Crystal structure of ethyl 6-methyl-2-oxo-4-(3,4,5-tri­meth­oxy­phen­yl)-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Novina, J.J.; Vasuki, G.; Suresh, M.; Padusha, M.S.A.

doi:10.1107/S2056989015003576

Crystal structure of ethyl 6-methyl-2-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

J. J. Novina, G. Vasuki, M. Suresh and M. S. A. Padusha

In the title compound, C₁₇H₂₂N₂O₆, the dihydropyrimidine ring adopts a flattened boat conformation. The dihedral angle between the benzene ring and the mean plane of the dihydropyrimidine ring is 75.25 (6)°. In the crystal, molecules are linked via pairs of N—H

O hydrogen bonds, forming inversion dimers with an R₂²(8) ring motif which are linked through N—H

O and weak C—H

O hydrogen bonds. These, together with π–π ring interactions [centroid–centroid distance = 3.7965 (10) Å], give an overall three-dimensional structure.

Keywords: crystal structure; pyrimidine; hydrogen bonds; centrosymmetric dimer.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015003576/zs2327sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015003576/zs2327Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015003576/zs2327Isup3.cml Supplementary material

CCDC reference: 1050728

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.050
wR factor = 0.154
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G The Model has Chirality at C13     (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Dihydropyrimidinones (DHPMs) occupy a special place in the areas of natural and synthetic organic chemistry, because of their therapeutic and pharmacological properties. The dihydropyrimidinone scaffold has emerged as an integral backbone for several drugs used as calcium channel blockers as well as anti-hypertensive and anti-cancer agents. DHPMs also exhibit anti-diabetic activity (Jawale et al., 2011). Furthermore, the 2-oxodihydropyrimidine-5-carboxylate core unit is also found in many marine natural products, including the batzelladine alkaloids, which were found to be potent HIV gp-120-CD4 inhibitors (Karade et al., 2007; Beşoluk et al., 2010). Because of this background and in order to obtain detailed information on its molecular conformation, the X-ray structure of the title compound, C₁₇H₂₂N₂O₂ has been determined and is presented herein.

In the racemic title compound (Fig. 1) the dihydropyrimidone ring adopts a flattened boat conformation with the atom C13 and N2 deviating by -0.1218 (11) and 0.1432 (12) Å, respectively from the least squares plane defined by the remaining atoms N1/C11/C12/C14 in the ring. The puckering parameters are q2 = 0.207 Å, q3 = -0.074 Å, Q = 0.220 Å, Θ = 109.7° and Φ = 35.0°. The C1—C6 benzene ring is twisted with respect to the dihydropyrimidinone ring, with an inter-ring dihedral angle of 75.25 (9)°. The ethyl acetate group attached to the pyrimidine ring shows an extended conformation [torsion angle C12—C15—O2—C16 = -177.55 (20)°]. The methoxy two substituent groups at C3 and C5 are almost coplanar with the benzene ring [torsion angles C2—C3—O3—C7 = 7.7 (3)° and C6—C5—O5—C9 = -5.1 (3)°] whereas the central group at C4 deviates significantly from the benzene plane [C3—C4—O4—C8 = 102.7 (2)°].

In the crystal, molecules are linked via a pair of N—H···O hydrogen bonds (Table 1) forming a centrosymmetric cyclic dimer with an R₂²(8) ring motif. The inter-dimer N2—H···O3ⁱⁱ and N2—H···O4ⁱⁱ interactions constitute a bifurcated association generating an asymmetric R²₁(5) ring motif. The one-dimensional chain structures extend across [101] (Fig. 2) while the crystal structure is further stabilized by weak C—H···O hydrogen bonds and by π–π stacking interactions between inversion-related benzene rings [ring centroid–centroid distance = 3.7965 (10)Å] (Fig. 3), giving an overall three-dimensional structure.

Related literature top

For general background and the biological activity of dihydropyrimidinones, see: Jawale et al. (2011); Beşoluk et al. (2010); Karade et al. (2007).

Experimental top

A mixture of ethyl acetoacetate (0.13 ml, 1 mmol), 3,4,5-trimethoxybenzaldehyde (0.196 g, 1 mmol), and urea (0.18 g, 3 mmol) in ethanol (5 ml) was heated under reflux in the presence of cerium chloride heptahydrate (25%) for 1 h (monitored by TLC). After the completion of the reaction, the reaction mixture was cooled to room temperature and poured onto crushed ice and stirred for 5–10 min. The solid was separated and filtered under suction, washed with ice-cold water (50 ml) and then recrystallized from hot ethanol to afford the pure product [m.p. 445 K; yield 96%].

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Cystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines (Table 1). For clarity only the H atoms participating in these interactions are shown.
	Fig. 3. A view showing the π–π interactions. The H atoms are omitted for the sake of clarity.

Ethyl 6-methyl-2-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₇H₂₂N₂O₆	Z = 2
M_r = 350.37	F(000) = 372
Triclinic, P1	D_x = 1.313 Mg m⁻³
Hall symbol: -P 1	Melting point: 445 K
a = 10.1447 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1919 (2) Å	Cell parameters from 3659 reflections
c = 10.8724 (2) Å	θ = 1.0–26.5°
α = 117.882 (1)°	µ = 0.10 mm⁻¹
β = 101.371 (1)°	T = 293 K
γ = 105.498 (1)°	Block, colourless
V = 886.40 (4) Å³	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	3009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
T_min = 0.970, T_max = 0.995	k = −12→12
13060 measured reflections	l = −13→13

Refinement top

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0769P)² + 0.2863P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3659 reflections	Δρ_max = 0.60 e Å⁻³
228 parameters	Δρ_min = −0.30 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

Crystal data top

C₁₇H₂₂N₂O₆	γ = 105.498 (1)°
M_r = 350.37	V = 886.40 (4) Å³
Triclinic, P1	Z = 2
a = 10.1447 (3) Å	Mo Kα radiation
b = 10.1919 (2) Å	µ = 0.10 mm⁻¹
c = 10.8724 (2) Å	T = 293 K
α = 117.882 (1)°	0.20 × 0.15 × 0.10 mm
β = 101.371 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3659 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3009 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.995	R_int = 0.020
13060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.154	H-atom parameters constrained
S = 1.06	Δρ_max = 0.60 e Å⁻³
3659 reflections	Δρ_min = −0.30 e Å⁻³
228 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	0.37112 (18)	0.3299 (2)	0.72474 (17)	0.0394 (4)
C2	0.44867 (19)	0.2873 (2)	0.80886 (18)	0.0410 (4)
H2	0.4009	0.1946	0.8073	0.049*
C3	0.59827 (19)	0.3837 (2)	0.89570 (18)	0.0415 (4)
C4	0.66902 (18)	0.5242 (2)	0.90186 (18)	0.0429 (4)
C5	0.5914 (2)	0.5645 (2)	0.8146 (2)	0.0477 (4)
C6	0.4429 (2)	0.4661 (2)	0.7249 (2)	0.0466 (4)
H6	0.3916	0.4918	0.6647	0.056*
C7	0.6280 (3)	0.2077 (3)	0.9753 (3)	0.0698 (6)
H7A	0.7016	0.2040	1.0427	0.105*
H7B	0.5992	0.1174	0.8743	0.105*
H7C	0.5433	0.2011	1.0028	0.105*
C8	0.9201 (2)	0.6153 (3)	0.9346 (2)	0.0652 (6)
H8A	1.0172	0.6907	1.0103	0.098*
H8B	0.9011	0.6404	0.8599	0.098*
H8C	0.9141	0.5062	0.8882	0.098*
C9	0.5979 (3)	0.7486 (3)	0.7382 (4)	0.0828 (8)
H9A	0.6640	0.8501	0.7591	0.124*
H9B	0.5124	0.7596	0.7590	0.124*
H9C	0.5679	0.6647	0.6343	0.124*
C10	0.0111 (2)	0.1030 (3)	0.2264 (2)	0.0599 (5)
H10A	−0.0726	0.1254	0.2006	0.090*
H10B	−0.0203	−0.0123	0.1806	0.090*
H10C	0.0824	0.1408	0.1908	0.090*
C11	0.07976 (19)	0.1893 (2)	0.39399 (19)	0.0445 (4)
