A—C15A—H16A	108.6	H17B—C16B—H18B	109.5
C15A—C16A—H17A	109.5	C15B—C16B—H19B	109.5
C15A—C16A—H18A	109.5	H17B—C16B—H19B	109.5
H17A—C16A—H18A	109.5	H18B—C16B—H19B	109.5
N7A—C1A—C2A—C3A	−177.8 (2)	N7B—C1B—C2B—C3B	178.7 (3)
C6A—C1A—C2A—C3A	5.1 (4)	C6B—C1B—C2B—C3B	−4.0 (4)
N7A—C1A—C2A—N21A	9.1 (4)	N7B—C1B—C2B—N21B	−8.7 (4)
C6A—C1A—C2A—N21A	−168.0 (2)	C6B—C1B—C2B—N21B	168.6 (2)
C3A—C2A—N21A—O21A	−172.0 (2)	C3B—C2B—N21B—O22B	−6.1 (4)
C1A—C2A—N21A—O21A	1.5 (4)	C1B—C2B—N21B—O22B	−179.2 (3)
C3A—C2A—N21A—O22A	4.6 (4)	C3B—C2B—N21B—O21B	171.0 (2)
C1A—C2A—N21A—O22A	178.1 (3)	C1B—C2B—N21B—O21B	−2.1 (4)
C1A—C2A—C3A—C4A	−3.1 (4)	C1B—C2B—C3B—C4B	2.8 (4)
N21A—C2A—C3A—C4A	170.5 (3)	N21B—C2B—C3B—C4B	−170.3 (3)
C2A—C3A—C4A—C5A	−0.6 (5)	C2B—C3B—C4B—C5B	0.0 (4)
C2A—C3A—C4A—C41A	−179.0 (3)	C2B—C3B—C4B—C41B	176.6 (3)
C3A—C4A—C41A—F41A	−130.1 (4)	C3B—C4B—C41B—F45B	−14.5 (13)
C5A—C4A—C41A—F41A	51.4 (5)	C5B—C4B—C41B—F45B	162.2 (12)
C3A—C4A—C41A—F46A	147.0 (9)	C3B—C4B—C41B—F43B	143.5 (4)
C5A—C4A—C41A—F46A	−31.5 (9)	C5B—C4B—C41B—F43B	−39.8 (5)
C3A—C4A—C41A—F42A	−9.8 (5)	C3B—C4B—C41B—F42B	22.8 (5)
C5A—C4A—C41A—F42A	171.7 (4)	C5B—C4B—C41B—F42B	−160.6 (4)
C3A—C4A—C41A—F43A	109.1 (4)	C3B—C4B—C41B—F46B	122.4 (13)
C5A—C4A—C41A—F43A	−69.4 (5)	C5B—C4B—C41B—F46B	−60.9 (13)
C3A—C4A—C41A—F44A	−98.5 (10)	C3B—C4B—C41B—F41B	−96.9 (5)
C5A—C4A—C41A—F44A	83.0 (10)	C5B—C4B—C41B—F41B	79.8 (5)
C3A—C4A—C41A—F45A	27.0 (12)	C3B—C4B—C41B—F44B	−128.4 (10)
C5A—C4A—C41A—F45A	−151.5 (11)	C5B—C4B—C41B—F44B	48.3 (10)
C3A—C4A—C5A—C6A	2.0 (5)	C3B—C4B—C5B—C6B	−1.5 (4)
C41A—C4A—C5A—C6A	−179.5 (3)	C41B—C4B—C5B—C6B	−178.2 (3)
C4A—C5A—C6A—C1A	0.3 (4)	C4B—C5B—C6B—C1B	0.2 (4)
N7A—C1A—C6A—C5A	179.1 (3)	N7B—C1B—C6B—C5B	179.9 (3)
C2A—C1A—C6A—C5A	−3.7 (4)	C2B—C1B—C6B—C5B	2.5 (4)
C6A—C1A—N7A—C8A	15.6 (4)	C6B—C1B—N7B—C12B	−16.0 (4)
C2A—C1A—N7A—C8A	−161.3 (3)	C2B—C1B—N7B—C12B	161.3 (3)
C6A—C1A—N7A—C12A	−119.1 (3)	C6B—C1B—N7B—C8B	118.6 (3)
C2A—C1A—N7A—C12A	63.9 (3)	C2B—C1B—N7B—C8B	−64.2 (3)
C1A—N7A—C8A—C9A	161.7 (2)	C1B—N7B—C8B—C9B	165.6 (2)
C12A—N7A—C8A—C9A	−60.5 (3)	C12B—N7B—C8B—C9B	−56.9 (3)
N7A—C8A—C9A—N10A	59.9 (3)	N7B—C8B—C9B—N10B	51.8 (3)
C8A—C9A—N10A—C13A	143.2 (2)	C8B—C9B—N10B—C13B	147.3 (2)
C8A—C9A—N10A—C11A	−57.5 (3)	C8B—C9B—N10B—C11B	−52.8 (3)
C13A—N10A—C11A—C12A	−146.8 (2)	C13B—N10B—C11B—C12B	−143.8 (2)
C9A—N10A—C11A—C12A	53.1 (3)	C9B—N10B—C11B—C12B	57.0 (3)
C1A—N7A—C12A—C11A	−164.9 (2)	C1B—N7B—C12B—C11B	−161.9 (2)
C8A—N7A—C12A—C11A	57.3 (3)	C8B—N7B—C12B—C11B	60.4 (3)
N10A—C11A—C12A—N7A	−52.2 (3)	N10B—C11B—C12B—N7B	−59.9 (3)
C9A—N10A—C13A—O13A	172.3 (2)	C11B—N10B—C13B—O13B	−171.7 (2)
C11A—N10A—C13A—O13A	14.1 (4)	C9B—N10B—C13B—O13B	−13.8 (4)
C9A—N10A—C13A—O14A	−10.6 (3)	C11B—N10B—C13B—O14B	10.0 (3)
C11A—N10A—C13A—O14A	−168.8 (2)	C9B—N10B—C13B—O14B	168.0 (2)
O13A—C13A—O14A—C15A	2.1 (4)	O13B—C13B—O14B—C15B	−3.0 (4)
N10A—C13A—O14A—C15A	−175.0 (2)	N10B—C13B—O14B—C15B	175.3 (2)
C13A—O14A—C15A—C16A	−159.1 (2)	C13B—O14B—C15B—C16B	160.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O22A	0.95	2.29	2.634 (4)	100
C6A—H6A···O13B^i	0.95	2.46	3.286 (3)	145
C8A—H81A···O13B^i	0.99	2.54	3.300 (3)	133
C9A—H91A···O14A	0.99	2.23	2.649 (3)	104
C11A—H12A···O13A	0.99	2.42	2.789 (3)	101
C11A—H12A···O13A^ii	0.99	2.59	3.411 (3)	140
C12A—H14A···O21A	0.99	2.30	2.830 (4)	113
C6B—H6B···O13A^ii	0.95	2.44	3.241 (4)	142
C8B—H81B···O21B	0.99	2.30	2.839 (4)	113
C9B—H91B···O13B	0.99	2.43	2.800 (4)	101
C9B—H91B···O13B^iii	0.99	2.59	3.401 (3)	139
C11B—H12B···O14B	0.99	2.24	2.651 (3)	104
C12B—H14B···O13A^ii	0.99	2.57	3.332 (3)	134

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+2, −y+1, −z+1.

