9-{[4-(Dimethyl­amino)­benzyl]amino}-5-(4-hy­droxy-3,5-dimeth­oxy­phenyl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one methanol monosolvate

Chen, H.; Tian, D.-L.; Chen, H.; Shi, S.-Y.; Ai, T.

doi:10.1107/S1600536811043054

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3042

doi:10.1107/S1600536811043054

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9-{[4-(Dimethylamino)benzyl]amino}-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one methanol monosolvate

Hong Chen,^a Dan-Li Tian,^b Hong Chen,^c,^b ^* Shao-Yu Shi ^b and Ting Ai ^b

^aAffiliated Hospital of the Medical College of the Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, ^bRoom of Pharmacognosy, Medical College of the Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, and ^cTianjin Key Laboratory for Biomarkers of Occupational and Environmental Hazards, Tianjin 300162, People's Republic of China
^*Correspondence e-mail: tjch2010@yahoo.cn

(Received 27 September 2011; accepted 17 October 2011; online 29 October 2011)

In the title compound, C₃₀H₃₂N₂O₇·CH₄O, the tetrahydrofuran ring and the six-membered ring fused to it both display envelope conformations, with the ring C atom opposite the carbonyl group and the adjacent bridgehead C atom as the flaps, respectively. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link all moieties into ribbons along [010]. Weak intermolecular C—H⋯O interactions consolidate the crystal packing further.

Related literature

For the crystal structures of related podophyllotoxin derivatives, see: Luo et al. (2011 ); Li et al. (2011 ).

Experimental

Crystal data

C₃₀H₃₂N₂O₇·CH₄O
M_r = 564.62
Monoclinic, P 2₁
a = 11.128 (4) Å
b = 8.757 (3) Å
c = 15.057 (5) Å
β = 105.093 (6)°
V = 1416.7 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.981, T_max = 0.989
14990 measured reflections
3602 independent reflections
3167 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.107
S = 1.06
3602 reflections
377 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O1	0.84	1.95	2.777 (3)	170
O6—H6A⋯O8ⁱ	0.84	1.97	2.756 (3)	156
C7—H7B⋯N1ⁱⁱ	0.99	2.62	3.473 (4)	145
C13—H13B⋯O6ⁱⁱⁱ	0.99	2.52	3.463 (4)	159
C24—H24A⋯O3^iv	0.95	2.35	3.242 (4)	156
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) x, y-1, z; (iii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (iv) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043054/cv5160sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043054/cv5160Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043054/cv5160Isup3.cml

checkCIF report

Comment top

In continuation of our structural study of new derivatives of Podophyllotoxin (Luo et al., 2011; Li et al., 2011), we report here the crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously for related compounds (Luo et al., 2011; Li et al., 2011). The tetrahydrofuran ring (C1/C2/C12/C13/O2) and the six-membered ring (C2–C4/C10–C12) fused to it both display envelope conformations. The dihedral angles between the benzene ring (C4–C6/C8–C10) of the benzo[d]-[1,3]dioxole and the other two benzene ring (C14–C19 and C23–C28) are 80.47 (3) and 71.32 (2)°, respectively.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link all moieties into ribbons in [010]. Weak intermolecular C—H···O interactions (Table 1) consolidate further the crystal packing.

Related literature top

For the crystal structures of related podophyllotoxin derivatives, see: Luo et al. (2011); Li et al. (2011).

Experimental top

The title compound was synthesized in two steps. A mixture of 4-dimethylamino carbaldehyde (0.179 g,1.2 mmol), 4β-amino-4-De methyl-epipodophyllotoxin (0.399 g,1 mmol) and two drops of acetic in 95% ethanol (30 ml) was stirred for 6 h, then an appropriate amount of NaBH₄ was added and the mixture stirred for 2 h at 273 K. After the addition of 5% HCl (5 ml) to end off the reaction, the mixture was concentrated in vacuo and the pH adjusted to basic conditions with a saturated NaHCO₃ solution. The reaction mixture was extracted with CH₂Cl₂, dried over MgSO₄ and concentrated in vacuo. The residue was dissolved in methanol and slow evaporation over two weeks at room temperature gave colourless crystal suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level. Dashed line denotes hydrogen bond.

9-{[4-(Dimethylamino)benzyl]amino}-5-(4-hydroxy-3,5-dimethoxyphenyl)- 5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol- 6(8H)-one methanol monosolvate top

Crystal data top

C₃₀H₃₂N₂O₇·CH₄O	F(000) = 600
M_r = 564.62	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3904 reflections
a = 11.128 (4) Å	θ = 1.4–27.9°
b = 8.757 (3) Å	µ = 0.10 mm⁻¹
c = 15.057 (5) Å	T = 113 K
β = 105.093 (6)°	Prism, colourless
V = 1416.7 (8) Å³	0.20 × 0.18 × 0.12 mm
Z = 2

Data collection top

Rigaku Saturn724 CCD diffractometer	3602 independent reflections
Radiation source: rotating anode	3167 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.060
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 1.4°
ω and ϕ scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −11→11
T_min = 0.981, T_max = 0.989	l = −19→19
14990 measured reflections

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0493P)²] where P = (F_o² + 2F_c²)/3
3602 reflections	(Δ/σ)_max < 0.001
377 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₃₀H₃₂N₂O₇·CH₄O	V = 1416.7 (8) Å³
M_r = 564.62	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.128 (4) Å	µ = 0.10 mm⁻¹
b = 8.757 (3) Å	T = 113 K
c = 15.057 (5) Å	0.20 × 0.18 × 0.12 mm
β = 105.093 (6)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3602 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3167 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.989	R_int = 0.060
14990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.107	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
3602 reflections	Δρ_min = −0.36 e Å⁻³
377 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.74921 (18)	0.6561 (3)	0.65328 (15)	0.0284 (5)
O2	0.95083 (18)	0.7007 (3)	0.66811 (13)	0.0252 (5)
O3	1.1227 (2)	−0.1440 (3)	0.94087 (15)	0.0310 (5)
O4	0.90857 (19)	−0.1737 (3)	0.89208 (14)	0.0286 (5)
O5	0.89789 (18)	0.0075 (3)	0.47434 (13)	0.0238 (5)
O6	0.67582 (17)	0.0835 (3)	0.37010 (12)	0.0228 (5)
H6A	0.5991	0.0978	0.3484	0.034*
O7	0.52790 (17)	0.2841 (3)	0.42785 (13)	0.0250 (5)
N1	1.1718 (2)	0.4576 (3)	0.89519 (15)	0.0218 (6)
H1A	1.1346	0.4563	0.9401	0.026*
N2	1.6236 (3)	0.5827 (4)	1.2607 (2)	0.0444 (8)
C1	0.8569 (3)	0.6166 (4)	0.68409 (19)	0.0221 (7)
C2	0.9091 (2)	0.4829 (4)	0.74486 (18)	0.0189 (6)
H2A	0.9185	0.5164	0.8098	0.023*
C3	0.8398 (2)	0.3297 (3)	0.73304 (18)	0.0170 (6)
H3A	0.7638	0.3427	0.7560	0.020*
C4	0.9242 (2)	0.2135 (4)	0.79506 (17)	0.0167 (6)
C5	0.8672 (3)	0.0786 (4)	0.81573 (18)	0.0197 (6)
H5A	0.7797	0.0649	0.7948	0.024*
C6	0.9408 (3)	−0.0313 (4)	0.86629 (18)	0.0201 (6)
C7	1.0196 (3)	−0.2290 (4)	0.9563 (2)	0.0255 (7)
H7A	1.0138	−0.2139	1.0202	0.031*
H7B	1.0307	−0.3393	0.9465	0.031*
C8	1.0694 (3)	−0.0135 (4)	0.89553 (19)	0.0226 (7)
C9	1.1282 (3)	0.1132 (4)	0.8767 (2)	0.0223 (6)
H9A	1.2162	0.1225	0.8971	0.027*
C10	1.0542 (3)	0.2319 (3)	0.82540 (17)	0.0178 (6)
C11	1.1241 (2)	0.3740 (4)	0.80762 (18)	0.0190 (6)
H11A	1.1972	0.3398	0.7857	0.023*
C12	1.0402 (2)	0.4690 (4)	0.73161 (19)	0.0194 (6)
H12A	1.0337	0.4155	0.6718	0.023*
C13	1.0703 (3)	0.6355 (4)	0.7195 (2)	0.0222 (7)
H13A	1.1012	0.6865	0.7798	0.027*
H13B	1.1337	0.6453	0.6843	0.027*
C14	0.7977 (2)	0.2702 (4)	0.63358 (18)	0.0171 (6)
C15	0.6814 (3)	0.3129 (3)	0.57749 (18)	0.0187 (6)
H15A	0.6304	0.3826	0.5995	0.022*
C16	0.6410 (2)	0.2524 (4)	0.48918 (18)	0.0186 (6)
C17	0.7132 (2)	0.1481 (3)	0.45567 (17)	0.0170 (6)
C18	0.8302 (2)	0.1073 (3)	0.51183 (18)	0.0172 (6)
C19	0.8707 (2)	0.1677 (4)	0.60009 (18)	0.0190 (6)
H19A	0.9496	0.1384	0.6381	0.023*
C20	1.0233 (3)	−0.0197 (4)	0.52667 (19)	0.0258 (7)
H20A	1.0682	0.0776	0.5386	0.039*
H20B	1.0648	−0.0871	0.4920	0.039*
H20C	1.0228	−0.0681	0.5852	0.039*
C21	0.4537 (3)	0.4016 (4)	0.4535 (2)	0.0284 (7)
H21A	0.4261	0.3681	0.5071	0.043*
H21B	0.3809	0.4219	0.4021	0.043*
H21C	0.5033	0.4950	0.4688	0.043*
C22	1.2890 (3)	0.5444 (4)	0.9001 (2)	0.0308 (8)
H22A	1.2676	0.6492	0.8766	0.037*
H22B	1.3351	0.4944	0.8600	0.037*
C23	1.3724 (3)	0.5531 (4)	0.9975 (2)	0.0258 (7)
C24	1.3635 (3)	0.6689 (4)	1.0581 (2)	0.0262 (7)
H24A	1.3000	0.7436	1.0396	0.031*
C25	1.4444 (3)	0.6788 (4)	1.1448 (2)	0.0264 (7)
H25A	1.4355	0.7599	1.1845	0.032*
C26	1.5391 (3)	0.5715 (4)	1.1750 (2)	0.0272 (7)
C27	1.5479 (3)	0.4538 (4)	1.1136 (2)	0.0363 (8)
H27A	1.6114	0.3790	1.1316	0.044*
C28	1.4656 (3)	0.4452 (4)	1.0276 (2)	0.0327 (8)
H28A	1.4728	0.3633	0.9880	0.039*
C29	1.6110 (3)	0.7020 (5)	1.3232 (2)	0.0388 (9)
H29A	1.6091	0.8013	1.2929	0.058*
H29B	1.6817	0.6985	1.3779	0.058*
H29C	1.5335	0.6874	1.3415	0.058*
C30	1.7049 (3)	0.4561 (5)	1.2954 (2)	0.0380 (9)
H30A	1.6581	0.3604	1.2817	0.057*
H30B	1.7381	0.4666	1.3621	0.057*
H30C	1.7738	0.4553	1.2660	0.057*
O8	0.56599 (19)	0.5632 (3)	0.73637 (15)	0.0331 (6)
H8A	0.6175	0.5836	0.7060	0.050*
C31	0.6124 (4)	0.6169 (5)	0.8287 (2)	0.0497 (11)
H31A	0.6190	0.7284	0.8285	0.075*
H31B	0.6948	0.5726	0.8556	0.075*
H31C	0.5554	0.5863	0.8653	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0194 (10)	0.0258 (13)	0.0372 (12)	0.0033 (10)	0.0024 (9)	0.0088 (10)
O2	0.0221 (10)	0.0231 (13)	0.0288 (11)	−0.0015 (10)	0.0037 (8)	0.0056 (10)
O3	0.0297 (12)	0.0226 (13)	0.0381 (13)	0.0027 (10)	0.0043 (10)	0.0112 (10)
O4	0.0281 (11)	0.0225 (13)	0.0316 (12)	−0.0024 (10)	0.0011 (9)	0.0097 (10)
O5	0.0195 (10)	0.0322 (14)	0.0181 (10)	0.0066 (10)	0.0018 (8)	−0.0052 (9)
O6	0.0207 (10)	0.0286 (13)	0.0166 (9)	0.0024 (10)	0.0005 (8)	−0.0058 (9)
O7	0.0170 (9)	0.0315 (14)	0.0231 (11)	0.0070 (10)	−0.0007 (8)	−0.0064 (9)
N1	0.0167 (11)	0.0306 (16)	0.0196 (12)	−0.0074 (11)	0.0073 (9)	−0.0027 (11)
N2	0.0411 (16)	0.041 (2)	0.0359 (16)	0.0159 (16)	−0.0173 (13)	−0.0133 (15)
C1	0.0224 (14)	0.0215 (18)	0.0220 (14)	0.0001 (13)	0.0051 (12)	0.0031 (12)
C2	0.0181 (13)	0.0211 (17)	0.0172 (13)	0.0006 (13)	0.0043 (11)	−0.0007 (12)
C3	0.0172 (13)	0.0169 (16)	0.0178 (13)	0.0006 (12)	0.0064 (11)	0.0029 (12)
C4	0.0183 (13)	0.0187 (15)	0.0130 (12)	0.0001 (13)	0.0038 (10)	−0.0006 (11)
C5	0.0194 (13)	0.0197 (16)	0.0193 (13)	0.0005 (13)	0.0039 (11)	0.0014 (12)
C6	0.0242 (14)	0.0179 (16)	0.0180 (13)	−0.0013 (14)	0.0052 (11)	0.0023 (12)
C7	0.0282 (15)	0.0200 (17)	0.0272 (16)	0.0000 (14)	0.0053 (13)	0.0079 (13)
C8	0.0250 (14)	0.0194 (17)	0.0206 (14)	0.0055 (14)	0.0009 (12)	0.0031 (13)
C9	0.0197 (13)	0.0203 (17)	0.0254 (15)	0.0009 (13)	0.0031 (12)	0.0003 (12)
C10	0.0208 (13)	0.0181 (16)	0.0148 (13)	−0.0007 (12)	0.0051 (11)	−0.0010 (11)
C11	0.0157 (13)	0.0221 (17)	0.0195 (14)	−0.0003 (12)	0.0052 (11)	−0.0016 (12)
C12	0.0184 (13)	0.0203 (16)	0.0192 (13)	−0.0010 (13)	0.0045 (11)	−0.0006 (12)
C13	0.0178 (13)	0.0265 (18)	0.0218 (14)	−0.0036 (13)	0.0043 (11)	0.0017 (13)
C14	0.0153 (12)	0.0183 (16)	0.0170 (13)	−0.0022 (12)	0.0029 (10)	0.0012 (11)
C15	0.0202 (13)	0.0171 (16)	0.0193 (14)	0.0018 (13)	0.0058 (11)	0.0008 (12)
C16	0.0135 (12)	0.0205 (17)	0.0196 (14)	0.0010 (11)	0.0001 (11)	0.0023 (12)
C17	0.0170 (12)	0.0160 (15)	0.0174 (13)	−0.0026 (12)	0.0036 (11)	−0.0009 (11)
C18	0.0169 (12)	0.0178 (16)	0.0171 (13)	0.0006 (12)	0.0050 (10)	−0.0004 (11)
C19	0.0157 (12)	0.0211 (16)	0.0197 (13)	0.0028 (12)	0.0036 (10)	0.0017 (12)
C20	0.0211 (14)	0.032 (2)	0.0228 (15)	0.0063 (15)	0.0036 (12)	−0.0011 (14)
C21	0.0219 (15)	0.0275 (19)	0.0329 (17)	0.0068 (14)	0.0020 (13)	−0.0038 (15)
C22	0.0268 (15)	0.040 (2)	0.0226 (15)	−0.0134 (16)	0.0014 (12)	0.0070 (15)
C23	0.0175 (13)	0.033 (2)	0.0254 (15)	−0.0080 (14)	0.0039 (12)	−0.0035 (14)
C24	0.0191 (14)	0.0296 (19)	0.0270 (15)	0.0054 (14)	0.0008 (12)	0.0025 (14)
C25	0.0236 (14)	0.0264 (19)	0.0281 (16)	0.0018 (14)	0.0050 (12)	−0.0032 (14)
C26	0.0198 (14)	0.0272 (19)	0.0297 (16)	0.0005 (14)	−0.0022 (12)	−0.0008 (14)
C27	0.0299 (17)	0.031 (2)	0.0398 (19)	0.0139 (17)	−0.0057 (15)	−0.0049 (17)
C28	0.0289 (16)	0.028 (2)	0.0371 (18)	0.0019 (16)	0.0023 (14)	−0.0139 (16)
C29	0.0393 (19)	0.047 (2)	0.0243 (17)	0.0024 (19)	−0.0011 (14)	−0.0085 (17)
C30	0.0266 (16)	0.042 (2)	0.0385 (19)	0.0024 (17)	−0.0042 (14)	0.0112 (18)
O8	0.0234 (11)	0.0408 (15)	0.0328 (12)	−0.0059 (12)	0.0029 (9)	0.0056 (12)
C31	0.044 (2)	0.063 (3)	0.044 (2)	−0.011 (2)	0.0152 (17)	−0.014 (2)

Geometric parameters (Å, º) top

O1—C1	1.217 (3)	C13—H13A	0.9900
O2—C1	1.351 (3)	C13—H13B	0.9900
O2—C13	1.468 (3)	C14—C19	1.390 (4)
O3—C8	1.384 (4)	C14—C15	1.399 (4)
O3—C7	1.437 (4)	C15—C16	1.393 (4)
O4—C6	1.382 (4)	C15—H15A	0.9500
O4—C7	1.440 (4)	C16—C17	1.394 (4)
O5—C18	1.368 (3)	C17—C18	1.402 (3)
O5—C20	1.433 (3)	C18—C19	1.392 (4)
O6—C17	1.369 (3)	C19—H19A	0.9500
O6—H6A	0.8400	C20—H20A	0.9800
O7—C16	1.382 (3)	C20—H20B	0.9800
O7—C21	1.434 (4)	C20—H20C	0.9800
N1—C11	1.480 (4)	C21—H21A	0.9800
N1—C22	1.495 (4)	C21—H21B	0.9800
N1—H1A	0.8800	C21—H21C	0.9800
N2—C26	1.389 (4)	C22—C23	1.520 (4)
N2—C29	1.437 (5)	C22—H22A	0.9900
N2—C30	1.440 (5)	C22—H22B	0.9900
C1—C2	1.506 (4)	C23—C24	1.385 (5)
C2—C12	1.528 (4)	C23—C28	1.388 (5)
C2—C3	1.534 (4)	C24—C25	1.381 (4)
C2—H2A	1.0000	C24—H24A	0.9500
C3—C4	1.528 (4)	C25—C26	1.397 (4)
C3—C14	1.539 (4)	C25—H25A	0.9500
C3—H3A	1.0000	C26—C27	1.405 (5)
C4—C10	1.408 (4)	C27—C28	1.379 (4)
C4—C5	1.413 (4)	C27—H27A	0.9500
C5—C6	1.361 (4)	C28—H28A	0.9500
C5—H5A	0.9500	C29—H29A	0.9800
C6—C8	1.392 (4)	C29—H29B	0.9800
C7—H7A	0.9900	C29—H29C	0.9800
C7—H7B	0.9900	C30—H30A	0.9800
C8—C9	1.355 (4)	C30—H30B	0.9800
C9—C10	1.422 (4)	C30—H30C	0.9800
C9—H9A	0.9500	O8—C31	1.431 (4)
C10—C11	1.528 (4)	O8—H8A	0.8400
C11—C12	1.522 (4)	C31—H31A	0.9800
C11—H11A	1.0000	C31—H31B	0.9800
C12—C13	1.518 (4)	C31—H31C	0.9800
C12—H12A	1.0000

C1—O2—C13	109.3 (2)	C15—C14—C3	119.7 (2)
C8—O3—C7	104.5 (2)	C16—C15—C14	119.5 (3)
C6—O4—C7	104.6 (2)	C16—C15—H15A	120.2
C18—O5—C20	116.2 (2)	C14—C15—H15A	120.2
C17—O6—H6A	109.5	O7—C16—C15	125.0 (3)
C16—O7—C21	116.9 (2)	O7—C16—C17	113.6 (2)
C11—N1—C22	113.6 (2)	C15—C16—C17	121.4 (2)
C11—N1—H1A	123.2	O6—C17—C16	123.3 (2)
C22—N1—H1A	123.2	O6—C17—C18	118.0 (2)
C26—N2—C29	120.1 (3)	C16—C17—C18	118.7 (2)
C26—N2—C30	119.5 (3)	O5—C18—C19	124.1 (2)
C29—N2—C30	118.8 (3)	O5—C18—C17	116.0 (2)
O1—C1—O2	120.5 (3)	C19—C18—C17	119.8 (3)
O1—C1—C2	129.7 (3)	C14—C19—C18	121.2 (2)
O2—C1—C2	109.7 (2)	C14—C19—H19A	119.4
C1—C2—C12	102.3 (2)	C18—C19—H19A	119.4
C1—C2—C3	120.4 (2)	O5—C20—H20A	109.5
C12—C2—C3	112.5 (3)	O5—C20—H20B	109.5
C1—C2—H2A	106.9	H20A—C20—H20B	109.5
C12—C2—H2A	106.9	O5—C20—H20C	109.5
C3—C2—H2A	106.9	H20A—C20—H20C	109.5
C4—C3—C2	107.5 (2)	H20B—C20—H20C	109.5
C4—C3—C14	110.6 (2)	O7—C21—H21A	109.5
C2—C3—C14	115.2 (2)	O7—C21—H21B	109.5
C4—C3—H3A	107.8	H21A—C21—H21B	109.5
C2—C3—H3A	107.8	O7—C21—H21C	109.5
C14—C3—H3A	107.8	H21A—C21—H21C	109.5
C10—C4—C5	120.4 (3)	H21B—C21—H21C	109.5
C10—C4—C3	122.6 (3)	N1—C22—C23	112.2 (2)
C5—C4—C3	116.8 (2)	N1—C22—H22A	109.2
C6—C5—C4	118.3 (3)	C23—C22—H22A	109.2
C6—C5—H5A	120.8	N1—C22—H22B	109.2
C4—C5—H5A	120.8	C23—C22—H22B	109.2
C5—C6—O4	129.3 (3)	H22A—C22—H22B	107.9
C5—C6—C8	121.2 (3)	C24—C23—C28	117.3 (3)
O4—C6—C8	109.5 (3)	C24—C23—C22	122.8 (3)
O3—C7—O4	107.4 (2)	C28—C23—C22	119.8 (3)
O3—C7—H7A	110.2	C25—C24—C23	121.8 (3)
O4—C7—H7A	110.2	C25—C24—H24A	119.1
O3—C7—H7B	110.2	C23—C24—H24A	119.1
O4—C7—H7B	110.2	C24—C25—C26	121.1 (3)
H7A—C7—H7B	108.5	C24—C25—H25A	119.5
C9—C8—O3	127.7 (3)	C26—C25—H25A	119.5
C9—C8—C6	122.6 (3)	N2—C26—C25	121.7 (3)
O3—C8—C6	109.7 (3)	N2—C26—C27	121.2 (3)
C8—C9—C10	117.9 (3)	C25—C26—C27	117.1 (3)
C8—C9—H9A	121.0	C28—C27—C26	121.0 (3)
C10—C9—H9A	121.0	C28—C27—H27A	119.5
C4—C10—C9	119.6 (3)	C26—C27—H27A	119.5
C4—C10—C11	124.3 (3)	C27—C28—C23	121.8 (3)
C9—C10—C11	116.1 (2)	C27—C28—H28A	119.1
N1—C11—C12	114.0 (3)	C23—C28—H28A	119.1
N1—C11—C10	109.1 (2)	N2—C29—H29A	109.5
C12—C11—C10	109.6 (2)	N2—C29—H29B	109.5
N1—C11—H11A	108.0	H29A—C29—H29B	109.5
C12—C11—H11A	108.0	N2—C29—H29C	109.5
C10—C11—H11A	108.0	H29A—C29—H29C	109.5
C13—C12—C11	120.2 (2)	H29B—C29—H29C	109.5
C13—C12—C2	100.8 (2)	N2—C30—H30A	109.5
C11—C12—C2	111.4 (2)	N2—C30—H30B	109.5
C13—C12—H12A	107.9	H30A—C30—H30B	109.5
C11—C12—H12A	107.9	N2—C30—H30C	109.5
C2—C12—H12A	107.9	H30A—C30—H30C	109.5
O2—C13—C12	103.8 (2)	H30B—C30—H30C	109.5
O2—C13—H13A	111.0	C31—O8—H8A	109.5
C12—C13—H13A	111.0	O8—C31—H31A	109.5
O2—C13—H13B	111.0	O8—C31—H31B	109.5
C12—C13—H13B	111.0	H31A—C31—H31B	109.5
H13A—C13—H13B	109.0	O8—C31—H31C	109.5
C19—C14—C15	119.3 (3)	H31A—C31—H31C	109.5
C19—C14—C3	120.9 (2)	H31B—C31—H31C	109.5

