7'-(2,5-Dimeth-oxy-phen-yl)-1',3',5',6',7',7a'-hexa-hydro-dispiro-[indan-2,5'-pyrrolo-[1,2-c][1,3]thia-zole-6',2''-indan]-1,3,1''-trione.

In the title compound, C(30)H(25)NO(5)S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intra-molecular C-H⋯O inter-actions stabilize the mol-ecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexa-hydro-pyrrolo-[1,2-c]thia-zole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Mol-ecules are linked by inter-molecular C-H⋯O inter-actions into a three-dimensional network. In addition, C-H⋯π and π-π inter-actions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.

Related literature

For related structures, see: Wei, Ali, Choon et al. (2011 ▶); Wei, Ali, Ismail et al. (2011 ▶); Wei, Ali, Yoon et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C30H25NO5S

M = 511.57

Triclinic,

a = 9.0425 (4) Å

b = 11.1127 (5) Å

c = 13.3005 (6) Å

α = 68.016 (1)°

β = 84.588 (1)°

γ = 79.735 (1)°

V = 1218.95 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.36 × 0.19 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.939, T max = 0.983

27399 measured reflections

7546 independent reflections

6172 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.03

7546 reflections

336 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003169/rz2700sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003169/rz2700Isup2.hkl

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

C30H25NO5S	Z = 2
Mr = 511.57	F(000) = 536
Triclinic, P1	Dx = 1.394 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0425 (4) Å	Cell parameters from 9674 reflections
b = 11.1127 (5) Å	θ = 2.3–30.7°
c = 13.3005 (6) Å	µ = 0.18 mm−1
α = 68.016 (1)°	T = 100 K
β = 84.588 (1)°	Plate, yellow
γ = 79.735 (1)°	0.36 × 0.19 × 0.10 mm
V = 1218.95 (9) Å3