(III) 1-[4-nitro-2-(trifluoromethyl)phenyl]-4-phenylpiperazine

Crystal data

C17H16F3N3O2	F(000) = 728
Mr = 351.33	Dx = 1.452 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12140 reflections
a = 13.390 (3) Å	θ = 2.9–30.5°
b = 9.853 (2) Å	µ = 0.12 mm^−1
c = 12.503 (3) Å	T = 150 K
β = 102.97 (3)°	Prism, colourless
V = 1607.5 (7) Å^3	0.24 × 0.16 × 0.14 mm
Z = 4

Data collection

Nonius KappaCCD area detector diffractometer	3659 independent reflections
Radiation source: Nonius FR591 rotating anode	2565 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→11
Tmin = 0.952, Tmax = 0.981	l = −16→16
12114 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0725P)^2 + 0.026P] where P = (Fo^2 + 2Fc^2)/3
3659 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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

6.4059 (0.0079) x + 1.4090 (0.0065) y + 9.2143 (0.0070) z = 6.3529 (0.0039)

* 0.0059 (0.0011) C1 * −0.0053 (0.0010) C2 * 0.0001 (0.0011) C3 * 0.0045 (0.0011) C4 * −0.0038 (0.0011) C5 * −0.0014 (0.0011) C6

Rms deviation of fitted atoms = 0.0041

5.6704 (0.0077) x − 6.0768 (0.0060) y + 6.8967 (0.0073) z = 4.3491 (0.0051)

Angle to previous plane (with approximate e.s.d.) = 46.42 (0.06)

* −0.0079 (0.0010) C13 * 0.0032 (0.0010) C14 * 0.0042 (0.0011) C15 * −0.0067 (0.0011) C16 * 0.0018 (0.0011) C17 * 0.0055 (0.0011) C18

Rms deviation of fitted atoms = 0.0053

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

	x	y	z	Uiso*/Ueq
C1	0.21549 (11)	0.15058 (16)	0.51727 (11)	0.0261 (3)
C2	0.15650 (11)	0.25895 (16)	0.54049 (12)	0.0273 (3)
C21	0.17209 (11)	0.39872 (17)	0.50038 (13)	0.0341 (4)
F21	0.26802 (7)	0.44574 (9)	0.53735 (7)	0.0380 (3)
F22	0.15390 (8)	0.40581 (10)	0.39104 (8)	0.0471 (3)
F23	0.11107 (8)	0.48987 (10)	0.53219 (11)	0.0598 (4)
C3	0.08033 (11)	0.23728 (17)	0.59735 (13)	0.0326 (4)
H3	0.0404	0.3108	0.6139	0.041*
C4	0.06353 (11)	0.10730 (16)	0.62938 (12)	0.0298 (4)
N41	−0.01770 (10)	0.08366 (17)	0.68912 (12)	0.0404 (4)
O41	−0.06792 (11)	0.17943 (16)	0.70715 (14)	0.0729 (5)
O42	−0.03109 (9)	−0.03161 (14)	0.71755 (10)	0.0499 (4)
C5	0.11872 (12)	−0.00173 (17)	0.60679 (13)	0.0333 (4)
H5	0.1049	−0.0906	0.6292	0.042*
C6	0.19522 (12)	0.02076 (17)	0.55042 (13)	0.0342 (4)
H6	0.2344	−0.0537	0.5342	0.043*
N7	0.29420 (9)	0.17663 (13)	0.45928 (9)	0.0276 (3)
C8	0.39715 (10)	0.17858 (16)	0.53107 (11)	0.0276 (3)
H81	0.4156	0.0862	0.5599	0.035*
H82	0.3978	0.2395	0.5942	0.035*
C9	0.47465 (11)	0.22715 (16)	0.46886 (12)	0.0279 (3)
H91	0.4595	0.3224	0.4455	0.035*
H92	0.5441	0.2242	0.5174	0.035*
N10	0.47196 (9)	0.14221 (12)	0.37263 (9)	0.0247 (3)
C11	0.36837 (11)	0.13431 (19)	0.30343 (12)	0.0359 (4)
H111	0.3682	0.0726	0.2409	0.045*
H112	0.3467	0.2254	0.2736	0.045*
C12	0.29369 (12)	0.08287 (19)	0.36834 (13)	0.0389 (4)
H121	0.2240	0.0775	0.3206	0.049*
H122	0.3140	−0.0091	0.3971	0.049*
C13	0.55177 (10)	0.15997 (14)	0.31675 (11)	0.0240 (3)
C14	0.62659 (11)	0.25970 (15)	0.34473 (12)	0.0284 (3)
H14	0.6239	0.3214	0.4024	0.036*
C15	0.70539 (11)	0.26988 (16)	0.28906 (13)	0.0322 (4)
H15	0.7559	0.3385	0.3092	0.040*
C16	0.71107 (11)	0.18199 (17)	0.20535 (13)	0.0333 (4)
H16	0.7644	0.1903	0.1669	0.042*
C17	0.63801 (11)	0.08141 (17)	0.17805 (12)	0.0323 (4)
H17	0.6418	0.0195	0.1209	0.040*
C18	0.55954 (11)	0.06957 (16)	0.23266 (12)	0.0295 (4)
H18	0.5103	−0.0007	0.2129	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0217 (7)	0.0351 (9)	0.0217 (7)	0.0005 (6)	0.0054 (6)	0.0021 (6)
C2	0.0246 (7)	0.0316 (9)	0.0268 (8)	−0.0008 (6)	0.0082 (6)	−0.0011 (6)
C21	0.0305 (8)	0.0342 (9)	0.0403 (9)	0.0026 (7)	0.0135 (7)	0.0001 (7)
F21	0.0379 (5)	0.0360 (6)	0.0409 (5)	−0.0093 (4)	0.0106 (4)	−0.0007 (4)
F22	0.0496 (6)	0.0476 (6)	0.0395 (6)	−0.0017 (5)	0.0004 (5)	0.0153 (5)
F23	0.0565 (7)	0.0334 (6)	0.1028 (9)	0.0099 (5)	0.0456 (7)	0.0039 (6)
C3	0.0271 (8)	0.0375 (9)	0.0352 (9)	0.0024 (7)	0.0113 (7)	−0.0039 (7)
C4	0.0209 (7)	0.0431 (10)	0.0267 (8)	−0.0028 (7)	0.0082 (6)	0.0021 (7)
N41	0.0286 (7)	0.0551 (10)	0.0414 (8)	−0.0053 (7)	0.0157 (6)	0.0047 (7)
O41	0.0612 (9)	0.0664 (10)	0.1121 (13)	0.0123 (8)	0.0639 (10)	0.0088 (9)
O42	0.0388 (7)	0.0636 (9)	0.0516 (8)	−0.0096 (6)	0.0191 (6)	0.0144 (7)
C5	0.0289 (8)	0.0384 (9)	0.0337 (8)	0.0000 (7)	0.0093 (7)	0.0102 (7)
C6	0.0318 (8)	0.0347 (9)	0.0388 (9)	0.0064 (7)	0.0138 (7)	0.0075 (7)
N7	0.0243 (6)	0.0364 (7)	0.0242 (6)	0.0001 (5)	0.0100 (5)	0.0006 (5)
C8	0.0267 (7)	0.0331 (9)	0.0236 (7)	0.0004 (6)	0.0069 (6)	−0.0021 (6)
C9	0.0256 (7)	0.0327 (9)	0.0265 (8)	0.0000 (6)	0.0078 (6)	−0.0052 (6)
N10	0.0228 (6)	0.0302 (7)	0.0226 (6)	−0.0007 (5)	0.0084 (5)	−0.0035 (5)
C11	0.0259 (8)	0.0589 (11)	0.0245 (8)	−0.0057 (8)	0.0091 (7)	−0.0069 (7)
C12	0.0291 (8)	0.0624 (12)	0.0280 (8)	−0.0129 (8)	0.0124 (7)	−0.0134 (8)
C13	0.0230 (7)	0.0265 (8)	0.0238 (7)	0.0025 (6)	0.0078 (6)	0.0042 (6)
C14	0.0276 (8)	0.0259 (8)	0.0331 (8)	0.0027 (6)	0.0097 (7)	−0.0003 (6)
C15	0.0274 (8)	0.0282 (9)	0.0433 (9)	−0.0012 (6)	0.0130 (7)	0.0060 (7)
C16	0.0282 (8)	0.0390 (9)	0.0365 (9)	0.0036 (7)	0.0151 (7)	0.0076 (7)
C17	0.0323 (8)	0.0393 (10)	0.0282 (8)	0.0024 (7)	0.0130 (7)	−0.0024 (7)
C18	0.0290 (8)	0.0324 (9)	0.0287 (8)	−0.0037 (7)	0.0099 (7)	−0.0022 (7)

