Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

The asymmetric unit of the title compound, C₁₂H₁₄N₂O₄, contains two independent mol­ecules. In one independent mol­ecule, the furanyl fragment is rotationally disordered between two orientations in a 0.625 (6):0.375 (6) ratio. In the crystal, inter­molecular pyrimidine–pyrimidinone N—H...O hydrogen bonds link the mol­ecules into centrosymmetric tetra­mers, which are further associated into ribbons extending in [010] via weak inter­molecular pyrimidine–carboxyl N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.071
• wR factor = 0.237
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
SYMMS01_ALERT_1_B  The cell setting should be one of the following
            *  triclinic
            *  monoclinic
            *  orthorhombic
            *  tetragonal
            *  rhombohedral
            *  trigonal
            *  hexagonal
            *  cubic
            Cell setting given = monoclinic'

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          7
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         13
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.       0.12
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................      10.00 Perc.
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      44.80 Deg.
              O2'  -C3   -C4      1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      35.00 Deg.
              O2   -C3   -C4'     1.555   1.555   1.555
PLAT793_ALERT_4_G The Model has Chirality at C2      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C14     (Verify) ....          S

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

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

---

S1. Comment

Biginelli reaction is a well known multicomponent reaction involving a one-pot cyclocondensation of an aldehyde, β-ketoester and urea/thiourea. It is the most important procedure in the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (Biginelli, 1893). Herewith we report the crystal structure of the title compound, (I), obtained by the three-component reaction of furfuraldehyde, acetoacetate and urea.

In (I) (Fig. 1), the dihydropyrimidinone rings adopt flattened boat conformation. The asymmetric unit contains two independent molecules. In one independent molecule, the furanyl fragment is rotationally disordered in a ratio 0.625 (6):0.375 (6). The bond lengths an angles are normal and comparable to the values observed in similar compounds (Nizam Mohideen et al., 2008; Qing-Fang et al., 2007) The dihedral angles between the furan rings (C3—C6/O2, C15—C18/O6) and the mean planes of the dihydropyrimidinone rings (N1/C1/N2/C9/C8, N3/C13/N4/C21/C20) unit in two independent molecules are 88.79 (4) ° and 86.73 (2)°, respectively, indicating that the furan rings and the dihydropyrimidinone rings are nearly perpendicular.

In the crystal structure, intermolecular N—H···O_pyrimidinone hydrogen bonds (Table 1) link the molecules into centrosymmetric tetramers. Tetramers are further associated into ribbons extended in direction [010] via the weak intermolecular N—H···O_carboxyl hydrogen bonds (Table 1).

Related literature

Biginelli reaction is the most important procedure in the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones, see: Biginelli et al. (1893). For related structures, see: Nizam Mohideen et al. (2008); Qing-Fang et al. (2007).

S2. Experimental

A mixture of ethylacetoacetate (0.5 mol), furfural (0.5 mol) and urea (0.6 mol) was refluxed in 50.0 ml of ethanol for 2.0 hrs. The reaction completion was monitored through thin layer chromatography and the reaction mixture was quenched in ice cold water. The precipitate obtained was filtered, dried and crystallized from methanol to obtain the title compound.

S3. Refinement

All H atoms were placed in geometrically idealized positions (N—H 0.86 and C—H = 0.93–0.97 Å) and treated as riding on their parent atoms, with U_iso(H) = 1.2U-1.5_eq(C, N). Atoms C4, C5, C6, O2 were treated as disordered between two positions, with refined occupancies of 0.375 (6) and 0.625 (6).

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids. Only major components of the disordered atoms are shown.

Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Crystal data

C12H14N2O4	F(000) = 1056
Mr = 250.25	Dx = 1.361 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1720 (14) Å	Cell parameters from 1664 reflections
b = 13.3180 (15) Å	θ = 2.3–22.3°
c = 17.116 (2) Å	µ = 0.10 mm^−1
β = 118.300 (2)°	T = 298 K
V = 2443.0 (5) Å^3	Block, yellow
Z = 8	0.48 × 0.45 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4298 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.952, Tmax = 0.983	k = −14→15
11604 measured reflections	l = −20→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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.237	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.1244P)^2] where P = (Fo^2 + 2Fc^2)/3
4298 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.23 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	Occ. (<1)
N1	0.0677 (3)	0.8975 (2)	0.4632 (2)	0.0478 (9)
H1	0.0351	0.9555	0.4437	0.057*
N2	0.0574 (3)	0.7467 (2)	0.5219 (2)	0.0479 (8)
H2	0.0468	0.7135	0.5609	0.057*
N3	0.8736 (3)	0.6124 (2)	0.7072 (2)	0.0499 (9)
H3	0.8988	0.5511	0.7182	0.060*
N4	0.8981 (3)	0.7698 (2)	0.6635 (2)	0.0497 (8)
H4	0.9196	0.8075	0.6321	0.060*
O1	−0.0199 (2)	0.88634 (18)	0.55364 (19)	0.0574 (8)
O2	0.3239 (6)	0.8613 (5)	0.5879 (5)	0.086 (2)	0.625 (6)
C4'	0.3192 (18)	0.9228 (13)	0.5941 (13)	0.086 (2)	0.375 (6)
H4'	0.2672	0.9425	0.6173	0.103*	0.375 (6)
O3	0.2203 (2)	0.7669 (2)	0.32562 (17)	0.0565 (8)
O4	0.1728 (3)	0.6108 (2)	0.3447 (2)	0.0686 (9)
O5	0.9657 (3)	0.63333 (18)	0.6200 (2)	0.0600 (8)
O6	0.6054 (4)	0.6411 (3)	0.5976 (3)	0.1107 (13)
O7	0.7327 (3)	0.7358 (2)	0.85737 (19)	0.0690 (9)
O8	0.7471 (3)	0.8936 (2)	0.8223 (2)	0.0780 (10)
C1	0.0329 (3)	0.8474 (3)	0.5145 (3)	0.0456 (10)
C2	0.1585 (3)	0.8589 (3)	0.4384 (3)	0.0429 (10)
H2A	0.1438	0.8907	0.3826	0.052*
C3	0.2873 (4)	0.8830 (3)	0.5074 (3)	0.0559 (11)
C4	0.3859 (8)	0.9166 (7)	0.4951 (7)	0.079 (2)	0.625 (6)
H4A	0.3852	0.9349	0.4424	0.094*	0.625 (6)
C5	0.4870 (15)	0.9164 (9)	0.5815 (12)	0.086 (4)	0.625 (6)
H5	0.5680	0.9359	0.5966	0.103*	0.625 (6)
C6	0.448 (2)	0.8828 (11)	0.6403 (17)	0.091 (4)	0.625 (6)
H6	0.4943	0.8764	0.7016	0.109*	0.625 (6)
O2'	0.3875 (9)	0.8450 (8)	0.5162 (7)	0.079 (2)	0.375 (6)
