6,8-Dimethyl-4-phenyl-2-tosylpyrrolo[3,4-c]pyrano[6,5-b]pyrimidine-7,9-dione

In the title compound, C₂₄H₂₅N₃O₅S, both the pyrrolidine and dihydro­pyran rings adopt envelope conformations, and are cis-fused. The tosyl group is equatorially attached to the pyrrolidine ring. The glide-related mol­ecules are linked by C—H...O hydrogen bonds, forming a C(6) chain along the c axis, and adjacent chains are cross-linked via C—H...O and C—H...π inter­actions, forming a two-dimensional network parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.138
• Data-to-parameter ratio = 31.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5     ..  C15     ..       2.94 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          S

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

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Pyranopyrimidine derivatives exhibit antiviral (Shamroukh et al., 2007) and antimicrobial activities (Bedair et al., 2000, 2001; Eid et al., 2004; Abdel Fattah et al., 2004). We report here the crystal structure of the title compound, a pyranopyrimidine derivative.

In the title molecule, all geometric parameters show normal values (Allen et al., 1987). The significant widening of the O1—S1—O2 [120.49 (6)°] angle from the ideal tetrahedral value is the result of the non-bonding interactions between the short S═O bonds. The sum of the angles around the pyrrolidine N atom (348.3 °) indicates sp³-hybridization.

The pyrrolidine ring has an envelope conformation, with C1, the envelope flap, lying 0.573 (2) Å from the plane defined by C2, C3, C4 and N1 atoms. The Cremer and Pople puckering parameters (Cremer & Pople, 1975) are q = 0.374 (1) Å and φ = 219.9 (2)°; the asymmetry parameter (Duax et al., 1976) ΔC_s[C1] is 1.6 (1)°. The tosyl group is equatorially attached to the pyrrolidine ring.

The dihydropyran ring (O3/C5/C2/C3/C7/C6) also adopts an enveope conformation, with atom C5 deviating from the O3/C2/C3/C7/C6 plane by 0.655 (2) Å; the lowest asymmetry parameter is ΔC_s[C5] = 7.7 (1)°, and the puckering parameters Q, θ and φ are 0.480 (1) Å, 123.4 (1)° and 252.4 (2)°, respectively. The phenyl ring is equatorially attached to the dihydropyran ring.

The C2—C4/N1 plane forms dihedral angles of 55.26 (5) and 84.93 (4)°, respectively, with the O3/C2/C3/C7/C6 and C8—C13 planes. The O3/C2/C3/C7/C6 plane forms dihedral angles of 7.04 (6) and 74.98 (4)°, respectively, with the pyrimidine (C7/C6/N2/C15/N3/C16) and pheny (C17—C22) planes. Atoms O4, O5, C23 and C24 deviate from the pyrimidine ring plane by 0.101 (2), 0.009 (2), 0.149 (2) and -0.072 (2) Å, respectively.

The glide-related molecules are linked to form a C(6) chain along the c axis by C10—H10···O1ⁱ hydrogen bonds. The molecules of the adjacent chains are cross-linked via C18—H18···O4ⁱⁱ and C20—H20···Cg1ⁱⁱⁱ (Cg1 is the C8—C13 ring centroid) interactions, forming a two-dimensional network parallel to the bc plane (Fig. 2). In the network, pairs of C18—H18···O4 hydrogen bonds generate R²₂(18) ring motif.

Related literature

For biological activities of pyranopyrimidine derivatives, see: Abdel Fattah et al. (2004); Bedair et al. (2000, 2001); Eid et al. (2004); Shamroukh et al. (2007). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976).

S2. Experimental

To a solution of 1,3-dimethyl-pyrimidine-2,4,6-trione (1 mmol) in dry toluene (20 ml), the corresponding 2-(N-cinnamyl-N-tosylamino)acetaldehyde (1 mmol) and catalytic amount of the base ethylenediamine-N,N'-diacetate (EDDA) were added and the reaction mixture was refluxed for 12 h. After completion of reaction, the solvent was evaporated under reduced pressure and the crude product was chromatographed using a hexane-ethyl acetate (8:2 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.

S3. Refinement

H atoms were positioned geometrically and constrained to ride on their parent atoms [for methyl H atoms, C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C), for aromatic C—H = 0.93 Å and methine C—H = 0.98 Å, and U_iso(H) = 1.2U_eq(C)]. A rotating group model was used for the methyl groups attached to aromatic rings.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures

Fig. 1. The molecular structure of the title compound, showing 80% probability displacement ellipsoids and the atomic numbering.

Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis. Dashed and dotted lines indicate C—H···O and C—H···π interactions, respectively. For the sake of clarity, H atoms not involved in the interactions have been omitted. Atoms labelled with the suffixes A, B and C are generated by the symmetry operations (x, 3/2 - y, 1/2 + z), (1 - x, 1 - y, -z) and (x, 1/2 - y, 1/2 + z), respectively.

6,8-Dimethyl-4-phenyl-2-tosylpyrrolo[3,4-c]pyrano[6,5-b] pyrimidine-7,9-dione

Crystal data

C24H25N3O5S	F(000) = 984
Mr = 467.53	Dx = 1.420 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8951 reflections
a = 16.2810 (2) Å	θ = 2.5–34.9°
b = 8.4063 (1) Å	µ = 0.19 mm^−1
c = 16.0030 (2) Å	T = 100 K
β = 93.400 (1)°	Block, colourless
V = 2186.36 (5) Å^3	0.42 × 0.19 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	9583 independent reflections
Radiation source: fine-focus sealed tube	7316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 1.3°
ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→13
Tmin = 0.924, Tmax = 0.967	l = −25→25
40900 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0688P)^2 + 0.5404P] where P = (Fo^2 + 2Fc^2)/3
9583 reflections	(Δ/σ)max = 0.001
301 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

