Diethyl 2,6-dihy-droxy-4-(3-nitro-phen-yl)-2,6-bis-(trifluoro-meth-yl)piperidine-3,5-dicarboxyl-ate.

In the title compound, C(19)H(20)F(6)N(2)O(8), the eth-oxy and ethyl groups are disordered over two sets of sites, with occupancy ratios of 0.212 (18):0.788 (18) and 0.746 (6):0.254 (6), respectively. The piperidine ring adopts a chair conformation. In the mol-ecule, intra-molecular O-H⋯O hydrogen bonds form two S(6) ring motifs. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds, forming dimers.

Related literature

For studies on 1,4-dihydro­pyridine and piperidones reported by our group, see: Palakshi Reddy et al. (2011a ▶,b ▶,c ▶); Rathore et al. (2009 ▶); Rajesh et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H20F6N2O8

M = 518.37

Monoclinic,

a = 17.7353 (16) Å

b = 15.2025 (14) Å

c = 17.3003 (16) Å

β = 91.049 (2)°

V = 4663.7 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.21 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.970, T max = 0.980

19801 measured reflections

5339 independent reflections

3229 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.02

5339 reflections

376 parameters

104 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055346/rz2690sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055346/rz2690Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055346/rz2690Isup3.cml

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

C19H20F6N2O8	F(000) = 2128
Mr = 518.37	Dx = 1.477 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4307 reflections
a = 17.7353 (16) Å	θ = 2.9–27.1°
b = 15.2025 (14) Å	µ = 0.14 mm−1
c = 17.3003 (16) Å	T = 296 K
β = 91.049 (2)°	Block, colourless
V = 4663.7 (7) Å3	0.21 × 0.21 × 0.14 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	5339 independent reflections
Radiation source: fine-focus sealed tube	3229 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→22
Tmin = 0.970, Tmax = 0.980	k = −19→19
19801 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0493P)2 + 2.0652P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5339 reflections	Δρmax = 0.21 e Å−3
376 parameters	Δρmin = −0.19 e Å−3
104 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00084 (15)

