Crystal structure of benzyl 3-oxo-2-oxa-5-aza­bicyclo­[2.2.1]heptane-5-carboxyl­ate

Krishnamurthy, S.; Jalli, V.; Vagvala, T.C.; Moriguchi, T.; Tsuge, A.

doi:10.1107/S2056989015010464

Crystal structure of benzyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

S. Krishnamurthy, V. Jalli, T. C. Vagvala, T. Moriguchi and A. Tsuge

The title compound, C₁₃H₁₃NO₄ (also known as N-benzyloxycarbonyl-4-hydroxy-L-proline lactone), crystallizes with two molecules in the asymmetric unit. They have slightly different conformations: the fused ring systems almost overlap, but different C—O—C—C torsion angles for the central chains of −155.5 (2) and −178.6 (2)° lead to different twists for the terminal benzene ring. In the crystal, the molecules are linked by C—H

O interactions, generating a three-dimensional network. The absolute structure was established based on an unchanging chiral centre in the synthesis.

Keywords: crystal structure; 4-hydroxyproline; C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015010464/hb7435sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015010464/hb7435Isup2.hkl Contains datablock I

CCDC reference: 1402251

checkCIF report

Key indicators

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.002 Å
R factor = 0.027
wR factor = 0.073
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.85 Note
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     --  C5      ..        5.4 su

Alert level G
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3     ..  C18     ..       2.99 Ang.
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C3      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C16     (Chiral SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          95 %

   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
   6 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Chemical context top

Four possible stereoisomers exists for 4-hydroxyproline. The (2S,4R)-isomer is mainly found in collagen and its presence in collagen is a very important factor for its triple helix stabilization (Erdmann & Wennemers, 2011). Moreover (2S,4S)- of 4-hydroxyproline isomer was found to have anticancer activity (Dickens et al. 2008)

For related derivatives and synthesis see (Krishnamurthy et al. 2014, Gomez-Vidal and Silverman, 2001)

Synthesis and crystallization top

(I) was prepared in exactly the same manner as described by (Lombardo et al. 2012). To a solution of Z-Hyp-OH (3.0 g, 11.3 mmol) and triphenylphosphine (3.5 g, 13.3 mmol) in dry THF (50 mL) at 0 °C, was added DEAD (40% in toluene, 5.7 mL, 12.4 mmol), under argon. The resulting solution was warmed to room temperature and stirred. After 12 h, the solvent was evaporated to give a crude residue which was purified directly by flash chromatography on silica gel (EtOAc:hexane, 40:60, v/v) to give I as a white solid ( 2 g, 72 %). (¹H NMR matched Lombardo et al. 2012)

Single crystals were obtained by vapour diffusion method at room temperature, i.e., pentane vapour was allowed to slowly diffuse into a EtOAc (0.3 ml) solution of I at room temperature. Single crystals were obtained after three days.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For biological background, see: Dickens et al. (2008); Erdmann & Wennemers (2011); Krishnamurthy et al. (2014); Gómez-Vidal & Silverman (2001). For the synthesis, see: Lombardo et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Molecular configuration for the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. Crystal packing diagram of the title compound.
	Fig. 3. Synthetic scheme for the title compound (I)

(I) top

Crystal data top

C₁₃H₁₃NO₄	Z = 4
M_r = 247.24	F(000) = 520
Monoclinic, P2₁	D_x = 1.393 Mg m⁻³
a = 11.212 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8943 (16) Å	µ = 0.10 mm⁻¹
c = 12.258 (2) Å	T = 90 K
β = 105.345 (2)°	Prism, colorless
V = 1178.8 (4) Å³	0.40 × 0.35 × 0.30 mm

Data collection top

Bruker APEX II KY CCD diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	4079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.333 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ϕandω–scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.709, T_max = 0.969	l = −14→14
11252 measured reflections

Refinement top

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0404P)² + 0.1656P] where P = (F_o² + 2F_c²)/3
4157 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₁₃NO₄	V = 1178.8 (4) Å³
M_r = 247.24	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.212 (2) Å	µ = 0.10 mm⁻¹
b = 8.8943 (16) Å	T = 90 K
c = 12.258 (2) Å	0.40 × 0.35 × 0.30 mm
β = 105.345 (2)°

Data collection top

Bruker APEX II KY CCD diffractometer	4157 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4079 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.969	R_int = 0.035
11252 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.073	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
4157 reflections	Δρ_min = −0.16 e Å⁻³
325 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.03159 (12)	0.45789 (16)	0.37070 (12)	0.0215 (3)
H1	−0.0256	0.4019	0.31	0.026*
C2	−0.02168 (13)	0.52285 (17)	0.46339 (12)	0.0235 (3)
H2A	−0.0862	0.5968	0.4356	0.028*
H2B	−0.0493	0.4465	0.5077	0.028*
C3	0.10287 (13)	0.59254 (17)	0.52422 (12)	0.0229 (3)
H3	0.1023	0.6507	0.592	0.027*
C4	0.19041 (13)	0.45866 (17)	0.54550 (11)	0.0229 (3)
H4A	0.2754	0.4888	0.5535	0.027*
H4B	0.1852	0.4018	0.6116	0.027*
C5	0.09010 (12)	0.59924 (16)	0.33634 (11)	0.0210 (3)
C6	0.19212 (13)	0.25806 (16)	0.39927 (12)	0.0218 (3)
C7	0.35825 (16)	0.0823 (2)	0.44690 (14)	0.0356 (4)
H7A	0.4176	0.1195	0.4083	0.043*
H7B	0.3012	0.0154	0.3961	0.043*
C8	0.42360 (14)	0.00050 (16)	0.55255 (13)	0.0265 (3)
C9	0.35980 (13)	−0.10101 (17)	0.60196 (15)	0.0319 (4)
H9	0.2765	−0.1189	0.5683	0.038*
C10	0.41768 (15)	−0.17599 (18)	0.70017 (15)	0.0341 (4)
H10	0.3731	−0.2425	0.7328	0.041*
C11	0.54297 (15)	−0.15203 (18)	0.75052 (14)	0.0310 (3)
H11	0.5828	−0.2035	0.8161	0.037*
C12	0.60744 (13)	−0.05120 (18)	0.70219 (13)	0.0290 (3)
H12	0.6911	−0.0349	0.7354	0.035*
C13	0.54857 (13)	0.02589 (18)	0.60467 (13)	0.0281 (3)
H13	0.5926	0.095	0.5737	0.034*
C14	0.96660 (12)	0.95675 (15)	0.18254 (11)	0.0199 (3)
H14	0.9969	0.9291	0.2625	0.024*
C15	1.06237 (13)	0.96354 (17)	0.11437 (12)	0.0228 (3)
H15A	1.1262	1.0383	0.1421	0.027*
H15B	1.0989	0.8666	0.1065	0.027*
C16	0.96511 (13)	1.01286 (16)	0.00832 (12)	0.0230 (3)
H16	0.9969	1.0321	−0.0575	0.028*
C17	0.86734 (13)	0.88969 (16)	−0.00859 (11)	0.0227 (3)
H17A	0.7863	0.926	−0.0497	0.027*
H17B	0.8892	0.8029	−0.0472	0.027*
C18	0.90739 (12)	1.11153 (16)	0.15699 (11)	0.0200 (3)
C19	0.81590 (12)	0.74552 (15)	0.15094 (12)	0.0190 (3)
C20	0.66990 (14)	0.54756 (16)	0.09787 (12)	0.0257 (3)
H20A	0.6144	0.5876	0.1394	0.031*
H20B	0.7242	0.4745	0.145	0.031*
C21	0.59844 (12)	0.47712 (16)	−0.01037 (12)	0.0224 (3)
C22	0.47838 (13)	0.52208 (17)	−0.06415 (13)	0.0259 (3)
H22	0.4391	0.5936	−0.0305	0.031*
C23	0.41709 (13)	0.46052 (18)	−0.16784 (13)	0.0280 (3)
H23	0.3365	0.49	−0.2028	0.034*
C24	0.47492 (14)	0.35578 (17)	−0.21940 (13)	0.0293 (3)
H24	0.4339	0.3158	−0.2894	0.035*
C25	0.59509 (15)	0.31033 (18)	−0.16600 (14)	0.0310 (3)
H25	0.6349	0.2404	−0.2006	0.037*
C26	0.65512 (13)	0.36930 (17)	−0.06153 (13)	0.0262 (3)
H26	0.7344	0.3364	−0.0251	0.031*
N1	0.13918 (11)	0.37446 (13)	0.43984 (10)	0.0227 (3)
N2	0.87336 (11)	0.85642 (14)	0.11057 (9)	0.0213 (2)
O1	0.10735 (9)	0.63621 (12)	0.24784 (8)	0.0278 (2)
O2	0.13217 (9)	0.68041 (11)	0.43299 (8)	0.0233 (2)
