N-Cyclo-propyl-N-[2-(2,4-difluoro-phen-yl)-2-hy-droxy-1-(1H-1,2,4-triazol-1-yl)prop-yl]-2-(5-methyl-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-1-yl)acetamide dichloro-methane 0.62-solvate.

In the title compound, C(21)H(22)F(2)N(6)O(4)·0.62CH(2)Cl(2), the difluoro-substituted benzene ring forms dihedral angles of 54.6 (3)° with the mean plane of the thymine ring and 50.9 (2)° with the triazole ring. The dihedral angle between the thymine and triazole rings is 7.4 (3)°. In the crystal, inter-molecular N-H⋯N and O-H⋯O hydrogen bonds link the main mol-ecules into chains along [10[Formula: see text]]. The CH(2)Cl(2) solvent mol-ecule was refined as partial occupancy over two sets of sites with refined occupancies of 0.308 (9) and 0.310 (8).

Related literature

For the applications of azole and triazole compounds as anti­fungal agents, see: Singh (2001 ▶); Richardson (2005 ▶); Hobson (2003 ▶); Slavin et al. (2002 ▶); Wingard & Leather (2004 ▶); Fridkin & Jarvis (1996 ▶); Gallis et al. (1990 ▶); Sheehan et al. (1999 ▶); Denning (2002 ▶); Aoyama et al. (1984 ▶); Lamb et al. (1999 ▶).

Experimental

Crystal data

C21H22F2N6O4·0.62CH2Cl2

M = 512.93

Triclinic,

a = 8.474 (2) Å

b = 12.464 (3) Å

c = 13.410 (4) Å

α = 62.942 (4)°

β = 73.187 (4)°

γ = 83.746 (4)°

V = 1207.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.30 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer

6058 measured reflections

4162 independent reflections

3053 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.092

wR(F 2) = 0.209

S = 1.16

4162 reflections

356 parameters

42 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034295/lh5302sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034295/lh5302Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034295/lh5302Isup3.cml

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

C21H22F2N6O4·0.62CH2Cl2	Z = 2
Mr = 512.93	F(000) = 532.2
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.474 (2) Å	Cell parameters from 1529 reflections
b = 12.464 (3) Å	θ = 2.5–24.6°
c = 13.410 (4) Å	µ = 0.24 mm−1
α = 62.942 (4)°	T = 298 K
β = 73.187 (4)°	Block, colourless
γ = 83.746 (4)°	0.30 × 0.16 × 0.14 mm
V = 1207.1 (6) Å3

Bruker SMART APEX diffractometer	3053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −10→8
6058 measured reflections	k = −14→11
4162 independent reflections	l = −15→10