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)
F1	0.36213 (8)	0.39434 (9)	0.23934 (8)	0.0892 (5)
F2	0.44369 (7)	0.30673 (10)	0.19217 (8)	0.0896 (5)
F3	0.37694 (9)	0.26642 (10)	0.28772 (7)	0.0906 (5)
F4	0.10958 (8)	0.36187 (10)	0.23426 (8)	0.0903 (5)
F5	0.04642 (7)	0.25576 (11)	0.18300 (8)	0.0940 (5)
F6	0.11954 (8)	0.23302 (10)	0.28156 (7)	0.0887 (5)
O1	0.26864 (19)	−0.15284 (15)	−0.12905 (13)	0.1564 (11)
O2	0.27330 (16)	−0.01793 (15)	−0.15351 (11)	0.1287 (9)
O3	0.4418 (19)	0.106 (3)	0.163 (2)	0.060 (4)	0.212 (18)
C13	0.4982 (16)	0.046 (2)	0.1072 (17)	0.103 (5)	0.212 (18)
H13A	0.4682	0.0137	0.0696	0.123*	0.212 (18)
H13B	0.5317	0.0851	0.0795	0.123*	0.212 (18)
C14	0.5328 (18)	−0.001 (2)	0.145 (2)	0.146 (8)	0.212 (18)
H14A	0.5785	−0.0162	0.1188	0.219*	0.212 (18)
H14B	0.5040	−0.0539	0.1532	0.219*	0.212 (18)
H14C	0.5449	0.0258	0.1934	0.219*	0.212 (18)
O3A	0.4362 (6)	0.0929 (8)	0.1583 (7)	0.085 (2)	0.788 (18)
C13A	0.5125 (4)	0.0683 (6)	0.1339 (4)	0.0949 (19)	0.788 (18)
H13C	0.5483	0.0687	0.1770	0.114*	0.788 (18)
H13D	0.5305	0.1067	0.0934	0.114*	0.788 (18)
C14A	0.4973 (5)	−0.0272 (5)	0.1033 (5)	0.127 (3)	0.788 (18)
H14D	0.5434	−0.0518	0.0846	0.191*	0.788 (18)
H14E	0.4604	−0.0253	0.0621	0.191*	0.788 (18)
H14F	0.4789	−0.0630	0.1446	0.191*	0.788 (18)
O4	0.41966 (8)	0.17953 (11)	0.05490 (9)	0.0736 (5)
O6	0.09483 (8)	0.14011 (10)	0.04494 (8)	0.0658 (4)
N1	0.24395 (8)	0.29412 (10)	0.19612 (8)	0.0462 (4)
H1N1	0.2380	0.3481	0.1947	0.069*
N2	0.27191 (15)	−0.07751 (16)	−0.10851 (13)	0.0909 (7)
O7	0.16066 (8)	0.30333 (9)	0.09062 (8)	0.0552 (4)
O8	0.32528 (8)	0.32280 (9)	0.09458 (8)	0.0551 (4)
C1	0.32495 (9)	0.17525 (12)	0.15245 (10)	0.0447 (4)
H1A	0.3228	0.1466	0.2031	0.054*
C2	0.25852 (9)	0.14162 (11)	0.10170 (9)	0.0413 (4)
H2A	0.2559	0.1780	0.0549	0.050*
C3	0.18628 (10)	0.15865 (12)	0.14797 (10)	0.0455 (4)
H3A	0.1924	0.1309	0.1988	0.055*
C4	0.17731 (10)	0.25802 (12)	0.16000 (10)	0.0471 (4)
C5	0.31612 (10)	0.27463 (12)	0.16372 (10)	0.0458 (4)
C6	0.26648 (11)	0.04661 (12)	0.07686 (10)	0.0480 (4)
C7	0.27170 (15)	−0.02213 (14)	0.12943 (13)	0.0756 (7)
H7A	0.2712	−0.0101	0.1821	0.091*
C8	0.27757 (19)	−0.10787 (16)	0.10466 (16)	0.0975 (10)
H8A	0.2809	−0.1532	0.1406	0.117*
C9	0.27849 (17)	−0.12666 (15)	0.02689 (16)	0.0892 (8)
H9A	0.2826	−0.1844	0.0097	0.107*
C10	0.27314 (13)	−0.05851 (14)	−0.02482 (12)	0.0649 (6)
C11	0.26732 (11)	0.02741 (13)	−0.00142 (11)	0.0525 (5)
H11A	0.2640	0.0724	−0.0378	0.063*
C12	0.39930 (11)	0.15197 (14)	0.11582 (12)	0.0543 (5)
C15	0.11874 (11)	0.11741 (14)	0.10727 (11)	0.0530 (5)
O5	0.09056 (9)	0.05249 (11)	0.14855 (9)	0.0774 (5)
C16	0.0290 (7)	0.0034 (8)	0.1123 (8)	0.088 (2)	0.746 (6)
H16A	0.0284	−0.0558	0.1331	0.105*	0.746 (6)
H16B	0.0375	−0.0007	0.0572	0.105*	0.746 (6)
C17	−0.0461 (2)	0.0461 (3)	0.1254 (3)	0.1125 (18)	0.746 (6)
H17A	−0.0856	0.0084	0.1062	0.169*	0.746 (6)
H17B	−0.0483	0.1014	0.0987	0.169*	0.746 (6)
H17C	−0.0524	0.0558	0.1798	0.169*	0.746 (6)
C16A	0.020 (2)	−0.006 (3)	0.121 (3)	0.110 (7)	0.254 (6)
H16C	−0.0045	−0.0335	0.1640	0.132*	0.254 (6)
H16D	−0.0160	0.0283	0.0908	0.132*	0.254 (6)
C17A	0.0617 (8)	−0.0715 (10)	0.0718 (8)	0.129 (6)	0.254 (6)
H17D	0.0261	−0.1119	0.0490	0.194*	0.254 (6)
H17E	0.0973	−0.1033	0.1035	0.194*	0.254 (6)
H17F	0.0879	−0.0411	0.0317	0.194*	0.254 (6)
C18	0.37467 (12)	0.31059 (15)	0.22174 (12)	0.0631 (6)
C19	0.11297 (13)	0.27698 (17)	0.21556 (12)	0.0662 (6)
H1O7	0.1249 (18)	0.270 (2)	0.0612 (18)	0.131 (12)*
H1O8	0.3669 (16)	0.3016 (18)	0.0676 (16)	0.107 (10)*

	U11	U22	U33	U12	U13	U23
F1	0.1027 (11)	0.0731 (9)	0.0911 (10)	−0.0184 (8)	−0.0143 (8)	−0.0273 (8)
F2	0.0528 (8)	0.1192 (12)	0.0964 (10)	−0.0196 (7)	−0.0136 (7)	−0.0125 (9)
F3	0.1094 (11)	0.1064 (11)	0.0548 (7)	−0.0210 (9)	−0.0313 (7)	0.0068 (7)
F4	0.0893 (10)	0.0979 (11)	0.0846 (9)	0.0251 (8)	0.0223 (7)	−0.0234 (8)
F5	0.0472 (7)	0.1460 (14)	0.0895 (10)	0.0020 (8)	0.0177 (7)	−0.0190 (9)
F6	0.0921 (10)	0.1193 (12)	0.0559 (8)	0.0020 (8)	0.0331 (7)	0.0065 (8)
O1	0.278 (4)	0.0839 (15)	0.1069 (17)	0.0169 (18)	−0.0065 (19)	−0.0513 (13)
O2	0.235 (3)	0.0943 (16)	0.0572 (11)	0.0125 (16)	0.0104 (14)	−0.0131 (11)
O3	0.044 (7)	0.079 (8)	0.057 (7)	0.004 (6)	−0.012 (6)	−0.002 (6)
C13	0.079 (8)	0.125 (10)	0.103 (10)	0.054 (8)	−0.009 (8)	−0.031 (9)
C14	0.138 (15)	0.166 (17)	0.132 (16)	0.080 (13)	−0.004 (13)	−0.017 (14)
O3A	0.073 (4)	0.105 (5)	0.078 (3)	0.048 (3)	0.006 (3)	0.011 (3)
C13A	0.078 (3)	0.126 (5)	0.080 (3)	0.052 (3)	−0.007 (2)	−0.012 (3)
C14A	0.142 (6)	0.118 (5)	0.123 (5)	0.060 (4)	0.038 (4)	0.009 (4)
O4	0.0514 (9)	0.1103 (13)	0.0595 (9)	0.0113 (8)	0.0097 (7)	0.0095 (9)
O6	0.0560 (9)	0.0897 (11)	0.0515 (8)	−0.0178 (7)	−0.0057 (7)	0.0130 (8)
N1	0.0508 (9)	0.0483 (9)	0.0396 (8)	−0.0002 (7)	0.0042 (7)	−0.0060 (7)
N2	0.132 (2)	0.0692 (15)	0.0711 (14)	0.0120 (13)	0.0019 (13)	−0.0252 (12)
O7	0.0592 (8)	0.0592 (9)	0.0471 (7)	0.0066 (7)	−0.0009 (6)	0.0057 (6)
O8	0.0608 (9)	0.0571 (8)	0.0475 (7)	−0.0029 (7)	0.0057 (6)	0.0089 (6)
C1	0.0440 (10)	0.0502 (10)	0.0399 (9)	0.0018 (8)	−0.0015 (7)	0.0017 (8)
C2	0.0446 (10)	0.0419 (10)	0.0375 (9)	−0.0009 (8)	0.0014 (7)	0.0024 (7)
C3	0.0443 (10)	0.0533 (11)	0.0389 (9)	−0.0062 (8)	0.0027 (7)	0.0050 (8)
C4	0.0442 (10)	0.0583 (12)	0.0391 (9)	−0.0002 (8)	0.0062 (8)	−0.0001 (8)
C5	0.0466 (10)	0.0516 (11)	0.0392 (9)	−0.0041 (8)	0.0007 (8)	0.0000 (8)
C6	0.0562 (11)	0.0420 (10)	0.0456 (10)	−0.0019 (8)	0.0001 (8)	0.0043 (8)
C7	0.120 (2)	0.0524 (13)	0.0545 (12)	0.0009 (13)	−0.0073 (12)	0.0081 (11)
C8	0.167 (3)	0.0501 (14)	0.0751 (17)	0.0019 (16)	−0.0128 (18)	0.0135 (13)
C9	0.136 (2)	0.0401 (12)	0.0913 (19)	0.0018 (14)	−0.0111 (17)	−0.0053 (13)
C10	0.0848 (16)	0.0515 (12)	0.0583 (12)	0.0006 (11)	−0.0009 (11)	−0.0111 (10)
C11	0.0652 (13)	0.0460 (11)	0.0462 (10)	0.0023 (9)	0.0020 (9)	0.0001 (9)
C12	0.0459 (11)	0.0676 (13)	0.0494 (11)	0.0056 (9)	−0.0035 (9)	−0.0047 (10)
C15	0.0502 (11)	0.0625 (13)	0.0466 (11)	−0.0102 (9)	0.0058 (9)	0.0052 (9)
O5	0.0769 (11)	0.0878 (11)	0.0671 (9)	−0.0391 (9)	−0.0074 (8)	0.0215 (8)
C16	0.082 (4)	0.095 (4)	0.086 (4)	−0.056 (3)	−0.011 (3)	0.019 (3)
C17	0.075 (3)	0.134 (4)	0.129 (4)	−0.032 (3)	0.012 (2)	−0.007 (3)
C16A	0.101 (14)	0.120 (13)	0.109 (12)	−0.031 (12)	−0.013 (10)	0.037 (10)
C17A	0.136 (11)	0.134 (12)	0.116 (10)	−0.064 (9)	−0.050 (8)	0.012 (8)
C18	0.0622 (14)	0.0700 (15)	0.0568 (12)	−0.0126 (11)	−0.0081 (10)	−0.0028 (11)
C19	0.0577 (13)	0.0868 (17)	0.0546 (12)	0.0053 (12)	0.0142 (10)	−0.0058 (12)