Special details

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
S1	0.832515 (17)	0.76601 (4)	0.138778 (16)	0.01501 (7)
O1	0.88386 (6)	0.74316 (12)	0.07011 (5)	0.02264 (19)
O2	0.78444 (6)	0.90866 (11)	0.14475 (5)	0.01949 (17)
O3	0.59556 (5)	0.28693 (11)	0.03949 (5)	0.01591 (15)
O4	0.33422 (5)	0.33580 (11)	0.12096 (6)	0.01933 (17)
O5	0.53895 (6)	0.56887 (12)	0.28523 (6)	0.02265 (19)
N1	0.76755 (6)	0.61871 (12)	0.13603 (6)	0.01536 (17)
N2	0.46544 (6)	0.31994 (12)	0.07934 (6)	0.01493 (17)
N3	0.43589 (6)	0.46118 (12)	0.20054 (6)	0.01647 (18)
C1	0.79886 (7)	0.45520 (14)	0.12820 (7)	0.0164 (2)
H1A	0.8357	0.4266	0.1757	0.020*
H1B	0.8272	0.4417	0.0770	0.020*
C2	0.71959 (7)	0.35804 (14)	0.12631 (7)	0.01415 (19)
H2	0.7309	0.2489	0.1452	0.017*
C3	0.66682 (7)	0.44598 (13)	0.18863 (7)	0.01388 (18)
H3	0.6778	0.3984	0.2441	0.017*
C4	0.69846 (7)	0.61972 (14)	0.19205 (7)	0.01552 (19)
H4A	0.6558	0.6932	0.1720	0.019*
H4B	0.7172	0.6491	0.2486	0.019*
C5	0.67726 (6)	0.35828 (13)	0.03792 (7)	0.01347 (18)
H5	0.6717	0.4683	0.0182	0.016*
C6	0.54775 (7)	0.34867 (13)	0.09687 (7)	0.01378 (18)
C7	0.57664 (7)	0.43028 (13)	0.16549 (7)	0.01420 (19)
C8	0.89543 (7)	0.74930 (13)	0.23173 (7)	0.01382 (19)
C9	0.86994 (7)	0.81965 (14)	0.30474 (7)	0.01478 (19)
H9	0.8205	0.8753	0.3042	0.018*
C10	0.91903 (7)	0.80569 (15)	0.37815 (7)	0.0167 (2)
H10	0.9023	0.8528	0.4269	0.020*
C11	0.99333 (7)	0.72184 (15)	0.38006 (7)	0.0172 (2)
C12	1.01751 (7)	0.65221 (15)	0.30632 (8)	0.0193 (2)
H12	1.0667	0.5957	0.3069	0.023*
C13	0.96929 (7)	0.66587 (15)	0.23177 (7)	0.0177 (2)
H13	0.9862	0.6199	0.1828	0.021*
C14	1.04485 (8)	0.70532 (19)	0.46063 (8)	0.0254 (3)
H14A	1.0955	0.6527	0.4501	0.038*
H14B	1.0155	0.6438	0.4996	0.038*
H14C	1.0565	0.8089	0.4837	0.038*
C15	0.40695 (7)	0.36841 (13)	0.13370 (7)	0.01505 (19)
C16	0.51885 (7)	0.49219 (14)	0.22172 (7)	0.0161 (2)
C17	0.72352 (7)	0.26413 (13)	−0.02389 (7)	0.01317 (18)
C18	0.76919 (7)	0.34268 (14)	−0.08228 (7)	0.0167 (2)
H18	0.7678	0.4531	−0.0856	0.020*
C19	0.81689 (8)	0.25623 (15)	−0.13557 (7)	0.0184 (2)
H19	0.8474	0.3090	−0.1743	0.022*
C20	0.81894 (7)	0.09128 (15)	−0.13105 (7)	0.0181 (2)
H20	0.8515	0.0338	−0.1662	0.022*
C21	0.77236 (8)	0.01197 (15)	−0.07405 (7)	0.0184 (2)
H21	0.7727	−0.0986	−0.0719	0.022*
C22	0.72519 (7)	0.09827 (14)	−0.02033 (7)	0.0163 (2)
H22	0.6946	0.0451	0.0182	0.020*
C23	0.43769 (8)	0.21169 (17)	0.01139 (8)	0.0220 (2)
H23A	0.4714	0.2259	−0.0352	0.033*
H23B	0.3814	0.2346	−0.0057	0.033*
H23C	0.4421	0.1037	0.0307	0.033*
C24	0.37563 (7)	0.52532 (16)	0.25595 (8)	0.0217 (2)
