Ethyl 3,4-bis­(acet­yloxy)-2-(4-meth­oxy­phen­yl)pyrrol­idine-1-carboxyl­ate

The title pyrrolidine compound, C₁₈H₂₃NO₇, is a tetra-substituted species in which the five-membered ring has a twisted conformation with the twist occurring in the C—C bond bearing the adjacent acet­yloxy substituents; the C_m—C_a—C_a—C_p torsion angle is −40.76 (18)° [m = methyl­ene, a = acet­yloxy and p = phen­yl]. The N atom, which is sp²-hybridized [sum of bond angles = 359.4°], bears an ethyl­carboxyl­ate substitutent and is connected to a methyl­ene-C atom on one side and a carbon atom bearing a 4-meth­oxy­phenyl group on the other side. Minor disorder is noted in the ethyl­carboxyl­ate substituent as well as in one of the acet­yloxy groups; the major components of the disorder have site occupancies of 0.729 (9) and 0.62 (3), respectively. The most notable feature of the mol­ecular packing is the formation of helical, supra­molecular chains aligned along the b-axis direction whereby the carbonyl-O atom not involved in a disordered residue accepts C—H...O inter­actions from methyl­ene-H and two-C atom separated methine-H atoms to form a six-membered {...HCCCH...O} synthon.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.140
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.154 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          5 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        27% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         10 Note
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), MarvinSketch (ChemAxon, 2010) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Ethyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate

Crystal data

C18H23NO7	F(000) = 776
Mr = 365.37	Dx = 1.252 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9429 (5) Å	Cell parameters from 6695 reflections
b = 9.3845 (5) Å	θ = 2.4–22.2°
c = 20.7845 (11) Å	µ = 0.10 mm^−1
β = 91.550 (2)°	T = 296 K
V = 1938.67 (18) Å^3	Slab, colourless
Z = 4	0.39 × 0.25 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer	2612 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.059
Absorption correction: multi-scan (SADABS; Bruker 2009)	θmax = 26.4°, θmin = 2.0°
