2-[(8-Meth-oxy-carbonyl-4b,8-dimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-3-yl)amino]-3,5-dinitro-benzoic acid ethyl acetate monosolvate.

The title compound, C(25)H(27)N(3)O(8)·C(4)H(8)O(2), has a diterpene skeleton in which the fused cyclo-hexane rings exhibit chair and half-chair conformations. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds are observed.

Related literature

For the synthesis of cis-deisopropyl­dehydro­abietate derivatives, see: Fonseca et al. (2001 ▶); Baleizao et al. (2004 ▶); Feio et al. (1999 ▶). For a related structures, see: Wang et al. (2006 ▶); Hamodrakas et al. (1978 ▶). For uses of dehydro­abietic acid (DAA), see: Bhatnagar (1983 ▶, 1984 ▶). For the geometry of diterpenic compounds, see: Allen et al. (1991 ▶);

Experimental

Crystal data

C25H27N3O8·C4H8O2

M = 585.60

Monoclinic,

a = 7.649 (4) Å

b = 13.591 (8) Å

c = 14.399 (8) Å

β = 101.371 (7)°

V = 1467.5 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.47 × 0.38 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.954, T max = 0.988

9128 measured reflections

5885 independent reflections

4688 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.03

5885 reflections

385 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032278/kp2429sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032278/kp2429Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032278/kp2429Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H27N3O8·C4H8O2	F(000) = 620
Mr = 585.60	Dx = 1.325 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3055 reflections
a = 7.649 (4) Å	θ = 2.8–24.0°
b = 13.591 (8) Å	µ = 0.10 mm−1
c = 14.399 (8) Å	T = 296 K
β = 101.371 (7)°	Block, orange
V = 1467.5 (15) Å3	0.47 × 0.38 × 0.12 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	5885 independent reflections
Radiation source: fine-focus sealed tube	4688 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.954, Tmax = 0.988	k = −17→14
9128 measured reflections	l = −16→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.058P)2 + 0.0376P] where P = (Fo2 + 2Fc2)/3
5885 reflections	(Δ/σ)max = 0.024
385 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.4541 (2)	0.20663 (15)	1.11523 (11)	0.0506 (4)
H1S	0.4165	0.2369	1.1599	0.061*
N2	1.1161 (3)	0.01668 (16)	1.21945 (16)	0.0627 (5)
N3	0.6957 (2)	0.1904 (2)	0.98090 (13)	0.0622 (6)
O1	0.1533 (2)	−0.19460 (12)	0.64103 (12)	0.0619 (4)
O2	0.2245 (2)	−0.05029 (12)	0.58598 (11)	0.0553 (4)
O3	1.1580 (3)	−0.01462 (18)	1.30023 (15)	0.0869 (6)
O4	1.2085 (3)	0.00787 (19)	1.16010 (15)	0.0920 (7)
O5	0.6401 (2)	0.10646 (14)	1.39061 (11)	0.0631 (4)
H5	0.5829	0.1229	1.4306	0.095*
O6	0.4375 (2)	0.19827 (14)	1.29741 (10)	0.0645 (5)
O7	0.6592 (3)	0.27809 (18)	0.97449 (14)	0.0812 (6)