H24A	0.3229	0.4778	0.2425	0.033*
H24B	0.3717	0.6385	0.2487	0.033*
H24C	0.3927	0.5018	0.3130	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01520 (12)	0.01894 (13)	0.01099 (11)	−0.00379 (10)	0.00169 (8)	0.00011 (9)
O1	0.0219 (4)	0.0333 (5)	0.0132 (4)	−0.0083 (4)	0.0058 (3)	−0.0025 (3)
O2	0.0211 (4)	0.0187 (4)	0.0183 (4)	−0.0010 (3)	−0.0017 (3)	0.0041 (3)
O3	0.0121 (3)	0.0194 (4)	0.0163 (4)	−0.0016 (3)	0.0014 (3)	−0.0051 (3)
O4	0.0121 (3)	0.0194 (4)	0.0263 (4)	0.0000 (3)	−0.0002 (3)	−0.0009 (3)
O5	0.0180 (4)	0.0287 (5)	0.0215 (4)	−0.0032 (4)	0.0029 (3)	−0.0104 (3)
N1	0.0138 (4)	0.0168 (4)	0.0157 (4)	−0.0024 (3)	0.0028 (3)	−0.0028 (3)
N2	0.0117 (4)	0.0159 (4)	0.0170 (4)	−0.0006 (3)	−0.0004 (3)	−0.0023 (3)
N3	0.0126 (4)	0.0167 (4)	0.0204 (4)	−0.0006 (3)	0.0037 (3)	−0.0042 (3)
C1	0.0125 (4)	0.0192 (5)	0.0173 (5)	−0.0010 (4)	0.0010 (4)	−0.0051 (4)
C2	0.0129 (4)	0.0154 (5)	0.0140 (4)	0.0004 (4)	0.0003 (3)	−0.0011 (3)
C3	0.0127 (4)	0.0165 (5)	0.0124 (4)	−0.0010 (4)	0.0010 (3)	−0.0018 (3)
C4	0.0129 (4)	0.0164 (5)	0.0175 (5)	−0.0023 (4)	0.0031 (4)	−0.0032 (4)
C5	0.0120 (4)	0.0145 (4)	0.0140 (4)	−0.0006 (4)	0.0012 (3)	−0.0012 (3)
C6	0.0122 (4)	0.0140 (4)	0.0152 (4)	−0.0003 (4)	0.0012 (3)	−0.0007 (3)
C7	0.0122 (4)	0.0151 (5)	0.0154 (4)	−0.0012 (4)	0.0011 (3)	−0.0020 (4)
C8	0.0128 (4)	0.0153 (5)	0.0135 (4)	−0.0026 (4)	0.0022 (3)	−0.0007 (3)
C9	0.0146 (4)	0.0163 (5)	0.0136 (4)	0.0008 (4)	0.0025 (3)	−0.0005 (4)
C10	0.0170 (5)	0.0205 (5)	0.0128 (4)	−0.0003 (4)	0.0018 (4)	−0.0004 (4)
C11	0.0144 (4)	0.0203 (5)	0.0169 (5)	−0.0029 (4)	0.0003 (4)	0.0035 (4)
C12	0.0144 (5)	0.0193 (5)	0.0244 (5)	0.0015 (4)	0.0018 (4)	0.0006 (4)
C13	0.0149 (4)	0.0200 (5)	0.0187 (5)	−0.0004 (4)	0.0036 (4)	−0.0043 (4)
C14	0.0166 (5)	0.0388 (8)	0.0204 (6)	−0.0009 (5)	−0.0026 (4)	0.0075 (5)
C15	0.0130 (4)	0.0124 (4)	0.0197 (5)	0.0010 (4)	0.0013 (4)	0.0002 (4)
C16	0.0142 (4)	0.0159 (5)	0.0185 (5)	−0.0015 (4)	0.0024 (4)	−0.0026 (4)
C17	0.0131 (4)	0.0141 (4)	0.0122 (4)	0.0004 (4)	−0.0002 (3)	−0.0010 (3)
C18	0.0187 (5)	0.0155 (5)	0.0161 (5)	0.0011 (4)	0.0028 (4)	0.0012 (4)
C19	0.0190 (5)	0.0212 (5)	0.0154 (5)	0.0019 (4)	0.0043 (4)	0.0011 (4)
C20	0.0191 (5)	0.0205 (5)	0.0146 (5)	0.0031 (4)	0.0002 (4)	−0.0043 (4)
C21	0.0211 (5)	0.0155 (5)	0.0185 (5)	0.0010 (4)	0.0001 (4)	−0.0033 (4)
C22	0.0179 (5)	0.0146 (5)	0.0163 (5)	−0.0007 (4)	0.0011 (4)	−0.0009 (4)
C23	0.0158 (5)	0.0243 (6)	0.0252 (6)	−0.0011 (4)	−0.0029 (4)	−0.0103 (5)
C24	0.0157 (5)	0.0225 (6)	0.0275 (6)	−0.0003 (4)	0.0066 (4)	−0.0067 (5)