Tmin = 0.470, Tmax = 0.745	h = −11→12
32581 measured reflections	k = −11→11
3970 independent reflections	l = −25→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.6202P] where P = (Fo^2 + 2Fc^2)/3
3970 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2–1.5U_equiv(C).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.60299 (14)	0.86994 (16)	0.30456 (8)	0.0696 (4)
O3	0.1472 (2)	1.0446 (2)	0.46704 (9)	0.1023 (6)
O6	0.3095 (2)	0.9713 (3)	0.00226 (10)	0.1187 (8)
O7	0.42775 (15)	0.89982 (16)	0.08920 (7)	0.0655 (4)
N1	0.52014 (15)	0.99253 (17)	0.21819 (8)	0.0528 (4)
C1	0.5423 (2)	1.0677 (2)	0.15739 (9)	0.0567 (5)
H1A	0.620254	1.030254	0.136003	0.068*
H1B	0.554466	1.169064	0.164517	0.068*
C2	0.4151 (2)	1.0384 (2)	0.11882 (10)	0.0558 (5)
H2	0.394852	1.113453	0.087240	0.067*
C3	0.31052 (19)	1.0297 (2)	0.17042 (9)	0.0517 (5)
H3	0.287218	1.125733	0.184930	0.062*
C4	0.37998 (18)	0.9470 (2)	0.22556 (9)	0.0491 (5)
H4	0.372923	0.844672	0.216805	0.059*
C5	0.6186 (2)	0.9499 (2)	0.25960 (10)	0.0554 (5)
O2A	0.73692 (14)	1.00916 (17)	0.24442 (8)	0.0705 (5)	0.729 (9)
C6A	0.8491 (2)	0.9829 (3)	0.28919 (14)	0.0823 (8)	0.729 (9)
H6A1	0.933380	0.995430	0.267481	0.099*	0.729 (9)
H6A2	0.845238	0.885715	0.304950	0.099*	0.729 (9)
C7A	0.8420 (6)	1.0823 (5)	0.3430 (3)	0.110 (3)	0.729 (9)
H7A1	0.842901	1.178292	0.327017	0.165*	0.729 (9)
H7A2	0.917881	1.067873	0.371778	0.165*	0.729 (9)
H7A3	0.760400	1.066240	0.365607	0.165*	0.729 (9)
O2B	0.73692 (14)	1.00916 (17)	0.24442 (8)	0.0705 (5)	0.271 (9)
C6B	0.8491 (2)	0.9829 (3)	0.28919 (14)	0.0823 (8)	0.271 (9)
H6B1	0.897975	0.898652	0.276247	0.099*	0.271 (9)
H6B2	0.816105	0.967127	0.332115	0.099*	0.271 (9)
C7B	0.9380 (13)	1.1074 (12)	0.2890 (8)	0.110 (7)	0.271 (9)
H7B1	0.953331	1.135652	0.245465	0.165*	0.271 (9)
H7B2	1.022237	1.083708	0.310020	0.165*	0.271 (9)
H7B3	0.896619	1.184482	0.311569	0.165*	0.271 (9)
C8	0.32267 (18)	0.97799 (19)	0.29014 (9)	0.0482 (5)
C9	0.2336 (2)	0.8822 (2)	0.31699 (10)	0.0572 (5)
H9	0.212147	0.798529	0.295049	0.069*
C10	0.1765 (2)	0.9086 (3)	0.37533 (11)	0.0688 (6)
H10	0.116135	0.843642	0.392146	0.083*
C11	0.2086 (2)	1.0308 (3)	0.40881 (11)	0.0660 (6)
C12	0.2958 (2)	1.1288 (2)	0.38331 (11)	0.0672 (6)