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0687P)2 + 1.6778P] where P = (Fo2 + 2Fc2)/3
4162 reflections	(Δ/σ)max < 0.001
356 parameters	Δρmax = 0.50 e Å−3
42 restraints	Δρmin = −0.34 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	Occ. (<1)
C1	0.4568 (7)	0.7140 (5)	1.3061 (5)	0.0602 (15)
H1	0.3778	0.7522	1.3425	0.072*
C2	0.5856 (6)	0.5787 (4)	1.2724 (4)	0.0416 (11)
H2	0.6213	0.5044	1.2752	0.050*
C3	0.7947 (5)	0.7116 (4)	1.0885 (3)	0.0320 (10)
H3A	0.8887	0.6649	1.1106	0.038*
H3B	0.8256	0.7963	1.0532	0.038*
C4	0.7508 (5)	0.6834 (4)	0.9990 (4)	0.0296 (9)
C5	0.5887 (5)	0.7388 (4)	0.9760 (3)	0.0291 (9)
C6	0.5620 (5)	0.8613 (4)	0.9364 (4)	0.0331 (10)
C7	0.4170 (6)	0.9142 (4)	0.9172 (4)	0.0481 (12)
H7	0.4040	0.9968	0.8914	0.058*
C8	0.2910 (6)	0.8396 (5)	0.9378 (5)	0.0537 (14)
C9	0.3077 (6)	0.7182 (4)	0.9764 (4)	0.0476 (12)
H9	0.2210	0.6695	0.9894	0.057*
C10	0.4563 (5)	0.6694 (4)	0.9955 (4)	0.0349 (10)
H10	0.4680	0.5866	1.0227	0.042*
C11	0.8951 (5)	0.7280 (4)	0.8885 (4)	0.0333 (10)
H11A	0.9135	0.8136	0.8603	0.040*
H11B	0.9940	0.6873	0.9079	0.040*
C12	0.7806 (6)	0.7963 (4)	0.7168 (4)	0.0421 (11)
H12	0.6619	0.7806	0.7371	0.051*
C13	0.8329 (10)	0.9254 (5)	0.6618 (5)	0.078 (2)
H13A	0.7476	0.9850	0.6514	0.094*
H13B	0.9264	0.9450	0.6791	0.094*
C14	0.8650 (8)	0.8592 (5)	0.5897 (4)	0.0644 (16)
H14A	0.9779	0.8385	0.5633	0.077*
H14B	0.7991	0.8785	0.5357	0.077*
C15	0.9161 (5)	0.6029 (4)	0.7912 (4)	0.0315 (10)
C16	0.8534 (5)	0.5732 (4)	0.7112 (4)	0.0375 (11)
H16A	0.7435	0.5370	0.7513	0.045*
H16B	0.8459	0.6471	0.6432	0.045*
C17	0.9241 (6)	0.3704 (4)	0.7248 (4)	0.0440 (12)
H17	0.8292	0.3407	0.7861	0.053*
C18	1.0177 (6)	0.2925 (4)	0.6907 (4)	0.0468 (12)
C19	0.9756 (9)	0.1617 (5)	0.7452 (6)	0.086 (2)
H19A	0.8814	0.1425	0.8114	0.129*
H19B	1.0675	0.1158	0.7697	0.129*
H19C	0.9508	0.1422	0.6898	0.129*
C20	1.1630 (6)	0.3403 (4)	0.5940 (4)	0.0430 (11)
C21	1.1004 (5)	0.5404 (4)	0.5851 (4)	0.0376 (10)
F1	0.6869 (3)	0.9347 (2)	0.9153 (3)	0.0508 (7)
F2	0.1460 (4)	0.8888 (3)	0.9206 (4)	0.0897 (12)
N1	0.5731 (5)	0.7741 (4)	1.2121 (4)	0.0512 (11)
N2	0.4584 (5)	0.5937 (4)	1.3470 (3)	0.0525 (11)
N3	0.6572 (4)	0.6839 (3)	1.1920 (3)	0.0322 (8)
N4	0.8680 (4)	0.7077 (3)	0.7957 (3)	0.0298 (8)
N5	0.9609 (4)	0.4908 (3)	0.6742 (3)	0.0351 (9)
N6	1.1926 (4)	0.4609 (3)	0.5494 (3)	0.0411 (9)
H6	1.2754	0.4935	0.5005	0.049*
O1	0.7269 (3)	0.5572 (2)	1.0449 (3)	0.0351 (7)
H1A	0.8101	0.5229	1.0622	0.053*
O2	0.9993 (4)	0.5299 (3)	0.8517 (3)	0.0455 (8)
O3	1.1376 (4)	0.6464 (3)	0.5414 (3)	0.0573 (10)
O4	1.2549 (5)	0.2801 (3)	0.5518 (3)	0.0655 (11)
C1A	0.332 (3)	0.799 (2)	0.626 (4)	0.104 (10)	0.308 (9)
H1AA	0.2307	0.7586	0.6801	0.125*	0.308 (9)
H1AB	0.3205	0.8252	0.5492	0.125*	0.308 (9)
Cl1	0.4739 (16)	0.7045 (11)	0.6375 (13)	0.193 (7)	0.308 (9)
Cl2	0.350 (3)	0.920 (2)	0.633 (2)	0.371 (15)	0.308 (9)
C1B	0.401 (4)	0.803 (2)	0.5671 (15)	0.103 (9)	0.310 (8)
H1BA	0.3007	0.7941	0.5521	0.123*	0.310 (8)
H1BB	0.4728	0.7448	0.5497	0.123*	0.310 (8)
Cl1'	0.3513 (16)	0.7336 (13)	0.7053 (12)	0.177 (6)	0.310 (8)
Cl2'	0.477 (3)	0.9237 (19)	0.453 (2)	0.340 (13)	0.310 (8)