Geometric parameters (Å, º)

S1—O1	1.4325 (9)	C8—C13	1.3920 (16)
S1—O2	1.4383 (10)	C8—C9	1.3944 (15)
S1—N1	1.6274 (10)	C9—C10	1.3862 (16)
S1—C8	1.7610 (11)	C9—H9	0.93
O3—C6	1.3430 (13)	C10—C11	1.3988 (17)
O3—C5	1.4606 (13)	C10—H10	0.93
O4—C15	1.2208 (13)	C11—C12	1.3947 (18)
O5—C16	1.2312 (14)	C11—C14	1.5023 (17)
N1—C1	1.4740 (15)	C12—C13	1.3935 (17)
N1—C4	1.4793 (14)	C12—H12	0.93
N2—C6	1.3741 (14)	C13—H13	0.93
N2—C15	1.3883 (15)	C14—H14A	0.96
N2—C23	1.4685 (15)	C14—H14B	0.96
N3—C15	1.3837 (15)	C14—H14C	0.96
N3—C16	1.3975 (15)	C17—C18	1.3945 (15)
N3—C24	1.4637 (15)	C17—C22	1.3956 (16)
C1—C2	1.5262 (16)	C18—C19	1.3918 (16)
C1—H1A	0.97	C18—H18	0.93
C1—H1B	0.97	C19—C20	1.3888 (18)
C2—C5	1.5362 (15)	C19—H19	0.93
C2—C3	1.5430 (15)	C20—C21	1.3907 (17)
C2—H2	0.98	C20—H20	0.93
C3—C7	1.4985 (15)	C21—C22	1.3904 (16)
C3—C4	1.5486 (16)	C21—H21	0.93
C3—H3	0.98	C22—H22	0.93
C4—H4A	0.97	C23—H23A	0.96
C4—H4B	0.97	C23—H23B	0.96
C5—C17	1.5035 (15)	C23—H23C	0.96
C5—H5	0.98	C24—H24A	0.96
C6—C7	1.3552 (15)	C24—H24B	0.96
C7—C16	1.4375 (15)	C24—H24C	0.96
O1—S1—O2	120.49 (6)	C10—C9—H9	120.4
O1—S1—N1	106.57 (5)	C8—C9—H9	120.4
O2—S1—N1	106.31 (5)	C9—C10—C11	121.04 (11)
O1—S1—C8	107.50 (5)	C9—C10—H10	119.5
O2—S1—C8	107.58 (5)	C11—C10—H10	119.5
N1—S1—C8	107.86 (5)	C12—C11—C10	118.69 (11)
C6—O3—C5	114.73 (8)	C12—C11—C14	121.07 (11)
C1—N1—C4	109.64 (9)	C10—C11—C14	120.23 (11)
C1—N1—S1	118.97 (8)	C13—C12—C11	121.12 (11)
C4—N1—S1	119.71 (8)	C13—C12—H12	119.4
C6—N2—C15	121.15 (9)	C11—C12—H12	119.4
C6—N2—C23	120.90 (9)	C8—C13—C12	118.99 (11)
C15—N2—C23	116.98 (9)	C8—C13—H13	120.5
C15—N3—C16	124.92 (9)	C12—C13—H13	120.5
C15—N3—C24	117.79 (9)	C11—C14—H14A	109.5
C16—N3—C24	117.21 (10)	C11—C14—H14B	109.5
N1—C1—C2	101.79 (9)	H14A—C14—H14B	109.5
N1—C1—H1A	111.4	C11—C14—H14C	109.5
C2—C1—H1A	111.4	H14A—C14—H14C	109.5
N1—C1—H1B	111.4	H14B—C14—H14C	109.5
C2—C1—H1B	111.4	O4—C15—N3	122.55 (10)
H1A—C1—H1B	109.3	O4—C15—N2	121.59 (10)
C1—C2—C5	110.50 (9)	N3—C15—N2	115.79 (9)
C1—C2—C3	103.50 (9)	O5—C16—N3	120.23 (10)
C5—C2—C3	110.97 (9)	O5—C16—C7	123.68 (10)
C1—C2—H2	110.6	N3—C16—C7	116.09 (10)
C5—C2—H2	110.6	C18—C17—C22	119.37 (10)
C3—C2—H2	110.6	C18—C17—C5	119.96 (10)
C7—C3—C2	111.90 (9)	C22—C17—C5	120.56 (10)
C7—C3—C4	114.26 (9)	C19—C18—C17	120.16 (11)
C2—C3—C4	106.13 (9)	C19—C18—H18	119.9
C7—C3—H3	108.1	C17—C18—H18	119.9
C2—C3—H3	108.1	C20—C19—C18	120.13 (11)
C4—C3—H3	108.1	C20—C19—H19	119.9
N1—C4—C3	103.68 (9)	C18—C19—H19	119.9
N1—C4—H4A	111.0	C19—C20—C21	120.03 (11)
C3—C4—H4A	111.0	C19—C20—H20	120.0
N1—C4—H4B	111.0	C21—C20—H20	120.0
C3—C4—H4B	111.0	C22—C21—C20	119.87 (11)
H4A—C4—H4B	109.0	C22—C21—H21	120.1
O3—C5—C17	106.69 (9)	C20—C21—H21	120.1
O3—C5—C2	110.06 (9)	C21—C22—C17	120.41 (11)
C17—C5—C2	112.97 (9)	C21—C22—H22	119.8
