Isopropyl 1-benzoyl-4-benzo-yloxy-2,6-di-phenyl-1,2,3,6-tetrahydropyridine-3-carboxyl-ate.

In the title compound, C35H31NO5, the piperidine ring has an envelope conformation, with the phenyl-substituted C atom adjacent to the methyl-ene C atom as the flap. This flap atom deviates by 0.633 (2) Å from the mean plane of the other five essentially coplanar atoms in the ring (r.m.s. deviation = 0.044 Å). Intra-molecular C-H⋯O hydrogen bonds form S(7) and S(9) ring motifs. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers with R (2) 2(16) loops.

Related literature

For general background to piperidine derivatives, see: Mishra & Ghosh (2011 ▶); Ramachandran et al. (2011 ▶); Natarajan & Mathews (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C35H31NO5

M = 545.61

Triclinic,

a = 10.1788 (6) Å

b = 11.4325 (7) Å

c = 13.1395 (9) Å

α = 81.847 (2)°

β = 86.662 (3)°

γ = 69.654 (2)°

V = 1419.08 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.952, T max = 0.959

25561 measured reflections

4996 independent reflections

3876 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.109

S = 1.02

4996 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015244/nk2218sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015244/nk2218Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015244/nk2218Isup3.cml

CCDC reference: 1010935

Additional supporting information: crystallographic information; 3D view; checkCIF report

C35H31NO5	V = 1419.08 (15) Å3
Mr = 545.61	Z = 2
Triclinic, P1	F(000) = 576
Hall symbol: -P 1	Dx = 1.277 Mg m−3
a = 10.1788 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4325 (7) Å	µ = 0.09 mm−1
c = 13.1395 (9) Å	T = 293 K
α = 81.847 (2)°	Block, white
β = 86.662 (3)°	0.22 × 0.19 × 0.17 mm
γ = 69.654 (2)°

Bruker SMART APEXII CCD diffractometer	4996 independent reflections
Radiation source: fine-focus sealed tube	3876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→12
Tmin = 0.952, Tmax = 0.959	k = −13→13
25561 measured reflections	l = −15→15