Geometric parameters (Å, º)

C1—C2	1.397 (2)	C13—C18	1.400 (2)
C1—C6	1.390 (2)	C14—C15	1.3921 (19)
C1—N7	1.4302 (17)	C15—C16	1.374 (2)
C2—C3	1.3844 (19)	C16—C17	1.380 (2)
C2—C21	1.496 (2)	C17—C18	1.381 (2)
C21—F21	1.3460 (18)	C3—H3	0.95
C21—F22	1.3355 (18)	C5—H5	0.95
C21—F23	1.3336 (18)	C6—H6	0.95
C3—C4	1.375 (2)	C8—H81	0.99
C4—C5	1.369 (2)	C8—H82	0.99
C4—N41	1.4697 (19)	C9—H91	0.99
N41—O41	1.2090 (19)	C9—H92	0.99
N41—O42	1.2153 (19)	C11—H111	0.99
C5—C6	1.385 (2)	C11—H112	0.99
N7—C12	1.464 (2)	C12—H121	0.99
N7—C8	1.4665 (19)	C12—H122	0.99
C8—C9	1.5076 (19)	C14—H14	0.95
C9—N10	1.4595 (18)	C15—H15	0.95
N10—C13	1.4128 (17)	C16—H16	0.95
N10—C11	1.4628 (19)	C17—H17	0.95
C11—C12	1.510 (2)	C18—H18	0.95
C13—C14	1.391 (2)
C6—C1—C2	118.95 (13)	C8—C9—H91	109.5
C6—C1—N7	122.13 (13)	N10—C9—H92	109.5
C2—C1—N7	118.92 (13)	C8—C9—H92	109.5
C3—C2—C1	120.33 (14)	H91—C9—H92	108.1
C3—C2—C21	119.24 (13)	C13—N10—C9	117.08 (11)
C1—C2—C21	120.40 (12)	C13—N10—C11	115.86 (11)
F23—C21—F22	106.67 (13)	C9—N10—C11	111.27 (11)
F23—C21—F21	105.49 (13)	N10—C11—C12	110.75 (12)
F22—C21—F21	105.92 (12)	N10—C11—H111	109.5
F23—C21—C2	112.27 (12)	C12—C11—H111	109.5
F22—C21—C2	112.59 (13)	N10—C11—H112	109.5
F21—C21—C2	113.32 (13)	C12—C11—H112	109.5
C4—C3—C2	118.73 (14)	H111—C11—H112	108.1
C4—C3—H3	120.6	N7—C12—C11	108.50 (13)
C2—C3—H3	120.6	N7—C12—H121	110.0
C5—C4—C3	122.66 (13)	C11—C12—H121	110.0
C5—C4—N41	118.42 (14)	N7—C12—H122	110.0
C3—C4—N41	118.92 (14)	C11—C12—H122	110.0
O41—N41—O42	123.38 (13)	H121—C12—H122	108.4
O41—N41—C4	118.50 (15)	C14—C13—C18	117.89 (12)
O42—N41—C4	118.12 (14)	C14—C13—N10	123.04 (12)
C4—C5—C6	118.32 (15)	C18—C13—N10	119.00 (13)
C4—C5—H5	120.8	C13—C14—C15	120.61 (14)
C6—C5—H5	120.8	C13—C14—H14	119.7
C5—C6—C1	121.00 (15)	C15—C14—H14	119.7
C5—C6—H6	119.5	C16—C15—C14	120.89 (14)
C1—C6—H6	119.5	C16—C15—H15	119.6
C1—N7—C12	113.89 (11)	C14—C15—H15	119.6
C1—N7—C8	112.98 (11)	C15—C16—C17	118.93 (13)
C12—N7—C8	108.88 (12)	C15—C16—H16	120.5
N7—C8—C9	110.47 (11)	C17—C16—H16	120.5
N7—C8—H81	109.6	C18—C17—C16	120.94 (14)
C9—C8—H81	109.6	C18—C17—H17	119.5
N7—C8—H82	109.6	C16—C17—H17	119.5
C9—C8—H82	109.6	C17—C18—C13	120.73 (14)
H81—C8—H82	108.1	C17—C18—H18	119.6
N10—C9—C8	110.54 (12)	C13—C18—H18	119.6
N10—C9—H91	109.5
C6—C1—C2—C3	1.1 (2)	C6—C1—N7—C8	−78.27 (18)
N7—C1—C2—C3	−179.42 (13)	C2—C1—N7—C8	102.29 (15)
C6—C1—C2—C21	−176.44 (14)	C1—N7—C8—C9	−171.41 (12)
N7—C1—C2—C21	3.0 (2)	C12—N7—C8—C9	61.01 (16)
C3—C2—C21—F23	3.9 (2)	N7—C8—C9—N10	−56.78 (16)
C1—C2—C21—F23	−178.53 (13)	C8—C9—N10—C13	−169.32 (12)
C3—C2—C21—F22	−116.54 (15)	C8—C9—N10—C11	54.23 (16)
C1—C2—C21—F22	61.05 (18)	C13—N10—C11—C12	166.59 (13)
C3—C2—C21—F21	123.27 (15)	C9—N10—C11—C12	−56.38 (18)
C1—C2—C21—F21	−59.14 (19)	C1—N7—C12—C11	171.06 (13)
C1—C2—C3—C4	−0.6 (2)	C8—N7—C12—C11	−61.87 (17)
C21—C2—C3—C4	177.01 (14)	N10—C11—C12—N7	59.96 (19)
C2—C3—C4—C5	−0.4 (2)	C9—N10—C13—C14	−4.7 (2)
C2—C3—C4—N41	−179.60 (13)	C11—N10—C13—C14	129.75 (16)
C5—C4—N41—O41	−178.49 (17)	C9—N10—C13—C18	172.11 (13)
C3—C4—N41—O41	0.8 (2)	C11—N10—C13—C18	−53.41 (19)
C5—C4—N41—O42	1.3 (2)	C18—C13—C14—C15	1.1 (2)
C3—C4—N41—O42	−179.47 (15)	N10—C13—C14—C15	177.95 (13)
C3—C4—C5—C6	0.7 (2)	C13—C14—C15—C16	0.0 (2)
N41—C4—C5—C6	179.97 (13)	C14—C15—C16—C17	−1.0 (2)
C4—C5—C6—C1	−0.2 (2)	C15—C16—C17—C18	0.8 (2)
C2—C1—C6—C5	−0.8 (2)	C16—C17—C18—C13	0.4 (2)
N7—C1—C6—C5	179.81 (13)	C14—C13—C18—C17	−1.3 (2)
C6—C1—N7—C12	46.6 (2)	N10—C13—C18—C17	−178.31 (13)
C2—C1—N7—C12	−132.80 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F23	0.95	2.34	2.679 (2)	100
C16—H16···O41^i	0.95	2.54	3.255 (2)	133
C12—H121···O42^ii	0.99	2.56	3.475 (2)	154

Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) −x, −y, −z+1.

(IV) 1-[2-nitro-4-(trifluoromethyl)phenyl]-4-phenylpiperazine

Crystal data

C17H16F3N3O2	F(000) = 1456
Mr = 351.33	Dx = 1.467 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16227 reflections
a = 30.6687 (12) Å	θ = 2.9–33.3°
b = 9.9731 (3) Å	µ = 0.12 mm^−1
c = 10.4592 (3) Å	T = 150 K
β = 95.8496 (10)°	Plate, yellow
V = 3182.41 (18) Å^3	0.20 × 0.15 × 0.04 mm
Z = 8

Data collection

Nonius KappaCCD area detector diffractometer	5553 independent reflections
Radiation source: Nonius FR591 rotating anode	2917 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ϕ and ω scans	h = −36→36
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.995, Tmax = 0.995	l = −12→12
14139 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0441P)^2] where P = (Fo^2 + 2Fc^2)/3
5553 reflections	(Δ/σ)max < 0.001
451 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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

17.4675 (0.0280) x + 2.9019 (0.0108) y − 8.6056 (0.0066) z = 1.8248 (0.0019)

* −0.0235 (0.0019) C1A * 0.0267 (0.0019) C2A * −0.0069 (0.0019) C3A * −0.0164 (0.0019) C4A * 0.0190 (0.0020) C5A * 0.0011 (0.0020) C6A

Rms deviation of fitted atoms = 0.0180

2.0698 (0.0327) x + 9.6511 (0.0028) y − 2.5986 (0.0111) z = 0.4878 (0.0099)

Angle to previous plane (with approximate e.s.d.) = 59.56 (0.10)

* 0.0092 (0.0018) C13A * −0.0043 (0.0018) C14A * −0.0031 (0.0020) C15A * 0.0057 (0.0020) C16A * −0.0008 (0.0019) C17A * −0.0067 (0.0019) C18A

Rms deviation of fitted atoms = 0.0056

− 6.5977 (0.0338) x + 4.1702 (0.0110) y + 9.4119 (0.0055) z = 5.3322 (0.0177)

Angle to previous plane (with approximate e.s.d.) = 79.87 (0.08)

* 0.0204 (0.0020) C1B * −0.0191 (0.0020) C2B * 0.0010 (0.0020) C3B * 0.0160 (0.0021) C4B * −0.0139 (0.0021) C5B * −0.0043 (0.0021) C6B

Rms deviation of fitted atoms = 0.0144

13.1915 (0.0303) x + 6.3461 (0.0091) y − 7.1215 (0.0088) z = 4.1912 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 66.94 (0.08)

* 0.0072 (0.0019) C13B * −0.0010 (0.0020) C14B * −0.0036 (0.0021) C15B * 0.0020 (0.0021) C16B * 0.0043 (0.0021) C17B * −0.0088 (0.0020) C18B