C5'	0.459 (4)	0.924 (2)	0.636 (3)	0.091 (4)	0.375 (6)
H5'	0.5116	0.9619	0.6855	0.109*	0.375 (6)
C6'	0.492 (3)	0.8685 (16)	0.598 (2)	0.086 (4)	0.375 (6)
H6'	0.5725	0.8445	0.6184	0.103*	0.375 (6)
C7	0.1783 (3)	0.6992 (3)	0.3629 (2)	0.0461 (9)
C8	0.1410 (3)	0.7470 (2)	0.4236 (2)	0.0408 (9)
C9	0.0980 (3)	0.6952 (3)	0.4705 (2)	0.0425 (9)
C10	0.0877 (4)	0.5845 (3)	0.4755 (3)	0.0621 (12)
H10A	0.0024	0.5646	0.4395	0.093*
H10B	0.1149	0.5652	0.5359	0.093*
H10C	0.1390	0.5523	0.4542	0.093*
C11	0.2614 (4)	0.7310 (3)	0.2650 (3)	0.0666 (12)
H11A	0.1938	0.6969	0.2155	0.080*
H11B	0.3299	0.6842	0.2946	0.080*
C12	0.3030 (4)	0.8203 (4)	0.2328 (3)	0.0828 (15)
H12A	0.2344	0.8660	0.2037	0.124*
H12B	0.3312	0.7988	0.1918	0.124*
H12C	0.3700	0.8533	0.2823	0.124*
C13	0.9139 (3)	0.6678 (3)	0.6603 (3)	0.0473 (10)
C14	0.7910 (3)	0.6476 (3)	0.7409 (3)	0.0477 (10)
H14	0.8183	0.6161	0.7989	0.057*
C15	0.6605 (4)	0.6159 (3)	0.6829 (3)	0.0588 (12)
C16	0.5810 (5)	0.5651 (4)	0.7005 (4)	0.0925 (17)
H16	0.5969	0.5387	0.7552	0.111*
C17	0.4691 (6)	0.5587 (5)	0.6215 (6)	0.113 (2)
H17	0.3961	0.5281	0.6141	0.136*
C18	0.4851 (6)	0.6031 (6)	0.5604 (6)	0.126 (3)
H18	0.4254	0.6087	0.5011	0.151*
C19	0.7596 (4)	0.8057 (3)	0.8129 (3)	0.0563 (11)
C20	0.8035 (3)	0.7603 (3)	0.7555 (2)	0.0452 (9)
C21	0.8509 (3)	0.8162 (3)	0.7128 (2)	0.0444 (9)
C22	0.8605 (4)	0.9280 (3)	0.7135 (3)	0.0591 (12)
H22A	0.7799	0.9562	0.6756	0.089*
H22B	0.9178	0.9474	0.6924	0.089*
H22C	0.8901	0.9524	0.7729	0.089*
C23	0.6852 (5)	0.7708 (4)	0.9158 (3)	0.0831 (15)
H23A	0.6148	0.8154	0.8839	0.100*
H23B	0.7496	0.8074	0.9654	0.100*
C24	0.6464 (5)	0.6833 (5)	0.9477 (4)	0.110 (2)
H24A	0.5780	0.6508	0.8987	0.165*
H24B	0.6206	0.7041	0.9903	0.165*
H24C	0.7150	0.6373	0.9753	0.165*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.047 (2)	0.0349 (18)	0.072 (2)	0.0098 (14)	0.037 (2)	0.0113 (15)
N2	0.058 (2)	0.0331 (19)	0.065 (2)	0.0014 (15)	0.0384 (19)	0.0075 (14)
N3	0.053 (2)	0.0363 (18)	0.074 (2)	0.0055 (14)	0.041 (2)	0.0085 (15)
N4	0.056 (2)	0.0355 (19)	0.068 (2)	0.0017 (15)	0.038 (2)	0.0059 (15)
O1	0.0673 (18)	0.0414 (16)	0.088 (2)	0.0067 (13)	0.0563 (18)	0.0067 (14)
O2	0.068 (3)	0.082 (5)	0.086 (4)	−0.010 (4)	0.019 (3)	0.002 (5)
C4'	0.068 (3)	0.082 (5)	0.086 (4)	−0.010 (4)	0.019 (3)	0.002 (5)