O3—C5—H5	109.0	C17—C22—H22	119.8
C17—C5—H5	109.0	N2—C23—H23A	109.5
C2—C5—H5	109.0	N2—C23—H23B	109.5
O3—C6—C7	124.21 (10)	H23A—C23—H23B	109.5
O3—C6—N2	112.98 (9)	N2—C23—H23C	109.5
C7—C6—N2	122.81 (10)	H23A—C23—H23C	109.5
C6—C7—C16	118.81 (10)	H23B—C23—H23C	109.5
C6—C7—C3	122.19 (10)	N3—C24—H24A	109.5
C16—C7—C3	118.78 (9)	N3—C24—H24B	109.5
C13—C8—C9	120.89 (10)	H24A—C24—H24B	109.5
C13—C8—S1	119.98 (8)	N3—C24—H24C	109.5
C9—C8—S1	119.13 (8)	H24A—C24—H24C	109.5
C10—C9—C8	119.26 (10)	H24B—C24—H24C	109.5
O1—S1—N1—C1	49.11 (10)	O1—S1—C8—C9	157.46 (9)
O2—S1—N1—C1	178.80 (8)	O2—S1—C8—C9	26.32 (11)
C8—S1—N1—C1	−66.07 (9)	N1—S1—C8—C9	−87.98 (10)
O1—S1—N1—C4	−171.57 (9)	C13—C8—C9—C10	−0.09 (17)
O2—S1—N1—C4	−41.89 (10)	S1—C8—C9—C10	179.52 (9)
C8—S1—N1—C4	73.25 (10)	C8—C9—C10—C11	−0.24 (18)
C4—N1—C1—C2	38.03 (11)	C9—C10—C11—C12	0.12 (18)
S1—N1—C1—C2	−178.92 (7)	C9—C10—C11—C14	−178.78 (12)
N1—C1—C2—C5	81.66 (10)	C10—C11—C12—C13	0.33 (18)
N1—C1—C2—C3	−37.21 (10)	C14—C11—C12—C13	179.23 (12)
C1—C2—C3—C7	149.83 (9)	C9—C8—C13—C12	0.53 (17)
C5—C2—C3—C7	31.29 (13)	S1—C8—C13—C12	−179.07 (9)
C1—C2—C3—C4	24.58 (11)	C11—C12—C13—C8	−0.65 (18)
C5—C2—C3—C4	−93.96 (10)	C16—N3—C15—O4	174.90 (11)
C1—N1—C4—C3	−22.41 (11)	C24—N3—C15—O4	−1.82 (17)
S1—N1—C4—C3	−165.14 (8)	C16—N3—C15—N2	−7.87 (17)
C7—C3—C4—N1	−126.07 (9)	C24—N3—C15—N2	175.41 (10)
C2—C3—C4—N1	−2.28 (11)	C6—N2—C15—O4	−175.92 (11)
C6—O3—C5—C17	174.84 (9)	C23—N2—C15—O4	−7.14 (17)
C6—O3—C5—C2	51.94 (12)	C6—N2—C15—N3	6.82 (16)
C1—C2—C5—O3	−171.08 (9)	C23—N2—C15—N3	175.60 (11)
C3—C2—C5—O3	−56.85 (12)	C15—N3—C16—O5	−175.86 (11)
C1—C2—C5—C17	69.79 (12)	C24—N3—C16—O5	0.88 (17)
C3—C2—C5—C17	−175.99 (9)	C15—N3—C16—C7	4.33 (17)
C5—O3—C6—C7	−20.84 (16)	C24—N3—C16—C7	−178.94 (11)
C5—O3—C6—N2	159.53 (9)	C6—C7—C16—O5	−179.37 (12)
C15—N2—C6—O3	177.01 (10)	C3—C7—C16—O5	5.85 (18)
C23—N2—C6—O3	8.66 (15)	C6—C7—C16—N3	0.43 (16)
C15—N2—C6—C7	−2.63 (17)	C3—C7—C16—N3	−174.34 (10)
C23—N2—C6—C7	−170.98 (11)	O3—C5—C17—C18	134.80 (10)
O3—C6—C7—C16	179.22 (11)	C2—C5—C17—C18	−104.13 (12)
N2—C6—C7—C16	−1.18 (17)	O3—C5—C17—C22	−48.98 (13)
O3—C6—C7—C3	−6.20 (18)	C2—C5—C17—C22	72.08 (13)
N2—C6—C7—C3	173.40 (10)	C22—C17—C18—C19	−0.94 (17)
C2—C3—C7—C6	−0.62 (15)	C5—C17—C18—C19	175.32 (11)
C4—C3—C7—C6	120.01 (12)	C17—C18—C19—C20	0.26 (18)
C2—C3—C7—C16	173.97 (10)	C18—C19—C20—C21	0.93 (18)
C4—C3—C7—C16	−65.40 (13)	C19—C20—C21—C22	−1.44 (18)
O1—S1—C8—C13	−22.94 (11)	C20—C21—C22—C17	0.76 (17)
O2—S1—C8—C13	−154.08 (9)	C18—C17—C22—C21	0.43 (17)
N1—S1—C8—C13	91.63 (10)	C5—C17—C22—C21	−175.81 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1^i	0.93	2.46	3.1846 (14)	134
C18—H18···O4^ii	0.93	2.47	3.2248 (15)	138
C20—H20···Cg1^iii	0.93	2.77	3.6038 (13)	149

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