Bruker SMART APEXII CCD diffractometer	7546 independent reflections
Radiation source: fine-focus sealed tube	6172 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 30.8°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.939, Tmax = 0.983	k = −15→16
27399 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.3649P] where P = (Fo2 + 2Fc2)/3
7546 reflections	(Δ/σ)max = 0.001
336 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.73773 (3)	0.75887 (3)	0.32247 (3)	0.02242 (8)
O1	0.48652 (10)	0.81440 (8)	0.08968 (7)	0.02018 (17)
O2	0.13926 (9)	0.78758 (9)	0.38401 (7)	0.01972 (17)
O3	0.22209 (10)	0.66773 (8)	0.08718 (6)	0.02009 (17)
O4	0.69120 (10)	0.08851 (8)	0.50375 (7)	0.02352 (18)
O5	0.42757 (10)	0.42066 (9)	0.12125 (7)	0.02060 (17)
N1	0.46129 (10)	0.70280 (9)	0.33292 (8)	0.01505 (17)
C1	0.53549 (13)	0.81258 (12)	0.32540 (10)	0.0197 (2)
H1A	0.5058	0.8389	0.3887	0.024*
H1B	0.5060	0.8890	0.2586	0.024*
C2	0.71655 (13)	0.62872 (12)	0.27699 (10)	0.0188 (2)
H2A	0.7143	0.6611	0.1969	0.023*
H2B	0.8001	0.5546	0.3019	0.023*
C3	0.56602 (12)	0.58616 (11)	0.32835 (9)	0.01487 (19)
H3A	0.5821	0.5197	0.4034	0.018*
C4	0.48564 (12)	0.53056 (11)	0.26182 (8)	0.01420 (19)
H4A	0.5193	0.5718	0.1844	0.017*
C5	0.31662 (12)	0.59219 (10)	0.27073 (8)	0.01339 (18)
C6	0.33703 (12)	0.73236 (11)	0.26064 (8)	0.01379 (19)
C7	0.36942 (12)	0.82428 (11)	0.14128 (9)	0.0156 (2)
C8	0.24279 (13)	0.93367 (11)	0.10817 (9)	0.0165 (2)
C9	0.22010 (14)	1.03660 (12)	0.00841 (10)	0.0206 (2)
H9A	0.2887	1.0420	−0.0512	0.025*
C10	0.09331 (15)	1.13115 (12)	−0.00065 (10)	0.0229 (2)
H10A	0.0747	1.2021	−0.0679	0.028*
C11	−0.00773 (14)	1.12392 (12)	0.08755 (10)	0.0233 (2)
H11A	−0.0937	1.1896	0.0789	0.028*
C12	0.01611 (13)	1.02212 (12)	0.18730 (10)	0.0208 (2)
H12A	−0.0514	1.0176	0.2474	0.025*
C13	0.14256 (13)	0.92684 (11)	0.19611 (9)	0.0167 (2)
C14	0.19522 (12)	0.81249 (11)	0.29325 (9)	0.01488 (19)
C15	0.22061 (12)	0.59216 (11)	0.18119 (8)	0.01511 (19)
C16	0.12391 (12)	0.49049 (11)	0.23166 (9)	0.01496 (19)