O3	0.0712 (19)	0.0502 (17)	0.0654 (18)	−0.0097 (13)	0.0466 (17)	−0.0051 (13)
O4	0.089 (2)	0.0406 (18)	0.097 (2)	−0.0088 (15)	0.061 (2)	−0.0133 (15)
O5	0.0728 (19)	0.0429 (17)	0.091 (2)	0.0006 (14)	0.0604 (19)	0.0001 (14)
O6	0.077 (3)	0.116 (3)	0.105 (3)	−0.018 (2)	0.015 (3)	0.006 (2)
O7	0.083 (2)	0.070 (2)	0.076 (2)	−0.0077 (16)	0.055 (2)	−0.0078 (16)
O8	0.100 (3)	0.052 (2)	0.105 (3)	−0.0020 (17)	0.066 (2)	−0.0134 (17)
C1	0.041 (2)	0.041 (2)	0.064 (3)	0.0000 (17)	0.032 (2)	0.0031 (19)
C2	0.044 (2)	0.037 (2)	0.055 (2)	−0.0022 (17)	0.030 (2)	0.0033 (17)
C3	0.049 (3)	0.041 (2)	0.074 (3)	−0.001 (2)	0.027 (3)	−0.004 (2)
C4	0.058 (3)	0.084 (6)	0.090 (5)	−0.003 (5)	0.031 (4)	−0.011 (5)
C5	0.052 (4)	0.090 (11)	0.100 (9)	−0.006 (8)	0.024 (6)	−0.015 (9)
C6	0.068 (6)	0.081 (14)	0.095 (6)	−0.007 (10)	0.016 (5)	−0.005 (11)
O2'	0.058 (3)	0.084 (6)	0.090 (5)	−0.003 (5)	0.031 (4)	−0.011 (5)
C5'	0.068 (6)	0.081 (14)	0.095 (6)	−0.007 (10)	0.016 (5)	−0.005 (11)
C6'	0.052 (4)	0.090 (11)	0.100 (9)	−0.006 (8)	0.024 (6)	−0.015 (9)
C7	0.043 (2)	0.045 (3)	0.053 (2)	−0.0040 (18)	0.025 (2)	−0.0023 (19)
C8	0.040 (2)	0.033 (2)	0.053 (2)	−0.0022 (16)	0.025 (2)	−0.0002 (16)
C9	0.041 (2)	0.037 (2)	0.057 (2)	−0.0012 (16)	0.029 (2)	−0.0004 (17)
C10	0.079 (3)	0.035 (2)	0.091 (3)	−0.009 (2)	0.055 (3)	−0.005 (2)
C11	0.075 (3)	0.070 (3)	0.071 (3)	−0.005 (2)	0.048 (3)	−0.004 (2)
C12	0.086 (4)	0.094 (4)	0.088 (4)	−0.023 (3)	0.057 (3)	−0.005 (3)
C13	0.044 (2)	0.039 (2)	0.064 (3)	0.0000 (17)	0.029 (2)	0.0050 (18)
C14	0.049 (2)	0.044 (2)	0.059 (3)	0.0016 (18)	0.033 (2)	0.0051 (18)
C15	0.054 (3)	0.049 (3)	0.081 (4)	−0.005 (2)	0.038 (3)	−0.007 (2)
C16	0.077 (4)	0.106 (5)	0.107 (5)	−0.027 (3)	0.054 (4)	−0.013 (3)
C17	0.068 (4)	0.110 (6)	0.161 (7)	−0.021 (4)	0.054 (5)	−0.043 (5)
C18	0.069 (5)	0.127 (6)	0.123 (7)	−0.007 (4)	−0.002 (5)	−0.019 (5)
C19	0.046 (3)	0.059 (3)	0.066 (3)	−0.005 (2)	0.028 (2)	−0.003 (2)
C20	0.038 (2)	0.041 (2)	0.057 (2)	0.0002 (17)	0.022 (2)	−0.0021 (18)
C21	0.038 (2)	0.037 (2)	0.058 (3)	−0.0007 (16)	0.022 (2)	−0.0011 (17)
C22	0.063 (3)	0.039 (2)	0.080 (3)	−0.0017 (19)	0.037 (3)	0.000 (2)
C23	0.103 (4)	0.090 (4)	0.082 (3)	−0.009 (3)	0.065 (3)	−0.013 (3)
C24	0.122 (5)	0.140 (6)	0.106 (4)	−0.030 (4)	0.084 (4)	−0.017 (4)

Geometric parameters (Å, º)

N1—C1	1.322 (4)	O2'—C6'	1.41 (3)
N1—C2	1.454 (4)	C5'—C6'	1.17 (6)
N1—H1	0.8600	C5'—H5'	0.9300
N2—C1	1.365 (4)	C6'—H6'	0.9300
N2—C9	1.379 (4)	C7—C8	1.462 (5)
N2—H2	0.8600	C8—C9	1.339 (5)
N3—C13	1.343 (5)	C9—C10	1.485 (5)
N3—C14	1.454 (4)	C10—H10A	0.9600
N3—H3	0.8600	C10—H10B	0.9600
N4—C21	1.373 (4)	C10—H10C	0.9600
N4—C13	1.377 (4)	C11—C12	1.496 (6)
N4—H4	0.8600	C11—H11A	0.9700
O1—C1	1.241 (4)	C11—H11B	0.9700
O2—C3	1.263 (8)	C12—H12A	0.9600
O2—C6	1.37 (2)	C12—H12B	0.9600
C4'—C3	1.44 (2)	C12—H12C	0.9600
C4'—C5'	1.50 (5)	C14—C15	1.480 (5)
C4'—H4'	0.9300	C14—C20	1.518 (5)
O3—C7	1.338 (4)	C14—H14	0.9800
O3—C11	1.430 (4)	C15—C16	1.327 (6)
O4—C7	1.211 (4)	C16—C17	1.395 (8)
O5—C13	1.224 (4)	C16—H16	0.9300
O6—C15	1.330 (6)	C17—C18	1.294 (9)
O6—C18	1.387 (7)	C17—H17	0.9300
O7—C19	1.337 (5)	C18—H18	0.9300
O7—C23	1.449 (5)	C19—C20	1.455 (5)
O8—C19	1.201 (4)	C20—C21	1.349 (5)
C2—C3	1.484 (5)	C21—C22	1.494 (5)
C2—C8	1.509 (5)	C22—H22A	0.9600
C2—H2A	0.9800	C22—H22B	0.9600
C3—O2'	1.262 (10)	C22—H22C	0.9600
C3—C4	1.387 (10)	C23—C24	1.458 (7)
C4—C5	1.405 (18)	C23—H23A	0.9700
C4—H4A	0.9300	C23—H23B	0.9700
C5—C6	1.38 (3)	C24—H24A	0.9600
C5—H5	0.9300	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C1—N1—C2	122.9 (3)	H10A—C10—H10B	109.5
C1—N1—H1	118.6	C9—C10—H10C	109.5
C2—N1—H1	118.6	H10A—C10—H10C	109.5
C1—N2—C9	123.9 (3)	H10B—C10—H10C	109.5
C1—N2—H2	118.0	O3—C11—C12	107.3 (4)
C9—N2—H2	118.0	O3—C11—H11A	110.3
C13—N3—C14	125.2 (3)	C12—C11—H11A	110.3
C13—N3—H3	117.4	O3—C11—H11B	110.3
C14—N3—H3	117.4	C12—C11—H11B	110.3
C21—N4—C13	125.1 (3)	H11A—C11—H11B	108.5
C21—N4—H4	117.5	C11—C12—H12A	109.5
C13—N4—H4	117.5	C11—C12—H12B	109.5
C3—O2—C6	112.1 (12)	H12A—C12—H12B	109.5
C3—C4'—C5'	101 (2)	C11—C12—H12C	109.5
C3—C4'—H4'	129.5	H12A—C12—H12C	109.5
C5'—C4'—H4'	129.5	H12B—C12—H12C	109.5
C7—O3—C11	117.6 (3)	O5—C13—N3	124.2 (4)
C15—O6—C18	106.5 (5)	O5—C13—N4	120.8 (3)
C19—O7—C23	117.0 (4)	N3—C13—N4	115.0 (4)
O1—C1—N1	123.9 (4)	N3—C14—C15	111.5 (3)