O3	0.15344 (9)	0.20350 (13)	0.30604 (9)	0.0302 (2)
O4	0.29114 (9)	0.20752 (12)	0.47981 (8)	0.0267 (2)
O5	0.85762 (8)	1.19197 (12)	0.21078 (8)	0.0252 (2)
O6	0.91040 (9)	1.14515 (11)	0.04972 (8)	0.0232 (2)
O7	0.82890 (8)	0.71808 (11)	0.25057 (8)	0.0224 (2)
O8	0.74174 (9)	0.66846 (11)	0.06459 (8)	0.0244 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0192 (6)	0.0193 (7)	0.0234 (7)	0.0006 (6)	0.0013 (5)	−0.0015 (6)
C2	0.0206 (7)	0.0251 (7)	0.0246 (7)	0.0012 (6)	0.0055 (6)	0.0036 (6)
C3	0.0257 (7)	0.0239 (7)	0.0195 (7)	0.0011 (6)	0.0068 (6)	0.0003 (6)
C4	0.0246 (7)	0.0232 (7)	0.0200 (7)	0.0005 (6)	0.0043 (5)	0.0000 (6)
C5	0.0185 (6)	0.0229 (7)	0.0204 (7)	0.0071 (5)	0.0031 (5)	0.0010 (5)
C6	0.0188 (6)	0.0196 (7)	0.0268 (7)	−0.0004 (5)	0.0056 (5)	0.0016 (6)
C7	0.0374 (9)	0.0358 (8)	0.0343 (8)	0.0174 (7)	0.0109 (7)	−0.0006 (7)
C8	0.0245 (7)	0.0228 (8)	0.0325 (8)	0.0074 (6)	0.0081 (6)	−0.0035 (6)
C9	0.0171 (7)	0.0253 (8)	0.0502 (10)	−0.0003 (6)	0.0031 (6)	−0.0034 (7)
C10	0.0282 (8)	0.0255 (8)	0.0497 (10)	0.0006 (6)	0.0123 (7)	0.0060 (7)
C11	0.0278 (8)	0.0301 (8)	0.0329 (8)	0.0075 (6)	0.0042 (6)	0.0019 (6)
C12	0.0172 (7)	0.0322 (8)	0.0360 (8)	0.0036 (6)	0.0041 (6)	−0.0069 (7)
C13	0.0242 (7)	0.0253 (7)	0.0383 (9)	0.0007 (6)	0.0144 (7)	−0.0027 (7)
C14	0.0181 (6)	0.0208 (7)	0.0198 (6)	−0.0006 (5)	0.0032 (5)	−0.0009 (5)
C15	0.0201 (7)	0.0227 (7)	0.0262 (7)	0.0004 (6)	0.0073 (5)	−0.0026 (6)
C16	0.0262 (7)	0.0216 (7)	0.0239 (7)	0.0022 (6)	0.0111 (6)	−0.0007 (6)
C17	0.0253 (7)	0.0238 (7)	0.0183 (7)	−0.0008 (6)	0.0047 (5)	−0.0011 (6)
C18	0.0147 (6)	0.0220 (7)	0.0225 (7)	−0.0046 (5)	0.0034 (5)	−0.0025 (5)
C19	0.0149 (6)	0.0178 (7)	0.0238 (7)	0.0030 (5)	0.0043 (5)	−0.0001 (5)
C20	0.0267 (7)	0.0222 (8)	0.0284 (8)	−0.0069 (6)	0.0075 (6)	0.0006 (6)
C21	0.0213 (7)	0.0200 (7)	0.0266 (7)	−0.0057 (6)	0.0077 (5)	0.0017 (6)
C22	0.0224 (7)	0.0222 (7)	0.0345 (8)	0.0009 (6)	0.0103 (6)	0.0006 (6)
C23	0.0174 (7)	0.0278 (7)	0.0362 (8)	−0.0019 (6)	0.0028 (6)	0.0057 (7)
C24	0.0284 (8)	0.0271 (8)	0.0295 (8)	−0.0064 (6)	0.0026 (6)	−0.0028 (6)
C25	0.0298 (8)	0.0269 (8)	0.0376 (8)	0.0013 (6)	0.0112 (6)	−0.0057 (7)
C26	0.0178 (7)	0.0252 (7)	0.0350 (8)	0.0008 (6)	0.0061 (6)	0.0018 (6)
N1	0.0230 (6)	0.0191 (6)	0.0225 (6)	0.0033 (5)	0.0001 (5)	−0.0003 (5)
N2	0.0221 (6)	0.0216 (6)	0.0182 (6)	−0.0028 (5)	0.0016 (5)	−0.0011 (5)
O1	0.0283 (5)	0.0338 (6)	0.0224 (5)	0.0082 (5)	0.0086 (4)	0.0067 (4)
O2	0.0272 (5)	0.0203 (5)	0.0220 (5)	−0.0007 (4)	0.0058 (4)	0.0011 (4)
O3	0.0254 (5)	0.0293 (6)	0.0332 (6)	0.0024 (5)	0.0028 (4)	−0.0082 (5)
O4	0.0253 (5)	0.0249 (5)	0.0288 (5)	0.0079 (4)	0.0052 (4)	0.0010 (4)
O5	0.0210 (5)	0.0265 (5)	0.0280 (5)	−0.0002 (4)	0.0060 (4)	−0.0053 (4)
O6	0.0266 (5)	0.0192 (5)	0.0239 (5)	0.0018 (4)	0.0068 (4)	0.0018 (4)
O7	0.0207 (5)	0.0234 (5)	0.0226 (5)	0.0002 (4)	0.0049 (4)	0.0023 (4)
O8	0.0253 (5)	0.0230 (5)	0.0239 (5)	−0.0070 (4)	0.0048 (4)	−0.0011 (4)

Geometric parameters (Å, º) top

C1—N1	1.4776 (17)	C14—N2	1.4763 (17)
C1—C5	1.528 (2)	C14—C18	1.525 (2)
C1—C2	1.530 (2)	C14—C15	1.5263 (19)
C1—H1	0.98	C14—H14	0.98
C2—C3	1.530 (2)	C15—C16	1.524 (2)
C2—H2A	0.97	C15—H15A	0.97
C2—H2B	0.97	C15—H15B	0.97
C3—O2	1.4710 (17)	C16—O6	1.4775 (16)
C3—C4	1.521 (2)	C16—C17	1.525 (2)
C3—H3	0.98	C16—H16	0.98
C4—N1	1.4746 (18)	C17—N2	1.4742 (18)
C4—H4A	0.97	C17—H17A	0.97
C4—H4B	0.97	C17—H17B	0.97
C5—O1	1.1973 (18)	C18—O5	1.2053 (17)
C5—O2	1.3606 (17)	C18—O6	1.3576 (17)
C6—O3	1.2113 (18)	C19—O7	1.2158 (17)
C6—N1	1.3519 (19)	C19—N2	1.3423 (18)
C6—O4	1.3526 (17)	C19—O8	1.3475 (16)
C7—O4	1.4592 (18)	C20—O8	1.4648 (16)
C7—C8	1.497 (2)	C20—C21	1.494 (2)
C7—H7A	0.97	C20—H20A	0.97
C7—H7B	0.97	C20—H20B	0.97
C8—C9	1.387 (2)	C21—C26	1.388 (2)
C8—C13	1.396 (2)	C21—C22	1.392 (2)
C9—C10	1.379 (2)	C22—C23	1.388 (2)
C9—H9	0.93	C22—H22	0.93
C10—C11	1.393 (2)	C23—C24	1.380 (2)
C10—H10	0.93	C23—H23	0.93
C11—C12	1.380 (2)	C24—C25	1.393 (2)
C11—H11	0.93	C24—H24	0.93
C12—C13	1.385 (2)	C25—C26	1.383 (2)
C12—H12	0.93	C25—H25	0.93
C13—H13	0.93	C26—H26	0.93