C17	0.03024 (13)	0.44286 (12)	0.18221 (9)	0.0189 (2)
H17A	0.0225	0.4761	0.1056	0.023*
C18	−0.05095 (13)	0.34581 (12)	0.24801 (10)	0.0209 (2)
H18A	−0.1146	0.3112	0.2164	0.025*
C19	−0.03949 (13)	0.29862 (12)	0.36080 (10)	0.0196 (2)
H19A	−0.0959	0.2322	0.4048	0.024*
C20	0.05276 (12)	0.34686 (11)	0.40993 (9)	0.0169 (2)
H20A	0.0591	0.3147	0.4866	0.020*
C21	0.13569 (12)	0.44365 (11)	0.34392 (9)	0.01400 (19)
C22	0.24062 (12)	0.51134 (11)	0.37847 (8)	0.01415 (19)
H22A	0.3162	0.4465	0.4285	0.017*
H22B	0.1843	0.5694	0.4148	0.017*
C23	0.52094 (12)	0.38279 (11)	0.29094 (9)	0.01523 (19)
C24	0.58450 (12)	0.29594 (11)	0.38738 (9)	0.0171 (2)
H24A	0.5980	0.3275	0.4426	0.020*
C25	0.62912 (12)	0.16255 (11)	0.40491 (10)	0.0183 (2)
C26	0.61226 (13)	0.11484 (12)	0.32496 (10)	0.0211 (2)
H26A	0.6467	0.0252	0.3355	0.025*
C27	0.54419 (14)	0.19992 (12)	0.22873 (10)	0.0218 (2)
H27A	0.5302	0.1675	0.1741	0.026*
C28	0.49688 (13)	0.33129 (11)	0.21227 (9)	0.0175 (2)
C29	0.75456 (15)	−0.04449 (12)	0.52243 (12)	0.0270 (3)
H29A	0.7961	−0.0853	0.5951	0.040*
H29B	0.8348	−0.0474	0.4681	0.040*
H29C	0.6764	−0.0923	0.5170	0.040*
C30	0.38015 (16)	0.37160 (14)	0.04664 (10)	0.0272 (3)
H30A	0.3236	0.4439	−0.0109	0.041*
H30B	0.3159	0.3050	0.0849	0.041*
H30C	0.4684	0.3322	0.0147	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.01879 (14)	0.01845 (15)	0.03543 (17)	−0.00579 (10)	−0.00349 (11)	−0.01403 (12)
O1	0.0222 (4)	0.0175 (4)	0.0211 (4)	−0.0063 (3)	0.0074 (3)	−0.0077 (3)
O2	0.0224 (4)	0.0204 (4)	0.0179 (4)	−0.0058 (3)	0.0050 (3)	−0.0088 (3)
O3	0.0277 (4)	0.0174 (4)	0.0149 (4)	−0.0050 (3)	−0.0012 (3)	−0.0048 (3)
O4	0.0283 (4)	0.0122 (4)	0.0293 (4)	0.0013 (3)	−0.0056 (3)	−0.0076 (3)
O5	0.0279 (4)	0.0197 (4)	0.0188 (4)	−0.0060 (3)	−0.0003 (3)	−0.0112 (3)
N1	0.0163 (4)	0.0122 (4)	0.0198 (4)	−0.0047 (3)	0.0002 (3)	−0.0085 (3)
C1	0.0189 (5)	0.0160 (5)	0.0294 (6)	−0.0068 (4)	0.0015 (4)	−0.0129 (5)
C2	0.0169 (5)	0.0157 (5)	0.0271 (5)	−0.0047 (4)	−0.0001 (4)	−0.0108 (4)