O8	0.7103 (3)	0.13644 (19)	0.91429 (12)	0.0894 (7)
O1S	0.3165 (2)	0.24418 (17)	0.61251 (13)	0.0775 (5)
O2S	0.4987 (2)	0.16498 (16)	0.53723 (12)	0.0749 (6)
C1	0.8417 (3)	0.08358 (16)	1.25915 (15)	0.0477 (5)
H1	0.8824	0.0633	1.3214	0.057*
C2	0.9446 (3)	0.06669 (17)	1.19241 (16)	0.0493 (5)
C3	0.8917 (3)	0.09838 (17)	1.10043 (16)	0.0513 (5)
H3	0.9632	0.0879	1.0561	0.062*
C4	0.7316 (3)	0.14554 (17)	1.07577 (13)	0.0478 (5)
C5	0.6150 (3)	0.16232 (16)	1.13960 (13)	0.0440 (5)
C6	0.6781 (3)	0.13053 (16)	1.23462 (13)	0.0441 (4)
C7	0.5720 (3)	0.14879 (17)	1.30933 (14)	0.0489 (5)
C8	0.3398 (3)	0.20904 (16)	1.02443 (13)	0.0446 (5)
C9	0.2480 (3)	0.29477 (18)	0.99475 (16)	0.0523 (5)
H9	0.2679	0.3517	1.0311	0.063*
C10	0.1267 (3)	0.29411 (17)	0.91050 (16)	0.0529 (5)
H10	0.0614	0.3509	0.8917	0.063*
C11	0.0978 (2)	0.21138 (16)	0.85216 (14)	0.0439 (5)
C12	0.1923 (2)	0.12511 (15)	0.88017 (13)	0.0396 (4)
C13	0.3113 (3)	0.12563 (16)	0.96844 (13)	0.0437 (4)
H13	0.3724	0.0682	0.9896	0.052*
C14	−0.0350 (3)	0.21756 (17)	0.76050 (15)	0.0514 (5)
H14A	0.0206	0.2489	0.7132	0.062*
H14B	−0.1345	0.2583	0.7695	0.062*
C15	−0.1040 (3)	0.11764 (17)	0.72472 (15)	0.0480 (5)
H15A	−0.1768	0.1243	0.6618	0.058*
H15B	−0.1785	0.0911	0.7660	0.058*
C16	0.0500 (2)	0.04646 (15)	0.72138 (13)	0.0393 (4)
H16	0.1279	0.0787	0.6842	0.047*
C17	0.1646 (3)	0.02907 (14)	0.82312 (13)	0.0402 (4)
C18	0.0684 (3)	−0.04380 (18)	0.87898 (15)	0.0540 (5)
H18A	0.1465	−0.0589	0.9389	0.065*
H18B	−0.0375	−0.0124	0.8927	0.065*
C19	0.0150 (4)	−0.13884 (19)	0.82600 (18)	0.0622 (6)
H19A	−0.0472	−0.1808	0.8633	0.075*
H19B	0.1209	−0.1733	0.8162	0.075*
C20	−0.1057 (3)	−0.11764 (19)	0.73048 (18)	0.0584 (6)
H20A	−0.2146	−0.0869	0.7409	0.070*
H20B	−0.1377	−0.1793	0.6976	0.070*
C21	−0.0177 (3)	−0.05074 (16)	0.66828 (14)	0.0444 (4)
C22	−0.1505 (3)	−0.0292 (2)	0.57444 (17)	0.0612 (6)
H22A	−0.1035	0.0220	0.5405	0.092*
H22B	−0.2626	−0.0086	0.5883	0.092*
H22C	−0.1677	−0.0878	0.5364	0.092*
C23	0.1299 (3)	−0.10728 (17)	0.63367 (14)	0.0460 (5)
C24	0.3485 (3)	−0.01273 (18)	0.81485 (15)	0.0499 (5)
H24A	0.4068	0.0322	0.7794	0.075*
H24B	0.3330	−0.0751	0.7829	0.075*
H24C	0.4200	−0.0213	0.8770	0.075*
C25	0.3532 (4)	−0.1005 (2)	0.5418 (2)	0.0760 (8)
H25A	0.4443	−0.1289	0.5897	0.114*
H25B	0.4062	−0.0545	0.5050	0.114*
H25C	0.2946	−0.1517	0.5012	0.114*
C1S	0.4227 (5)	0.3569 (3)	0.7347 (3)	0.1153 (14)
H1S1	0.4138	0.4133	0.6939	0.173*
H1S2	0.5131	0.3683	0.7901	0.173*
H1S3	0.3103	0.3460	0.7531	0.173*
C2S	0.4685 (4)	0.2728 (3)	0.6858 (2)	0.1023 (12)
H2S1	0.5012	0.2190	0.7300	0.123*
H2S2	0.5701	0.2878	0.6572	0.123*
C3S	0.3494 (3)	0.19013 (19)	0.54227 (16)	0.0568 (6)
C4S	0.1866 (4)	0.1646 (2)	0.47246 (19)	0.0685 (7)
H4S1	0.1995	0.1859	0.4106	0.103*
H4S2	0.0855	0.1966	0.4894	0.103*
H4S3	0.1693	0.0946	0.4721	0.103*