O1—C1—N2	120.4 (3)	N3—C14—C20	110.5 (3)
N1—C1—N2	115.6 (3)	C15—C14—C20	112.6 (3)
N1—C2—C3	110.7 (3)	N3—C14—H14	107.3
N1—C2—C8	109.4 (3)	C15—C14—H14	107.3
C3—C2—C8	111.0 (3)	C20—C14—H14	107.3
N1—C2—H2A	108.5	C16—C15—O6	109.7 (5)
C3—C2—H2A	108.5	C16—C15—C14	131.2 (5)
C8—C2—H2A	108.5	O6—C15—C14	119.1 (4)
O2'—C3—O2	87.6 (7)	C15—C16—C17	107.0 (6)
O2'—C3—C4	44.8 (5)	C15—C16—H16	126.5
O2—C3—C4	110.9 (6)	C17—C16—H16	126.5
O2'—C3—C4'	104.6 (10)	C18—C17—C16	107.7 (6)
O2—C3—C4'	35.0 (6)	C18—C17—H17	126.2
C4—C3—C4'	101.9 (9)	C16—C17—H17	126.2
O2'—C3—C2	127.2 (6)	C17—C18—O6	109.1 (7)
O2—C3—C2	120.8 (5)	C17—C18—H18	125.4
C4—C3—C2	127.8 (6)	O6—C18—H18	125.4
C4'—C3—C2	124.4 (9)	O8—C19—O7	121.5 (4)
C3—C4—C5	103.2 (10)	O8—C19—C20	127.3 (4)
C3—C4—H4A	128.4	O7—C19—C20	111.3 (4)
C5—C4—H4A	128.4	C21—C20—C19	121.7 (4)
C6—C5—C4	109.5 (15)	C21—C20—C14	119.5 (3)
C6—C5—H5	125.2	C19—C20—C14	118.8 (3)
C4—C5—H5	125.2	C20—C21—N4	119.7 (3)
O2—C6—C5	104.1 (18)	C20—C21—C22	126.7 (3)
O2—C6—H6	127.9	N4—C21—C22	113.5 (3)
C5—C6—H6	127.9	C21—C22—H22A	109.5
C3—O2'—C6'	113.1 (15)	C21—C22—H22B	109.5
C6'—C5'—C4'	110 (3)	H22A—C22—H22B	109.5
C6'—C5'—H5'	125.2	C21—C22—H22C	109.5
C4'—C5'—H5'	125.2	H22A—C22—H22C	109.5
C5'—C6'—O2'	108 (3)	H22B—C22—H22C	109.5
C5'—C6'—H6'	125.9	O7—C23—C24	107.9 (4)
O2'—C6'—H6'	125.9	O7—C23—H23A	110.1
O4—C7—O3	121.3 (3)	C24—C23—H23A	110.1
O4—C7—C8	127.4 (3)	O7—C23—H23B	110.1
O3—C7—C8	111.2 (3)	C24—C23—H23B	110.1
C9—C8—C7	122.9 (3)	H23A—C23—H23B	108.4
C9—C8—C2	118.2 (3)	C23—C24—H24A	109.5
C7—C8—C2	118.9 (3)	C23—C24—H24B	109.5
C8—C9—N2	119.1 (3)	H24A—C24—H24B	109.5
C8—C9—C10	127.9 (3)	C23—C24—H24C	109.5
N2—C9—C10	113.0 (3)	H24A—C24—H24C	109.5
C9—C10—H10A	109.5	H24B—C24—H24C	109.5
C9—C10—H10B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.12	2.924 (4)	156
N2—H2···O5^ii	0.86	2.02	2.851 (4)	162
N3—H3···O4^iii	0.86	2.38	3.077 (4)	138
N4—H4···O1^iv	0.86	2.10	2.952 (4)	174

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