F1—C18	1.329 (3)	C1—C2	1.544 (2)
F2—C18	1.337 (2)	C1—H1A	0.9800
F3—C18	1.324 (2)	C2—C6	1.514 (2)
F4—C19	1.332 (3)	C2—C3	1.545 (2)
F5—C19	1.338 (3)	C2—H2A	0.9800
F6—C19	1.326 (3)	C3—C15	1.514 (3)
O1—N2	1.200 (3)	C3—C4	1.534 (3)
O2—N2	1.195 (3)	C3—H3A	0.9800
O3—C12	1.31 (4)	C4—C19	1.533 (3)
O3—C13	1.67 (5)	C5—C18	1.532 (3)
C13—C14	1.14 (5)	C6—C11	1.386 (2)
C13—H13A	0.9700	C6—C7	1.387 (3)
C13—H13B	0.9700	C7—C8	1.377 (3)
C14—H14A	0.9600	C7—H7A	0.9300
C14—H14B	0.9600	C8—C9	1.376 (3)
C14—H14C	0.9600	C8—H8A	0.9300
O3A—C12	1.326 (12)	C9—C10	1.371 (3)
O3A—C13A	1.473 (13)	C9—H9A	0.9300
C13A—C14A	1.567 (18)	C10—C11	1.372 (3)
C13A—H13C	0.9700	C11—H11A	0.9300
C13A—H13D	0.9700	C15—O5	1.322 (2)
C14A—H14D	0.9600	O5—C16	1.454 (11)
C14A—H14E	0.9600	O5—C16A	1.59 (4)
C14A—H14F	0.9600	C16—C17	1.503 (14)
O4—C12	1.196 (2)	C16—H16A	0.9700
O6—C15	1.202 (2)	C16—H16B	0.9700
N1—C4	1.436 (2)	C17—H17A	0.9600
N1—C5	1.438 (2)	C17—H17B	0.9600
N1—H1N1	0.8269	C17—H17C	0.9600
N2—C10	1.476 (3)	C16A—C17A	1.51 (4)
O7—C4	1.410 (2)	C16A—H16C	0.9700
O7—H1O7	0.95 (3)	C16A—H16D	0.9700
O8—C5	1.414 (2)	C17A—H17D	0.9600
O8—H1O8	0.94 (3)	C17A—H17E	0.9600
C1—C12	1.515 (3)	C17A—H17F	0.9600
C1—C5	1.532 (3)
C12—O3—C13	106 (3)	C11—C6—C7	118.70 (18)
C14—C13—O3	110 (3)	C11—C6—C2	118.75 (16)
C14—C13—H13A	111.0	C7—C6—C2	122.54 (17)
O3—C13—H13A	109.7	C8—C7—C6	120.9 (2)
C14—C13—H13B	109.7	C8—C7—H7A	119.5
O3—C13—H13B	109.7	C6—C7—H7A	119.5
H13A—C13—H13B	108.2	C9—C8—C7	120.2 (2)
C12—O3A—C13A	117.4 (10)	C9—C8—H8A	119.9
O3A—C13A—C14A	100.3 (9)	C7—C8—H8A	119.9
O3A—C13A—H13C	111.7	C10—C9—C8	118.6 (2)
C14A—C13A—H13C	111.7	C10—C9—H9A	120.7
O3A—C13A—H13D	111.7	C8—C9—H9A	120.7
C14A—C13A—H13D	111.7	C9—C10—C11	122.1 (2)
H13C—C13A—H13D	109.5	C9—C10—N2	119.5 (2)
C13A—C14A—H14D	109.5	C11—C10—N2	118.4 (2)
C13A—C14A—H14E	109.5	C10—C11—C6	119.42 (18)
H14D—C14A—H14E	109.5	C10—C11—H11A	120.3
C13A—C14A—H14F	109.5	C6—C11—H11A	120.3
H14D—C14A—H14F	109.5	O4—C12—O3	123.9 (19)
H14E—C14A—H14F	109.5	O4—C12—O3A	124.9 (6)
C4—N1—C5	118.89 (14)	O4—C12—C1	124.46 (18)
C4—N1—H1N1	105.3	O3—C12—C1	111.2 (19)
C5—N1—H1N1	107.8	O3A—C12—C1	110.6 (6)
O2—N2—O1	122.1 (2)	O6—C15—O5	124.63 (18)
O2—N2—C10	119.4 (2)	O6—C15—C3	124.15 (17)
O1—N2—C10	118.5 (3)	O5—C15—C3	111.21 (16)
C4—O7—H1O7	109.0 (19)	C15—O5—C16	116.0 (6)
C5—O8—H1O8	110.3 (17)	C15—O5—C16A	123.6 (17)
C12—C1—C5	112.05 (15)	O5—C16—C17	112.0 (8)
C12—C1—C2	110.23 (14)	O5—C16—H16A	109.2
C5—C1—C2	108.68 (14)	C17—C16—H16A	109.2
C12—C1—H1A	108.6	O5—C16—H16B	109.2
C5—C1—H1A	108.6	C17—C16—H16B	109.2
C2—C1—H1A	108.6	H16A—C16—H16B	107.9
C6—C2—C1	113.77 (14)	C17A—C16A—O5	99 (2)
C6—C2—C3	112.92 (14)	C17A—C16A—H16C	112.0
C1—C2—C3	106.34 (13)	O5—C16A—H16C	112.0
C6—C2—H2A	107.9	C17A—C16A—H16D	112.0
C1—C2—H2A	107.9	O5—C16A—H16D	112.0
C3—C2—H2A	107.9	H16C—C16A—H16D	109.7
C15—C3—C4	112.82 (16)	C16A—C17A—H17D	109.5
C15—C3—C2	110.25 (15)	C16A—C17A—H17E	109.5
C4—C3—C2	108.93 (14)	H17D—C17A—H17E	109.5
C15—C3—H3A	108.2	C16A—C17A—H17F	109.5
C4—C3—H3A	108.2	H17D—C17A—H17F	109.5
C2—C3—H3A	108.2	H17E—C17A—H17F	109.5
O7—C4—N1	109.97 (15)	F3—C18—F1	106.91 (18)
O7—C4—C19	107.16 (15)	F3—C18—F2	107.10 (19)
N1—C4—C19	105.75 (15)	F1—C18—F2	106.74 (18)
O7—C4—C3	112.72 (14)	F3—C18—C5	113.17 (17)
N1—C4—C3	110.43 (15)	F1—C18—C5	112.19 (18)
C19—C4—C3	110.53 (16)	F2—C18—C5	110.38 (17)
O8—C5—N1	109.87 (15)	F6—C19—F4	106.42 (18)
O8—C5—C1	112.92 (14)	F6—C19—F5	107.68 (19)
N1—C5—C1	110.29 (14)	F4—C19—F5	107.00 (19)
O8—C5—C18	106.40 (15)	F6—C19—C4	112.99 (18)
N1—C5—C18	105.58 (15)	F4—C19—C4	111.84 (19)
C1—C5—C18	111.45 (16)	F5—C19—C4	110.60 (17)
C12—O3—C13—C14	−174 (4)	C7—C6—C11—C10	0.1 (3)
C12—O3A—C13A—C14A	−108.6 (8)	C2—C6—C11—C10	−178.85 (18)
C12—C1—C2—C6	48.7 (2)	C13—O3—C12—O4	−33 (3)
C5—C1—C2—C6	171.81 (14)	C13—O3—C12—O3A	66 (13)
C12—C1—C2—C3	173.59 (15)	C13—O3—C12—C1	153.9 (18)
C5—C1—C2—C3	−63.26 (17)	C13A—O3A—C12—O4	8.6 (12)
C6—C2—C3—C15	−47.4 (2)	C13A—O3A—C12—O3	−80 (14)
C1—C2—C3—C15	−172.88 (15)	C13A—O3A—C12—C1	−175.2 (8)
C6—C2—C3—C4	−171.73 (14)	C5—C1—C12—O4	−57.3 (3)
C1—C2—C3—C4	62.81 (17)	C2—C1—C12—O4	63.8 (3)
C5—N1—C4—O7	−74.3 (2)	C5—C1—C12—O3	115.9 (16)
C5—N1—C4—C19	170.28 (16)	C2—C1—C12—O3	−123.0 (16)
C5—N1—C4—C3	50.7 (2)	C5—C1—C12—O3A	126.5 (5)
