2,4-Diphenyl-6-trifluoro-methyl-2,3-dihydro-1H,5H-pyrrolo-[3,4-c]pyrrole-1,3-dione.

The asymmetric unit of the title compound, C(19)H(11)F(3)N(2)O(2), contains two crystallographically unique mol-ecules which differ in the rotation of a phenyl ring and a -CF(3) substituent. The dihedral angles involving the pyrrole ring and the attached phenyl ring are 62.82 (8) and 71.54 (7)° in the two molecules. The difference in the rotation of the CF(3) groups with respect to the pyrrolo rings to which they are attached is 23.5(1)°. For one mol-ecule, there is a close contact between an H atom and the centroid of the phenyl ring of an adjacent mol-ecule (2.572 Å). A similar contact is lacking in the second mol-ecule. In the crystal, N-H⋯O inter-actions connect adjacent mol-ecules into a chain normal to (01[Formula: see text]). Crystallographically unique mol-ecules alternate along the hydrogen-bonded chains.

Related literature

For background information on the biological activity of compounds with pyrrol-3,4-dicarboximide scaffolds, see: Malinka et al. (1999 ▶, 2005 ▶); Shen et al. (2010 ▶). For a description of structurally similar lamellarins, see: Yu et al. (2011 ▶).

Experimental

Crystal data

C19H11F3N2O2

M = 356.30

Triclinic,

a = 10.4730 (4) Å

b = 12.2394 (5) Å

c = 13.4379 (5) Å

α = 67.542 (2)°

β = 82.511 (2)°

γ = 80.294 (2)°

V = 1564.98 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.86, T max = 0.98

32220 measured reflections

6660 independent reflections

5882 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 0.98

6660 reflections

469 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶), Mercury (Macrae et al., 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶).; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001675/nk2128sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001675/nk2128Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001675/nk2128Isup3.cml