	U11	U22	U33	U12	U13	U23
C1	0.051 (3)	0.067 (4)	0.056 (4)	0.010 (3)	0.005 (3)	−0.036 (3)
C2	0.045 (3)	0.046 (3)	0.030 (2)	0.003 (2)	−0.003 (2)	−0.017 (2)
C3	0.028 (2)	0.041 (2)	0.032 (2)	0.0028 (18)	−0.0105 (18)	−0.019 (2)
C4	0.027 (2)	0.030 (2)	0.032 (2)	0.0003 (17)	−0.0059 (18)	−0.0146 (18)
C5	0.027 (2)	0.036 (2)	0.024 (2)	−0.0010 (18)	−0.0036 (17)	−0.0159 (18)
C6	0.027 (2)	0.034 (2)	0.043 (3)	−0.0028 (18)	−0.0070 (19)	−0.021 (2)
C7	0.047 (3)	0.038 (3)	0.059 (3)	0.010 (2)	−0.016 (2)	−0.022 (2)
C8	0.035 (3)	0.054 (3)	0.074 (4)	0.009 (2)	−0.022 (3)	−0.027 (3)
C9	0.033 (3)	0.050 (3)	0.062 (3)	−0.006 (2)	−0.015 (2)	−0.024 (3)
C10	0.033 (2)	0.037 (2)	0.034 (2)	−0.0029 (19)	−0.0070 (19)	−0.016 (2)
C11	0.025 (2)	0.044 (3)	0.038 (3)	0.0033 (18)	−0.0082 (19)	−0.026 (2)
C12	0.048 (3)	0.040 (3)	0.036 (3)	0.008 (2)	−0.012 (2)	−0.016 (2)
C13	0.137 (6)	0.041 (3)	0.054 (4)	0.002 (3)	−0.031 (4)	−0.015 (3)
C14	0.093 (4)	0.051 (3)	0.037 (3)	0.001 (3)	−0.014 (3)	−0.011 (3)
C15	0.020 (2)	0.042 (2)	0.029 (2)	0.0004 (18)	−0.0021 (18)	−0.016 (2)
C16	0.035 (2)	0.050 (3)	0.035 (2)	0.005 (2)	−0.009 (2)	−0.026 (2)
C17	0.048 (3)	0.052 (3)	0.031 (2)	−0.013 (2)	−0.005 (2)	−0.017 (2)
C18	0.058 (3)	0.043 (3)	0.044 (3)	−0.001 (2)	−0.012 (2)	−0.025 (2)
C19	0.107 (5)	0.048 (3)	0.094 (5)	−0.012 (3)	−0.007 (4)	−0.034 (4)
C20	0.050 (3)	0.051 (3)	0.046 (3)	0.012 (2)	−0.023 (2)	−0.032 (2)
C21	0.042 (3)	0.040 (3)	0.033 (2)	−0.001 (2)	−0.011 (2)	−0.017 (2)
F1	0.0455 (16)	0.0343 (14)	0.075 (2)	−0.0060 (12)	−0.0167 (14)	−0.0245 (14)
F2	0.0437 (18)	0.082 (2)	0.143 (4)	0.0242 (17)	−0.048 (2)	−0.041 (2)
N1	0.057 (3)	0.048 (2)	0.049 (3)	0.008 (2)	−0.002 (2)	−0.030 (2)
N2	0.050 (3)	0.060 (3)	0.036 (2)	−0.005 (2)	0.003 (2)	−0.019 (2)
N3	0.0328 (19)	0.043 (2)	0.0258 (19)	0.0026 (16)	−0.0049 (15)	−0.0214 (17)
N4	0.0309 (19)	0.036 (2)	0.0232 (18)	0.0019 (15)	−0.0046 (15)	−0.0153 (15)
N5	0.036 (2)	0.043 (2)	0.030 (2)	−0.0042 (16)	−0.0038 (16)	−0.0212 (17)
N6	0.039 (2)	0.050 (2)	0.033 (2)	−0.0022 (18)	−0.0007 (17)	−0.0214 (18)
O1	0.0352 (17)	0.0327 (16)	0.0405 (18)	0.0086 (13)	−0.0139 (14)	−0.0183 (14)
O2	0.0464 (19)	0.057 (2)	0.047 (2)	0.0239 (16)	−0.0270 (16)	−0.0315 (17)
O3	0.060 (2)	0.045 (2)	0.054 (2)	−0.0065 (17)	0.0030 (18)	−0.0210 (18)
O4	0.071 (3)	0.071 (2)	0.074 (3)	0.018 (2)	−0.018 (2)	−0.052 (2)
C1A	0.102 (13)	0.108 (13)	0.095 (12)	−0.001 (9)	−0.034 (9)	−0.034 (9)
Cl1	0.178 (9)	0.167 (9)	0.210 (10)	0.003 (6)	0.005 (7)	−0.096 (7)
Cl2	0.363 (17)	0.382 (18)	0.371 (18)	0.015 (10)	−0.130 (10)	−0.153 (11)
C1B	0.073 (11)	0.102 (12)	0.104 (13)	0.007 (8)	−0.023 (9)	−0.022 (9)
Cl1'	0.162 (9)	0.207 (9)	0.181 (9)	−0.023 (6)	−0.020 (6)	−0.112 (7)
Cl2'	0.310 (15)	0.319 (15)	0.367 (16)	0.024 (9)	−0.121 (10)	−0.119 (10)