C3	0.0174 (5)	0.0113 (5)	0.0178 (5)	−0.0040 (4)	−0.0007 (4)	−0.0066 (4)
C4	0.0162 (5)	0.0127 (5)	0.0159 (4)	−0.0053 (4)	0.0019 (3)	−0.0069 (4)
C5	0.0164 (4)	0.0115 (5)	0.0135 (4)	−0.0050 (4)	0.0010 (3)	−0.0051 (4)
C6	0.0155 (4)	0.0121 (5)	0.0148 (4)	−0.0040 (4)	0.0022 (3)	−0.0058 (4)
C7	0.0201 (5)	0.0118 (5)	0.0162 (5)	−0.0057 (4)	0.0028 (4)	−0.0060 (4)
C8	0.0199 (5)	0.0120 (5)	0.0183 (5)	−0.0048 (4)	0.0016 (4)	−0.0058 (4)
C9	0.0255 (6)	0.0163 (5)	0.0196 (5)	−0.0075 (4)	0.0022 (4)	−0.0048 (4)
C10	0.0290 (6)	0.0155 (5)	0.0221 (5)	−0.0043 (4)	−0.0036 (4)	−0.0033 (4)
C11	0.0256 (6)	0.0179 (6)	0.0263 (6)	0.0006 (4)	−0.0039 (5)	−0.0089 (5)
C12	0.0216 (5)	0.0193 (6)	0.0226 (5)	−0.0013 (4)	0.0006 (4)	−0.0099 (5)
C13	0.0190 (5)	0.0135 (5)	0.0188 (5)	−0.0042 (4)	0.0010 (4)	−0.0068 (4)
C14	0.0164 (5)	0.0136 (5)	0.0173 (5)	−0.0054 (4)	0.0019 (4)	−0.0078 (4)
C15	0.0178 (5)	0.0137 (5)	0.0153 (4)	−0.0030 (4)	0.0002 (4)	−0.0068 (4)
C16	0.0155 (5)	0.0143 (5)	0.0168 (5)	−0.0034 (4)	0.0000 (4)	−0.0071 (4)
C17	0.0184 (5)	0.0213 (6)	0.0205 (5)	−0.0034 (4)	−0.0018 (4)	−0.0111 (4)
C18	0.0174 (5)	0.0208 (6)	0.0299 (6)	−0.0051 (4)	−0.0015 (4)	−0.0143 (5)
C19	0.0161 (5)	0.0136 (5)	0.0294 (6)	−0.0049 (4)	0.0005 (4)	−0.0073 (4)
C20	0.0160 (5)	0.0134 (5)	0.0202 (5)	−0.0035 (4)	−0.0001 (4)	−0.0046 (4)
C21	0.0134 (4)	0.0120 (5)	0.0174 (5)	−0.0028 (4)	0.0003 (3)	−0.0061 (4)
C22	0.0170 (5)	0.0136 (5)	0.0133 (4)	−0.0062 (4)	0.0002 (3)	−0.0049 (4)
C23	0.0153 (4)	0.0134 (5)	0.0196 (5)	−0.0051 (4)	0.0031 (4)	−0.0085 (4)
C24	0.0175 (5)	0.0142 (5)	0.0222 (5)	−0.0045 (4)	0.0012 (4)	−0.0092 (4)
C25	0.0166 (5)	0.0138 (5)	0.0256 (5)	−0.0042 (4)	0.0014 (4)	−0.0081 (4)
C26	0.0206 (5)	0.0146 (5)	0.0319 (6)	−0.0050 (4)	0.0030 (4)	−0.0127 (5)
C27	0.0248 (6)	0.0196 (6)	0.0279 (6)	−0.0067 (4)	0.0030 (4)	−0.0159 (5)
C28	0.0187 (5)	0.0172 (5)	0.0201 (5)	−0.0059 (4)	0.0025 (4)	−0.0101 (4)
C29	0.0288 (6)	0.0130 (6)	0.0360 (7)	0.0018 (5)	−0.0007 (5)	−0.0077 (5)
C30	0.0384 (7)	0.0295 (7)	0.0210 (5)	−0.0110 (6)	−0.0008 (5)	−0.0149 (5)