C13—O2—C1—O1	175.0 (3)	C3—C2—C12—C13	164.5 (2)
C13—O2—C1—C2	−2.7 (3)	C1—C2—C12—C11	162.5 (2)
O1—C1—C2—C12	162.1 (3)	C3—C2—C12—C11	−66.8 (3)
O2—C1—C2—C12	−20.5 (3)	C1—O2—C13—C12	25.1 (3)
O1—C1—C2—C3	36.4 (5)	C11—C12—C13—O2	−158.8 (2)
O2—C1—C2—C3	−146.1 (2)	C2—C12—C13—O2	−36.0 (3)
C1—C2—C3—C4	172.5 (2)	C4—C3—C14—C19	−27.4 (4)
C12—C2—C3—C4	51.8 (3)	C2—C3—C14—C19	94.8 (3)
C1—C2—C3—C14	48.7 (3)	C4—C3—C14—C15	149.1 (3)
C12—C2—C3—C14	−72.0 (3)	C2—C3—C14—C15	−88.8 (3)
C2—C3—C4—C10	−22.5 (3)	C19—C14—C15—C16	−0.1 (4)
C14—C3—C4—C10	104.1 (3)	C3—C14—C15—C16	−176.7 (3)
C2—C3—C4—C5	162.2 (2)	C21—O7—C16—C15	7.7 (4)
C14—C3—C4—C5	−71.3 (3)	C21—O7—C16—C17	−173.9 (2)
C10—C4—C5—C6	0.7 (4)	C14—C15—C16—O7	179.2 (3)
C3—C4—C5—C6	176.2 (2)	C14—C15—C16—C17	0.9 (4)
C4—C5—C6—O4	−177.2 (3)	O7—C16—C17—O6	0.2 (4)
C4—C5—C6—C8	−1.3 (4)	C15—C16—C17—O6	178.6 (3)
C7—O4—C6—C5	−171.1 (3)	O7—C16—C17—C18	179.9 (3)
C7—O4—C6—C8	12.7 (3)	C15—C16—C17—C18	−1.7 (4)
C8—O3—C7—O4	20.3 (3)	C20—O5—C18—C19	−7.7 (4)
C6—O4—C7—O3	−20.4 (3)	C20—O5—C18—C17	172.4 (3)
C7—O3—C8—C9	170.1 (3)	O6—C17—C18—O5	1.3 (4)
C7—O3—C8—C6	−12.6 (3)	C16—C17—C18—O5	−178.5 (2)
C5—C6—C8—C9	0.8 (5)	O6—C17—C18—C19	−178.6 (3)
O4—C6—C8—C9	177.4 (3)	C16—C17—C18—C19	1.7 (4)
C5—C6—C8—O3	−176.6 (3)	C15—C14—C19—C18	0.1 (4)
O4—C6—C8—O3	−0.1 (3)	C3—C14—C19—C18	176.6 (3)
O3—C8—C9—C10	177.3 (3)	O5—C18—C19—C14	179.2 (3)
C6—C8—C9—C10	0.4 (5)	C17—C18—C19—C14	−0.9 (4)
C5—C4—C10—C9	0.4 (4)	C11—N1—C22—C23	−148.1 (3)
C3—C4—C10—C9	−174.8 (3)	N1—C22—C23—C24	−89.1 (4)
C5—C4—C10—C11	−179.2 (3)	N1—C22—C23—C28	93.5 (4)
C3—C4—C10—C11	5.6 (4)	C28—C23—C24—C25	0.7 (5)
C8—C9—C10—C4	−0.9 (4)	C22—C23—C24—C25	−176.7 (3)
C8—C9—C10—C11	178.7 (2)	C23—C24—C25—C26	0.0 (5)
C22—N1—C11—C12	−86.8 (3)	C29—N2—C26—C25	3.5 (5)
C22—N1—C11—C10	150.3 (3)	C30—N2—C26—C25	168.9 (3)
C4—C10—C11—N1	109.5 (3)	C29—N2—C26—C27	−178.5 (3)
C9—C10—C11—N1	−70.1 (3)	C30—N2—C26—C27	−13.1 (5)
C4—C10—C11—C12	−16.0 (4)	C24—C25—C26—N2	177.9 (3)