C1—N1	1.306 (6)	C15—O2	1.226 (5)
C1—N2	1.342 (6)	C15—N4	1.348 (5)
C1—H1	0.9300	C15—C16	1.519 (6)
C2—N2	1.304 (6)	C16—N5	1.460 (5)
C2—N3	1.326 (5)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—N3	1.455 (5)	C17—C18	1.345 (6)
C3—C4	1.541 (6)	C17—N5	1.364 (6)
C3—H3A	0.9700	C17—H17	0.9300
C3—H3B	0.9700	C18—C20	1.444 (7)
C4—O1	1.418 (5)	C18—C19	1.487 (7)
C4—C5	1.517 (6)	C19—H19A	0.9600
C4—C11	1.533 (6)	C19—H19B	0.9600
C5—C10	1.383 (6)	C19—H19C	0.9600
C5—C6	1.386 (6)	C20—O4	1.222 (5)
C6—F1	1.356 (4)	C20—N6	1.362 (6)
C6—C7	1.364 (6)	C21—O3	1.211 (5)
C7—C8	1.376 (7)	C21—N6	1.366 (6)
C7—H7	0.9300	C21—N5	1.370 (5)
C8—F2	1.346 (5)	N1—N3	1.355 (5)
C8—C9	1.364 (7)	N6—H6	0.8013
C9—C10	1.378 (6)	O1—H1A	0.8200
C9—H9	0.9300	C1A—Cl1	1.580 (12)
C10—H10	0.9300	C1A—Cl2	1.581 (12)
C11—N4	1.460 (5)	C1A—H1AA	0.9600
C11—H11A	0.9700	C1A—H1AB	0.9601
C11—H11B	0.9700	C1A—H1BA	1.1262
C12—N4	1.448 (5)	Cl1—H1BB	1.0513
C12—C13	1.489 (7)	C1B—Cl1'	1.590 (12)
C12—C14	1.495 (7)	C1B—Cl2'	1.599 (12)
C12—H12	0.9800	C1B—H1AB	0.7735
C13—C14	1.488 (8)	C1B—H1BA	0.9600
C13—H13A	0.9700	C1B—H1BB	0.9601
C13—H13B	0.9700	Cl1'—H1AA	1.1355
C14—H14A	0.9700	Cl2'—H1AB	1.6877
C14—H14B	0.9700
N1—C1—N2	115.8 (4)	N5—C16—C15	112.0 (3)
N1—C1—H1	122.1	N5—C16—H16A	109.2
N2—C1—H1	122.1	C15—C16—H16A	109.2
N2—C2—N3	110.8 (4)	N5—C16—H16B	109.2
N2—C2—H2	124.6	C15—C16—H16B	109.2
N3—C2—H2	124.6	H16A—C16—H16B	107.9
N3—C3—C4	111.7 (3)	C18—C17—N5	123.5 (4)
N3—C3—H3A	109.3	C18—C17—H17	118.3
C4—C3—H3A	109.3	N5—C17—H17	118.3
N3—C3—H3B	109.3	C17—C18—C20	117.6 (4)
C4—C3—H3B	109.3	C17—C18—C19	123.2 (5)
H3A—C3—H3B	107.9	C20—C18—C19	119.2 (5)
O1—C4—C5	106.0 (3)	C18—C19—H19A	109.5
O1—C4—C11	109.8 (3)	C18—C19—H19B	109.5
C5—C4—C11	112.6 (3)	H19A—C19—H19B	109.5
O1—C4—C3	109.4 (3)	C18—C19—H19C	109.5
C5—C4—C3	111.1 (3)	H19A—C19—H19C	109.5