H12	0.316983	1.212179	0.405547	0.081*
C13	0.3513 (2)	1.1015 (2)	0.32416 (10)	0.0606 (5)
H13	0.409538	1.167959	0.306848	0.073*
C14	0.1867 (4)	1.1555 (4)	0.50790 (14)	0.1162 (11)
H14A	0.279515	1.143361	0.520688	0.174*
H14B	0.132295	1.154781	0.545354	0.174*
H14C	0.175574	1.244718	0.485817	0.174*
O4A	0.0923 (11)	1.1555 (11)	0.1225 (4)	0.094 (3)	0.62 (3)
O5A	0.19114 (13)	0.95503 (14)	0.14977 (7)	0.0627 (4)	0.62 (3)
C15A	0.0847 (2)	1.0321 (3)	0.12979 (13)	0.0698 (6)	0.62 (3)
C16A	−0.0280 (3)	0.9405 (4)	0.10542 (16)	0.1058 (10)	0.62 (3)
H16A	−0.088795	0.996594	0.079195	0.159*	0.62 (3)
H16B	−0.075114	0.901846	0.141146	0.159*	0.62 (3)
H16C	0.007324	0.864149	0.080204	0.159*	0.62 (3)
O4B	0.0711 (19)	1.1544 (18)	0.149 (2)	0.143 (8)	0.38 (3)
O5B	0.19114 (13)	0.95503 (14)	0.14977 (7)	0.0627 (4)	0.38 (3)
C15B	0.0847 (2)	1.0321 (3)	0.12979 (13)	0.0698 (6)	0.38 (3)
C16B	−0.0280 (3)	0.9405 (4)	0.10542 (16)	0.1058 (10)	0.38 (3)
H16D	−0.112233	0.984766	0.114881	0.159*	0.38 (3)
H16E	−0.022720	0.848987	0.125949	0.159*	0.38 (3)
H16F	−0.021632	0.928836	0.059714	0.159*	0.38 (3)
C17	0.3671 (3)	0.8794 (3)	0.03155 (12)	0.0788 (7)
C18	0.3816 (3)	0.7291 (3)	0.01004 (14)	0.1128 (11)
H18A	0.306152	0.674432	0.023937	0.169*
H18B	0.463131	0.689770	0.028367	0.169*
H18C	0.384959	0.726180	−0.036058	0.169*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0625 (9)	0.0584 (9)	0.0870 (11)	0.0014 (7)	−0.0158 (8)	0.0222 (8)
O3	0.1082 (15)	0.1215 (16)	0.0783 (12)	0.0018 (12)	0.0220 (11)	−0.0096 (12)
O6	0.143 (2)	0.1322 (19)	0.0783 (13)	0.0106 (15)	−0.0538 (13)	−0.0073 (12)
O7	0.0731 (10)	0.0659 (9)	0.0566 (8)	−0.0001 (7)	−0.0147 (7)	−0.0110 (7)
N1	0.0451 (9)	0.0578 (10)	0.0548 (10)	−0.0031 (7)	−0.0115 (7)	0.0042 (8)
C1	0.0545 (12)	0.0601 (12)	0.0549 (12)	−0.0054 (9)	−0.0077 (9)	0.0005 (10)
C2	0.0628 (12)	0.0494 (11)	0.0544 (11)	−0.0025 (9)	−0.0142 (9)	0.0007 (9)
C3	0.0489 (11)	0.0449 (10)	0.0602 (12)	−0.0030 (8)	−0.0167 (9)	−0.0027 (9)
C4	0.0484 (10)	0.0419 (10)	0.0562 (11)	−0.0016 (8)	−0.0112 (9)	0.0001 (8)
C5	0.0511 (11)	0.0462 (11)	0.0680 (13)	0.0012 (9)	−0.0132 (10)	0.0013 (10)
O2A	0.0485 (8)	0.0791 (10)	0.0827 (11)	−0.0087 (7)	−0.0197 (7)	0.0185 (8)
C6A	0.0513 (13)	0.0856 (17)	0.108 (2)	0.0014 (12)	−0.0293 (13)	0.0188 (16)
C7A	0.111 (4)	0.087 (3)	0.128 (4)	0.018 (3)	−0.070 (4)	−0.013 (3)
O2B	0.0485 (8)	0.0791 (10)	0.0827 (11)	−0.0087 (7)	−0.0197 (7)	0.0185 (8)
C6B	0.0513 (13)	0.0856 (17)	0.108 (2)	0.0014 (12)	−0.0293 (13)	0.0188 (16)
C7B	0.070 (8)	0.090 (8)	0.165 (14)	−0.003 (6)	−0.069 (9)	0.013 (8)
C8	0.0443 (10)	0.0444 (10)	0.0550 (11)	0.0012 (8)	−0.0132 (8)	0.0024 (8)
C9	0.0505 (11)	0.0522 (12)	0.0682 (13)	−0.0048 (9)	−0.0091 (10)	0.0006 (10)
C10	0.0554 (13)	0.0735 (15)	0.0774 (15)	−0.0079 (11)	0.0009 (11)	0.0085 (12)
C11	0.0610 (13)	0.0792 (16)	0.0576 (13)	0.0100 (12)	0.0009 (11)	0.0034 (12)
C12	0.0784 (15)	0.0598 (13)	0.0627 (14)	0.0030 (11)	−0.0107 (12)	−0.0080 (11)
C13	0.0685 (13)	0.0491 (11)	0.0639 (13)	−0.0068 (10)	−0.0045 (10)	−0.0005 (10)
C14	0.163 (3)	0.108 (2)	0.0780 (19)	0.025 (2)	0.014 (2)	−0.0093 (18)
O4A	0.077 (4)	0.077 (4)	0.125 (5)	0.006 (3)	−0.035 (3)	0.032 (4)
O5A	0.0529 (8)	0.0548 (8)	0.0789 (10)	−0.0057 (6)	−0.0255 (7)	−0.0020 (7)
C15A	0.0505 (13)	0.0730 (16)	0.0848 (17)	−0.0012 (11)	−0.0194 (11)	0.0147 (14)
C16A	0.0675 (16)	0.120 (2)	0.128 (2)	−0.0181 (16)	−0.0458 (17)	0.011 (2)
O4B	0.062 (5)	0.065 (6)	0.30 (2)	0.019 (4)	−0.034 (11)	−0.042 (10)
O5B	0.0529 (8)	0.0548 (8)	0.0789 (10)	−0.0057 (6)	−0.0255 (7)	−0.0020 (7)
C15B	0.0505 (13)	0.0730 (16)	0.0848 (17)	−0.0012 (11)	−0.0194 (11)	0.0147 (14)
C16B	0.0675 (16)	0.120 (2)	0.128 (2)	−0.0181 (16)	−0.0458 (17)	0.011 (2)
C17	0.0763 (16)	0.098 (2)	0.0609 (15)	−0.0115 (14)	−0.0149 (12)	−0.0149 (14)
C18	0.131 (3)	0.113 (2)	0.094 (2)	−0.020 (2)	−0.0115 (18)	−0.0440 (19)

Geometric parameters (Å, º)

O1—C5	1.212 (2)	C7B—H7B1	0.9600
O3—C11	1.376 (3)	C7B—H7B2	0.9600
O3—C14	1.393 (4)	C7B—H7B3	0.9600
O6—C17	1.193 (3)	C8—C13	1.383 (3)
O7—C17	1.341 (3)	C8—C9	1.389 (3)
O7—C2	1.446 (2)	C9—C10	1.375 (3)
N1—C5	1.347 (2)	C9—H9	0.9300
N1—C1	1.469 (3)	C10—C11	1.375 (3)
N1—C4	1.469 (2)	C10—H10	0.9300
C1—C2	1.504 (3)	C11—C12	1.380 (3)
C1—H1A	0.9700	C12—C13	1.385 (3)
C1—H1B	0.9700	C12—H12	0.9300
C2—C3	1.516 (3)	C13—H13	0.9300
C2—H2	0.9800	C14—H14A	0.9600
C3—O5B	1.434 (2)	C14—H14B	0.9600
C3—O5A	1.434 (2)	C14—H14C	0.9600
C3—C4	1.533 (3)	O4A—C15A	1.171 (10)
C3—H3	0.9800	O5A—C15A	1.338 (2)
C4—C8	1.501 (3)	C15A—C16A	1.490 (3)
C4—H4	0.9800	C16A—H16A	0.9600
C5—O2B	1.346 (3)	C16A—H16B	0.9600
C5—O2A	1.346 (3)	C16A—H16C	0.9600
O2A—C6A	1.454 (2)	O4B—C15B	1.225 (19)
C6A—C7A	1.460 (5)	O5B—C15B	1.338 (2)
C6A—H6A1	0.9700	C15B—C16B	1.490 (3)
C6A—H6A2	0.9700	C16B—H16D	0.9600
C7A—H7A1	0.9600	C16B—H16E	0.9600
C7A—H7A2	0.9600	C16B—H16F	0.9600
C7A—H7A3	0.9600	C17—C18	1.488 (4)
O2B—C6B	1.454 (2)	C18—H18A	0.9600
C6B—C7B	1.466 (12)	C18—H18B	0.9600
C6B—H6B1	0.9700	C18—H18C	0.9600
C6B—H6B2	0.9700
C11—O3—C14	118.8 (2)	H7B1—C7B—H7B2	109.5
C17—O7—C2	117.81 (19)	C6B—C7B—H7B3	109.5
C5—N1—C1	124.68 (17)	H7B1—C7B—H7B3	109.5
C5—N1—C4	121.50 (16)	H7B2—C7B—H7B3	109.5
C1—N1—C4	113.18 (14)	C13—C8—C9	117.48 (19)
N1—C1—C2	103.15 (16)	C13—C8—C4	122.78 (18)
N1—C1—H1A	111.1	C9—C8—C4	119.71 (17)
C2—C1—H1A	111.1	C10—C9—C8	121.4 (2)
N1—C1—H1B	111.1	C10—C9—H9	119.3
C2—C1—H1B	111.1	C8—C9—H9	119.3
H1A—C1—H1B	109.1	C11—C10—C9	120.1 (2)
O7—C2—C1	108.04 (16)	C11—C10—H10	120.0
O7—C2—C3	108.80 (16)	C9—C10—H10	120.0
C1—C2—C3	102.45 (15)	C10—C11—O3	114.9 (2)
O7—C2—H2	112.3	C10—C11—C12	120.1 (2)
C1—C2—H2	112.3	O3—C11—C12	125.0 (2)
C3—C2—H2	112.3	C11—C12—C13	119.2 (2)
O5B—C3—C2	113.11 (15)	C11—C12—H12	120.4
O5A—C3—C2	113.11 (15)	C13—C12—H12	120.4
O5B—C3—C4	109.21 (15)	C8—C13—C12	121.8 (2)
O5A—C3—C4	109.21 (15)	C8—C13—H13	119.1
C2—C3—C4	104.62 (15)	C12—C13—H13	119.1
O5A—C3—H3	109.9	O3—C14—H14A	109.5
C2—C3—H3	109.9	O3—C14—H14B	109.5
C4—C3—H3	109.9	H14A—C14—H14B	109.5
N1—C4—C8	114.91 (15)	O3—C14—H14C	109.5
N1—C4—C3	100.63 (15)	H14A—C14—H14C	109.5
C8—C4—C3	113.36 (16)	H14B—C14—H14C	109.5
N1—C4—H4	109.2	C15A—O5A—C3	118.03 (16)
C8—C4—H4	109.2	O4A—C15A—O5A	121.4 (5)
C3—C4—H4	109.2	O4A—C15A—C16A	125.3 (5)
O1—C5—O2B	124.58 (18)	O5A—C15A—C16A	112.0 (2)
O1—C5—O2A	124.58 (18)	C15A—C16A—H16A	109.5
O1—C5—N1	124.77 (19)	C15A—C16A—H16B	109.5
O2B—C5—N1	110.65 (18)	H16A—C16A—H16B	109.5
O2A—C5—N1	110.65 (18)	C15A—C16A—H16C	109.5
C5—O2A—C6A	116.09 (17)	H16A—C16A—H16C	109.5
O2A—C6A—C7A	109.3 (2)	H16B—C16A—H16C	109.5
O2A—C6A—H6A1	109.8	C15B—O5B—C3	118.03 (16)
C7A—C6A—H6A1	109.8	O4B—C15B—O5B	119.9 (10)
O2A—C6A—H6A2	109.8	O4B—C15B—C16B	124.3 (8)
C7A—C6A—H6A2	109.8	O5B—C15B—C16B	112.0 (2)
H6A1—C6A—H6A2	108.3	C15B—C16B—H16D	109.5
C6A—C7A—H7A1	109.5	C15B—C16B—H16E	109.5
C6A—C7A—H7A2	109.5	H16D—C16B—H16E	109.5
H7A1—C7A—H7A2	109.5	C15B—C16B—H16F	109.5
C6A—C7A—H7A3	109.5	H16D—C16B—H16F	109.5
H7A1—C7A—H7A3	109.5	H16E—C16B—H16F	109.5
H7A2—C7A—H7A3	109.5	O6—C17—O7	123.4 (2)
C5—O2B—C6B	116.09 (17)	O6—C17—C18	125.5 (2)
O2B—C6B—C7B	108.4 (4)	O7—C17—C18	111.0 (3)
O2B—C6B—H6B1	110.0	C17—C18—H18A	109.5
C7B—C6B—H6B1	110.0	C17—C18—H18B	109.5
O2B—C6B—H6B2	110.0	H18A—C18—H18B	109.5
C7B—C6B—H6B2	110.0	C17—C18—H18C	109.5
H6B1—C6B—H6B2	108.4	H18A—C18—H18C	109.5
C6B—C7B—H7B1	109.5	H18B—C18—H18C	109.5
C6B—C7B—H7B2	109.5
C5—N1—C1—C2	158.14 (18)	C5—O2A—C6A—C7A	−81.8 (4)
C4—N1—C1—C2	−12.8 (2)	O1—C5—O2B—C6B	−5.5 (3)
C17—O7—C2—C1	−147.52 (19)	N1—C5—O2B—C6B	174.16 (18)
C17—O7—C2—C3	102.0 (2)	C5—O2B—C6B—C7B	−147.9 (8)
N1—C1—C2—O7	−82.60 (19)	N1—C4—C8—C13	38.0 (2)
N1—C1—C2—C3	32.16 (19)	C3—C4—C8—C13	−77.0 (2)
O7—C2—C3—O5B	−45.3 (2)	N1—C4—C8—C9	−144.04 (17)
C1—C2—C3—O5B	−159.51 (15)	C3—C4—C8—C9	101.0 (2)
O7—C2—C3—O5A	−45.3 (2)	C13—C8—C9—C10	−0.3 (3)
C1—C2—C3—O5A	−159.51 (15)	C4—C8—C9—C10	−178.40 (18)
O7—C2—C3—C4	73.45 (17)	C8—C9—C10—C11	−0.9 (3)
C1—C2—C3—C4	−40.76 (18)	C9—C10—C11—O3	−178.9 (2)
C5—N1—C4—C8	54.7 (2)	C9—C10—C11—C12	1.4 (3)
C1—N1—C4—C8	−134.09 (17)	C14—O3—C11—C10	171.9 (2)
C5—N1—C4—C3	176.83 (17)	C14—O3—C11—C12	−8.5 (4)
C1—N1—C4—C3	−11.9 (2)	C10—C11—C12—C13	−0.7 (3)
O5B—C3—C4—N1	153.37 (15)	O3—C11—C12—C13	179.6 (2)
O5A—C3—C4—N1	153.37 (15)	C9—C8—C13—C12	1.0 (3)
C2—C3—C4—N1	32.01 (18)	C4—C8—C13—C12	179.05 (18)
O5B—C3—C4—C8	−83.41 (19)	C11—C12—C13—C8	−0.5 (3)
O5A—C3—C4—C8	−83.41 (19)	C2—C3—O5A—C15A	−98.4 (2)
C2—C3—C4—C8	155.23 (15)	C4—C3—O5A—C15A	145.5 (2)
C1—N1—C5—O1	−168.3 (2)	C3—O5A—C15A—O4A	8.2 (7)
C4—N1—C5—O1	1.8 (3)	C3—O5A—C15A—C16A	175.8 (2)
C1—N1—C5—O2B	12.0 (3)	C2—C3—O5B—C15B	−98.4 (2)
C4—N1—C5—O2B	−177.78 (16)	C4—C3—O5B—C15B	145.5 (2)
C1—N1—C5—O2A	12.0 (3)	C3—O5B—C15B—O4B	−25 (2)
C4—N1—C5—O2A	−177.78 (16)	C3—O5B—C15B—C16B	175.8 (2)
O1—C5—O2A—C6A	−5.5 (3)	C2—O7—C17—O6	3.9 (4)
N1—C5—O2A—C6A	174.16 (18)	C2—O7—C17—C18	−176.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1^i	0.97	2.54	3.289 (2)	134
C3—H3···O1^i	0.98	2.55	3.344 (2)	139

Symmetry code: (i) −x+1, y+1/2, −z+1/2.