Rms deviation of fitted atoms = 0.0053

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

	x	y	z	Uiso*/Ueq
C1A	0.09429 (9)	0.1451 (3)	0.0310 (3)	0.0213 (7)
C2A	0.06807 (9)	0.2612 (2)	0.0111 (2)	0.0202 (7)
N21A	0.08262 (9)	0.3937 (2)	0.0587 (2)	0.0284 (6)
O21A	0.12176 (7)	0.42108 (19)	0.0617 (2)	0.0394 (6)
O22A	0.05467 (7)	0.47313 (18)	0.08779 (19)	0.0402 (6)
C3A	0.02849 (9)	0.2609 (3)	−0.0655 (3)	0.0242 (7)
H3A	0.0109	0.3395	−0.0727	0.030*
C4A	0.01447 (9)	0.1455 (3)	−0.1317 (3)	0.0224 (7)
C41A	−0.02757 (10)	0.1464 (3)	−0.2158 (3)	0.0299 (8)
F41A	−0.04239 (5)	0.02284 (15)	−0.24613 (16)	0.0416 (5)
F42A	−0.05967 (5)	0.20914 (16)	−0.16140 (16)	0.0454 (5)
F43A	−0.02484 (5)	0.20959 (16)	−0.32835 (16)	0.0431 (5)
C5A	0.04093 (9)	0.0334 (3)	−0.1199 (3)	0.0269 (7)
H5A	0.0324	−0.0447	−0.1681	0.034*
C6A	0.07947 (9)	0.0321 (3)	−0.0400 (3)	0.0254 (7)
H6A	0.0965	−0.0476	−0.0329	0.032*
N7A	0.13233 (7)	0.1413 (2)	0.1165 (2)	0.0230 (6)
C8A	0.12967 (9)	0.1877 (3)	0.2488 (3)	0.0251 (7)
H81A	0.1153	0.1182	0.2974	0.031*
H82A	0.1117	0.2702	0.2476	0.031*
C9A	0.17492 (8)	0.2161 (3)	0.3145 (3)	0.0248 (7)
H91A	0.1887	0.2889	0.2685	0.031*
H92A	0.1726	0.2462	0.4038	0.031*
N10A	0.20232 (7)	0.0947 (2)	0.3160 (2)	0.0223 (6)
C11A	0.20436 (9)	0.0436 (3)	0.1865 (3)	0.0273 (7)
H10A	0.2214	−0.0409	0.1906	0.034*
H11A	0.2198	0.1093	0.1363	0.034*
C12A	0.15895 (9)	0.0179 (3)	0.1186 (3)	0.0257 (7)
H12A	0.1615	−0.0123	0.0295	0.032*
H13A	0.1444	−0.0540	0.1638	0.032*
C13A	0.24301 (9)	0.1055 (2)	0.3942 (3)	0.0240 (7)
C14A	0.24276 (10)	0.1389 (3)	0.5232 (3)	0.0286 (8)
H14A	0.2156	0.1529	0.5576	0.036*
C15A	0.28161 (11)	0.1520 (3)	0.6022 (3)	0.0380 (9)
H15A	0.2809	0.1752	0.6900	0.047*
C16A	0.32162 (11)	0.1312 (3)	0.5536 (3)	0.0391 (9)
H16A	0.3483	0.1410	0.6074	0.049*
C17A	0.32200 (10)	0.0965 (3)	0.4273 (3)	0.0360 (8)
H17A	0.3493	0.0816	0.3939	0.045*
C18A	0.28327 (9)	0.0824 (3)	0.3465 (3)	0.0301 (8)
H18A	0.2842	0.0572	0.2593	0.038*
C1B	0.42414 (10)	0.6388 (3)	0.5830 (3)	0.0283 (7)
C2B	0.45093 (9)	0.7455 (3)	0.5503 (3)	0.0263 (7)
N21B	0.43331 (8)	0.8595 (2)	0.4719 (3)	0.0329 (7)
O21B	0.40595 (7)	0.8366 (2)	0.3810 (2)	0.0464 (6)
O22B	0.44769 (7)	0.9713 (2)	0.4996 (2)	0.0491 (7)
C3B	0.49575 (9)	0.7473 (3)	0.5831 (3)	0.0296 (8)
H3B	0.5125	0.8226	0.5618	0.037*
C4B	0.51600 (9)	0.6397 (3)	0.6465 (3)	0.0289 (8)
C41B	0.56374 (11)	0.6436 (3)	0.6882 (3)	0.0414 (9)
F41B	0.58253 (5)	0.52277 (17)	0.69733 (17)	0.0507 (5)
F42B	0.57224 (6)	0.69977 (17)	0.80571 (19)	0.0583 (6)
F43B	0.58638 (6)	0.71653 (19)	0.6102 (2)	0.0647 (6)
C5B	0.49123 (10)	0.5304 (3)	0.6744 (3)	0.0357 (8)
H5B	0.5052	0.4543	0.7150	0.045*
C6B	0.44634 (10)	0.5300 (3)	0.6441 (3)	0.0338 (8)
H6B	0.4300	0.4537	0.6654	0.042*
N7B	0.37900 (7)	0.6412 (2)	0.5570 (2)	0.0290 (6)
C8B	0.35391 (9)	0.5169 (3)	0.5639 (3)	0.0326 (8)
H81B	0.3475	0.5005	0.6534	0.041*
H82B	0.3711	0.4401	0.5360	0.041*
C9B	0.31135 (9)	0.5306 (3)	0.4763 (3)	0.0299 (8)
H91B	0.3181	0.5428	0.3865	0.037*
H92B	0.2940	0.4473	0.4803	0.037*
N10B	0.28563 (7)	0.6441 (2)	0.5139 (2)	0.0252 (6)
C11B	0.31132 (9)	0.7689 (3)	0.5122 (3)	0.0296 (8)
H10B	0.2941	0.8444	0.5423	0.037*
H11B	0.3177	0.7885	0.4233	0.037*
C12B	0.35379 (9)	0.7553 (3)	0.5982 (3)	0.0297 (8)
H12B	0.3712	0.8385	0.5944	0.037*
H13B	0.3474	0.7418	0.6882	0.037*
C13B	0.24282 (9)	0.6581 (3)	0.4467 (3)	0.0245 (7)
C14B	0.22729 (10)	0.5759 (3)	0.3458 (3)	0.0333 (8)
H14B	0.2454	0.5066	0.3182	0.042*
C15B	0.18538 (11)	0.5938 (3)	0.2845 (3)	0.0393 (9)
H15B	0.1751	0.5365	0.2153	0.049*
C16B	0.15846 (10)	0.6934 (3)	0.3226 (3)	0.0385 (9)
H16B	0.1298	0.7056	0.2801	0.048*
C17B	0.17397 (10)	0.7755 (3)	0.4242 (3)	0.0395 (9)
H17B	0.1558	0.8451	0.4511	0.049*
C18B	0.21527 (10)	0.7575 (3)	0.4865 (3)	0.0313 (8)
H18B	0.2251	0.8133	0.5572	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0187 (18)	0.0259 (16)	0.0203 (16)	−0.0005 (13)	0.0062 (14)	0.0007 (14)
C2A	0.0226 (18)	0.0161 (15)	0.0217 (16)	−0.0027 (13)	0.0020 (14)	−0.0038 (13)
N21A	0.0318 (17)	0.0238 (14)	0.0290 (16)	0.0025 (13)	−0.0007 (13)	0.0004 (12)
O21A	0.0252 (14)	0.0364 (12)	0.0556 (15)	−0.0088 (11)	0.0003 (12)	−0.0049 (11)
O22A	0.0388 (15)	0.0283 (12)	0.0528 (15)	0.0073 (11)	0.0018 (12)	−0.0115 (10)
C3A	0.0209 (18)	0.0244 (16)	0.0282 (18)	0.0048 (13)	0.0061 (14)	0.0029 (14)
C4A	0.0197 (17)	0.0241 (17)	0.0234 (18)	−0.0002 (13)	0.0017 (14)	0.0037 (14)
C41A	0.031 (2)	0.0256 (18)	0.033 (2)	−0.0013 (15)	0.0011 (17)	0.0038 (15)
F41A	0.0330 (11)	0.0294 (10)	0.0589 (13)	−0.0087 (8)	−0.0123 (9)	−0.0013 (9)
F42A	0.0219 (11)	0.0570 (11)	0.0560 (13)	0.0094 (9)	−0.0023 (9)	−0.0108 (10)
F43A	0.0415 (12)	0.0474 (11)	0.0379 (11)	−0.0040 (9)	−0.0083 (9)	0.0126 (9)
C5A	0.029 (2)	0.0241 (17)	0.0272 (18)	−0.0033 (14)	−0.0002 (15)	−0.0022 (14)
C6A	0.0241 (19)	0.0218 (16)	0.0301 (18)	0.0036 (14)	0.0009 (15)	0.0017 (14)
N7A	0.0180 (14)	0.0265 (13)	0.0242 (15)	0.0059 (11)	0.0010 (12)	−0.0051 (11)
C8A	0.0189 (18)	0.0286 (16)	0.0282 (18)	0.0034 (14)	0.0043 (14)	−0.0036 (14)
C9A	0.0214 (18)	0.0271 (17)	0.0255 (17)	0.0011 (14)	0.0010 (14)	−0.0052 (13)
N10A	0.0181 (14)	0.0245 (13)	0.0238 (15)	0.0027 (11)	0.0003 (11)	−0.0019 (11)
C11A	0.0228 (19)	0.0260 (16)	0.0331 (19)	0.0050 (13)	0.0032 (15)	−0.0037 (14)
C12A	0.0193 (18)	0.0267 (16)	0.0302 (18)	0.0055 (14)	−0.0016 (14)	−0.0058 (14)
C13A	0.0222 (18)	0.0176 (15)	0.031 (2)	−0.0019 (13)	−0.0038 (15)	0.0035 (13)
C14A	0.0223 (19)	0.0317 (17)	0.031 (2)	0.0030 (14)	0.0008 (16)	−0.0015 (15)
C15A	0.042 (2)	0.0324 (18)	0.036 (2)	0.0002 (16)	−0.0099 (19)	−0.0027 (15)
C16A	0.027 (2)	0.0340 (19)	0.051 (2)	−0.0030 (16)	−0.0168 (19)	0.0033 (17)
C17A	0.0201 (19)	0.0383 (19)	0.049 (2)	−0.0008 (15)	−0.0010 (17)	0.0080 (17)
C18A	0.0227 (19)	0.0328 (17)	0.035 (2)	0.0030 (15)	0.0021 (16)	0.0033 (15)
C1B	0.0207 (19)	0.0298 (17)	0.0342 (19)	−0.0037 (14)	0.0021 (15)	0.0001 (15)
C2B	0.0205 (18)	0.0258 (16)	0.0321 (19)	0.0026 (14)	0.0006 (15)	0.0032 (14)
N21B	0.0221 (16)	0.0355 (17)	0.0417 (18)	−0.0015 (13)	0.0052 (14)	0.0064 (14)
O21B	0.0406 (16)	0.0540 (14)	0.0421 (15)	−0.0092 (12)	−0.0081 (13)	0.0150 (12)
O22B	0.0403 (15)	0.0262 (13)	0.0784 (18)	−0.0052 (11)	−0.0052 (13)	0.0075 (12)
C3B	0.0240 (19)	0.0288 (17)	0.0368 (19)	−0.0058 (14)	0.0065 (15)	−0.0048 (15)
C4B	0.0221 (19)	0.0296 (18)	0.035 (2)	0.0010 (15)	0.0017 (15)	−0.0020 (15)
C41B	0.026 (2)	0.038 (2)	0.059 (3)	−0.0001 (17)	−0.0034 (19)	−0.0050 (19)
F41B	0.0280 (11)	0.0421 (11)	0.0798 (15)	0.0127 (9)	−0.0045 (10)	−0.0072 (10)
F42B	0.0377 (13)	0.0573 (12)	0.0746 (15)	0.0084 (10)	−0.0202 (11)	−0.0250 (11)
F43B	0.0197 (11)	0.0688 (13)	0.1061 (18)	−0.0045 (10)	0.0091 (11)	0.0236 (13)
C5B	0.027 (2)	0.0341 (19)	0.045 (2)	0.0073 (16)	0.0005 (17)	0.0071 (16)
C6B	0.025 (2)	0.0311 (18)	0.045 (2)	−0.0047 (15)	0.0021 (16)	0.0100 (15)
N7B	0.0170 (15)	0.0241 (13)	0.0461 (17)	−0.0041 (11)	0.0042 (13)	−0.0007 (12)
C8B	0.0198 (18)	0.0250 (17)	0.054 (2)	−0.0014 (14)	0.0069 (16)	0.0047 (15)
C9B	0.0218 (19)	0.0221 (16)	0.046 (2)	−0.0064 (14)	0.0039 (16)	0.0010 (15)
N10B	0.0167 (14)	0.0202 (13)	0.0384 (16)	−0.0006 (11)	0.0024 (12)	−0.0007 (11)
C11B	0.0228 (19)	0.0246 (16)	0.041 (2)	−0.0010 (14)	0.0016 (15)	−0.0006 (14)
C12B	0.0196 (18)	0.0286 (17)	0.041 (2)	−0.0030 (14)	0.0031 (16)	−0.0016 (15)
C13B	0.0207 (18)	0.0241 (16)	0.0283 (18)	−0.0039 (14)	0.0000 (15)	0.0064 (14)
C14B	0.027 (2)	0.0359 (18)	0.037 (2)	−0.0034 (15)	−0.0005 (16)	0.0014 (16)
C15B	0.038 (2)	0.038 (2)	0.041 (2)	−0.0138 (17)	−0.0058 (18)	0.0030 (17)
C16B	0.025 (2)	0.041 (2)	0.047 (2)	−0.0068 (17)	−0.0095 (17)	0.0201 (18)
C17B	0.026 (2)	0.0285 (18)	0.063 (2)	0.0029 (15)	0.0014 (18)	0.0115 (17)
C18B	0.0253 (19)	0.0253 (17)	0.043 (2)	−0.0045 (14)	0.0004 (16)	−0.0013 (15)