N1—C1—C5	103.08 (11)	C15—C14—H14	116.7
N1—C1—C2	100.58 (11)	C16—C15—C14	91.73 (10)
C5—C1—C2	100.05 (11)	C16—C15—H15A	113.3
N1—C1—H1	116.8	C14—C15—H15A	113.3
C5—C1—H1	116.8	C16—C15—H15B	113.3
C2—C1—H1	116.8	C14—C15—H15B	113.3
C3—C2—C1	91.69 (11)	H15A—C15—H15B	110.7
C3—C2—H2A	113.3	O6—C16—C15	101.81 (10)
C1—C2—H2A	113.3	O6—C16—C17	105.66 (10)
C3—C2—H2B	113.3	C15—C16—C17	103.63 (11)
C1—C2—H2B	113.3	O6—C16—H16	114.8
H2A—C2—H2B	110.7	C15—C16—H16	114.8
O2—C3—C4	106.41 (11)	C17—C16—H16	114.8
O2—C3—C2	101.74 (11)	N2—C17—C16	99.60 (11)
C4—C3—C2	103.34 (12)	N2—C17—H17A	111.9
O2—C3—H3	114.6	C16—C17—H17A	111.9
C4—C3—H3	114.6	N2—C17—H17B	111.9
C2—C3—H3	114.6	C16—C17—H17B	111.9
N1—C4—C3	99.40 (11)	H17A—C17—H17B	109.6
N1—C4—H4A	111.9	O5—C18—O6	122.20 (13)
C3—C4—H4A	111.9	O5—C18—C14	131.54 (13)
N1—C4—H4B	111.9	O6—C18—C14	106.07 (11)
C3—C4—H4B	111.9	O7—C19—N2	125.19 (13)
H4A—C4—H4B	109.6	O7—C19—O8	124.89 (12)
O1—C5—O2	122.78 (14)	N2—C19—O8	109.92 (12)
O1—C5—C1	131.28 (13)	O8—C20—C21	105.41 (11)
O2—C5—C1	105.77 (11)	O8—C20—H20A	110.7
O3—C6—N1	124.85 (13)	C21—C20—H20A	110.7
O3—C6—O4	125.12 (13)	O8—C20—H20B	110.7
N1—C6—O4	109.97 (12)	C21—C20—H20B	110.7
O4—C7—C8	107.58 (12)	H20A—C20—H20B	108.8
O4—C7—H7A	110.2	C26—C21—C22	119.05 (13)
C8—C7—H7A	110.2	C26—C21—C20	119.26 (13)
O4—C7—H7B	110.2	C22—C21—C20	121.62 (13)
C8—C7—H7B	110.2	C23—C22—C21	120.20 (14)
H7A—C7—H7B	108.5	C23—C22—H22	119.9
C9—C8—C13	118.47 (14)	C21—C22—H22	119.9
C9—C8—C7	120.22 (14)	C24—C23—C22	120.46 (14)
C13—C8—C7	121.29 (14)	C24—C23—H23	119.8
C10—C9—C8	121.21 (14)	C22—C23—H23	119.8
C10—C9—H9	119.4	C23—C24—C25	119.60 (14)
C8—C9—H9	119.4	C23—C24—H24	120.2
C9—C10—C11	119.95 (15)	C25—C24—H24	120.2
C9—C10—H10	120.0	C26—C25—C24	119.89 (15)
C11—C10—H10	120.0	C26—C25—H25	120.1
C12—C11—C10	119.38 (15)	C24—C25—H25	120.1
C12—C11—H11	120.3	C25—C26—C21	120.76 (13)
C10—C11—H11	120.3	C25—C26—H26	119.6
C11—C12—C13	120.54 (14)	C21—C26—H26	119.6
C11—C12—H12	119.7	C6—N1—C4	127.24 (12)
C13—C12—H12	119.7	C6—N1—C1	123.02 (11)
C12—C13—C8	120.43 (14)	C4—N1—C1	108.53 (11)
C12—C13—H13	119.8	C19—N2—C17	127.75 (12)
C8—C13—H13	119.8	C19—N2—C14	123.84 (11)
N2—C14—C18	102.83 (10)	C17—N2—C14	108.07 (11)
N2—C14—C15	100.74 (11)	C5—O2—C3	106.52 (11)
C18—C14—C15	100.54 (11)	C6—O4—C7	115.82 (11)
N2—C14—H14	116.7	C18—O6—C16	106.04 (10)
C18—C14—H14	116.7	C19—O8—C20	115.16 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.98	2.42	3.3493 (18)	159
C2—H2A···O7ⁱⁱ	0.97	2.46	3.2116 (18)	134
C3—H3···O5ⁱⁱⁱ	0.98	2.37	3.2816 (18)	155
C4—H4B···O7ⁱⁱⁱ	0.97	2.39	3.3408 (18)	168
C15—H15A···O3^iv	0.97	2.44	3.1382 (19)	128
C16—H16···O1^v	0.98	2.49	3.2207 (18)	131
C26—H26···O6^vi	0.93	2.58	3.4584 (19)	157

Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1; (iv) x+1, y+1, z; (v) −x+1, y+1/2, −z; (vi) x, y−1, z.