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

The di­hydro­pyrimidine ring in the title ester adopts a flattened envelope conformation. An intra­molecular C—H...O hydrogen bond generates an S(6) ring. Mol­ecules are linked via pairs of N—H...O hydrogen bonds, forming inversion dimers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.121
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         22 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00500 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
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         17 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
   8 ALERT level G = General information/check it is not something unexpected

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 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.

Author Response: The role of the authors is as follows: M. Syed Ali Padusha and M. Suresh synthesized the title compound.

 J. Josephine Novina and G. Vasuki were involved in
 preparing write-up for the paper.

 Vijayan Viswanathan and Devadasan Velmurugan were involved in
 refining the  structure.


   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

---

S1. Chemical context

Pyrimidine derivatives have been investigated extensively due to their great biological significance and as the main constituent of nucleic acids. Pyrimidines and their derivatives are considered to be important for drugs and agricultural chemicals. They are also found to exhibit remarkable pharmacological activities such as anti-cancer, anti-tumor, anti-inflammatory and anti­fungal etc and are used widely as agrochemicals, pharmaceuticals, dyes, organic additives in electroplating of steel and in the polymerization process (Sharma et al., 2014; Vaisalini et al., 2012). Di­hydro­pyrimidino­nes, the product of the Biginelli reaction, are also widely used in the pharmaceutical industry as calcium channel blockers and alpha-1 antagonists (Beena & Akelesh, 2012). Moreover, some bioactive alkaloids such as batzelladine B, containing the di­hydro­pyrimidine unit, which has been isolated from marine sources, show anti-HIV activity (Asghari et al., 2011). Our inter­est in the preparation of pharmacologically active compounds led us to synthesize the title compound (I) and we report its crystal structure herein.

S2. Structural commentary

\ The molecular structure of (I) is shown in Fig. 1. The di­hydro­pyrimidine ring adopts a flattened envelope conformation. Atoms N1/N2/C11/C12/C14 are essentially planar with a maximum deviation of 0.0305 (17) Å for C11 while atom C13 is displaced by 0.1311 (17) Å from this plane, forming the flap. The puckering parameters are q2 = 0.0935, q3 = -0.0317, Q = 0.0987 Å, Θ = 108.7 and Φ = 22.9°. The benzene ring is almost perpendicular to the least-squares plane of the six-membered tetra­hydro­pyrimidine ring, making a dihedral angle of 88.09 (6)°. In comparison, this dihedral angle in the structure of ethyl 6-eth­oxy­carbonyl­methyl-4-(2-hy­droxy­phenyl)-2-oxo-1,2,3,4-\ tetra­hydro­pyrimidine-5-carboxyl­ate, (II), is 87.7 (2)° (Kettmann et al., 2008), in ethyl-6-(chloro­methyl)-4-(4-chloro­phenyl)-2-oxo-1,2,3,4- tetra­hydro­pyrimidine-5-carboxyl­ate, (III), it is 87.08 (9)° (Bharanidharan et al., 2014), and in the crystal structure of ethyl 6-methyl-2-oxo-4-(3,4,5-tri­meth­oxy­phenyl)-1,2,3,4-tetra­hydro­pyrimidine-5-\ carboxyl­ate, (IV), it is 75.25 (6)° (Novina et al., 2015). The ethyl acetate group attached to the pyrimidine ring shows an extended conformation [torsion angle C12—C15—O2—C16 = -175.83 (15)°]. The meth­oxy group at C4 is essentially coplanar with the benzene ring [C5—C4—O5—C7 = -1.3 (3)°], whereas the two meth­oxy substituent groups at C2 and C3 deviate significantly from the benzene plane [C3—C2—O3—C9 = 71.6 (2) and C2—C3—O4—C8 = 71.6 (2)°]. The molecular structure is partially stabilized by the C10—H10A···O1 intra­molecular inter­action (Table 1), which generates an S(6) ring motif.

S3. Supra­molecular features

In the crystal, both N—H groups participate in separate inter­molecular hydrogen-bonding associations (Table 1) giving centrosymmetric cyclic motifs [graph sets R₂²(8) and R₂²(14)], resulting in ribbons parallel to [111] (Fig. 2). The molecular packing (Fig. 3) is further stabilized by weak C—H···π inter­actions between the methyl H atoms of the ethyl groups and the pyrimidine rings of inversion-related molecules.