	U11	U22	U33	U12	U13	U23
N1	0.0465 (9)	0.0698 (13)	0.0344 (8)	0.0096 (9)	0.0056 (7)	−0.0083 (8)
N2	0.0529 (11)	0.0655 (14)	0.0658 (14)	0.0085 (9)	0.0023 (10)	−0.0114 (10)
N3	0.0460 (10)	0.0995 (19)	0.0428 (10)	−0.0062 (11)	0.0133 (8)	−0.0005 (11)
O1	0.0686 (10)	0.0477 (10)	0.0715 (11)	0.0040 (8)	0.0189 (9)	−0.0004 (8)
O2	0.0591 (9)	0.0528 (9)	0.0593 (9)	0.0054 (7)	0.0249 (7)	0.0035 (7)
O3	0.0812 (13)	0.1000 (15)	0.0742 (13)	0.0356 (11)	0.0025 (10)	0.0020 (11)
O4	0.0618 (11)	0.129 (2)	0.0892 (14)	0.0323 (11)	0.0234 (11)	−0.0025 (12)
O5	0.0734 (11)	0.0769 (12)	0.0417 (8)	0.0163 (9)	0.0178 (8)	0.0080 (8)
O6	0.0606 (9)	0.0897 (13)	0.0448 (8)	0.0209 (9)	0.0144 (7)	−0.0002 (8)
O7	0.0831 (13)	0.0916 (17)	0.0666 (12)	−0.0033 (11)	0.0091 (10)	0.0213 (11)
O8	0.0761 (12)	0.154 (2)	0.0423 (9)	0.0142 (13)	0.0212 (8)	−0.0121 (11)
O1S	0.0567 (10)	0.1045 (15)	0.0693 (11)	0.0140 (10)	0.0071 (9)	−0.0255 (10)
O2S	0.0632 (10)	0.1121 (17)	0.0497 (9)	0.0202 (10)	0.0117 (8)	−0.0045 (9)
C1	0.0501 (12)	0.0453 (12)	0.0436 (11)	−0.0005 (9)	−0.0007 (9)	−0.0074 (9)
C2	0.0429 (11)	0.0503 (13)	0.0528 (13)	0.0018 (9)	0.0051 (9)	−0.0129 (9)
C3	0.0452 (11)	0.0621 (14)	0.0476 (12)	−0.0033 (10)	0.0115 (9)	−0.0154 (10)
C4	0.0440 (11)	0.0609 (14)	0.0374 (10)	−0.0035 (9)	0.0054 (8)	−0.0080 (9)
C5	0.0428 (10)	0.0505 (12)	0.0376 (10)	−0.0016 (9)	0.0058 (8)	−0.0083 (8)
C6	0.0459 (10)	0.0475 (12)	0.0377 (10)	−0.0017 (9)	0.0057 (8)	−0.0073 (9)
C7	0.0529 (12)	0.0546 (14)	0.0384 (11)	0.0010 (10)	0.0070 (9)	−0.0061 (9)
C8	0.0405 (10)	0.0557 (13)	0.0374 (10)	0.0030 (9)	0.0072 (8)	−0.0016 (9)