C11—C4—C3	107.9 (3)	H19B—C19—H19C	109.5
C10—C5—C6	115.5 (4)	O4—C20—N6	120.5 (5)
C10—C5—C4	121.8 (4)	O4—C20—C18	124.1 (5)
C6—C5—C4	122.7 (4)	N6—C20—C18	115.3 (4)
F1—C6—C7	117.1 (4)	O3—C21—N6	123.1 (4)
F1—C6—C5	118.6 (4)	O3—C21—N5	122.3 (4)
C7—C6—C5	124.4 (4)	N6—C21—N5	114.5 (4)
C6—C7—C8	116.9 (4)	C1—N1—N3	101.6 (4)
C6—C7—H7	121.6	C2—N2—C1	102.3 (4)
C8—C7—H7	121.6	C2—N3—N1	109.6 (3)
F2—C8—C9	119.3 (4)	C2—N3—C3	130.1 (4)
F2—C8—C7	118.3 (4)	N1—N3—C3	120.2 (3)
C9—C8—C7	122.3 (4)	C15—N4—C12	122.2 (3)
C8—C9—C10	118.4 (4)	C15—N4—C11	118.4 (3)
C8—C9—H9	120.8	C12—N4—C11	119.2 (3)
C10—C9—H9	120.8	C17—N5—C21	121.4 (4)
C9—C10—C5	122.6 (4)	C17—N5—C16	121.9 (4)
C9—C10—H10	118.7	C21—N5—C16	116.7 (4)
C5—C10—H10	118.7	C20—N6—C21	127.5 (4)
N4—C11—C4	113.4 (3)	C20—N6—H6	121.9
N4—C11—H11A	108.9	C21—N6—H6	110.3
C4—C11—H11A	108.9	C4—O1—H1A	109.5
N4—C11—H11B	108.9	Cl1—C1A—Cl2	122 (2)
C4—C11—H11B	108.9	Cl1—C1A—H1AA	108.7
H11A—C11—H11B	107.7	Cl2—C1A—H1AA	108.8
N4—C12—C13	118.6 (4)	Cl1—C1A—H1AB	104.8
N4—C12—C14	119.8 (4)	Cl2—C1A—H1AB	104.5
C13—C12—C14	59.8 (3)	H1AA—C1A—H1AB	107.3
N4—C12—H12	115.7	Cl1—C1A—H1BA	96.4
C13—C12—H12	115.7	Cl2—C1A—H1BA	124.6
C14—C12—H12	115.7	H1AA—C1A—H1BA	92.2
C14—C13—C12	60.3 (3)	H1AB—C1A—H1BA	21.3
C14—C13—H13A	117.7	C1A—Cl1—H1BB	73.9
C12—C13—H13A	117.7	Cl1'—C1B—Cl2'	147 (2)
C14—C13—H13B	117.7	Cl1'—C1B—H1AB	106.6
C12—C13—H13B	117.7	Cl2'—C1B—H1AB	82.9
H13A—C13—H13B	114.9	Cl1'—C1B—H1BA	100.4
C13—C14—C12	59.9 (3)	Cl2'—C1B—H1BA	100.3
C13—C14—H14A	117.8	H1AB—C1B—H1BA	25.2
C12—C14—H14A	117.8	Cl1'—C1B—H1BB	99.5
C13—C14—H14B	117.8	Cl2'—C1B—H1BB	100.0
C12—C14—H14B	117.8	H1AB—C1B—H1BB	125.7
H14A—C14—H14B	114.9	H1BA—C1B—H1BB	104.4
O2—C15—N4	123.6 (4)	C1B—Cl1'—H1AA	74.3
O2—C15—C16	119.6 (4)	C1B—Cl2'—H1AB	27.0
N4—C15—C16	116.7 (4)
N3—C3—C4—O1	−66.7 (4)	C17—C18—C20—N6	2.0 (7)
N3—C3—C4—C5	50.0 (4)	C19—C18—C20—N6	−179.9 (5)
N3—C3—C4—C11	173.9 (3)	N2—C1—N1—N3	−0.6 (6)
O1—C4—C5—C10	−2.4 (5)	N3—C2—N2—C1	0.6 (6)
C11—C4—C5—C10	117.7 (4)	N1—C1—N2—C2	0.1 (7)
C3—C4—C5—C10	−121.1 (4)	N2—C2—N3—N1	−1.0 (5)
O1—C4—C5—C6	176.4 (4)	N2—C2—N3—C3	−175.6 (4)
C11—C4—C5—C6	−63.5 (5)	C1—N1—N3—C2	1.0 (5)
C3—C4—C5—C6	57.7 (5)	C1—N1—N3—C3	176.2 (4)
C10—C5—C6—F1	−179.9 (4)	C4—C3—N3—C2	65.9 (6)
C4—C5—C6—F1	1.3 (6)	C4—C3—N3—N1	−108.2 (4)
C10—C5—C6—C7	0.3 (6)	O2—C15—N4—C12	175.1 (4)
C4—C5—C6—C7	−178.5 (4)	C16—C15—N4—C12	−8.5 (5)
F1—C6—C7—C8	179.4 (4)	O2—C15—N4—C11	−9.3 (6)
C5—C6—C7—C8	−0.8 (7)	C16—C15—N4—C11	167.1 (3)
C6—C7—C8—F2	179.5 (5)	C13—C12—N4—C15	−135.1 (5)
C6—C7—C8—C9	0.5 (8)	C14—C12—N4—C15	−65.5 (6)
F2—C8—C9—C10	−178.8 (5)	C13—C12—N4—C11	49.3 (6)
C7—C8—C9—C10	0.2 (8)	C14—C12—N4—C11	118.9 (5)
C8—C9—C10—C5	−0.7 (7)	C4—C11—N4—C15	−89.6 (4)
C6—C5—C10—C9	0.4 (6)	C4—C11—N4—C12	86.1 (5)
C4—C5—C10—C9	179.3 (4)	C18—C17—N5—C21	−1.3 (7)
O1—C4—C11—N4	61.5 (4)	C18—C17—N5—C16	178.0 (4)
C5—C4—C11—N4	−56.3 (5)	O3—C21—N5—C17	−177.8 (4)
C3—C4—C11—N4	−179.4 (3)	N6—C21—N5—C17	2.6 (6)
N4—C12—C13—C14	109.7 (5)	O3—C21—N5—C16	2.8 (6)
N4—C12—C14—C13	−107.7 (5)	N6—C21—N5—C16	−176.7 (4)
O2—C15—C16—N5	−27.8 (6)	C15—C16—N5—C17	100.4 (5)
N4—C15—C16—N5	155.7 (3)	C15—C16—N5—C21	−80.3 (5)
N5—C17—C18—C20	−1.1 (7)	O4—C20—N6—C21	178.6 (4)
N5—C17—C18—C19	−179.2 (5)	C18—C20—N6—C21	−0.6 (7)
C17—C18—C20—O4	−177.2 (5)	O3—C21—N6—C20	178.8 (5)
C19—C18—C20—O4	0.9 (8)	N5—C21—N6—C20	−1.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N2i	0.80	2.11	2.893 (5)	167.
O1—H1A···O2ii	0.82	2.13	2.903 (4)	158.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N2i	0.80	2.11	2.893 (5)	167
O1—H1A⋯O2ii	0.82	2.13	2.903 (4)	158

Symmetry codes: (i) ; (ii) .