S4. Synthesis and crystallization

To an ethano­lic solution of ethyl 4-chloro­aceto acetate (2 ml, 0.012 mol), 2,3,4-tri­meth­oxy benzaldehyde (2.4 g, 0.012 mol), and urea (2.25 g, 0.037 mol) were added followed by CeCl₃.7H₂O (931 mg). The reaction mixture was taken in a round-bottom flask and refluxed for 2 h. Then the reaction mixture was cooled and poured into crushed ice taken in a beaker with constant stirring. The solid separated out was filtered, washed with ice-cold water and then recrystallized from hot ethanol to afford the product [yield: 92%; m.p. 425–427 K] as X-ray quality crystals.

S5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2₁. H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances fixed in the range 0.93–0.98 Å and N—H = 0.86 Å with U_iso(H) = 1.5U _eq(CH₃) and 1.2U_eq(CH₂,CH, NH).

Related literature

For general background and the biological activity of dihydropyrimidinones, see: Sharma et al. (2014); Asghari et al. (2011); Vaisalini et al. (2012); Beena & Akelesh (2012). For related structures, see: Kettmann et al. (2008); Bharanidharan et al. (2014); Novina et al. (2015).

Computing details

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); software used to prepare material for publication: PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates the intramolecular C10—H10A···O1 hydrogen bond.
	Fig. 2. Partial crystal packing diagram for the title compound, showing the R2^2(8) and R2^2(14) ring motifs. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Part of the crystal packing of the title compound, showing C—H···π interactions and N—H···O hydrogen bonds as dashed lines.

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

Crystal data

C17H21ClN2O6	Z = 2
Mr = 384.81	F(000) = 404
Triclinic, P1	Dx = 1.421 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.479 (5) Å	Cell parameters from 3737 reflections
b = 10.080 (5) Å	θ = 1.0–26.6°
c = 10.320 (5) Å	µ = 0.25 mm^−1
α = 108.552 (5)°	T = 293 K
β = 102.886 (5)°	Block, colourless
γ = 94.406 (5)°	0.20 × 0.15 × 0.10 mm
V = 899.5 (8) Å^3

Data collection

Bruker Kappa APEXII CCD diffractometer	3737 independent reflections
Radiation source: fine-focus sealed tube	3025 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and ϕ scan	θmax = 26.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.952, Tmax = 0.976	k = −12→12
12878 measured reflections	l = −12→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 0.3029P] where P = (Fo^2 + 2Fc^2)/3
3737 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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
C7	0.3380 (3)	−0.2172 (2)	−0.3248 (3)	0.0695 (6)
H7A	0.3999	−0.1501	−0.3444	0.104*
H7B	0.3213	−0.3077	−0.3989	0.104*
H7C	0.3848	−0.2260	−0.2360	0.104*
C4	0.2052 (2)	−0.03983 (17)	−0.22112 (17)	0.0417 (4)
C5	0.33170 (19)	0.04788 (18)	−0.12747 (18)	0.0428 (4)
H5	0.4230	0.0206	−0.1293	0.051*
C6	0.32077 (18)	0.17612 (18)	−0.03140 (17)	0.0404 (4)
H6	0.4058	0.2338	0.0317	0.049*
C1	0.18792 (17)	0.22104 (16)	−0.02627 (16)	0.0353 (3)
C2	0.06034 (17)	0.13322 (17)	−0.12190 (17)	0.0375 (4)
C3	0.06932 (19)	0.00217 (17)	−0.21729 (17)	0.0409 (4)
C8	−0.1441 (3)	−0.0596 (3)	−0.4122 (2)	0.0685 (6)
H8A	−0.1575	0.0377	−0.3781	0.103*
H8B	−0.2377	−0.1197	−0.4467	0.103*
H8C	−0.0969	−0.0740	−0.4877	0.103*
C9	−0.1707 (3)	0.1099 (3)	−0.0726 (3)	0.0690 (6)
H9A	−0.1769	0.0092	−0.1149	0.104*
H9B	−0.2658	0.1358	−0.0970	0.104*
H9C	−0.1365	0.1373	0.0285	0.104*
C13	0.17802 (17)	0.35901 (16)	0.08517 (16)	0.0360 (3)
H13	0.0787	0.3807	0.0601	0.043*
C12	0.28624 (17)	0.48334 (16)	0.09400 (16)	0.0357 (3)
C11	0.39561 (18)	0.54845 (16)	0.21121 (17)	0.0376 (4)
C14	0.31732 (19)	0.40206 (18)	0.33668 (17)	0.0417 (4)
C10	0.5076 (2)	0.67371 (18)	0.23650 (19)	0.0451 (4)
H10A	0.5094	0.6851	0.1470	0.054*
H10B	0.6041	0.6582	0.2793	0.054*
C15	0.26590 (19)	0.52688 (17)	−0.03168 (17)	0.0391 (4)
C16	0.1095 (2)	0.4838 (2)	−0.2602 (2)	0.0548 (5)
H16A	0.1940	0.4739	−0.2989	0.066*
H16B	0.0869	0.5787	−0.2469	0.066*
C17	−0.0182 (3)	0.3764 (3)	−0.3576 (2)	0.0816 (8)
H17A	0.0067	0.2832	−0.3725	0.122*
H17B	−0.0438	0.3916	−0.4466	0.122*
H17C	−0.1001	0.3852	−0.3166	0.122*
N2	0.20306 (15)	0.34077 (15)	0.22426 (14)	0.0414 (3)
H2N	0.1367	0.2844	0.2341	0.050*
N1	0.41333 (16)	0.50454 (16)	0.32654 (15)	0.0478 (4)
H1N	0.4894	0.5439	0.3964	0.057*
O5	0.20239 (16)	−0.16966 (14)	−0.31766 (15)	0.0586 (4)
O4	−0.05528 (14)	−0.09329 (13)	−0.29991 (14)	0.0536 (4)
O3	−0.07186 (13)	0.17960 (13)	−0.12314 (14)	0.0471 (3)
O1	0.34931 (16)	0.60863 (16)	−0.05290 (15)	0.0615 (4)
O2	0.13972 (14)	0.45913 (14)	−0.12663 (13)	0.0495 (3)
O6	0.33671 (15)	0.37184 (15)	0.44510 (13)	0.0595 (4)
Cl	0.46401 (7)	0.83004 (5)	0.35072 (6)	0.06618 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C7	0.0724 (15)	0.0561 (13)	0.0664 (14)	0.0167 (11)	0.0202 (11)	−0.0003 (10)
C4	0.0495 (10)	0.0351 (8)	0.0351 (8)	0.0004 (7)	0.0089 (7)	0.0082 (7)
C5	0.0384 (9)	0.0438 (9)	0.0440 (9)	0.0025 (7)	0.0120 (7)	0.0123 (7)
C6	0.0355 (8)	0.0396 (8)	0.0382 (8)	−0.0058 (7)	0.0033 (6)	0.0097 (7)
C1	0.0371 (8)	0.0317 (7)	0.0324 (7)	−0.0034 (6)	0.0034 (6)	0.0106 (6)
C2	0.0355 (8)	0.0346 (8)	0.0371 (8)	−0.0010 (6)	0.0016 (6)	0.0119 (6)
C3	0.0411 (9)	0.0340 (8)	0.0369 (8)	−0.0066 (7)	−0.0003 (7)	0.0082 (7)
C8	0.0629 (13)	0.0710 (14)	0.0475 (11)	−0.0165 (11)	−0.0123 (9)	0.0127 (10)
C9	0.0669 (14)	0.0783 (15)	0.0892 (17)	0.0250 (12)	0.0395 (13)	0.0495 (14)
C13	0.0343 (8)	0.0352 (8)	0.0316 (7)	−0.0030 (6)	0.0020 (6)	0.0087 (6)
C12	0.0380 (8)	0.0294 (7)	0.0348 (8)	0.0013 (6)	0.0059 (6)	0.0078 (6)
C11	0.0393 (9)	0.0320 (8)	0.0371 (8)	−0.0010 (6)	0.0078 (7)	0.0089 (6)
C14	0.0439 (9)	0.0385 (8)	0.0351 (8)	−0.0059 (7)	0.0025 (7)	0.0107 (7)
C10	0.0469 (10)	0.0373 (9)	0.0426 (9)	−0.0075 (7)	0.0076 (7)	0.0082 (7)
C15	0.0424 (9)	0.0337 (8)	0.0384 (8)	0.0052 (7)	0.0088 (7)	0.0100 (7)
C16	0.0629 (12)	0.0611 (12)	0.0402 (9)	0.0124 (10)	0.0058 (8)	0.0220 (9)
C17	0.0997 (19)	0.0735 (16)	0.0466 (12)	0.0001 (14)	−0.0117 (12)	0.0114 (11)
N2	0.0422 (8)	0.0407 (7)	0.0328 (7)	−0.0115 (6)	0.0035 (6)	0.0096 (6)
N1	0.0463 (8)	0.0482 (8)	0.0369 (7)	−0.0168 (7)	−0.0066 (6)	0.0160 (6)
O5	0.0615 (9)	0.0436 (7)	0.0531 (8)	0.0061 (6)	0.0102 (6)	−0.0030 (6)
O4	0.0483 (7)	0.0383 (6)	0.0535 (7)	−0.0110 (5)	−0.0075 (6)	0.0066 (6)
O3	0.0359 (6)	0.0398 (6)	0.0581 (8)	−0.0001 (5)	0.0015 (5)	0.0154 (6)
O1	0.0604 (9)	0.0675 (9)	0.0557 (8)	−0.0128 (7)	0.0036 (6)	0.0334 (7)
O2	0.0519 (7)	0.0511 (7)	0.0386 (6)	−0.0040 (6)	−0.0016 (5)	0.0180 (5)
O6	0.0628 (9)	0.0630 (9)	0.0412 (7)	−0.0235 (7)	−0.0084 (6)	0.0250 (6)
Cl	0.0771 (4)	0.0375 (3)	0.0716 (4)	0.0020 (2)	0.0145 (3)	0.0072 (2)

Geometric parameters (Å, º)

C7—O5	1.415 (3)	C13—N2	1.474 (2)
C7—H7A	0.9600	C13—C12	1.523 (2)
C7—H7B	0.9600	C13—H13	0.9800
C7—H7C	0.9600	C12—C11	1.341 (2)
C4—O5	1.364 (2)	C12—C15	1.475 (2)
C4—C5	1.389 (2)	C11—N1	1.378 (2)
C4—C3	1.391 (3)	C11—C10	1.500 (2)
C5—C6	1.384 (3)	C14—O6	1.230 (2)
C5—H5	0.9300	C14—N2	1.335 (2)
C6—C1	1.377 (3)	C14—N1	1.369 (2)
C6—H6	0.9300	C10—Cl	1.783 (2)
C1—C2	1.403 (2)	C10—H10A	0.9700
C1—C13	1.522 (2)	C10—H10B	0.9700
C2—O3	1.370 (2)	C15—O1	1.202 (2)
C2—C3	1.396 (2)	C15—O2	1.335 (2)
C3—O4	1.3791 (19)	C16—O2	1.448 (2)
C8—O4	1.424 (3)	C16—C17	1.487 (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—O3	1.412 (2)	C17—H17B	0.9600
C9—H9A	0.9600	C17—H17C	0.9600
C9—H9B	0.9600	N2—H2N	0.8600
C9—H9C	0.9600	N1—H1N	0.8600
O5—C7—H7A	109.5	C12—C13—H13	108.2
O5—C7—H7B	109.5	C11—C12—C15	122.12 (15)
H7A—C7—H7B	109.5	C11—C12—C13	120.78 (14)
O5—C7—H7C	109.5	C15—C12—C13	117.09 (13)
H7A—C7—H7C	109.5	C12—C11—N1	120.98 (14)
H7B—C7—H7C	109.5	C12—C11—C10	126.74 (15)
O5—C4—C5	124.55 (17)	N1—C11—C10	112.26 (14)
O5—C4—C3	115.73 (15)	O6—C14—N2	123.26 (15)
C5—C4—C3	119.71 (16)	O6—C14—N1	120.67 (14)
C6—C5—C4	119.45 (17)	N2—C14—N1	116.06 (15)
C6—C5—H5	120.3	C11—C10—Cl	109.90 (13)
C4—C5—H5	120.3	C11—C10—H10A	109.7
C1—C6—C5	122.07 (15)	Cl—C10—H10A	109.7
C1—C6—H6	119.0	C11—C10—H10B	109.7
C5—C6—H6	119.0	Cl—C10—H10B	109.7
C6—C1—C2	118.47 (15)	H10A—C10—H10B	108.2
C6—C1—C13	121.07 (13)	O1—C15—O2	122.11 (16)
C2—C1—C13	120.39 (15)	O1—C15—C12	127.08 (15)
O3—C2—C3	120.68 (14)	O2—C15—C12	110.79 (14)
O3—C2—C1	119.18 (15)	O2—C16—C17	107.07 (17)
C3—C2—C1	120.11 (16)	O2—C16—H16A	110.3
O4—C3—C4	118.51 (15)	C17—C16—H16A	110.3
O4—C3—C2	121.07 (16)	O2—C16—H16B	110.3
C4—C3—C2	120.16 (14)	C17—C16—H16B	110.3
O4—C8—H8A	109.5	H16A—C16—H16B	108.6
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
O3—C9—H9A	109.5	H17B—C17—H17C	109.5
O3—C9—H9B	109.5	C14—N2—C13	127.23 (14)
H9A—C9—H9B	109.5	C14—N2—H2N	116.4
O3—C9—H9C	109.5	C13—N2—H2N	116.4
H9A—C9—H9C	109.5	C14—N1—C11	124.02 (14)
H9B—C9—H9C	109.5	C14—N1—H1N	118.0
N2—C13—C1	109.46 (13)	C11—N1—H1N	118.0
N2—C13—C12	109.91 (12)	C4—O5—C7	117.72 (15)
C1—C13—C12	112.61 (13)	C3—O4—C8	117.15 (15)
N2—C13—H13	108.2	C2—O3—C9	116.65 (15)
C1—C13—H13	108.2	C15—O2—C16	117.05 (14)
O5—C4—C5—C6	−178.30 (16)	C13—C12—C11—N1	0.2 (3)
C3—C4—C5—C6	0.0 (3)	C15—C12—C11—C10	2.3 (3)
C4—C5—C6—C1	−0.7 (3)	C13—C12—C11—C10	−178.40 (16)
C5—C6—C1—C2	0.0 (2)	C12—C11—C10—Cl	103.68 (19)
C5—C6—C1—C13	176.89 (15)	N1—C11—C10—Cl	−75.01 (18)
C6—C1—C2—O3	−176.62 (14)	C11—C12—C15—O1	9.9 (3)
C13—C1—C2—O3	6.5 (2)	C13—C12—C15—O1	−169.41 (18)
C6—C1—C2—C3	1.4 (2)	C11—C12—C15—O2	−171.87 (16)
C13—C1—C2—C3	−175.49 (14)	C13—C12—C15—O2	8.8 (2)
O5—C4—C3—O4	5.7 (2)	O6—C14—N2—C13	−173.33 (17)
C5—C4—C3—O4	−172.75 (15)	N1—C14—N2—C13	7.7 (3)
O5—C4—C3—C2	179.86 (15)	C1—C13—N2—C14	112.29 (19)
C5—C4—C3—C2	1.4 (3)	C12—C13—N2—C14	−11.9 (2)
O3—C2—C3—O4	−10.1 (2)	O6—C14—N1—C11	−177.08 (18)
C1—C2—C3—O4	171.86 (15)	N2—C14—N1—C11	1.9 (3)
O3—C2—C3—C4	175.89 (15)	C12—C11—N1—C14	−5.6 (3)
C1—C2—C3—C4	−2.1 (2)	C10—C11—N1—C14	173.14 (17)
C6—C1—C13—N2	−72.80 (18)	C5—C4—O5—C7	−1.3 (3)
C2—C1—C13—N2	104.02 (16)	C3—C4—O5—C7	−179.67 (18)
C6—C1—C13—C12	49.8 (2)	C4—C3—O4—C8	−114.3 (2)
C2—C1—C13—C12	−133.40 (15)	C2—C3—O4—C8	71.6 (2)
N2—C13—C12—C11	7.4 (2)	C3—C2—O3—C9	71.6 (2)
C1—C13—C12—C11	−114.95 (17)	C1—C2—O3—C9	−110.4 (2)
N2—C13—C12—C15	−173.26 (14)	O1—C15—O2—C16	2.5 (3)
C1—C13—C12—C15	64.41 (19)	C12—C15—O2—C16	−175.83 (15)
C15—C12—C11—N1	−179.15 (15)	C17—C16—O2—C15	168.35 (19)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the N1/C11–C13/N2/C14 pyrimidine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6^i	0.86	1.95	2.812 (2)	178
N2—H2N···O4^ii	0.86	2.37	3.160 (2)	153
C17—H17C···Cg^iii	0.96	2.83	3.676 (4)	147
C10—H10A···O1	0.97	2.14	2.864 (3)	131

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