S1—C2	1.8083 (12)	C11—C12	1.3891 (17)
S1—C1	1.8213 (12)	C11—H11A	0.9500
O1—C7	1.2174 (13)	C12—C13	1.3939 (16)
O2—C14	1.2142 (13)	C12—H12A	0.9500
O3—C15	1.2180 (13)	C13—C14	1.4771 (16)
O4—C25	1.3729 (14)	C15—C16	1.4715 (15)
O4—C29	1.4229 (15)	C16—C21	1.3928 (14)
O5—C28	1.3660 (14)	C16—C17	1.3985 (15)
O5—C30	1.4264 (14)	C17—C18	1.3864 (17)
N1—C6	1.4595 (14)	C17—H17A	0.9500
N1—C1	1.4617 (14)	C18—C19	1.3990 (17)
N1—C3	1.4802 (14)	C18—H18A	0.9500
C1—H1A	0.9900	C19—C20	1.3909 (16)
C1—H1B	0.9900	C19—H19A	0.9500
C2—C3	1.5347 (16)	C20—C21	1.3951 (15)
C2—H2A	0.9900	C20—H20A	0.9500
C2—H2B	0.9900	C21—C22	1.5075 (14)
C3—C4	1.5439 (14)	C22—H22A	0.9900
C3—H3A	1.0000	C22—H22B	0.9900
C4—C23	1.5195 (15)	C23—C24	1.3862 (16)
C4—C5	1.5724 (15)	C23—C28	1.4162 (14)
C4—H4A	1.0000	C24—C25	1.4001 (16)
C5—C15	1.5387 (14)	C24—H24A	0.9500
C5—C22	1.5503 (15)	C25—C26	1.3845 (16)
C5—C6	1.5555 (15)	C26—C27	1.3951 (18)
C6—C14	1.5501 (15)	C26—H26A	0.9500
C6—C7	1.5666 (15)	C27—C28	1.3848 (16)
C7—C8	1.4768 (15)	C27—H27A	0.9500
C8—C9	1.3937 (16)	C29—H29A	0.9800
C8—C13	1.3977 (15)	C29—H29B	0.9800
C9—C10	1.3910 (17)	C29—H29C	0.9800
C9—H9A	0.9500	C30—H30A	0.9800
C10—C11	1.4039 (18)	C30—H30B	0.9800
C10—H10A	0.9500	C30—H30C	0.9800
C2—S1—C1	92.41 (5)	C8—C13—C14	110.52 (10)
C25—O4—C29	117.86 (10)	O2—C14—C13	125.67 (10)
C28—O5—C30	117.49 (10)	O2—C14—C6	125.75 (10)
C6—N1—C1	116.85 (9)	C13—C14—C6	108.55 (9)
C6—N1—C3	109.94 (8)	O3—C15—C16	127.44 (10)
C1—N1—C3	114.03 (9)	O3—C15—C5	124.96 (10)
N1—C1—S1	107.80 (8)	C16—C15—C5	107.52 (9)
N1—C1—H1A	110.1	C21—C16—C17	121.64 (10)
S1—C1—H1A	110.1	C21—C16—C15	109.33 (9)
N1—C1—H1B	110.1	C17—C16—C15	129.03 (10)
S1—C1—H1B	110.1	C18—C17—C16	118.22 (10)
H1A—C1—H1B	108.5	C18—C17—H17A	120.9
C3—C2—S1	104.63 (7)	C16—C17—H17A	120.9
C3—C2—H2A	110.8	C17—C18—C19	120.29 (10)
S1—C2—H2A	110.8	C17—C18—H18A	119.9
C3—C2—H2B	110.8	C19—C18—H18A	119.9
S1—C2—H2B	110.8	C20—C19—C18	121.43 (11)
H2A—C2—H2B	108.9	C20—C19—H19A	119.3
N1—C3—C2	108.88 (9)	C18—C19—H19A	119.3
N1—C3—C4	105.18 (8)	C19—C20—C21	118.44 (10)
C2—C3—C4	113.74 (9)	C19—C20—H20A	120.8
N1—C3—H3A	109.6	C21—C20—H20A	120.8
C2—C3—H3A	109.6	C16—C21—C20	119.98 (10)
C4—C3—H3A	109.6	C16—C21—C22	112.13 (9)
C23—C4—C3	115.74 (9)	C20—C21—C22	127.88 (10)
C23—C4—C5	117.58 (9)	C21—C22—C5	104.02 (8)
C3—C4—C5	102.55 (8)	C21—C22—H22A	111.0
C23—C4—H4A	106.7	C5—C22—H22A	111.0
C3—C4—H4A	106.7	C21—C22—H22B	111.0
C5—C4—H4A	106.7	C5—C22—H22B	111.0
C15—C5—C22	104.83 (8)	H22A—C22—H22B	109.0