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.1791P] where P = (Fo2 + 2Fc2)/3
4996 reflections	(Δ/σ)max = 0.001
372 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 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
C20	0.96506 (16)	0.08716 (14)	0.67253 (11)	0.0519 (4)
H20	0.8967	0.0763	0.6347	0.062*
C21	1.09259 (18)	0.08065 (17)	0.62695 (13)	0.0646 (5)
H21	1.1096	0.0652	0.5589	0.078*
C22	1.19444 (18)	0.09692 (18)	0.68161 (14)	0.0673 (5)
H22	1.2805	0.0924	0.6510	0.081*
C23	1.16822 (16)	0.11983 (17)	0.78179 (13)	0.0614 (4)
H23	1.2365	0.1317	0.8189	0.074*
C24	1.04077 (15)	0.12537 (14)	0.82808 (12)	0.0490 (4)
H24	1.0246	0.1399	0.8963	0.059*
C19	0.93736 (14)	0.10950 (12)	0.77359 (10)	0.0405 (3)
C1	0.79798 (13)	0.10671 (12)	0.82094 (10)	0.0395 (3)
H1	0.7885	0.0281	0.8069	0.047*
C2	0.78325 (14)	0.10737 (12)	0.93686 (10)	0.0415 (3)
H2B	0.7113	0.0729	0.9625	0.050*
H2A	0.8709	0.0539	0.9692	0.050*
C3	0.74623 (13)	0.23572 (12)	0.96537 (10)	0.0386 (3)
C4	0.69662 (13)	0.34103 (12)	0.90037 (10)	0.0386 (3)
C5	0.65643 (14)	0.33967 (12)	0.79121 (10)	0.0392 (3)
H5	0.5551	0.3845	0.7874	0.047*
C6	0.72113 (14)	0.41264 (12)	0.70991 (10)	0.0407 (3)
C7	0.84932 (16)	0.42433 (14)	0.72253 (12)	0.0520 (4)
H7	0.9004	0.3847	0.7818	0.062*
C8	0.90280 (18)	0.49434 (16)	0.64800 (13)	0.0622 (4)
H8	0.9897	0.5011	0.6571	0.075*
C9	0.8275 (2)	0.55393 (15)	0.56055 (13)	0.0617 (4)
H9	0.8636	0.6008	0.5104	0.074*
C10	0.6998 (2)	0.54443 (14)	0.54719 (11)	0.0586 (4)
H10	0.6488	0.5851	0.4881	0.070*
C11	0.64622 (16)	0.47421 (13)	0.62156 (11)	0.0482 (4)
H11	0.5590	0.4683	0.6121	0.058*
C32	0.66009 (14)	0.46966 (13)	0.93018 (10)	0.0428 (3)
C33	0.72277 (18)	0.59541 (14)	1.03681 (13)	0.0607 (4)
H33	0.6229	0.6459	1.0317	0.073*
C34	0.7649 (3)	0.56499 (19)	1.14784 (15)	0.0892 (6)
H34A	0.8630	0.5163	1.1528	0.134*
H34B	0.7118	0.5175	1.1849	0.134*
H34C	0.7469	0.6417	1.1768	0.134*
C35	0.8054 (3)	0.6625 (2)	0.97090 (19)	0.0940 (7)
H35A	0.7820	0.7460	0.9887	0.141*
H35B	0.7838	0.6671	0.9000	0.141*
H35C	0.9036	0.6175	0.9816	0.141*
N1	0.67724 (11)	0.21014 (10)	0.77234 (8)	0.0401 (3)
O1	0.56508 (11)	0.55833 (9)	0.89218 (8)	0.0572 (3)
O2	0.74703 (10)	0.47477 (9)	1.00008 (8)	0.0530 (3)
O3	0.74902 (9)	0.24164 (9)	1.07066 (7)	0.0441 (2)
O4	0.98397 (11)	0.18061 (10)	1.06863 (8)	0.0535 (3)
O5	0.48623 (13)	0.27894 (10)	0.67147 (10)	0.0748 (4)
C25	0.87486 (15)	0.21460 (12)	1.11539 (11)	0.0409 (3)
C26	0.86017 (15)	0.23327 (12)	1.22445 (10)	0.0430 (3)
C13	0.58887 (14)	0.05921 (14)	0.70980 (11)	0.0468 (4)
C12	0.58068 (15)	0.19148 (14)	0.71550 (11)	0.0484 (4)
C31	0.73276 (17)	0.26105 (15)	1.27588 (12)	0.0569 (4)
H31	0.6523	0.2683	1.2417	0.068*
C27	0.97936 (17)	0.22454 (14)	1.27551 (12)	0.0523 (4)
H27	1.0651	0.2061	1.2410	0.063*
C14	0.62173 (17)	0.00964 (16)	0.61776 (13)	0.0605 (4)
H14	0.6427	0.0573	0.5599	0.073*
C18	0.55352 (17)	−0.01192 (15)	0.79366 (13)	0.0552 (4)
H18	0.5299	0.0206	0.8558	0.066*
C17	0.55295 (18)	−0.13089 (16)	0.78597 (15)	0.0656 (5)
H17	0.5275	−0.1776	0.8425	0.079*
C30	0.7256 (2)	0.27799 (17)	1.37821 (13)	0.0691 (5)
H30	0.6404	0.2951	1.4134	0.083*
C28	0.9705 (2)	0.24314 (16)	1.37712 (13)	0.0638 (5)
H28	1.0503	0.2377	1.4113	0.077*
C29	0.8442 (2)	0.26963 (16)	1.42834 (13)	0.0690 (5)
H29	0.8388	0.2820	1.4971	0.083*
C16	0.58985 (19)	−0.18005 (17)	0.69509 (16)	0.0696 (5)
H16	0.5920	−0.2611	0.6904	0.084*
C15	0.62343 (19)	−0.11043 (18)	0.61150 (16)	0.0704 (5)
H15	0.6477	−0.1440	0.5498	0.084*