C9—C10—C11—C12	164.4 (2)	C24—C25—C26—C27	−0.2 (5)
N1—C11—C12—C13	39.2 (3)	N2—C26—C27—C28	−178.4 (4)
C10—C11—C12—C13	161.8 (2)	C25—C26—C27—C28	−0.3 (5)
N1—C11—C12—C2	−78.3 (3)	C26—C27—C28—C23	1.1 (6)
C10—C11—C12—C2	44.3 (3)	C24—C23—C28—C27	−1.2 (5)
C1—C2—C12—C13	33.8 (3)	C22—C23—C28—C27	176.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O1	0.84	1.95	2.777 (3)	170
O6—H6A···O8ⁱ	0.84	1.97	2.756 (3)	156
C7—H7B···N1ⁱⁱ	0.99	2.62	3.473 (4)	145
C13—H13B···O6ⁱⁱⁱ	0.99	2.52	3.463 (4)	159
C24—H24A···O3^iv	0.95	2.35	3.242 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₃₀H₃₂N₂O₇·CH₄O
M_r	564.62
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	11.128 (4), 8.757 (3), 15.057 (5)
β (°)	105.093 (6)
V (Å³)	1416.7 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.981, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	14990, 3602, 3167
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.107, 1.06
No. of reflections	3602
No. of parameters	377
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.36

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O1	0.84	1.95	2.777 (3)	169.9
O6—H6A···O8ⁱ	0.84	1.97	2.756 (3)	155.7
C7—H7B···N1ⁱⁱ	0.99	2.62	3.473 (4)	144.5
C13—H13B···O6ⁱⁱⁱ	0.99	2.52	3.463 (4)	158.7
C24—H24A···O3^iv	0.95	2.35	3.242 (4)	155.5

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

References

Li, Y., Wang, H., Chen, H., Chen, L.-T. & Liu, J. (2011). Acta Cryst. E67, o1538–o1539. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luo, G., Chen, H., Zhou, J., Tian, D.-L. & Zhang, S. (2011). Acta Cryst. E67, o2087. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3042

doi:10.1107/S1600536811043054

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

9-{[4-(Di­methyl­amino)­benzyl]amino}-5-(4-hy­dr­oxy-3,5-dimeth­­oxy­phenyl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

9-{[4-(Dimethylamino)benzyl]amino}-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one methanol monosolvate