C12	0.15090 (18)	0.1416 (2)	0.47179 (19)	0.0425 (4)
C13	0.20307 (18)	0.2357 (2)	0.64192 (18)	0.0410 (4)
H13	0.1699	0.1573	0.6694	0.049*
C14	0.0864 (2)	0.4142 (2)	0.62100 (19)	0.0455 (4)
C15	0.1840 (2)	−0.0008 (2)	0.3951 (2)	0.0496 (4)
C16	0.2722 (3)	−0.1808 (3)	0.4190 (3)	0.0833 (8)
H16A	0.3437	−0.1572	0.3764	0.100*
H16B	0.1855	−0.2781	0.3388	0.100*
C17	0.3362 (5)	−0.2078 (4)	0.5344 (4)	0.1191 (13)
H17A	0.3634	−0.2977	0.4898	0.179*
H17B	0.2647	−0.2321	0.5754	0.179*
H17C	0.4223	−0.1113	0.6131	0.179*
N1	0.06044 (18)	0.33131 (19)	0.47041 (16)	0.0507 (4)
H1N	0.0304	0.3699	0.4205	0.061*
N2	0.13307 (16)	0.34918 (19)	0.69333 (16)	0.0447 (4)
H2N	0.1210	0.3761	0.7766	0.054*
O1	0.1753 (2)	−0.07004 (19)	0.26618 (17)	0.0744 (5)
O2	0.23206 (16)	−0.04531 (16)	0.48721 (16)	0.0609 (4)
O3	0.68614 (15)	0.35473 (16)	0.98399 (14)	0.0559 (4)
O4	0.81300 (14)	0.62806 (16)	1.00213 (14)	0.0542 (4)
O5	0.67016 (17)	0.70646 (19)	0.8294 (2)	0.0717 (5)
O6	0.06186 (17)	0.53697 (18)	0.68139 (15)	0.0598 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0405 (8)	0.0409 (8)	0.0349 (8)	0.0214 (7)	0.0128 (7)	0.0178 (7)
C2	0.0455 (9)	0.0391 (8)	0.0371 (8)	0.0222 (7)	0.0126 (7)	0.0189 (7)
C3	0.0465 (9)	0.0450 (9)	0.0316 (8)	0.0272 (7)	0.0116 (7)	0.0170 (7)
C4	0.0390 (8)	0.0457 (9)	0.0338 (8)	0.0192 (7)	0.0105 (6)	0.0153 (7)
C5	0.0468 (9)	0.0465 (9)	0.0505 (10)	0.0197 (8)	0.0179 (8)	0.0273 (8)
C6	0.0450 (9)	0.0532 (10)	0.0487 (10)	0.0246 (8)	0.0138 (8)	0.0324 (8)
C7	0.0782 (15)	0.0662 (13)	0.0680 (13)	0.0347 (12)	0.0081 (11)	0.0440 (11)
C8	0.0440 (10)	0.0744 (14)	0.0590 (12)	0.0240 (10)	0.0159 (9)	0.0256 (11)
C9	0.0771 (16)	0.0827 (17)	0.117 (2)	0.0329 (14)	0.0329 (15)	0.0762 (17)
C10	0.0654 (12)	0.0652 (12)	0.0397 (10)	0.0334 (10)	0.0109 (9)	0.0223 (9)
C11	0.0431 (9)	0.0451 (9)	0.0386 (9)	0.0197 (7)	0.0121 (7)	0.0190 (7)
C12	0.0385 (8)	0.0399 (8)	0.0397 (9)	0.0160 (7)	0.0099 (7)	0.0174 (7)
C13	0.0402 (8)	0.0438 (9)	0.0409 (9)	0.0207 (7)	0.0127 (7)	0.0240 (7)
C14	0.0454 (9)	0.0535 (10)	0.0405 (9)	0.0290 (8)	0.0156 (7)	0.0237 (8)
C15	0.0433 (9)	0.0399 (9)	0.0471 (10)	0.0154 (7)	0.0070 (7)	0.0157 (8)
C16	0.0882 (17)	0.0513 (12)	0.0835 (17)	0.0417 (12)	0.0098 (13)	0.0202 (12)
C17	0.142 (3)	0.094 (2)	0.107 (2)	0.079 (2)	0.012 (2)	0.0433 (19)
N1	0.0662 (10)	0.0574 (9)	0.0382 (8)	0.0390 (8)	0.0178 (7)	0.0269 (7)
N2	0.0461 (8)	0.0586 (9)	0.0364 (7)	0.0312 (7)	0.0170 (6)	0.0257 (7)
O1	0.0979 (12)	0.0630 (9)	0.0499 (9)	0.0456 (9)	0.0243 (8)	0.0172 (7)
O2	0.0668 (9)	0.0449 (7)	0.0571 (8)	0.0302 (7)	0.0086 (7)	0.0203 (6)
O3	0.0544 (8)	0.0581 (8)	0.0487 (7)	0.0271 (6)	0.0034 (6)	0.0289 (6)
O4	0.0419 (7)	0.0570 (8)	0.0397 (7)	0.0149 (6)	0.0088 (5)	0.0152 (6)
O5	0.0554 (8)	0.0653 (9)	0.0974 (12)	0.0163 (7)	0.0160 (8)	0.0564 (9)
O6	0.0778 (10)	0.0686 (9)	0.0446 (7)	0.0525 (8)	0.0231 (7)	0.0277 (7)

