A cyclic carbo-isosteric penta-depsipeptide: cyclo(Phe¹–D-Ala²–Gly³–Phe⁴–APO⁵)

Cyclo(Phe¹–D-Ala²–Gly³–Phe⁴–APO⁵) is the minor diastereoisomer of a cyclic penta-peptidomimetic analogue containing a novel 2-amino­propyl lactone (APO) motif, which displays the same number of atoms as the native amino acid glycine and has a methyl group in place of the carbonyl O atom.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.112
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.14 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          3 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT791_ALERT_4_G The Model has Chirality at C8      .............          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C10     .............          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     .............          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C20     .............          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          85 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

3,12-Dibenzyl-9,14-dimethyl-1-oxa-4,7,10,13-tetraazacyclopentadecane-2,5,8,11-tetrone

Crystal data

C26H32N4O5	Dx = 1.360 Mg m^−3
Mr = 480.56	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 9940 reflections
a = 10.126 (9) Å	θ = 4.1–68.8°
b = 15.096 (14) Å	µ = 0.78 mm^−1
c = 15.355 (13) Å	T = 100 K
V = 2347 (4) Å^3	Block, colourless
Z = 4	0.12 × 0.07 × 0.05 mm
F(000) = 1024

Data collection

Bruker SMART 6000 CCD diffractometer	4133 independent reflections
Radiation source: Microstar rotating anode generator	3847 reflections with I > 2σ(I)
Incoatec multilayer mirrors monochromator	Rint = 0.075
Detector resolution: 5.6 pixels mm^-1	θmax = 66.6°, θmin = 4.1°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −17→17
Tmin = 0.486, Tmax = 0.753	l = −18→18
23011 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0764P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.011
4133 reflections	Δρmax = 0.31 e Å^−3
330 parameters	Δρmin = −0.43 e Å^−3
0 restraints	Absolute structure: Flack x determined using 1590 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons & Flack, 2004)
0 constraints	Absolute structure parameter: 0.10 (11)
Primary atom site location: structure-invariant direct methods