C15—C3—C4—O7	−54.4 (2)	C2—C1—C12—O3A	−112.3 (5)
C2—C3—C4—O7	68.37 (18)	C4—C3—C15—O6	57.1 (3)
C15—C3—C4—N1	−177.85 (14)	C2—C3—C15—O6	−65.0 (3)
C2—C3—C4—N1	−55.08 (18)	C4—C3—C15—O5	−124.01 (18)
C15—C3—C4—C19	65.5 (2)	C2—C3—C15—O5	113.95 (18)
C2—C3—C4—C19	−171.74 (15)	O6—C15—O5—C16	3.6 (7)
C4—N1—C5—O8	73.9 (2)	C3—C15—O5—C16	−175.3 (6)
C4—N1—C5—C1	−51.2 (2)	O6—C15—O5—C16A	0(2)
C4—N1—C5—C18	−171.71 (16)	C3—C15—O5—C16A	−179 (2)
C12—C1—C5—O8	54.7 (2)	C15—O5—C16—C17	−85.9 (8)
C2—C1—C5—O8	−67.35 (18)	C16A—O5—C16—C17	74 (16)
C12—C1—C5—N1	178.06 (14)	C15—O5—C16A—C17A	84 (3)
C2—C1—C5—N1	56.01 (18)	C16—O5—C16A—C17A	63 (15)
C12—C1—C5—C18	−65.0 (2)	O8—C5—C18—F3	−174.73 (17)
C2—C1—C5—C18	172.94 (15)	N1—C5—C18—F3	68.5 (2)
C1—C2—C6—C11	−120.73 (19)	C1—C5—C18—F3	−51.2 (2)
C3—C2—C6—C11	117.93 (19)	O8—C5—C18—F1	64.2 (2)
C1—C2—C6—C7	60.4 (2)	N1—C5—C18—F1	−52.5 (2)
C3—C2—C6—C7	−61.0 (2)	C1—C5—C18—F1	−172.31 (16)
C11—C6—C7—C8	0.0 (4)	O8—C5—C18—F2	−54.7 (2)
C2—C6—C7—C8	178.9 (2)	N1—C5—C18—F2	−171.46 (17)
C6—C7—C8—C9	0.1 (5)	C1—C5—C18—F2	68.8 (2)
C7—C8—C9—C10	−0.3 (5)	O7—C4—C19—F6	175.74 (18)
C8—C9—C10—C11	0.3 (4)	N1—C4—C19—F6	−67.0 (2)
C8—C9—C10—N2	−178.3 (3)	C3—C4—C19—F6	52.6 (2)
O2—N2—C10—C9	−174.1 (3)	O7—C4—C19—F4	−64.2 (2)
O1—N2—C10—C9	6.8 (4)	N1—C4—C19—F4	53.1 (2)
O2—N2—C10—C11	7.2 (4)	C3—C4—C19—F4	172.61 (17)
O1—N2—C10—C11	−171.9 (3)	O7—C4—C19—F5	55.0 (2)
C9—C10—C11—C6	−0.2 (4)	N1—C4—C19—F5	172.24 (18)
N2—C10—C11—C6	178.4 (2)	C3—C4—C19—F5	−68.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1O7···O6	0.95 (3)	2.06 (3)	2.848 (2)	139 (3)
O8—H1O8···O4	0.94 (3)	2.09 (3)	2.839 (2)	136 (2)
O7—H1O7···O4i	0.95 (3)	2.28 (3)	2.882 (2)	121 (2)
O8—H1O8···O6i	0.94 (3)	2.26 (3)	2.877 (2)	123 (2)
C11—H11A···O7i	0.93	2.50	3.272 (2)	141
C11—H11A···O8i	0.93	2.44	3.222 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1O7⋯O6	0.95 (3)	2.06 (3)	2.848 (2)	139 (3)
O8—H1O8⋯O4	0.94 (3)	2.09 (3)	2.839 (2)	136 (2)
O7—H1O7⋯O4i	0.95 (3)	2.28 (3)	2.882 (2)	121 (2)
O8—H1O8⋯O6i	0.94 (3)	2.26 (3)	2.877 (2)	123 (2)
C11—H11A⋯O7i	0.93	2.50	3.272 (2)	141
C11—H11A⋯O8i	0.93	2.44	3.222 (2)	142

Symmetry code: (i) .