C15—C5—C6	113.28 (9)	C24—C23—C28	117.81 (10)
C22—C5—C6	115.15 (8)	C24—C23—C4	123.85 (9)
C15—C5—C4	112.77 (8)	C28—C23—C4	118.21 (10)
C22—C5—C4	111.13 (8)	C23—C24—C25	121.22 (10)
C6—C5—C4	99.96 (8)	C23—C24—H24A	119.4
N1—C6—C14	112.51 (8)	C25—C24—H24A	119.4
N1—C6—C5	101.36 (8)	O4—C25—C26	124.86 (11)
C14—C6—C5	114.44 (9)	O4—C25—C24	114.81 (10)
N1—C6—C7	113.84 (9)	C26—C25—C24	120.32 (11)
C14—C6—C7	101.90 (8)	C25—C26—C27	119.25 (11)
C5—C6—C7	113.32 (8)	C25—C26—H26A	120.4
O1—C7—C8	125.97 (10)	C27—C26—H26A	120.4
O1—C7—C6	125.21 (10)	C28—C27—C26	120.45 (10)
C8—C7—C6	108.37 (9)	C28—C27—H27A	119.8
C9—C8—C13	121.07 (11)	C26—C27—H27A	119.8
C9—C8—C7	128.86 (10)	O5—C28—C27	124.19 (10)
C13—C8—C7	109.99 (10)	O5—C28—C23	114.99 (10)
C10—C9—C8	117.57 (11)	C27—C28—C23	120.81 (11)
C10—C9—H9A	121.2	O4—C29—H29A	109.5
C8—C9—H9A	121.2	O4—C29—H29B	109.5
C9—C10—C11	121.34 (11)	H29A—C29—H29B	109.5
C9—C10—H10A	119.3	O4—C29—H29C	109.5
C11—C10—H10A	119.3	H29A—C29—H29C	109.5
C12—C11—C10	120.99 (11)	H29B—C29—H29C	109.5
C12—C11—H11A	119.5	O5—C30—H30A	109.5
C10—C11—H11A	119.5	O5—C30—H30B	109.5
C11—C12—C13	117.65 (11)	H30A—C30—H30B	109.5
C11—C12—H12A	121.2	O5—C30—H30C	109.5
C13—C12—H12A	121.2	H30A—C30—H30C	109.5
C12—C13—C8	121.37 (11)	H30B—C30—H30C	109.5
C12—C13—C14	128.06 (10)
C6—N1—C1—S1	−134.10 (8)	C8—C13—C14—O2	173.06 (11)
C3—N1—C1—S1	−3.99 (11)	C12—C13—C14—C6	177.49 (11)
C2—S1—C1—N1	21.48 (9)	C8—C13—C14—C6	−5.04 (12)
C1—S1—C2—C3	−31.84 (8)	N1—C6—C14—O2	−48.10 (15)
C6—N1—C3—C2	113.37 (10)	C5—C6—C14—O2	66.90 (14)
C1—N1—C3—C2	−20.09 (12)	C7—C6—C14—O2	−170.40 (11)
C6—N1—C3—C4	−8.87 (11)	N1—C6—C14—C13	129.99 (9)
C1—N1—C3—C4	−142.33 (9)	C5—C6—C14—C13	−115.01 (10)
S1—C2—C3—N1	34.39 (10)	C7—C6—C14—C13	7.69 (11)
S1—C2—C3—C4	151.30 (8)	C22—C5—C15—O3	162.88 (11)
N1—C3—C4—C23	−149.38 (9)	C6—C5—C15—O3	36.55 (15)
C2—C3—C4—C23	91.57 (11)	C4—C5—C15—O3	−76.08 (14)
N1—C3—C4—C5	−20.04 (10)	C22—C5—C15—C16	−14.21 (11)
C2—C3—C4—C5	−139.09 (9)	C6—C5—C15—C16	−140.54 (9)
C23—C4—C5—C15	−71.71 (12)	C4—C5—C15—C16	106.83 (10)
C3—C4—C5—C15	160.10 (9)	O3—C15—C16—C21	−168.21 (11)
C23—C4—C5—C22	45.66 (12)	C5—C15—C16—C21	8.79 (12)
C3—C4—C5—C22	−82.53 (10)	O3—C15—C16—C17	11.16 (19)
C23—C4—C5—C6	167.69 (9)	C5—C15—C16—C17	−171.85 (11)
C3—C4—C5—C6	39.51 (9)	C21—C16—C17—C18	−0.56 (17)
C1—N1—C6—C14	−71.05 (12)	C15—C16—C17—C18	−179.85 (11)
C3—N1—C6—C14	156.95 (9)	C16—C17—C18—C19	0.60 (17)
C1—N1—C6—C5	166.27 (9)	C17—C18—C19—C20	−0.08 (18)
C3—N1—C6—C5	34.26 (10)	C18—C19—C20—C21	−0.51 (17)