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6916 (2)	0.75967 (14)	0.68262 (14)	0.0209 (4)
H1	0.6894	0.7333	0.7388	0.025*
C2	0.6031 (2)	0.82691 (14)	0.66282 (14)	0.0227 (4)
H2	0.5431	0.8475	0.7058	0.027*
C3	0.6026 (2)	0.86397 (14)	0.58022 (15)	0.0223 (4)
H3	0.5413	0.9095	0.5663	0.027*
C4	0.6915 (2)	0.83465 (15)	0.51801 (14)	0.0231 (4)
H4	0.6904	0.8594	0.4611	0.028*
C5	0.7827 (2)	0.76883 (14)	0.53901 (13)	0.0206 (4)
H5	0.8450	0.7501	0.4966	0.025*
C6	0.7835 (2)	0.73002 (14)	0.62175 (13)	0.0191 (4)
C7	0.8833 (2)	0.65948 (13)	0.64407 (13)	0.0191 (4)
H7A	0.9203	0.6354	0.5893	0.023*
H7B	0.8374	0.6105	0.6744	0.023*
C8	0.9979 (2)	0.69186 (13)	0.70179 (13)	0.0178 (4)
H8	1.0399	0.7448	0.6741	0.021*
N9	1.09594 (18)	0.62140 (11)	0.70982 (11)	0.0188 (4)
H9	1.056 (2)	0.5716 (19)	0.7369 (18)	0.023*
C10	1.2144 (2)	0.64565 (14)	0.76043 (13)	0.0196 (4)
H10	1.1909	0.6941	0.8021	0.024*
C11	1.2647 (2)	0.56634 (14)	0.81143 (14)	0.0213 (4)
H11A	1.2632	0.5130	0.7739	0.026*
H11B	1.3571	0.5770	0.8297	0.026*
O12	1.18248 (15)	0.55144 (9)	0.88820 (9)	0.0204 (3)
C13	1.0956 (2)	0.48517 (13)	0.88625 (14)	0.0196 (4)
C14	1.0182 (2)	0.48060 (14)	0.97123 (13)	0.0198 (4)
H14	1.0780	0.4536	1.0158	0.024*
N15	0.98462 (18)	0.56809 (12)	1.00179 (11)	0.0191 (4)
H15	0.949 (3)	0.6021 (18)	0.9664 (19)	0.023*
C16	1.0227 (2)	0.59836 (14)	1.08029 (13)	0.0184 (4)
C17	0.9816 (2)	0.69272 (14)	1.10269 (13)	0.0212 (4)
H17A	0.9236	0.6904	1.1545	0.025*
H17B	1.0619	0.7261	1.1194	0.025*
N18	0.9139 (2)	0.74228 (11)	1.03547 (11)	0.0197 (4)
H18	0.828 (3)	0.7378 (18)	1.0336 (17)	0.024*
C19	0.9831 (2)	0.77969 (13)	0.96966 (13)	0.0175 (4)
C20	0.8968 (2)	0.82801 (14)	0.90145 (13)	0.0197 (4)
H20	0.8026	0.8097	0.9090	0.024*
N21	0.94164 (18)	0.80253 (12)	0.81497 (12)	0.0188 (4)
H21	0.953 (3)	0.8414 (19)	0.7802 (19)	0.023*
C22	0.94722 (18)	0.71732 (13)	0.79294 (13)	0.0165 (4)
O23	0.91694 (15)	0.65798 (9)	0.84460 (9)	0.0196 (3)
C24	1.3230 (2)	0.67838 (15)	0.69969 (15)	0.0236 (5)
H24A	1.3504	0.6301	0.6610	0.035*
H24B	1.3988	0.6982	0.7342	0.035*
H24C	1.2896	0.7279	0.6647	0.035*
O25	1.08111 (16)	0.43461 (10)	0.82577 (10)	0.0245 (3)
C26	0.8961 (2)	0.42006 (14)	0.96385 (15)	0.0238 (5)
H26A	0.9245	0.3609	0.9434	0.029*
H26B	0.8563	0.4128	1.0223	0.029*
C27	0.7928 (2)	0.45570 (14)	0.90239 (15)	0.0222 (5)
C28	0.7071 (2)	0.52271 (15)	0.92819 (15)	0.0244 (5)
H28	0.7078	0.5426	0.9869	0.029*
C29	0.6201 (2)	0.56087 (15)	0.86874 (17)	0.0275 (5)
H29	0.5631	0.6072	0.8872	0.033*
C30	0.6156 (2)	0.53217 (15)	0.78319 (16)	0.0271 (5)
H30	0.5568	0.5590	0.7428	0.033*
C31	0.6983 (2)	0.46364 (15)	0.75708 (15)	0.0254 (5)
H31	0.6950	0.4426	0.6988	0.030*
C32	0.7853 (2)	0.42612 (15)	0.81573 (15)	0.0245 (5)
H32	0.8413	0.3793	0.7971	0.029*
O33	1.08418 (17)	0.55439 (10)	1.13399 (10)	0.0268 (4)
O34	1.10326 (14)	0.77972 (10)	0.96627 (9)	0.0220 (3)
C35	0.9080 (3)	0.92754 (14)	0.91424 (15)	0.0258 (5)
H35A	1.0002	0.9458	0.9067	0.039*
H35B	0.8783	0.9431	0.9730	0.039*
H35C	0.8527	0.9579	0.8712	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0215 (10)	0.0231 (10)	0.0180 (10)	−0.0008 (9)	0.0012 (8)	0.0021 (8)
C2	0.0219 (10)	0.0258 (10)	0.0206 (11)	0.0004 (9)	0.0018 (8)	−0.0027 (8)
C3	0.0211 (10)	0.0214 (10)	0.0244 (11)	0.0019 (9)	−0.0031 (9)	−0.0020 (8)
C4	0.0258 (11)	0.0238 (10)	0.0197 (10)	−0.0018 (9)	−0.0035 (9)	0.0019 (9)
C5	0.0214 (11)	0.0239 (11)	0.0163 (10)	0.0001 (8)	−0.0017 (8)	−0.0022 (8)
C6	0.0191 (10)	0.0199 (10)	0.0183 (10)	−0.0038 (8)	−0.0030 (8)	−0.0015 (8)
C7	0.0221 (10)	0.0192 (10)	0.0160 (9)	−0.0009 (8)	−0.0005 (8)	−0.0017 (8)
C8	0.0202 (10)	0.0172 (9)	0.0161 (9)	−0.0002 (8)	−0.0009 (8)	0.0029 (7)
N9	0.0199 (9)	0.0186 (9)	0.0180 (9)	0.0007 (7)	−0.0003 (7)	−0.0003 (7)
C10	0.0206 (11)	0.0209 (10)	0.0174 (10)	−0.0004 (8)	−0.0006 (8)	−0.0028 (8)
C11	0.0191 (10)	0.0262 (11)	0.0186 (10)	0.0001 (8)	0.0023 (8)	0.0007 (9)
O12	0.0213 (7)	0.0245 (8)	0.0153 (7)	−0.0021 (6)	0.0003 (6)	0.0002 (6)
C13	0.0207 (10)	0.0161 (9)	0.0221 (10)	0.0023 (8)	−0.0013 (8)	0.0006 (8)
C14	0.0248 (11)	0.0190 (10)	0.0157 (9)	0.0008 (9)	−0.0005 (8)	0.0021 (8)
N15	0.0253 (9)	0.0165 (8)	0.0155 (9)	0.0030 (7)	−0.0023 (7)	0.0015 (7)
C16	0.0187 (10)	0.0229 (10)	0.0137 (9)	−0.0011 (8)	0.0009 (8)	0.0029 (8)
C17	0.0284 (11)	0.0204 (10)	0.0148 (10)	−0.0001 (9)	0.0004 (9)	−0.0001 (7)
N18	0.0205 (9)	0.0203 (9)	0.0183 (9)	0.0002 (7)	0.0008 (7)	0.0006 (7)
C19	0.0228 (11)	0.0151 (9)	0.0145 (9)	0.0016 (8)	0.0000 (8)	−0.0030 (7)
C20	0.0217 (10)	0.0193 (10)	0.0182 (10)	0.0019 (9)	0.0007 (8)	−0.0003 (8)
N21	0.0260 (9)	0.0169 (9)	0.0134 (8)	−0.0004 (7)	0.0001 (7)	0.0023 (7)
C22	0.0154 (9)	0.0188 (10)	0.0153 (10)	−0.0001 (7)	−0.0038 (7)	0.0012 (8)
O23	0.0240 (7)	0.0194 (7)	0.0153 (7)	−0.0010 (6)	0.0002 (6)	0.0011 (5)
C24	0.0233 (10)	0.0239 (10)	0.0237 (11)	0.0002 (9)	−0.0006 (9)	−0.0003 (8)
O25	0.0272 (8)	0.0244 (7)	0.0219 (8)	0.0005 (7)	−0.0011 (6)	−0.0057 (6)
C26	0.0273 (11)	0.0189 (10)	0.0251 (11)	−0.0004 (9)	0.0024 (9)	0.0027 (8)
C27	0.0200 (10)	0.0173 (10)	0.0294 (11)	−0.0052 (8)	0.0027 (9)	0.0024 (8)
C28	0.0225 (11)	0.0234 (10)	0.0273 (11)	−0.0047 (9)	0.0041 (9)	−0.0040 (9)
C29	0.0189 (11)	0.0236 (11)	0.0399 (14)	−0.0003 (9)	0.0004 (9)	−0.0027 (10)
C30	0.0207 (10)	0.0233 (11)	0.0374 (13)	−0.0024 (9)	−0.0028 (9)	0.0022 (10)
C31	0.0220 (11)	0.0266 (11)	0.0275 (12)	−0.0054 (9)	−0.0004 (9)	−0.0038 (9)
C32	0.0220 (11)	0.0205 (10)	0.0309 (11)	−0.0016 (9)	0.0025 (9)	−0.0034 (9)
O33	0.0357 (9)	0.0265 (8)	0.0183 (7)	0.0055 (7)	−0.0044 (7)	0.0016 (6)
O34	0.0221 (8)	0.0232 (7)	0.0206 (7)	−0.0003 (6)	−0.0016 (6)	−0.0003 (6)
C35	0.0357 (12)	0.0195 (10)	0.0221 (10)	0.0034 (10)	−0.0016 (9)	−0.0014 (8)

Geometric parameters (Å, º)

C1—C2	1.387 (3)	C16—C17	1.523 (3)
C1—C6	1.393 (3)	C17—N18	1.447 (3)
C1—H1	0.9500	C17—H17A	0.9900
C2—C3	1.386 (3)	C17—H17B	0.9900
C2—H2	0.9500	N18—C19	1.353 (3)
C3—C4	1.385 (3)	N18—H18	0.87 (3)
C3—H3	0.9500	C19—O34	1.218 (3)
C4—C5	1.394 (3)	C19—C20	1.546 (3)
C4—H4	0.9500	C20—N21	1.455 (3)
C5—C6	1.399 (3)	C20—C35	1.519 (3)
C5—H5	0.9500	C20—H20	1.0000
C6—C7	1.507 (3)	N21—C22	1.331 (3)
C7—C8	1.540 (3)	N21—H21	0.80 (3)
C7—H7A	0.9900	C22—O23	1.235 (3)
C7—H7B	0.9900	C24—H24A	0.9800
C8—N9	1.460 (3)	C24—H24B	0.9800
C8—C22	1.539 (3)	C24—H24C	0.9800
C8—H8	1.0000	C26—C27	1.508 (3)
N9—C10	1.475 (3)	C26—H26A	0.9900
N9—H9	0.95 (3)	C26—H26B	0.9900
C10—C11	1.519 (3)	C27—C28	1.391 (3)
C10—C24	1.524 (3)	C27—C32	1.406 (4)
C10—H10	1.0000	C28—C29	1.393 (4)
C11—O12	1.461 (3)	C28—H28	0.9500
C11—H11A	0.9900	C29—C30	1.384 (4)
C11—H11B	0.9900	C29—H29	0.9500
O12—C13	1.333 (3)	C30—C31	1.390 (4)
C13—O25	1.211 (3)	C30—H30	0.9500
C13—C14	1.523 (3)	C31—C32	1.381 (4)
C14—N15	1.442 (3)	C31—H31	0.9500
C14—C26	1.542 (3)	C32—H32	0.9500
C14—H14	1.0000	C35—H35A	0.9800
N15—C16	1.345 (3)	C35—H35B	0.9800
N15—H15	0.83 (3)	C35—H35C	0.9800
C16—O33	1.228 (3)
C2—C1—C6	121.3 (2)	N18—C17—C16	116.85 (18)
C2—C1—H1	119.4	N18—C17—H17A	108.1
C6—C1—H1	119.4	C16—C17—H17A	108.1
C3—C2—C1	119.9 (2)	N18—C17—H17B	108.1
C3—C2—H2	120.1	C16—C17—H17B	108.1
C1—C2—H2	120.1	H17A—C17—H17B	107.3
C4—C3—C2	120.0 (2)	C19—N18—C17	120.2 (2)
C4—C3—H3	120.0	C19—N18—H18	121.6 (18)
C2—C3—H3	120.0	C17—N18—H18	117.1 (18)
C3—C4—C5	119.9 (2)	O34—C19—N18	123.31 (19)
C3—C4—H4	120.0	O34—C19—C20	122.35 (19)
C5—C4—H4	120.0	N18—C19—C20	114.24 (19)
C4—C5—C6	120.81 (19)	N21—C20—C35	110.87 (18)
C4—C5—H5	119.6	N21—C20—C19	108.49 (17)
C6—C5—H5	119.6	C35—C20—C19	109.68 (18)
C1—C6—C5	118.1 (2)	N21—C20—H20	109.3
C1—C6—C7	121.49 (19)	C35—C20—H20	109.3
C5—C6—C7	120.40 (18)	C19—C20—H20	109.3
C6—C7—C8	114.32 (17)	C22—N21—C20	120.04 (18)
C6—C7—H7A	108.7	C22—N21—H21	122.1 (19)
C8—C7—H7A	108.7	C20—N21—H21	117.4 (19)
C6—C7—H7B	108.7	O23—C22—N21	121.80 (19)
C8—C7—H7B	108.7	O23—C22—C8	119.05 (18)
H7A—C7—H7B	107.6	N21—C22—C8	119.11 (18)
N9—C8—C22	109.38 (16)	C10—C24—H24A	109.5
N9—C8—C7	109.26 (17)	C10—C24—H24B	109.5
C22—C8—C7	110.56 (17)	H24A—C24—H24B	109.5
N9—C8—H8	109.2	C10—C24—H24C	109.5
C22—C8—H8	109.2	H24A—C24—H24C	109.5
C7—C8—H8	109.2	H24B—C24—H24C	109.5
C8—N9—C10	114.60 (16)	C27—C26—C14	113.00 (18)
C8—N9—H9	109.2 (15)	C27—C26—H26A	109.0
C10—N9—H9	107.9 (15)	C14—C26—H26A	109.0
N9—C10—C11	110.42 (17)	C27—C26—H26B	109.0
N9—C10—C24	110.16 (18)	C14—C26—H26B	109.0
C11—C10—C24	109.20 (18)	H26A—C26—H26B	107.8
N9—C10—H10	109.0	C28—C27—C32	117.8 (2)
C11—C10—H10	109.0	C28—C27—C26	120.9 (2)
C24—C10—H10	109.0	C32—C27—C26	121.1 (2)
O12—C11—C10	110.26 (17)	C27—C28—C29	120.6 (2)
O12—C11—H11A	109.6	C27—C28—H28	119.7
C10—C11—H11A	109.6	C29—C28—H28	119.7
O12—C11—H11B	109.6	C30—C29—C28	120.9 (2)
C10—C11—H11B	109.6	C30—C29—H29	119.6
H11A—C11—H11B	108.1	C28—C29—H29	119.6
C13—O12—C11	118.28 (16)	C29—C30—C31	119.2 (2)
O25—C13—O12	124.8 (2)	C29—C30—H30	120.4
O25—C13—C14	124.47 (19)	C31—C30—H30	120.4
O12—C13—C14	110.74 (17)	C32—C31—C30	120.1 (2)
N15—C14—C13	111.01 (17)	C32—C31—H31	120.0
N15—C14—C26	112.16 (19)	C30—C31—H31	120.0
C13—C14—C26	112.10 (18)	C31—C32—C27	121.4 (2)
N15—C14—H14	107.1	C31—C32—H32	119.3
C13—C14—H14	107.1	C27—C32—H32	119.3
C26—C14—H14	107.1	C20—C35—H35A	109.5
C16—N15—C14	122.33 (19)	C20—C35—H35B	109.5
C16—N15—H15	120.0 (18)	H35A—C35—H35B	109.5
C14—N15—H15	117.2 (18)	C20—C35—H35C	109.5
O33—C16—N15	124.3 (2)	H35A—C35—H35C	109.5
O33—C16—C17	119.49 (19)	H35B—C35—H35C	109.5
N15—C16—C17	116.21 (18)
C6—C1—C2—C3	2.0 (3)	O33—C16—C17—N18	177.65 (19)
C1—C2—C3—C4	−0.9 (3)	N15—C16—C17—N18	−4.0 (3)
C2—C3—C4—C5	−1.0 (3)	C16—C17—N18—C19	−79.0 (3)
C3—C4—C5—C6	1.7 (3)	C17—N18—C19—O34	−5.5 (3)
C2—C1—C6—C5	−1.2 (3)	C17—N18—C19—C20	178.25 (17)
C2—C1—C6—C7	177.58 (19)	O34—C19—C20—N21	49.5 (3)
C4—C5—C6—C1	−0.6 (3)	N18—C19—C20—N21	−134.16 (19)
C4—C5—C6—C7	−179.45 (19)	O34—C19—C20—C35	−71.7 (3)
C1—C6—C7—C8	−75.1 (3)	N18—C19—C20—C35	104.6 (2)
C5—C6—C7—C8	103.7 (2)	C35—C20—N21—C22	175.89 (19)
C6—C7—C8—N9	−172.90 (16)	C19—C20—N21—C22	55.4 (2)
C6—C7—C8—C22	66.7 (2)	C20—N21—C22—O23	−1.1 (3)
C22—C8—N9—C10	−61.6 (2)	C20—N21—C22—C8	−178.64 (17)
C7—C8—N9—C10	177.27 (17)	N9—C8—C22—O23	−45.8 (2)
C8—N9—C10—C11	145.33 (18)	C7—C8—C22—O23	74.5 (2)
C8—N9—C10—C24	−94.0 (2)	N9—C8—C22—N21	131.84 (19)
N9—C10—C11—O12	−77.0 (2)	C7—C8—C22—N21	−107.8 (2)
C24—C10—C11—O12	161.69 (17)	N15—C14—C26—C27	59.4 (2)
C10—C11—O12—C13	103.6 (2)	C13—C14—C26—C27	−66.3 (2)
C11—O12—C13—O25	1.6 (3)	C14—C26—C27—C28	−78.9 (3)
C11—O12—C13—C14	−179.37 (16)	C14—C26—C27—C32	97.2 (2)
O25—C13—C14—N15	−140.7 (2)	C32—C27—C28—C29	−2.1 (3)
O12—C13—C14—N15	40.3 (2)	C26—C27—C28—C29	174.1 (2)
O25—C13—C14—C26	−14.4 (3)	C27—C28—C29—C30	1.0 (3)
O12—C13—C14—C26	166.61 (17)	C28—C29—C30—C31	0.7 (3)
C13—C14—N15—C16	−121.6 (2)	C29—C30—C31—C32	−1.2 (3)
C26—C14—N15—C16	112.1 (2)	C30—C31—C32—C27	0.0 (3)
C14—N15—C16—O33	−2.8 (3)	C28—C27—C32—C31	1.7 (3)
C14—N15—C16—C17	178.95 (19)	C26—C27—C32—C31	−174.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O25	0.95 (3)	2.49 (3)	3.338 (3)	149 (2)
N15—H15···O23	0.83 (3)	2.08 (3)	2.853 (3)	155 (2)
N18—H18···O34^i	0.87 (3)	2.29 (3)	3.163 (4)	177 (3)
N21—H21···O25^ii	0.80 (3)	2.18 (3)	2.949 (3)	161 (3)

Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) −x+2, y+1/2, −z+3/2.