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

C19H11F3N2O2	Z = 4
Mr = 356.30	F(000) = 728
Triclinic, P1	Dx = 1.512 Mg m−3
a = 10.4730 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2394 (5) Å	Cell parameters from 9948 reflections
c = 13.4379 (5) Å	θ = 2.5–26.7°
α = 67.542 (2)°	µ = 0.12 mm−1
β = 82.511 (2)°	T = 100 K
γ = 80.294 (2)°	Prismatic, white
V = 1564.98 (11) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII DUO CCD diffractometer	6660 independent reflections
Radiation source: fine-focus sealed tube	5882 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 8.3333 pixels mm-1	θmax = 26.8°, θmin = 1.6°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −15→15
Tmin = 0.86, Tmax = 0.98	l = −17→16
32220 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0353P)2 + 1.1733P] where P = (Fo2 + 2Fc2)/3
6660 reflections	(Δ/σ)max < 0.001
469 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 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
N1	0.35532 (11)	0.26068 (9)	0.56592 (9)	0.0148 (2)
H1	0.325	0.3322	0.5223	0.018*
N2	0.50857 (11)	−0.07836 (9)	0.78471 (9)	0.0160 (2)
F2	0.21712 (9)	0.35605 (8)	0.72938 (8)	0.0317 (2)
F3	0.14763 (10)	0.18726 (8)	0.81133 (8)	0.0427 (3)
F1	0.08781 (9)	0.30162 (10)	0.65371 (8)	0.0374 (2)
O1	0.34017 (9)	−0.03336 (8)	0.89917 (8)	0.0201 (2)
O2	0.65695 (9)	−0.06867 (8)	0.63809 (8)	0.0202 (2)
C12	0.63795 (13)	0.15446 (12)	0.41080 (11)	0.0177 (3)
H12	0.6364	0.0713	0.4483	0.021*
C1	0.30092 (12)	0.20234 (11)	0.66742 (10)	0.0152 (3)
C6	0.46392 (12)	0.19190 (11)	0.54172 (10)	0.0143 (2)
C3	0.39775 (12)	−0.00958 (11)	0.81056 (10)	0.0151 (3)
C2	0.37467 (12)	0.09388 (11)	0.70964 (10)	0.0148 (2)
C7	0.55052 (12)	0.23597 (11)	0.44434 (10)	0.0152 (3)
C4	0.56091 (12)	−0.02501 (11)	0.67653 (10)	0.0152 (3)
C5	0.47444 (12)	0.08653 (11)	0.63056 (10)	0.0141 (2)
C13	0.56303 (13)	−0.19193 (11)	0.85754 (11)	0.0171 (3)
C8	0.55377 (13)	0.35825 (12)	0.38800 (11)	0.0182 (3)
H8	0.4948	0.4143	0.4099	0.022*
C9	0.64284 (14)	0.39777 (13)	0.30042 (11)	0.0220 (3)
H9	0.6443	0.4809	0.2623	0.026*
C14	0.56688 (14)	−0.29193 (12)	0.83170 (12)	0.0214 (3)
H14	0.5332	−0.2851	0.767	0.026*
C11	0.72685 (14)	0.19496 (13)	0.32298 (11)	0.0218 (3)
H11	0.7857	0.1394	0.3004	0.026*
C18	0.61225 (15)	−0.20018 (13)	0.95143 (12)	0.0243 (3)
H18	0.6099	−0.1312	0.9683	0.029*
C10	0.72999 (14)	0.31659 (13)	0.26804 (11)	0.0232 (3)
H10	0.7916	0.3441	0.2085	0.028*
C15	0.62048 (15)	−0.40205 (13)	0.90134 (13)	0.0279 (3)
H15	0.6235	−0.4711	0.8844	0.034*
C16	0.66956 (16)	−0.41145 (14)	0.99549 (13)	0.0323 (4)
H16	0.7063	−0.4869	1.043	0.039*
C17	0.66517 (17)	−0.31135 (15)	1.02056 (12)	0.0326 (4)
H17	0.6985	−0.3185	1.0855	0.039*
C19	0.18769 (13)	0.26076 (12)	0.71546 (11)	0.0189 (3)
F4	0.44762 (10)	0.84161 (10)	0.14618 (8)	0.0383 (3)
F5	0.31060 (9)	0.84493 (9)	0.27591 (8)	0.0373 (2)
F6	0.44468 (11)	0.68802 (9)	0.29453 (10)	0.0485 (3)
O4	0.25551 (9)	0.48629 (8)	0.41050 (7)	0.0179 (2)
O3	−0.02763 (9)	0.49810 (8)	0.17043 (8)	0.0192 (2)
N3	0.23046 (11)	0.79102 (10)	0.08260 (9)	0.0165 (2)
H3	0.2561	0.8585	0.0371	0.02*
N4	0.10361 (11)	0.46869 (9)	0.30785 (9)	0.0154 (2)
C22	0.19988 (12)	0.52244 (11)	0.32763 (10)	0.0147 (2)
C26	0.06391 (12)	0.78966 (12)	−0.03297 (10)	0.0157 (3)
C25	0.13700 (12)	0.73589 (11)	0.06384 (10)	0.0151 (3)
C21	0.21500 (12)	0.62799 (11)	0.22789 (10)	0.0152 (3)
C23	0.05479 (12)	0.53067 (11)	0.20333 (10)	0.0151 (3)
C24	0.12802 (12)	0.63298 (11)	0.15423 (10)	0.0150 (3)
C20	0.27846 (13)	0.72673 (12)	0.18161 (11)	0.0168 (3)
C31	0.00339 (14)	0.71767 (12)	−0.06663 (11)	0.0190 (3)
H31	0.0126	0.6338	−0.0286	0.023*
C32	0.05449 (13)	0.36364 (11)	0.38542 (10)	0.0157 (3)
C28	−0.02495 (14)	0.96323 (12)	−0.17831 (11)	0.0217 (3)
H28	−0.0347	1.0471	−0.2165	0.026*
C27	0.04938 (13)	0.91299 (12)	−0.08956 (11)	0.0187 (3)
H27	0.0905	0.9625	−0.0672	0.022*
C37	0.13017 (14)	0.25396 (12)	0.40797 (11)	0.0193 (3)
H37	0.2151	0.248	0.3739	0.023*
C36	0.08002 (15)	0.15257 (12)	0.48124 (12)	0.0236 (3)
H36	0.1313	0.0768	0.4983	0.028*
C30	−0.07021 (14)	0.76880 (13)	−0.15566 (12)	0.0224 (3)
H30	−0.1108	0.7196	−0.1787	0.027*
C34	−0.11889 (14)	0.27239 (13)	0.50622 (12)	0.0242 (3)
H34	−0.2041	0.2783	0.5397	0.029*
C33	−0.06943 (14)	0.37408 (12)	0.43446 (11)	0.0206 (3)
H33	−0.1198	0.4501	0.419	0.025*
C29	−0.08508 (14)	0.89119 (13)	−0.21134 (11)	0.0222 (3)
H29	−0.1362	0.9257	−0.2719	0.027*
C38	0.37168 (14)	0.77383 (12)	0.22422 (11)	0.0199 (3)
C35	−0.04424 (15)	0.16186 (13)	0.52922 (11)	0.0245 (3)
H35	−0.0787	0.0922	0.5782	0.029*

	U11	U22	U33	U12	U13	U23
N1	0.0173 (5)	0.0114 (5)	0.0137 (5)	−0.0008 (4)	−0.0019 (4)	−0.0026 (4)
N2	0.0183 (5)	0.0130 (5)	0.0143 (5)	−0.0014 (4)	−0.0012 (4)	−0.0026 (4)
F2	0.0338 (5)	0.0266 (5)	0.0431 (6)	−0.0007 (4)	−0.0007 (4)	−0.0242 (4)
F3	0.0475 (6)	0.0241 (5)	0.0342 (5)	0.0060 (4)	0.0236 (5)	0.0010 (4)
F1	0.0219 (5)	0.0552 (6)	0.0438 (6)	0.0131 (4)	−0.0119 (4)	−0.0324 (5)
O1	0.0212 (5)	0.0188 (5)	0.0164 (5)	−0.0041 (4)	0.0026 (4)	−0.0030 (4)
O2	0.0202 (5)	0.0185 (5)	0.0189 (5)	0.0020 (4)	0.0005 (4)	−0.0061 (4)
C12	0.0195 (6)	0.0172 (6)	0.0164 (6)	−0.0021 (5)	−0.0031 (5)	−0.0055 (5)
C1	0.0164 (6)	0.0139 (6)	0.0149 (6)	−0.0025 (5)	−0.0018 (5)	−0.0044 (5)
C6	0.0151 (6)	0.0142 (6)	0.0147 (6)	−0.0015 (5)	−0.0037 (5)	−0.0058 (5)
C3	0.0160 (6)	0.0132 (6)	0.0167 (6)	−0.0043 (5)	−0.0012 (5)	−0.0053 (5)
C2	0.0158 (6)	0.0143 (6)	0.0150 (6)	−0.0035 (5)	−0.0008 (5)	−0.0057 (5)
C7	0.0157 (6)	0.0171 (6)	0.0129 (6)	−0.0035 (5)	−0.0027 (5)	−0.0047 (5)
C4	0.0172 (6)	0.0140 (6)	0.0146 (6)	−0.0032 (5)	−0.0028 (5)	−0.0045 (5)
C5	0.0148 (6)	0.0141 (6)	0.0142 (6)	−0.0024 (5)	−0.0018 (5)	−0.0058 (5)
C13	0.0170 (6)	0.0139 (6)	0.0153 (6)	−0.0010 (5)	−0.0004 (5)	−0.0003 (5)
C8	0.0195 (6)	0.0171 (6)	0.0182 (6)	−0.0026 (5)	−0.0024 (5)	−0.0063 (5)
C9	0.0243 (7)	0.0197 (7)	0.0192 (7)	−0.0074 (5)	−0.0024 (5)	−0.0022 (5)
C14	0.0233 (7)	0.0179 (7)	0.0211 (7)	−0.0019 (5)	−0.0024 (5)	−0.0052 (6)
C11	0.0193 (7)	0.0268 (7)	0.0190 (7)	−0.0002 (5)	−0.0001 (5)	−0.0096 (6)
C18	0.0283 (8)	0.0243 (7)	0.0186 (7)	−0.0010 (6)	−0.0029 (6)	−0.0067 (6)
C10	0.0207 (7)	0.0296 (8)	0.0161 (7)	−0.0070 (6)	0.0021 (5)	−0.0044 (6)
C15	0.0309 (8)	0.0157 (7)	0.0307 (8)	0.0000 (6)	0.0024 (6)	−0.0042 (6)
C16	0.0350 (9)	0.0228 (8)	0.0229 (8)	0.0068 (6)	−0.0013 (6)	0.0047 (6)
C17	0.0379 (9)	0.0355 (9)	0.0163 (7)	0.0030 (7)	−0.0077 (6)	−0.0020 (6)
C19	0.0212 (7)	0.0153 (6)	0.0180 (6)	−0.0004 (5)	−0.0002 (5)	−0.0049 (5)
F4	0.0402 (6)	0.0568 (6)	0.0266 (5)	−0.0341 (5)	0.0090 (4)	−0.0172 (5)
F5	0.0337 (5)	0.0514 (6)	0.0435 (6)	−0.0149 (4)	0.0028 (4)	−0.0339 (5)
F6	0.0552 (7)	0.0263 (5)	0.0633 (7)	−0.0056 (5)	−0.0444 (6)	−0.0029 (5)
O4	0.0207 (5)	0.0152 (4)	0.0159 (5)	−0.0006 (4)	−0.0047 (4)	−0.0032 (4)
O3	0.0220 (5)	0.0173 (5)	0.0189 (5)	−0.0057 (4)	−0.0032 (4)	−0.0056 (4)
N3	0.0199 (6)	0.0138 (5)	0.0142 (5)	−0.0054 (4)	−0.0022 (4)	−0.0018 (4)
N4	0.0181 (5)	0.0121 (5)	0.0143 (5)	−0.0025 (4)	−0.0014 (4)	−0.0027 (4)
C22	0.0156 (6)	0.0127 (6)	0.0153 (6)	0.0001 (5)	0.0002 (5)	−0.0058 (5)
C26	0.0159 (6)	0.0173 (6)	0.0121 (6)	−0.0017 (5)	0.0002 (5)	−0.0041 (5)
C25	0.0164 (6)	0.0138 (6)	0.0155 (6)	−0.0021 (5)	0.0002 (5)	−0.0062 (5)
C21	0.0158 (6)	0.0142 (6)	0.0148 (6)	−0.0009 (5)	−0.0008 (5)	−0.0048 (5)
C23	0.0168 (6)	0.0123 (6)	0.0148 (6)	0.0004 (5)	−0.0001 (5)	−0.0049 (5)
C24	0.0158 (6)	0.0141 (6)	0.0145 (6)	−0.0010 (5)	−0.0010 (5)	−0.0053 (5)
C20	0.0184 (6)	0.0161 (6)	0.0148 (6)	−0.0026 (5)	−0.0017 (5)	−0.0040 (5)
C31	0.0239 (7)	0.0163 (6)	0.0165 (6)	−0.0037 (5)	−0.0021 (5)	−0.0049 (5)
C32	0.0211 (6)	0.0129 (6)	0.0123 (6)	−0.0042 (5)	−0.0024 (5)	−0.0027 (5)
C28	0.0240 (7)	0.0166 (6)	0.0201 (7)	−0.0017 (5)	−0.0042 (5)	−0.0014 (5)
C27	0.0205 (7)	0.0176 (6)	0.0178 (6)	−0.0038 (5)	−0.0019 (5)	−0.0057 (5)
C37	0.0240 (7)	0.0159 (6)	0.0177 (6)	−0.0008 (5)	−0.0018 (5)	−0.0064 (5)
C36	0.0369 (8)	0.0127 (6)	0.0201 (7)	−0.0017 (6)	−0.0052 (6)	−0.0044 (5)
C30	0.0255 (7)	0.0239 (7)	0.0203 (7)	−0.0059 (6)	−0.0048 (6)	−0.0087 (6)
C34	0.0221 (7)	0.0286 (8)	0.0188 (7)	−0.0081 (6)	0.0004 (5)	−0.0039 (6)
C33	0.0210 (7)	0.0176 (6)	0.0193 (7)	−0.0008 (5)	−0.0018 (5)	−0.0033 (5)
C29	0.0218 (7)	0.0252 (7)	0.0174 (7)	−0.0027 (6)	−0.0062 (5)	−0.0039 (6)
C38	0.0218 (7)	0.0193 (7)	0.0173 (7)	−0.0067 (5)	−0.0031 (5)	−0.0033 (5)
C35	0.0368 (8)	0.0197 (7)	0.0160 (7)	−0.0138 (6)	−0.0029 (6)	−0.0010 (5)

N1—C1	1.3731 (16)	F4—C38	1.3269 (16)
N1—C6	1.3776 (16)	F5—C38	1.3444 (17)
N1—H1	0.8800	F6—C38	1.3190 (17)
N2—C3	1.4018 (17)	O4—C22	1.2170 (16)
N2—C4	1.4240 (16)	O3—C23	1.2040 (16)
N2—C13	1.4332 (16)	N3—C20	1.3723 (17)
F2—C19	1.3391 (16)	N3—C25	1.3761 (17)
F3—C19	1.3213 (16)	N3—H3	0.8800
F1—C19	1.3288 (17)	N4—C22	1.3954 (17)
O1—C3	1.2139 (16)	N4—C23	1.4324 (16)
O2—C4	1.2076 (16)	N4—C32	1.4366 (16)
C12—C11	1.3884 (19)	C22—C21	1.4769 (17)
C12—C7	1.4018 (18)	C26—C31	1.3964 (19)
C12—H12	0.9500	C26—C27	1.3985 (18)
C1—C2	1.3689 (18)	C26—C25	1.4654 (18)
C1—C19	1.4837 (18)	C25—C24	1.3827 (18)
C6—C5	1.3823 (18)	C21—C20	1.3704 (18)
C6—C7	1.4636 (18)	C21—C24	1.4083 (18)
C3—C2	1.4735 (18)	C23—C24	1.4670 (18)
C2—C5	1.4074 (18)	C20—C38	1.4835 (18)
C7—C8	1.3996 (18)	C31—C30	1.3867 (19)
C4—C5	1.4663 (17)	C31—H31	0.9500
C13—C18	1.386 (2)	C32—C37	1.3840 (18)
C13—C14	1.3873 (19)	C32—C33	1.3858 (19)
C8—C9	1.3858 (19)	C28—C27	1.3881 (19)
C8—H8	0.9500	C28—C29	1.389 (2)
C9—C10	1.389 (2)	C28—H28	0.9500
C9—H9	0.9500	C27—H27	0.9500
C14—C15	1.388 (2)	C37—C36	1.3917 (19)
C14—H14	0.9500	C37—H37	0.9500
C11—C10	1.390 (2)	C36—C35	1.382 (2)
C11—H11	0.9500	C36—H36	0.9500
C18—C17	1.391 (2)	C30—C29	1.387 (2)
C18—H18	0.9500	C30—H30	0.9500
C10—H10	0.9500	C34—C33	1.3847 (19)
C15—C16	1.384 (2)	C34—C35	1.387 (2)
C15—H15	0.9500	C34—H34	0.9500
C16—C17	1.382 (2)	C33—H33	0.9500
C16—H16	0.9500	C29—H29	0.9500
C17—H17	0.9500	C35—H35	0.9500
C1—N1—C6	110.75 (10)	C20—N3—C25	111.02 (11)
C1—N1—H1	124.6	C20—N3—H3	124.5
C6—N1—H1	124.6	C25—N3—H3	124.5
C3—N2—C4	112.92 (10)	C22—N4—C23	113.47 (10)
C3—N2—C13	124.26 (11)	C22—N4—C32	123.71 (11)
C4—N2—C13	122.80 (11)	C23—N4—C32	122.80 (11)
C11—C12—C7	120.19 (12)	O4—C22—N4	125.38 (12)
C11—C12—H12	119.9	O4—C22—C21	130.17 (12)
C7—C12—H12	119.9	N4—C22—C21	104.44 (11)
C2—C1—N1	107.49 (11)	C31—C26—C27	119.49 (12)
C2—C1—C19	131.11 (12)	C31—C26—C25	119.70 (12)
N1—C1—C19	121.27 (11)	C27—C26—C25	120.75 (12)
N1—C6—C5	105.48 (11)	N3—C25—C24	105.57 (11)
N1—C6—C7	123.03 (11)	N3—C25—C26	122.20 (11)
C5—C6—C7	131.18 (12)	C24—C25—C26	132.11 (12)
O1—C3—N2	125.03 (12)	C20—C21—C24	107.44 (11)
O1—C3—C2	130.37 (12)	C20—C21—C22	143.29 (12)
N2—C3—C2	104.56 (10)	C24—C21—C22	109.19 (11)
C1—C2—C5	107.14 (11)	O3—C23—N4	123.71 (12)
C1—C2—C3	142.97 (12)	O3—C23—C24	132.10 (12)
C5—C2—C3	109.22 (11)	N4—C23—C24	104.19 (10)
C8—C7—C12	119.19 (12)	C25—C24—C21	108.83 (11)
C8—C7—C6	121.21 (12)	C25—C24—C23	142.33 (12)
C12—C7—C6	119.47 (12)	C21—C24—C23	108.72 (11)
O2—C4—N2	123.74 (12)	C21—C20—N3	107.14 (11)
O2—C4—C5	131.42 (12)	C21—C20—C38	131.64 (12)
N2—C4—C5	104.84 (11)	N3—C20—C38	120.92 (11)
C6—C5—C2	109.10 (11)	C30—C31—C26	119.88 (12)
C6—C5—C4	142.06 (12)	C30—C31—H31	120.1
C2—C5—C4	108.36 (11)	C26—C31—H31	120.1
C18—C13—C14	121.11 (13)	C37—C32—C33	121.29 (12)
C18—C13—N2	119.90 (12)	C37—C32—N4	119.62 (12)
C14—C13—N2	118.98 (12)	C33—C32—N4	119.07 (12)
C9—C8—C7	120.18 (13)	C27—C28—C29	120.13 (13)
C9—C8—H8	119.9	C27—C28—H28	119.9
C7—C8—H8	119.9	C29—C28—H28	119.9
C8—C9—C10	120.40 (13)	C28—C27—C26	120.12 (13)
C8—C9—H9	119.8	C28—C27—H27	119.9
C10—C9—H9	119.8	C26—C27—H27	119.9
C13—C14—C15	119.34 (14)	C32—C37—C36	118.99 (13)
C13—C14—H14	120.3	C32—C37—H37	120.5
C15—C14—H14	120.3	C36—C37—H37	120.5
C12—C11—C10	120.19 (13)	C35—C36—C37	120.13 (13)
C12—C11—H11	119.9	C35—C36—H36	119.9
C10—C11—H11	119.9	C37—C36—H36	119.9
C13—C18—C17	118.80 (14)	C31—C30—C29	120.55 (13)
C13—C18—H18	120.6	C31—C30—H30	119.7
C17—C18—H18	120.6	C29—C30—H30	119.7
C9—C10—C11	119.85 (13)	C33—C34—C35	120.09 (14)
C9—C10—H10	120.1	C33—C34—H34	120.0
C11—C10—H10	120.1	C35—C34—H34	120.0
C16—C15—C14	120.06 (15)	C34—C33—C32	119.20 (13)
C16—C15—H15	120.0	C34—C33—H33	120.4
C14—C15—H15	120.0	C32—C33—H33	120.4
C17—C16—C15	120.17 (14)	C30—C29—C28	119.82 (13)
C17—C16—H16	119.9	C30—C29—H29	120.1
C15—C16—H16	119.9	C28—C29—H29	120.1
C16—C17—C18	120.51 (15)	F6—C38—F4	109.15 (12)
C16—C17—H17	119.7	F6—C38—F5	106.22 (12)
C18—C17—H17	119.7	F4—C38—F5	104.84 (11)
F3—C19—F1	108.45 (12)	F6—C38—C20	112.20 (11)
F3—C19—F2	106.94 (12)	F4—C38—C20	112.23 (11)
F1—C19—F2	105.21 (11)	F5—C38—C20	111.78 (11)
F3—C19—C1	111.26 (11)	C36—C35—C34	120.29 (13)
F1—C19—C1	113.09 (11)	C36—C35—H35	119.9
F2—C19—C1	111.52 (11)	C34—C35—H35	119.9
C6—N1—C1—C2	−0.33 (14)	C23—N4—C22—O4	179.89 (12)
C6—N1—C1—C19	175.96 (11)	C32—N4—C22—O4	1.8 (2)
C1—N1—C6—C5	1.50 (14)	C23—N4—C22—C21	−0.01 (14)
C1—N1—C6—C7	−172.82 (11)	C32—N4—C22—C21	−178.08 (11)
C4—N2—C3—O1	−175.96 (12)	C20—N3—C25—C24	−0.67 (15)
C13—N2—C3—O1	5.5 (2)	C20—N3—C25—C26	175.96 (12)
C4—N2—C3—C2	2.17 (14)	C31—C26—C25—N3	159.02 (12)
C13—N2—C3—C2	−176.41 (11)	C27—C26—C25—N3	−23.69 (19)
N1—C1—C2—C5	−0.97 (14)	C31—C26—C25—C24	−25.4 (2)
C19—C1—C2—C5	−176.76 (13)	C27—C26—C25—C24	151.93 (14)
N1—C1—C2—C3	167.80 (16)	O4—C22—C21—C20	−3.9 (3)
C19—C1—C2—C3	−8.0 (3)	N4—C22—C21—C20	176.03 (18)
O1—C3—C2—C1	6.3 (3)	O4—C22—C21—C24	−179.59 (13)
N2—C3—C2—C1	−171.73 (17)	N4—C22—C21—C24	0.30 (14)
O1—C3—C2—C5	174.89 (13)	C22—N4—C23—O3	179.29 (12)
N2—C3—C2—C5	−3.10 (14)	C32—N4—C23—O3	−2.62 (19)
C11—C12—C7—C8	0.25 (19)	C22—N4—C23—C24	−0.26 (14)
C11—C12—C7—C6	−175.56 (12)	C32—N4—C23—C24	177.83 (11)
N1—C6—C7—C8	20.70 (19)	N3—C25—C24—C21	1.02 (14)
C5—C6—C7—C8	−152.02 (14)	C26—C25—C24—C21	−175.14 (13)
N1—C6—C7—C12	−163.58 (12)	N3—C25—C24—C23	176.03 (16)
C5—C6—C7—C12	23.7 (2)	C26—C25—C24—C23	−0.1 (3)
C3—N2—C4—O2	179.17 (12)	C20—C21—C24—C25	−1.01 (15)
C13—N2—C4—O2	−2.2 (2)	C22—C21—C24—C25	176.32 (11)
C3—N2—C4—C5	−0.48 (14)	C20—C21—C24—C23	−177.80 (11)
C13—N2—C4—C5	178.13 (11)	C22—C21—C24—C23	−0.47 (14)
N1—C6—C5—C2	−2.08 (14)	O3—C23—C24—C25	5.9 (3)
C7—C6—C5—C2	171.59 (13)	N4—C23—C24—C25	−174.58 (17)
N1—C6—C5—C4	−172.55 (16)	O3—C23—C24—C21	−179.05 (14)
C7—C6—C5—C4	1.1 (3)	N4—C23—C24—C21	0.44 (13)
C1—C2—C5—C6	1.93 (15)	C24—C21—C20—N3	0.58 (15)
C3—C2—C5—C6	−170.94 (11)	C22—C21—C20—N3	−175.20 (17)
C1—C2—C5—C4	175.77 (11)	C24—C21—C20—C38	174.17 (14)
C3—C2—C5—C4	2.91 (14)	C22—C21—C20—C38	−1.6 (3)
O2—C4—C5—C6	−10.6 (3)	C25—N3—C20—C21	0.06 (15)
N2—C4—C5—C6	168.98 (16)	C25—N3—C20—C38	−174.36 (12)
O2—C4—C5—C2	178.85 (14)	C27—C26—C31—C30	0.1 (2)
N2—C4—C5—C2	−1.54 (13)	C25—C26—C31—C30	177.41 (13)
C3—N2—C13—C18	−63.64 (18)	C22—N4—C32—C37	−73.65 (17)
C4—N2—C13—C18	117.91 (15)	C23—N4—C32—C37	108.45 (14)
C3—N2—C13—C14	117.16 (15)	C22—N4—C32—C33	107.80 (15)
C4—N2—C13—C14	−61.29 (17)	C23—N4—C32—C33	−70.09 (17)
C12—C7—C8—C9	−0.22 (19)	C29—C28—C27—C26	−0.1 (2)
C6—C7—C8—C9	175.51 (12)	C31—C26—C27—C28	0.2 (2)
C7—C8—C9—C10	−0.3 (2)	C25—C26—C27—C28	−177.12 (12)
C18—C13—C14—C15	0.3 (2)	C33—C32—C37—C36	0.1 (2)
N2—C13—C14—C15	179.44 (13)	N4—C32—C37—C36	−178.38 (12)
C7—C12—C11—C10	0.2 (2)	C32—C37—C36—C35	0.9 (2)
C14—C13—C18—C17	−0.5 (2)	C26—C31—C30—C29	−0.4 (2)
N2—C13—C18—C17	−179.69 (13)	C35—C34—C33—C32	0.7 (2)
C12—C11—C10—C9	−0.7 (2)	C37—C32—C33—C34	−0.9 (2)
C8—C9—C10—C11	0.8 (2)	N4—C32—C33—C34	177.59 (12)
C13—C14—C15—C16	0.0 (2)	C31—C30—C29—C28	0.5 (2)
C14—C15—C16—C17	0.1 (2)	C27—C28—C29—C30	−0.3 (2)
C15—C16—C17—C18	−0.4 (3)	C21—C20—C38—F6	32.2 (2)
C13—C18—C17—C16	0.6 (2)	N3—C20—C38—F6	−154.97 (13)
C2—C1—C19—F3	−7.4 (2)	C21—C20—C38—F4	155.50 (14)
N1—C1—C19—F3	177.30 (12)	N3—C20—C38—F4	−31.64 (18)
C2—C1—C19—F1	−129.75 (15)	C21—C20—C38—F5	−87.03 (18)
N1—C1—C19—F1	54.95 (17)	N3—C20—C38—F5	85.83 (15)
C2—C1—C19—F2	111.91 (16)	C37—C36—C35—C34	−1.2 (2)
N1—C1—C19—F2	−63.39 (16)	C33—C34—C35—C36	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.88	2.01	2.8395 (14)	156.
N1—H1···O4	0.88	2.00	2.8757 (14)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.88	2.01	2.8395 (14)	156
N1—H1⋯O4	0.88	2.00	2.8757 (14)	173

Symmetry code: (i) .