	U11	U22	U33	U12	U13	U23
C20	0.0513 (9)	0.0568 (9)	0.0435 (9)	−0.0144 (7)	−0.0085 (7)	−0.0009 (7)
C21	0.0614 (11)	0.0797 (12)	0.0432 (9)	−0.0157 (9)	0.0018 (8)	−0.0006 (8)
C22	0.0450 (9)	0.0867 (13)	0.0607 (11)	−0.0155 (9)	0.0049 (8)	0.0003 (9)
C23	0.0402 (9)	0.0773 (11)	0.0652 (11)	−0.0170 (8)	−0.0040 (8)	−0.0111 (9)
C24	0.0401 (8)	0.0544 (9)	0.0483 (9)	−0.0094 (7)	−0.0061 (7)	−0.0082 (7)
C19	0.0381 (7)	0.0337 (7)	0.0433 (8)	−0.0055 (6)	−0.0063 (6)	−0.0001 (6)
C1	0.0383 (7)	0.0337 (7)	0.0432 (8)	−0.0086 (6)	−0.0095 (6)	−0.0002 (5)
C2	0.0384 (7)	0.0381 (7)	0.0443 (8)	−0.0107 (6)	−0.0072 (6)	0.0032 (6)
C3	0.0324 (7)	0.0455 (7)	0.0350 (7)	−0.0104 (6)	−0.0019 (5)	−0.0027 (6)
C4	0.0333 (7)	0.0388 (7)	0.0404 (7)	−0.0090 (6)	−0.0033 (6)	−0.0021 (6)
C5	0.0349 (7)	0.0350 (7)	0.0430 (8)	−0.0066 (5)	−0.0080 (6)	−0.0003 (5)
C6	0.0444 (8)	0.0334 (7)	0.0402 (8)	−0.0081 (6)	−0.0023 (6)	−0.0043 (5)
C7	0.0480 (9)	0.0497 (8)	0.0536 (9)	−0.0139 (7)	−0.0062 (7)	0.0039 (7)
C8	0.0566 (10)	0.0623 (10)	0.0680 (11)	−0.0247 (8)	0.0062 (8)	−0.0013 (8)
C9	0.0815 (12)	0.0510 (9)	0.0515 (10)	−0.0248 (9)	0.0148 (9)	−0.0041 (7)
C10	0.0828 (12)	0.0497 (9)	0.0387 (8)	−0.0182 (8)	−0.0062 (8)	−0.0005 (7)
C11	0.0579 (9)	0.0428 (8)	0.0416 (8)	−0.0138 (7)	−0.0097 (7)	−0.0030 (6)
C32	0.0387 (8)	0.0426 (8)	0.0432 (8)	−0.0103 (6)	0.0004 (6)	−0.0031 (6)
C33	0.0617 (10)	0.0438 (8)	0.0788 (12)	−0.0160 (7)	−0.0105 (9)	−0.0162 (8)
C34	0.1236 (18)	0.0702 (12)	0.0775 (14)	−0.0304 (12)	−0.0076 (13)	−0.0259 (10)
C35	0.1025 (16)	0.0748 (13)	0.1143 (18)	−0.0469 (12)	−0.0037 (13)	−0.0003 (12)
N1	0.0372 (6)	0.0365 (6)	0.0442 (7)	−0.0098 (5)	−0.0112 (5)	−0.0007 (5)
O1	0.0547 (6)	0.0426 (6)	0.0625 (7)	−0.0012 (5)	−0.0115 (5)	−0.0040 (5)
O2	0.0485 (6)	0.0433 (5)	0.0659 (7)	−0.0095 (5)	−0.0121 (5)	−0.0138 (5)
O3	0.0385 (5)	0.0524 (6)	0.0362 (5)	−0.0103 (4)	−0.0044 (4)	−0.0017 (4)
O4	0.0424 (6)	0.0679 (7)	0.0501 (6)	−0.0175 (5)	0.0011 (5)	−0.0118 (5)
O5	0.0707 (8)	0.0547 (7)	0.0959 (9)	−0.0160 (6)	−0.0504 (7)	0.0059 (6)
C25	0.0406 (8)	0.0381 (7)	0.0432 (8)	−0.0138 (6)	−0.0051 (6)	0.0002 (6)
C26	0.0478 (8)	0.0384 (7)	0.0410 (8)	−0.0131 (6)	−0.0058 (6)	−0.0011 (6)
C13	0.0383 (8)	0.0504 (8)	0.0533 (9)	−0.0164 (6)	−0.0131 (6)	−0.0038 (7)
C12	0.0448 (8)	0.0490 (8)	0.0505 (9)	−0.0156 (7)	−0.0148 (7)	0.0013 (7)
C31	0.0519 (9)	0.0659 (10)	0.0482 (9)	−0.0143 (8)	−0.0031 (7)	−0.0063 (7)
C27	0.0542 (9)	0.0510 (8)	0.0509 (9)	−0.0172 (7)	−0.0117 (7)	−0.0016 (7)
C14	0.0596 (10)	0.0691 (11)	0.0584 (10)	−0.0285 (8)	−0.0030 (8)	−0.0091 (8)
C18	0.0555 (9)	0.0579 (9)	0.0561 (10)	−0.0241 (8)	−0.0056 (7)	−0.0064 (7)
C17	0.0631 (11)	0.0602 (10)	0.0787 (12)	−0.0308 (8)	−0.0044 (9)	0.0007 (9)
C30	0.0712 (12)	0.0734 (12)	0.0476 (10)	−0.0059 (9)	0.0054 (9)	−0.0097 (8)
C28	0.0780 (13)	0.0586 (10)	0.0557 (10)	−0.0214 (9)	−0.0236 (9)	−0.0063 (8)
C29	0.0971 (15)	0.0557 (10)	0.0447 (9)	−0.0107 (9)	−0.0136 (10)	−0.0104 (8)
C16	0.0620 (11)	0.0574 (10)	0.0978 (15)	−0.0262 (9)	−0.0010 (10)	−0.0222 (10)
C15	0.0672 (11)	0.0764 (12)	0.0767 (12)	−0.0284 (10)	0.0042 (9)	−0.0319 (10)