C9	0.0539 (12)	0.0534 (14)	0.0484 (12)	0.0042 (10)	0.0075 (10)	−0.0078 (10)
C10	0.0536 (12)	0.0484 (13)	0.0542 (13)	0.0127 (10)	0.0048 (10)	0.0010 (10)
C11	0.0396 (10)	0.0485 (12)	0.0420 (11)	0.0067 (9)	0.0043 (8)	0.0024 (9)
C12	0.0366 (9)	0.0459 (11)	0.0363 (9)	0.0033 (8)	0.0072 (7)	0.0033 (8)
C13	0.0413 (10)	0.0502 (12)	0.0387 (10)	0.0084 (9)	0.0059 (8)	0.0029 (9)
C14	0.0490 (12)	0.0506 (13)	0.0505 (12)	0.0127 (10)	−0.0005 (9)	0.0036 (10)
C15	0.0405 (10)	0.0548 (13)	0.0454 (11)	0.0089 (9)	0.0007 (9)	0.0001 (10)
C16	0.0345 (9)	0.0438 (11)	0.0392 (10)	0.0012 (8)	0.0060 (8)	0.0031 (8)
C17	0.0411 (10)	0.0419 (11)	0.0364 (10)	0.0053 (8)	0.0048 (8)	0.0016 (8)
C18	0.0690 (14)	0.0514 (13)	0.0444 (11)	0.0034 (11)	0.0177 (10)	0.0085 (10)
C19	0.0843 (17)	0.0474 (14)	0.0618 (15)	−0.0087 (12)	0.0312 (13)	0.0079 (11)
C20	0.0551 (13)	0.0555 (15)	0.0683 (16)	−0.0136 (11)	0.0211 (12)	−0.0086 (11)
C21	0.0388 (10)	0.0475 (12)	0.0456 (11)	−0.0003 (9)	0.0055 (8)	−0.0004 (9)
C22	0.0495 (13)	0.0671 (16)	0.0598 (14)	0.0015 (11)	−0.0069 (10)	−0.0117 (12)
C23	0.0441 (11)	0.0488 (13)	0.0430 (11)	−0.0010 (9)	0.0033 (9)	−0.0014 (9)
C24	0.0423 (11)	0.0553 (13)	0.0485 (12)	0.0117 (9)	0.0004 (9)	−0.0027 (10)
C25	0.0725 (17)	0.0785 (19)	0.088 (2)	0.0140 (14)	0.0429 (16)	0.0006 (14)
C1S	0.100 (3)	0.107 (3)	0.142 (3)	−0.026 (2)	0.031 (2)	−0.049 (3)
C2S	0.077 (2)	0.136 (3)	0.083 (2)	0.019 (2)	−0.0077 (17)	−0.041 (2)
C3S	0.0628 (14)	0.0618 (15)	0.0457 (12)	0.0060 (12)	0.0103 (10)	0.0077 (11)
C4S	0.0693 (16)	0.0697 (17)	0.0609 (15)	−0.0036 (12)	−0.0010 (12)	0.0105 (12)