Geometric parameters (Å, º) top

C1—C2	1.384 (2)	C10—C11	1.501 (2)
C1—C6	1.384 (2)	C10—H10A	0.9600
C1—C13	1.533 (2)	C10—H10B	0.9600
C2—C3	1.389 (2)	C10—H10C	0.9600
C2—H2	0.9300	C11—C12	1.344 (2)
C3—O3	1.368 (2)	C11—N1	1.383 (2)
C3—C4	1.383 (3)	C12—C15	1.468 (2)
C4—O4	1.382 (2)	C12—C13	1.518 (2)
C4—C5	1.390 (3)	C13—N2	1.464 (2)
C5—O5	1.368 (2)	C13—H13	0.9800
C5—C6	1.387 (3)	C14—O6	1.233 (2)
C6—H6	0.9300	C14—N2	1.338 (2)
C7—O3	1.406 (3)	C14—N1	1.371 (2)
C7—H7A	0.9600	C15—O1	1.210 (2)
C7—H7B	0.9600	C15—O2	1.340 (2)
C7—H7C	0.9600	C16—O2	1.444 (3)
C8—O4	1.428 (2)	C16—C17	1.472 (3)
C8—H8A	0.9600	C16—H16A	0.9700
C8—H8B	0.9600	C16—H16B	0.9700
C8—H8C	0.9600	C17—H17A	0.9600
C9—O5	1.410 (3)	C17—H17B	0.9600
C9—H9A	0.9600	C17—H17C	0.9600
C9—H9B	0.9600	N1—H1N	0.8600
C9—H9C	0.9600	N2—H2N	0.8600

C2—C1—C6	120.13 (15)	H10B—C10—H10C	109.5
C2—C1—C13	120.26 (15)	C12—C11—N1	119.53 (15)
C6—C1—C13	119.40 (15)	C12—C11—C10	127.51 (17)
C1—C2—C3	119.70 (16)	N1—C11—C10	112.94 (15)
C1—C2—H2	120.1	C11—C12—C15	120.97 (16)
C3—C2—H2	120.2	C11—C12—C13	121.07 (15)
O3—C3—C4	114.49 (15)	C15—C12—C13	117.94 (15)
O3—C3—C2	125.05 (16)	N2—C13—C12	109.34 (13)
C4—C3—C2	120.42 (15)	N2—C13—C1	109.29 (14)
O4—C4—C3	119.43 (15)	C12—C13—C1	114.52 (14)
O4—C4—C5	120.85 (16)	N2—C13—H13	107.8
C3—C4—C5	119.58 (16)	C12—C13—H13	107.8
O5—C5—C6	124.58 (17)	C1—C13—H13	107.8
O5—C5—C4	115.35 (16)	O6—C14—N2	123.56 (16)
C6—C5—C4	120.03 (17)	O6—C14—N1	120.72 (16)
C1—C6—C5	120.03 (16)	N2—C14—N1	115.66 (15)
C1—C6—H6	120.0	O1—C15—O2	122.09 (18)
C5—C6—H6	120.0	O1—C15—C12	125.98 (18)
O3—C7—H7A	109.5	O2—C15—C12	111.89 (16)
O3—C7—H7B	109.5	O2—C16—C17	109.0 (2)
H7A—C7—H7B	109.5	O2—C16—H16A	109.9
O3—C7—H7C	109.5	C17—C16—H16A	109.9
H7A—C7—H7C	109.5	O2—C16—H16B	109.9
H7B—C7—H7C	109.5	C17—C16—H16B	109.9
O4—C8—H8A	109.5	H16A—C16—H16B	108.3
O4—C8—H8B	109.5	C16—C17—H17A	109.5
H8A—C8—H8B	109.5	C16—C17—H17B	109.5
O4—C8—H8C	109.5	H17A—C17—H17B	109.5
H8A—C8—H8C	109.5	C16—C17—H17C	109.5
H8B—C8—H8C	109.5	H17A—C17—H17C	109.5
O5—C9—H9A	109.5	H17B—C17—H17C	109.5
O5—C9—H9B	109.5	C14—N1—C11	123.90 (15)
H9A—C9—H9B	109.5	C14—N1—H1N	118.1
O5—C9—H9C	109.5	C11—N1—H1N	118.1
H9A—C9—H9C	109.5	C14—N2—C13	125.19 (14)
H9B—C9—H9C	109.5	C14—N2—H2N	117.4
C11—C10—H10A	109.5	C13—N2—H2N	117.4
C11—C10—H10B	109.5	C15—O2—C16	114.13 (17)
H10A—C10—H10B	109.5	C3—O3—C7	118.70 (15)
C11—C10—H10C	109.5	C4—O4—C8	113.93 (14)
H10A—C10—H10C	109.5	C5—O5—C9	117.35 (17)