Geometric parameters (Å, º)

C1A—N7A	1.396 (3)	C1B—N7B	1.383 (3)
C1A—C6A	1.400 (3)	C1B—C6B	1.400 (4)
C1A—C2A	1.413 (3)	C1B—C2B	1.408 (4)
C2A—C3A	1.384 (3)	C2B—C3B	1.383 (4)
C2A—N21A	1.465 (3)	C2B—N21B	1.472 (3)
N21A—O22A	1.228 (3)	N21B—O22B	1.223 (3)
N21A—O21A	1.228 (3)	N21B—O21B	1.224 (3)
C3A—C4A	1.389 (3)	C3B—C4B	1.376 (4)
C4A—C5A	1.379 (3)	C4B—C5B	1.377 (4)
C4A—C41A	1.485 (4)	C4B—C41B	1.485 (4)
C41A—F41A	1.340 (3)	C41B—F41B	1.335 (3)
C41A—F42A	1.341 (3)	C41B—F43B	1.339 (4)
C41A—F43A	1.345 (3)	C41B—F42B	1.351 (3)
C5A—C6A	1.376 (3)	C5B—C6B	1.381 (4)
N7A—C8A	1.469 (3)	N7B—C12B	1.464 (3)
N7A—C12A	1.475 (3)	N7B—C8B	1.465 (3)
C8A—C9A	1.512 (3)	C8B—C9B	1.522 (3)
C9A—N10A	1.473 (3)	C9B—N10B	1.456 (3)
N10A—C13A	1.425 (3)	N10B—C13B	1.431 (3)
N10A—C11A	1.454 (3)	N10B—C11B	1.474 (3)
C11A—C12A	1.519 (3)	C11B—C12B	1.511 (3)
C13A—C14A	1.391 (4)	C13B—C14B	1.382 (4)
C13A—C18A	1.397 (4)	C13B—C18B	1.394 (4)
C14A—C15A	1.385 (4)	C14B—C15B	1.388 (4)
C15A—C16A	1.391 (4)	C15B—C16B	1.376 (4)
C16A—C17A	1.367 (4)	C16B—C17B	1.387 (4)
C17A—C18A	1.393 (4)	C17B—C18B	1.376 (4)
C3A—H3A	0.95	C3B—H3B	0.95
C5A—H5A	0.95	C5B—H5B	0.95
C6A—H6A	0.95	C6B—H6B	0.95
C8A—H81A	0.99	C8B—H81B	0.99
C8A—H82A	0.99	C8B—H82B	0.99
C9A—H91A	0.99	C9B—H91B	0.99
C9A—H92A	0.99	C9B—H92B	0.99
C11A—H10A	0.99	C11B—H10B	0.99
C11A—H11A	0.99	C11B—H11B	0.99
C12A—H12A	0.99	C12B—H12B	0.99
C12A—H13A	0.99	C12B—H13B	0.99
C14A—H14A	0.95	C14B—H14B	0.95
C15A—H15A	0.95	C15B—H15B	0.95
C16A—H16A	0.95	C16B—H16B	0.95
C17A—H17A	0.95	C17B—H17B	0.95
C18A—H18A	0.95	C18B—H18B	0.95
N7A—C1A—C6A	121.5 (2)	N7B—C1B—C6B	122.3 (3)
N7A—C1A—C2A	122.9 (2)	N7B—C1B—C2B	122.4 (2)
C6A—C1A—C2A	115.6 (2)	C6B—C1B—C2B	115.3 (3)
C3A—C2A—C1A	122.4 (2)	C3B—C2B—C1B	122.7 (3)
C3A—C2A—N21A	114.7 (2)	C3B—C2B—N21B	115.3 (2)
C1A—C2A—N21A	122.6 (2)	C1B—C2B—N21B	121.9 (2)
O22A—N21A—O21A	123.7 (2)	O22B—N21B—O21B	123.8 (2)
O22A—N21A—C2A	118.0 (2)	O22B—N21B—C2B	118.0 (2)
O21A—N21A—C2A	118.2 (2)	O21B—N21B—C2B	118.2 (2)
C2A—C3A—C4A	119.9 (2)	C4B—C3B—C2B	119.9 (3)
C2A—C3A—H3A	120.0	C4B—C3B—H3B	120.1
C4A—C3A—H3A	120.0	C2B—C3B—H3B	120.1
C5A—C4A—C3A	118.5 (2)	C3B—C4B—C5B	119.2 (3)
C5A—C4A—C41A	121.7 (2)	C3B—C4B—C41B	120.3 (3)
C3A—C4A—C41A	119.7 (2)	C5B—C4B—C41B	120.5 (3)
F41A—C41A—F42A	106.5 (2)	F41B—C41B—F43B	106.7 (3)
F41A—C41A—F43A	105.9 (2)	F41B—C41B—F42B	105.5 (2)
F42A—C41A—F43A	105.5 (2)	F43B—C41B—F42B	105.4 (3)
F41A—C41A—C4A	112.8 (2)	F41B—C41B—C4B	113.8 (3)
F42A—C41A—C4A	112.5 (2)	F43B—C41B—C4B	113.1 (3)
F43A—C41A—C4A	113.2 (2)	F42B—C41B—C4B	111.8 (3)
C6A—C5A—C4A	121.5 (3)	C4B—C5B—C6B	120.8 (3)
C6A—C5A—H5A	119.2	C4B—C5B—H5B	119.6
C4A—C5A—H5A	119.2	C6B—C5B—H5B	119.6
C5A—C6A—C1A	121.8 (3)	C5B—C6B—C1B	122.0 (3)
C5A—C6A—H6A	119.1	C5B—C6B—H6B	119.0
C1A—C6A—H6A	119.1	C1B—C6B—H6B	119.0
C1A—N7A—C8A	118.1 (2)	C1B—N7B—C12B	120.2 (2)
C1A—N7A—C12A	117.2 (2)	C1B—N7B—C8B	119.7 (2)
C8A—N7A—C12A	109.4 (2)	C12B—N7B—C8B	110.3 (2)
N7A—C8A—C9A	110.6 (2)	N7B—C8B—C9B	108.5 (2)
N7A—C8A—H81A	109.5	N7B—C8B—H81B	110.0
C9A—C8A—H81A	109.5	C9B—C8B—H81B	110.0
N7A—C8A—H82A	109.5	N7B—C8B—H82B	110.0
C9A—C8A—H82A	109.5	C9B—C8B—H82B	110.0
H81A—C8A—H82A	108.1	H81B—C8B—H82B	108.4
N10A—C9A—C8A	110.3 (2)	N10B—C9B—C8B	111.3 (2)
N10A—C9A—H91A	109.6	N10B—C9B—H91B	109.4
C8A—C9A—H91A	109.6	C8B—C9B—H91B	109.4
N10A—C9A—H92A	109.6	N10B—C9B—H92B	109.4
C8A—C9A—H92A	109.6	C8B—C9B—H92B	109.4
H91A—C9A—H92A	108.1	H91B—C9B—H92B	108.0
C13A—N10A—C11A	116.3 (2)	C13B—N10B—C9B	116.0 (2)
C13A—N10A—C9A	114.2 (2)	C13B—N10B—C11B	112.1 (2)
C11A—N10A—C9A	110.9 (2)	C9B—N10B—C11B	110.4 (2)
N10A—C11A—C12A	111.7 (2)	N10B—C11B—C12B	110.3 (2)
N10A—C11A—H10A	109.3	N10B—C11B—H10B	109.6
C12A—C11A—H10A	109.3	C12B—C11B—H10B	109.6
N10A—C11A—H11A	109.3	N10B—C11B—H11B	109.6
C12A—C11A—H11A	109.3	C12B—C11B—H11B	109.6
H10A—C11A—H11A	107.9	H10B—C11B—H11B	108.1
N7A—C12A—C11A	110.2 (2)	N7B—C12B—C11B	110.1 (2)
N7A—C12A—H12A	109.6	N7B—C12B—H12B	109.6
C11A—C12A—H12A	109.6	C11B—C12B—H12B	109.6
N7A—C12A—H13A	109.6	N7B—C12B—H13B	109.6