N1—C5	1.353 (3)	C14—H14B	0.9700
N1—C8	1.423 (3)	C15—C16	1.532 (3)
N1—H1S	0.8600	C15—H15A	0.9700
N2—O4	1.217 (3)	C15—H15B	0.9700
N2—O3	1.221 (3)	C16—C21	1.562 (3)
N2—C2	1.461 (3)	C16—C17	1.570 (3)
N3—O7	1.223 (3)	C16—H16	0.9800
N3—O8	1.230 (3)	C17—C24	1.543 (3)
N3—C4	1.472 (3)	C17—C18	1.550 (3)
O1—C23	1.202 (3)	C18—C19	1.515 (4)
O2—C23	1.338 (3)	C18—H18A	0.9700
O2—C25	1.445 (3)	C18—H18B	0.9700
O5—C7	1.316 (3)	C19—C20	1.525 (4)
O5—H5	0.8200	C19—H19A	0.9700
O6—C7	1.213 (3)	C19—H19B	0.9700
O1S—C3S	1.314 (3)	C20—C21	1.523 (3)
O1S—C2S	1.461 (4)	C20—H20A	0.9700
O2S—C3S	1.209 (3)	C20—H20B	0.9700
C1—C2	1.376 (3)	C21—C23	1.528 (3)
C1—C6	1.387 (3)	C21—C22	1.550 (3)
C1—H1	0.9300	C22—H22A	0.9600
C2—C3	1.376 (3)	C22—H22B	0.9600
C3—C4	1.365 (3)	C22—H22C	0.9600
C3—H3	0.9300	C24—H24A	0.9600
C4—C5	1.420 (3)	C24—H24B	0.9600
C5—C6	1.425 (3)	C24—H24C	0.9600
C6—C7	1.491 (3)	C25—H25A	0.9600
C8—C13	1.383 (3)	C25—H25B	0.9600
C8—C9	1.384 (3)	C25—H25C	0.9600
C9—C10	1.374 (3)	C1S—C2S	1.422 (5)
C9—H9	0.9300	C1S—H1S1	0.9600
C10—C11	1.395 (3)	C1S—H1S2	0.9600
C10—H10	0.9300	C1S—H1S3	0.9600
C11—C12	1.394 (3)	C2S—H2S1	0.9700
C11—C14	1.501 (3)	C2S—H2S2	0.9700
C12—C13	1.410 (3)	C3S—C4S	1.479 (4)
C12—C17	1.534 (3)	C4S—H4S1	0.9600
C13—H13	0.9300	C4S—H4S2	0.9600
C14—C15	1.510 (3)	C4S—H4S3	0.9600
C14—H14A	0.9700
C5—N1—C8	127.69 (16)	C24—C17—C18	109.75 (18)
C5—N1—H1S	116.2	C12—C17—C16	111.36 (16)
C8—N1—H1S	116.2	C24—C17—C16	109.47 (15)
O4—N2—O3	123.7 (2)	C18—C17—C16	110.21 (17)
O4—N2—C2	118.3 (2)	C19—C18—C17	113.07 (18)
O3—N2—C2	118.0 (2)	C19—C18—H18A	109.0
O7—N3—O8	125.2 (2)	C17—C18—H18A	109.0
O7—N3—C4	118.2 (2)	C19—C18—H18B	109.0
O8—N3—C4	116.6 (3)	C17—C18—H18B	109.0
C23—O2—C25	115.90 (19)	H18A—C18—H18B	107.8
C7—O5—H5	109.5	C18—C19—C20	110.4 (2)
C3S—O1S—C2S	117.3 (2)	C18—C19—H19A	109.6
C2—C1—C6	120.7 (2)	C20—C19—H19A	109.6
C2—C1—H1	119.7	C18—C19—H19B	109.6
C6—C1—H1	119.7	C20—C19—H19B	109.6
C1—C2—C3	121.4 (2)	H19A—C19—H19B	108.1
C1—C2—N2	119.9 (2)	C19—C20—C21	112.58 (18)
C3—C2—N2	118.7 (2)	C19—C20—H20A	109.1
C4—C3—C2	118.41 (19)	C21—C20—H20A	109.1
C4—C3—H3	120.8	C19—C20—H20B	109.1
C2—C3—H3	120.8	C21—C20—H20B	109.1
C3—C4—C5	123.6 (2)	H20A—C20—H20B	107.8
C3—C4—N3	115.45 (18)	C20—C21—C23	109.39 (18)
C5—C4—N3	120.53 (19)	C20—C21—C22	109.59 (19)
N1—C5—C4	124.00 (18)	C23—C21—C22	102.13 (17)
N1—C5—C6	120.19 (17)	C20—C21—C16	111.04 (17)
C4—C5—C6	115.80 (19)	C23—C21—C16	112.97 (16)
C1—C6—C5	120.14 (18)	C22—C21—C16	111.35 (18)
C1—C6—C7	119.03 (19)	C21—C22—H22A	109.5
C5—C6—C7	120.83 (19)	C21—C22—H22B	109.5
O6—C7—O5	122.96 (19)	H22A—C22—H22B	109.5
O6—C7—C6	123.90 (19)	C21—C22—H22C	109.5
O5—C7—C6	113.13 (19)	H22A—C22—H22C	109.5
C13—C8—C9	119.86 (18)	H22B—C22—H22C	109.5
C13—C8—N1	120.96 (18)	O1—C23—O2	122.0 (2)
C9—C8—N1	119.06 (19)	O1—C23—C21	125.1 (2)
C10—C9—C8	118.7 (2)	O2—C23—C21	112.64 (19)
C10—C9—H9	120.6	C17—C24—H24A	109.5
C8—C9—H9	120.6	C17—C24—H24B	109.5
C9—C10—C11	122.41 (19)	H24A—C24—H24B	109.5
C9—C10—H10	118.8	C17—C24—H24C	109.5
C11—C10—H10	118.8	H24A—C24—H24C	109.5
C12—C11—C10	119.49 (18)	H24B—C24—H24C	109.5
C12—C11—C14	121.58 (18)	O2—C25—H25A	109.5
C10—C11—C14	118.94 (18)	O2—C25—H25B	109.5
C11—C12—C13	117.52 (18)	H25A—C25—H25B	109.5
C11—C12—C17	123.47 (16)	O2—C25—H25C	109.5
C13—C12—C17	118.90 (16)	H25A—C25—H25C	109.5
C8—C13—C12	121.94 (18)	H25B—C25—H25C	109.5
C8—C13—H13	119.0	C2S—C1S—H1S1	109.5
C12—C13—H13	119.0	C2S—C1S—H1S2	109.5
C11—C14—C15	112.35 (17)	H1S1—C1S—H1S2	109.5
C11—C14—H14A	109.1	C2S—C1S—H1S3	109.5
C15—C14—H14A	109.1	H1S1—C1S—H1S3	109.5
C11—C14—H14B	109.1	H1S2—C1S—H1S3	109.5
C15—C14—H14B	109.1	C1S—C2S—O1S	109.5 (3)
H14A—C14—H14B	107.9	C1S—C2S—H2S1	109.8
C14—C15—C16	111.05 (18)	O1S—C2S—H2S1	109.8
C14—C15—H15A	109.4	C1S—C2S—H2S2	109.8
C16—C15—H15A	109.4	O1S—C2S—H2S2	109.8
C14—C15—H15B	109.4	H2S1—C2S—H2S2	108.2
C16—C15—H15B	109.4	O2S—C3S—O1S	122.1 (2)
H15A—C15—H15B	108.0	O2S—C3S—C4S	124.9 (2)
C15—C16—C21	111.52 (17)	O1S—C3S—C4S	113.0 (2)
C15—C16—C17	110.93 (16)	C3S—C4S—H4S1	109.5
C21—C16—C17	113.55 (16)	C3S—C4S—H4S2	109.5
C15—C16—H16	106.8	H4S1—C4S—H4S2	109.5
C21—C16—H16	106.8	C3S—C4S—H4S3	109.5
C17—C16—H16	106.8	H4S1—C4S—H4S3	109.5
C12—C17—C24	108.83 (16)	H4S2—C4S—H4S3	109.5
C12—C17—C18	107.17 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1S···O6	0.86	2.02	2.654 (3)	129
O5—H5···O2Si	0.82	1.87	2.676 (3)	168
C4S—H4S3···O2	0.96	2.54	3.332 (4)	139
C15—H15B···O8	0.97	2.53	3.326 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1S⋯O6	0.86	2.02	2.654 (3)	129
O5—H5⋯O2S i	0.82	1.87	2.676 (3)	168
C4S—H4S3⋯O2	0.96	2.54	3.332 (4)	139
C15—H15B⋯O8	0.97	2.53	3.326 (4)	140

Symmetry code: (i) .