C6—C1—C2—C3	1.3 (2)	C6—C1—C13—N2	−52.6 (2)
C13—C1—C2—C3	−173.41 (15)	C2—C1—C13—C12	−114.87 (17)
C1—C2—C3—O3	179.57 (16)	C6—C1—C13—C12	70.4 (2)
C1—C2—C3—C4	1.8 (2)	C11—C12—C15—O1	12.9 (3)
O3—C3—C4—O4	−5.5 (2)	C13—C12—C15—O1	−165.48 (19)
C2—C3—C4—O4	172.46 (15)	C11—C12—C15—O2	−169.40 (16)
O3—C3—C4—C5	178.81 (15)	C13—C12—C15—O2	12.2 (2)
C2—C3—C4—C5	−3.2 (3)	O6—C14—N1—C11	−177.32 (18)
O4—C4—C5—O5	3.7 (3)	N2—C14—N1—C11	0.0 (3)
C3—C4—C5—O5	179.34 (16)	C12—C11—N1—C14	−11.8 (3)
O4—C4—C5—C6	−174.07 (16)	C10—C11—N1—C14	166.62 (18)
C3—C4—C5—C6	1.6 (3)	O6—C14—N2—C13	−161.54 (18)
C2—C1—C6—C5	−2.9 (3)	N1—C14—N2—C13	21.2 (3)
C13—C1—C6—C5	171.79 (16)	C12—C13—N2—C14	−27.1 (2)
O5—C5—C6—C1	−176.06 (17)	C1—C13—N2—C14	98.96 (19)
C4—C5—C6—C1	1.5 (3)	O1—C15—O2—C16	0.3 (3)
N1—C11—C12—C15	−174.94 (16)	C12—C15—O2—C16	−177.52 (18)
C10—C11—C12—C15	6.9 (3)	C17—C16—O2—C15	174.6 (2)
N1—C11—C12—C13	3.4 (3)	C4—C3—O3—C7	−174.43 (18)
C10—C11—C12—C13	−174.76 (18)	C2—C3—O3—C7	7.7 (3)
C11—C12—C13—N2	13.6 (2)	C3—C4—O4—C8	102.7 (2)
C15—C12—C13—N2	−167.97 (15)	C5—C4—O4—C8	−81.7 (2)
C11—C12—C13—C1	−109.38 (18)	C6—C5—O5—C9	−5.1 (3)
C15—C12—C13—C1	69.0 (2)	C4—C5—O5—C9	177.3 (2)
C2—C1—C13—N2	122.09 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6ⁱ	0.86	2.01	2.867 (2)	171
N2—H2N···O3ⁱⁱ	0.86	2.56	3.0629 (19)	118
N2—H2N···O4ⁱⁱ	0.86	2.39	3.1331 (19)	145
C8—H8A···O1ⁱⁱⁱ	0.96	2.46	3.325 (3)	149
C9—H9A···O1^iv	0.96	2.56	3.491 (3)	163

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