C11A—C12A—H13A	109.6	C11B—C12B—H13B	109.6
H12A—C12A—H13A	108.1	H12B—C12B—H13B	108.2
C14A—C13A—C18A	118.6 (3)	C14B—C13B—C18B	118.5 (3)
C14A—C13A—N10A	118.9 (3)	C14B—C13B—N10B	123.0 (3)
C18A—C13A—N10A	122.5 (3)	C18B—C13B—N10B	118.5 (2)
C15A—C14A—C13A	120.8 (3)	C13B—C14B—C15B	120.5 (3)
C15A—C14A—H14A	119.6	C13B—C14B—H14B	119.8
C13A—C14A—H14A	119.6	C15B—C14B—H14B	119.8
C14A—C15A—C16A	120.4 (3)	C16B—C15B—C14B	120.9 (3)
C14A—C15A—H15A	119.8	C16B—C15B—H15B	119.5
C16A—C15A—H15A	119.8	C14B—C15B—H15B	119.5
C17A—C16A—C15A	119.1 (3)	C15B—C16B—C17B	118.6 (3)
C17A—C16A—H16A	120.5	C15B—C16B—H16B	120.7
C15A—C16A—H16A	120.5	C17B—C16B—H16B	120.7
C16A—C17A—C18A	121.4 (3)	C18B—C17B—C16B	120.9 (3)
C16A—C17A—H17A	119.3	C18B—C17B—H17B	119.6
C18A—C17A—H17A	119.3	C16B—C17B—H17B	119.6
C17A—C18A—C13A	119.8 (3)	C17B—C18B—C13B	120.5 (3)
C17A—C18A—H18A	120.1	C17B—C18B—H18B	119.7
C13A—C18A—H18A	120.1	C13B—C18B—H18B	119.7
N7A—C1A—C2A—C3A	−174.3 (3)	N7B—C1B—C2B—C3B	175.9 (3)
C6A—C1A—C2A—C3A	5.0 (4)	C6B—C1B—C2B—C3B	−3.9 (4)
N7A—C1A—C2A—N21A	12.1 (4)	N7B—C1B—C2B—N21B	−7.8 (4)
C6A—C1A—C2A—N21A	−168.6 (2)	C6B—C1B—C2B—N21B	172.4 (3)
C3A—C2A—N21A—O22A	36.5 (3)	C3B—C2B—N21B—O22B	−41.7 (4)
C1A—C2A—N21A—O22A	−149.4 (3)	C1B—C2B—N21B—O22B	141.8 (3)
C3A—C2A—N21A—O21A	−140.2 (3)	C3B—C2B—N21B—O21B	136.6 (3)
C1A—C2A—N21A—O21A	33.9 (4)	C1B—C2B—N21B—O21B	−40.0 (4)
C1A—C2A—C3A—C4A	−3.6 (4)	C1B—C2B—C3B—C4B	2.2 (4)
N21A—C2A—C3A—C4A	170.4 (2)	N21B—C2B—C3B—C4B	−174.3 (3)
C2A—C3A—C4A—C5A	−0.5 (4)	C2B—C3B—C4B—C5B	1.2 (4)
C2A—C3A—C4A—C41A	−178.8 (3)	C2B—C3B—C4B—C41B	−176.8 (3)
C5A—C4A—C41A—F41A	18.2 (4)	C3B—C4B—C41B—F41B	−153.2 (3)
C3A—C4A—C41A—F41A	−163.6 (2)	C5B—C4B—C41B—F41B	28.9 (4)
C5A—C4A—C41A—F42A	138.6 (3)	C3B—C4B—C41B—F43B	−31.3 (4)
C3A—C4A—C41A—F42A	−43.2 (4)	C5B—C4B—C41B—F43B	150.8 (3)
C5A—C4A—C41A—F43A	−102.0 (3)	C3B—C4B—C41B—F42B	87.4 (4)
C3A—C4A—C41A—F43A	76.2 (3)	C5B—C4B—C41B—F42B	−90.5 (3)
C3A—C4A—C5A—C6A	3.0 (4)	C3B—C4B—C5B—C6B	−2.6 (5)
C41A—C4A—C5A—C6A	−178.8 (3)	C41B—C4B—C5B—C6B	175.3 (3)
C4A—C5A—C6A—C1A	−1.5 (4)	C4B—C5B—C6B—C1B	0.7 (5)
N7A—C1A—C6A—C5A	176.9 (3)	N7B—C1B—C6B—C5B	−177.4 (3)
C2A—C1A—C6A—C5A	−2.5 (4)	C2B—C1B—C6B—C5B	2.4 (4)
C6A—C1A—N7A—C8A	−127.8 (3)	C6B—C1B—N7B—C12B	127.5 (3)
C2A—C1A—N7A—C8A	51.5 (4)	C2B—C1B—N7B—C12B	−52.2 (4)
C6A—C1A—N7A—C12A	6.5 (4)	C6B—C1B—N7B—C8B	−15.1 (4)
C2A—C1A—N7A—C12A	−174.1 (2)	C2B—C1B—N7B—C8B	165.1 (3)
C1A—N7A—C8A—C9A	−162.9 (2)	C1B—N7B—C8B—C9B	−154.3 (2)
C12A—N7A—C8A—C9A	59.5 (3)	C12B—N7B—C8B—C9B	59.7 (3)
N7A—C8A—C9A—N10A	−58.6 (3)	N7B—C8B—C9B—N10B	−58.8 (3)
C8A—C9A—N10A—C13A	−170.2 (2)	C8B—C9B—N10B—C13B	−173.6 (2)
C8A—C9A—N10A—C11A	56.1 (3)	C8B—C9B—N10B—C11B	57.5 (3)
C13A—N10A—C11A—C12A	172.0 (2)	C13B—N10B—C11B—C12B	172.7 (2)
C9A—N10A—C11A—C12A	−55.4 (3)	C9B—N10B—C11B—C12B	−56.3 (3)
C1A—N7A—C12A—C11A	164.2 (2)	C1B—N7B—C12B—C11B	154.1 (2)
C8A—N7A—C12A—C11A	−57.8 (3)	C8B—N7B—C12B—C11B	−60.1 (3)
N10A—C11A—C12A—N7A	56.4 (3)	N10B—C11B—C12B—N7B	57.6 (3)
C11A—N10A—C13A—C14A	−172.7 (2)	C9B—N10B—C13B—C14B	−4.5 (4)
C9A—N10A—C13A—C14A	56.2 (3)	C11B—N10B—C13B—C14B	123.6 (3)
C11A—N10A—C13A—C18A	6.6 (3)	C9B—N10B—C13B—C18B	174.3 (2)
C9A—N10A—C13A—C18A	−124.5 (3)	C11B—N10B—C13B—C18B	−57.7 (3)
C18A—C13A—C14A—C15A	1.4 (4)	C18B—C13B—C14B—C15B	1.0 (4)
N10A—C13A—C14A—C15A	−179.2 (2)	N10B—C13B—C14B—C15B	179.7 (3)
C13A—C14A—C15A—C16A	−0.3 (4)	C13B—C14B—C15B—C16B	0.0 (5)
C14A—C15A—C16A—C17A	−0.7 (4)	C14B—C15B—C16B—C17B	−0.3 (5)
C15A—C16A—C17A—C18A	0.4 (4)	C15B—C16B—C17B—C18B	−0.5 (4)
C16A—C17A—C18A—C13A	0.7 (4)	C16B—C17B—C18B—C13B	1.5 (5)
C14A—C13A—C18A—C17A	−1.6 (4)	C14B—C13B—C18B—C17B	−1.8 (4)
N10A—C13A—C18A—C17A	179.1 (2)	N10B—C13B—C18B—C17B	179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···F43A^i	0.95	2.46	3.303 (3)	148
C3B—H3B···O22B^ii	0.95	2.51	3.455 (3)	176
C16B—H16B···F42A^iii	0.95	2.52	3.453 (3)	167
C15B—H15B···O21A	0.95	2.46	3.358 (4)	158

Symmetry codes: (i) −x, y−1/2, −z−1/2; (ii) −x+1, −y+2, −z+1; (iii) −x, −y+1, −z.