C20—C21	1.380 (2)	C33—O2	1.4609 (17)
C20—C19	1.382 (2)	C33—C35	1.490 (3)
C20—H20	0.9300	C33—C34	1.503 (2)
C21—C22	1.373 (2)	C33—H33	0.9800
C21—H21	0.9300	C34—H34A	0.9600
C22—C23	1.371 (2)	C34—H34B	0.9600
C22—H22	0.9300	C34—H34C	0.9600
C23—C24	1.385 (2)	C35—H35A	0.9600
C23—H23	0.9300	C35—H35B	0.9600
C24—C19	1.3823 (19)	C35—H35C	0.9600
C24—H24	0.9300	N1—C12	1.3586 (17)
C19—C1	1.5244 (19)	O3—C25	1.3574 (16)
C1—N1	1.4775 (16)	O4—C25	1.2042 (16)
C1—C2	1.5225 (19)	O5—C12	1.2210 (17)
C1—H1	0.9800	C25—C26	1.4700 (19)
C2—C3	1.4800 (18)	C26—C31	1.383 (2)
C2—H2B	0.9700	C26—C27	1.387 (2)
C2—H2A	0.9700	C13—C18	1.381 (2)
C3—C4	1.3303 (18)	C13—C14	1.382 (2)
C3—O3	1.3970 (16)	C13—C12	1.498 (2)
C4—C32	1.4901 (19)	C31—C30	1.380 (2)
C4—C5	1.5179 (19)	C31—H31	0.9300
C5—N1	1.4761 (16)	C27—C28	1.374 (2)
C5—C6	1.5225 (19)	C27—H27	0.9300
C5—H5	0.9800	C14—C15	1.381 (2)
C6—C7	1.379 (2)	C14—H14	0.9300
C6—C11	1.3866 (19)	C18—C17	1.380 (2)
C7—C8	1.384 (2)	C18—H18	0.9300
C7—H7	0.9300	C17—C16	1.369 (3)
C8—C9	1.375 (2)	C17—H17	0.9300
C8—H8	0.9300	C30—C29	1.377 (3)
C9—C10	1.364 (2)	C30—H30	0.9300
C9—H9	0.9300	C28—C29	1.372 (3)
C10—C11	1.385 (2)	C28—H28	0.9300
C10—H10	0.9300	C29—H29	0.9300
C11—H11	0.9300	C16—C15	1.362 (3)
C32—O1	1.2013 (16)	C16—H16	0.9300
C32—O2	1.3326 (17)	C15—H15	0.9300
C21—C20—C19	121.03 (15)	O2—C33—C34	106.04 (13)
C21—C20—H20	119.5	C35—C33—C34	113.85 (17)
C19—C20—H20	119.5	O2—C33—H33	109.5
C22—C21—C20	120.23 (16)	C35—C33—H33	109.5
C22—C21—H21	119.9	C34—C33—H33	109.5
C20—C21—H21	119.9	C33—C34—H34A	109.5
C23—C22—C21	119.41 (16)	C33—C34—H34B	109.5
C23—C22—H22	120.3	H34A—C34—H34B	109.5
C21—C22—H22	120.3	C33—C34—H34C	109.5
C22—C23—C24	120.53 (16)	H34A—C34—H34C	109.5
C22—C23—H23	119.7	H34B—C34—H34C	109.5
C24—C23—H23	119.7	C33—C35—H35A	109.5
C19—C24—C23	120.50 (14)	C33—C35—H35B	109.5
C19—C24—H24	119.8	H35A—C35—H35B	109.5
C23—C24—H24	119.8	C33—C35—H35C	109.5
C20—C19—C24	118.30 (13)	H35A—C35—H35C	109.5
C20—C19—C1	118.08 (12)	H35B—C35—H35C	109.5
C24—C19—C1	123.50 (13)	C12—N1—C5	118.36 (10)
N1—C1—C2	107.94 (10)	C12—N1—C1	123.35 (11)
N1—C1—C19	112.29 (10)	C5—N1—C1	118.21 (10)
C2—C1—C19	116.08 (11)	C32—O2—C33	118.20 (11)
N1—C1—H1	106.7	C25—O3—C3	118.50 (10)
C2—C1—H1	106.7	O4—C25—O3	122.40 (13)
C19—C1—H1	106.7	O4—C25—C26	125.44 (13)
C3—C2—C1	111.93 (10)	O3—C25—C26	112.16 (12)
C3—C2—H2B	109.2	C31—C26—C27	119.87 (14)
C1—C2—H2B	109.2	C31—C26—C25	122.37 (13)
C3—C2—H2A	109.2	C27—C26—C25	117.75 (13)
C1—C2—H2A	109.2	C18—C13—C14	118.73 (14)
H2B—C2—H2A	107.9	C18—C13—C12	120.89 (14)
C4—C3—O3	119.97 (12)	C14—C13—C12	120.19 (14)
C4—C3—C2	124.51 (12)	O5—C12—N1	122.03 (13)
O3—C3—C2	115.02 (10)	O5—C12—C13	119.46 (12)
C3—C4—C32	123.90 (12)	N1—C12—C13	118.48 (12)
C3—C4—C5	121.79 (12)	C30—C31—C26	119.66 (16)
C32—C4—C5	113.95 (11)	C30—C31—H31	120.2
N1—C5—C4	110.68 (10)	C26—C31—H31	120.2
N1—C5—C6	114.62 (11)	C28—C27—C26	119.90 (16)
C4—C5—C6	113.74 (11)	C28—C27—H27	120.1
N1—C5—H5	105.6	C26—C27—H27	120.1
C4—C5—H5	105.6	C15—C14—C13	120.17 (16)
C6—C5—H5	105.6	C15—C14—H14	119.9
C7—C6—C11	118.44 (13)	C13—C14—H14	119.9
C7—C6—C5	122.49 (12)	C17—C18—C13	120.56 (16)
C11—C6—C5	119.02 (12)	C17—C18—H18	119.7
C6—C7—C8	120.72 (14)	C13—C18—H18	119.7
C6—C7—H7	119.6	C16—C17—C18	119.94 (17)
C8—C7—H7	119.6	C16—C17—H17	120.0
C9—C8—C7	120.01 (16)	C18—C17—H17	120.0
C9—C8—H8	120.0	C29—C30—C31	120.16 (17)
C7—C8—H8	120.0	C29—C30—H30	119.9
C10—C9—C8	120.09 (15)	C31—C30—H30	119.9
C10—C9—H9	120.0	C29—C28—C27	120.19 (16)
C8—C9—H9	120.0	C29—C28—H28	119.9
C9—C10—C11	120.01 (15)	C27—C28—H28	119.9
C9—C10—H10	120.0	C28—C29—C30	120.21 (16)
C11—C10—H10	120.0	C28—C29—H29	119.9
C10—C11—C6	120.73 (15)	C30—C29—H29	119.9
C10—C11—H11	119.6	C15—C16—C17	120.10 (16)
C6—C11—H11	119.6	C15—C16—H16	120.0
O1—C32—O2	124.75 (13)	C17—C16—H16	120.0
O1—C32—C4	122.82 (13)	C16—C15—C14	120.44 (17)
O2—C32—C4	112.39 (11)	C16—C15—H15	119.8
O2—C33—C35	108.43 (15)	C14—C15—H15	119.8
C19—C20—C21—C22	−0.3 (2)	C4—C5—N1—C1	−36.21 (15)
C20—C21—C22—C23	−0.1 (3)	C6—C5—N1—C1	94.06 (13)
C21—C22—C23—C24	0.6 (3)	C2—C1—N1—C12	−117.56 (14)
C22—C23—C24—C19	−0.8 (2)	C19—C1—N1—C12	113.23 (14)
C21—C20—C19—C24	0.1 (2)	C2—C1—N1—C5	59.05 (14)
C21—C20—C19—C1	−175.99 (13)	C19—C1—N1—C5	−70.17 (14)
C23—C24—C19—C20	0.5 (2)	O1—C32—O2—C33	2.6 (2)
C23—C24—C19—C1	176.31 (14)	C4—C32—O2—C33	−179.61 (12)
C20—C19—C1—N1	−66.15 (15)	C35—C33—O2—C32	−91.49 (17)
C24—C19—C1—N1	118.01 (14)	C34—C33—O2—C32	145.87 (15)
C20—C19—C1—C2	169.00 (12)	C4—C3—O3—C25	−108.81 (14)
C24—C19—C1—C2	−6.84 (18)	C2—C3—O3—C25	78.95 (14)
N1—C1—C2—C3	−45.79 (14)	C3—O3—C25—O4	−3.28 (18)
C19—C1—C2—C3	81.25 (14)	C3—O3—C25—C26	176.06 (10)
C1—C2—C3—C4	16.21 (18)	O4—C25—C26—C31	−173.77 (14)
C1—C2—C3—O3	−171.96 (10)	O3—C25—C26—C31	6.91 (18)
O3—C3—C4—C32	8.7 (2)	O4—C25—C26—C27	7.4 (2)
C2—C3—C4—C32	−179.86 (12)	O3—C25—C26—C27	−171.88 (11)
O3—C3—C4—C5	−163.98 (11)	C5—N1—C12—O5	7.5 (2)
C2—C3—C4—C5	7.5 (2)	C1—N1—C12—O5	−175.88 (14)
C3—C4—C5—N1	1.40 (17)	C5—N1—C12—C13	−170.63 (12)
C32—C4—C5—N1	−171.94 (10)	C1—N1—C12—C13	6.0 (2)
C3—C4—C5—C6	−129.34 (13)	C18—C13—C12—O5	−106.54 (18)
C32—C4—C5—C6	57.32 (15)	C14—C13—C12—O5	68.5 (2)
N1—C5—C6—C7	−98.31 (15)	C18—C13—C12—N1	71.66 (19)
C4—C5—C6—C7	30.45 (18)	C14—C13—C12—N1	−113.33 (16)
N1—C5—C6—C11	84.44 (15)	C27—C26—C31—C30	−1.0 (2)
C4—C5—C6—C11	−146.80 (13)	C25—C26—C31—C30	−179.75 (14)
C11—C6—C7—C8	−1.0 (2)	C31—C26—C27—C28	0.2 (2)
C5—C6—C7—C8	−178.23 (14)	C25—C26—C27—C28	179.03 (13)
C6—C7—C8—C9	0.5 (2)	C18—C13—C14—C15	−2.1 (2)
C7—C8—C9—C10	0.2 (3)	C12—C13—C14—C15	−177.24 (14)
C8—C9—C10—C11	−0.3 (2)	C14—C13—C18—C17	0.9 (2)
C9—C10—C11—C6	−0.2 (2)	C12—C13—C18—C17	175.96 (14)
C7—C6—C11—C10	0.8 (2)	C13—C18—C17—C16	1.1 (3)
C5—C6—C11—C10	178.19 (13)	C26—C31—C30—C29	1.2 (3)
C3—C4—C32—O1	−146.00 (15)	C26—C27—C28—C29	0.4 (2)
C5—C4—C32—O1	27.18 (18)	C27—C28—C29—C30	−0.1 (3)
C3—C4—C32—O2	36.14 (18)	C31—C30—C29—C28	−0.7 (3)
C5—C4—C32—O2	−150.68 (12)	C18—C17—C16—C15	−1.8 (3)
C4—C5—N1—C12	140.57 (12)	C17—C16—C15—C14	0.5 (3)
C6—C5—N1—C12	−89.16 (14)	C13—C14—C15—C16	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O5i	0.93	2.57	3.500 (2)	173
C11—H11···O5	0.93	2.53	3.171 (2)	126
C24—H24···O4	0.93	2.36	3.2898 (19)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O5i	0.93	2.57	3.500 (2)	173
C11—H11⋯O5	0.93	2.53	3.171 (2)	126
C24—H24⋯O4	0.93	2.36	3.2898 (19)	179

Symmetry code: (i) .