C1—N1—C6—C7	44.24 (12)	C17—C16—C21—C20	−0.02 (16)
C3—N1—C6—C7	−87.76 (11)	C15—C16—C21—C20	179.40 (10)
C15—C5—C6—N1	−164.96 (8)	C17—C16—C21—C22	−178.82 (10)
C22—C5—C6—N1	74.39 (10)	C15—C16—C21—C22	0.60 (12)
C4—C5—C6—N1	−44.74 (9)	C19—C20—C21—C16	0.55 (16)
C15—C5—C6—C14	73.69 (11)	C19—C20—C21—C22	179.14 (10)
C22—C5—C6—C14	−46.96 (12)	C16—C21—C22—C5	−9.50 (12)
C4—C5—C6—C14	−166.09 (8)	C20—C21—C22—C5	171.82 (10)
C15—C5—C6—C7	−42.58 (12)	C15—C5—C22—C21	13.99 (11)
C22—C5—C6—C7	−163.23 (9)	C6—C5—C22—C21	139.16 (9)
C4—C5—C6—C7	77.64 (10)	C4—C5—C22—C21	−108.12 (9)
N1—C6—C7—O1	43.42 (15)	C3—C4—C23—C24	17.73 (15)
C14—C6—C7—O1	164.81 (11)	C5—C4—C23—C24	−103.87 (12)
C5—C6—C7—O1	−71.73 (14)	C3—C4—C23—C28	−157.93 (10)
N1—C6—C7—C8	−129.22 (9)	C5—C4—C23—C28	80.47 (12)
C14—C6—C7—C8	−7.83 (11)	C28—C23—C24—C25	2.52 (16)
C5—C6—C7—C8	115.62 (10)	C4—C23—C24—C25	−173.15 (10)
O1—C7—C8—C9	9.64 (19)	C29—O4—C25—C26	5.59 (17)
C6—C7—C8—C9	−177.79 (11)	C29—O4—C25—C24	−173.03 (11)
O1—C7—C8—C13	−167.21 (11)	C23—C24—C25—O4	179.56 (10)
C6—C7—C8—C13	5.37 (12)	C23—C24—C25—C26	0.87 (17)
C13—C8—C9—C10	−0.76 (17)	O4—C25—C26—C27	178.59 (11)
C7—C8—C9—C10	−177.30 (11)	C24—C25—C26—C27	−2.86 (18)
C8—C9—C10—C11	0.45 (18)	C25—C26—C27—C28	1.39 (18)
C9—C10—C11—C12	0.35 (19)	C30—O5—C28—C27	10.24 (17)
C10—C11—C12—C13	−0.82 (18)	C30—O5—C28—C23	−170.86 (10)
C11—C12—C13—C8	0.51 (17)	C26—C27—C28—O5	−179.08 (11)
C11—C12—C13—C14	177.73 (11)	C26—C27—C28—C23	2.08 (18)
C9—C8—C13—C12	0.29 (17)	C24—C23—C28—O5	177.07 (10)
C7—C8—C13—C12	177.43 (10)	C4—C23—C28—O5	−7.01 (15)
C9—C8—C13—C14	−177.38 (10)	C24—C23—C28—C27	−3.99 (16)
C7—C8—C13—C14	−0.24 (13)	C4—C23—C28—C27	171.93 (10)
C12—C13—C14—O2	−4.42 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.99	2.58	3.2234 (15)	123
C4—H4A···O1	1.00	2.49	3.1289 (15)	122
C22—H22B···O2	0.99	2.27	3.0697 (16)	137
C11—H11A···O3i	0.95	2.44	3.1210 (15)	129
C20—H20A···O2ii	0.95	2.48	3.1176 (14)	124
C1—H1A···O4iii	0.99	2.40	3.2806 (16)	148
C30—H30C···O1iv	0.98	2.47	3.2433 (18)	136
C2—H2B···Cg1v	0.99	2.58	3.5224 (14)	160

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1	0.99	2.58	3.2234 (15)	123
C4—H4A⋯O1	1.00	2.49	3.1289 (15)	122
C22—H22B⋯O2	0.99	2.27	3.0697 (16)	137
C11—H11A⋯O3i	0.95	2.44	3.1210 (15)	129
C20—H20A⋯O2ii	0.95	2.48	3.1176 (14)	124
C1—H1A⋯O4iii	0.99	2.40	3.2806 (16)	148
C30—H30C⋯O1iv	0.98	2.47	3.2433 (18)	136
C2—H2B⋯Cg1v	0.99	2.58	3.5224 (14)	160

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .