1,6,6-Trimethyl-1,2,6,7,8,9-hexa­hydro­phen­anthro[1,2-b]furan-10,11-dione

Zhang, L.; Wang, J.-K.; Qu, Y.

doi:10.1107/S1600536805027303

Buy article online - an online subscription or single-article purchase is required to access this article.

1,6,6-Trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione

L. Zhang, J.-K. Wang and Y. Qu

The title compound, C₁₉H₂₀O₃, is widely used in China to treat coronary heart diseases. The asymmetric unit contains two independent molecules in which both the five- and the terminal six-membered rings adopt half-chair conformations.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027303/ci6603sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027303/ci6603Isup2.hkl Contains datablock I

CCDC reference: 287504

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.047
wR factor = 0.132
Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C19
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H21B   ..  H23D    ..       1.73 Ang.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.67 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C24'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
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        C17
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C30    -C32           1.45 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C30    -C32           0.22 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C11    -C13           0.22 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C33    -   C34    ...       1.56 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C14    -   C15    ...       1.55 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               3906
           Count of symmetry unique reflns         3921
           Completeness (_total/calc)             99.62%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

Comment top

The title compound, (I), the main active component isolated from the rhizome of Salvia miltiorrhiza Bunge and Salvia przewalskii Maxim (Labiatae), has been used widely in China to treat coronary heart diseases, particularly angina pectoris and myocardial infarction (Xue et al., 1999). We report here the crystal strucure of (I).

The asymmetric unit of (I) contains two crystallographically independent molecules (Fig. 1). The corresponding bond lengths and angles of these two molecules agree with each other (Table 1). The C14—C15 and C33—C34 bond distances agree with the corresponding distance of 1.5628 (19) Å, reported for 8,9-dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione (Qin et al., 2005). In one of the moleules, the cyclohexene ring A is disordered. In both molecules, ring A adopts a half-chair conformation and the five-membered ring D adopts a distorted half-chair conformation. Intramolecular C—H···O hydrogen bonds are observed in the molecular structure (Table 2), but no intermolecular hydrogen bonding is observed in the crystal structure.

Experimental top

Compound (I) was obtained from the Tasly Group, a pharmaceutical company in Tianjin. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The asymmetric unit of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. In one of the molecules, both components of the disodered cyclohexene ring are shown.

1,6,6-Trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione top

Crystal data top

C₁₉H₂₀O₃	D_x = 1.291 Mg m⁻³
M_r = 296.35	Melting point: 460.2 K
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 29524 reflections
a = 14.458 (3) Å	θ = 3.1–27.5°
b = 21.356 (4) Å	µ = 0.09 mm⁻¹
c = 9.874 (2) Å	T = 293 K
V = 3048.7 (11) Å³	Plate, orange
Z = 8	0.67 × 0.23 × 0.06 mm
F(000) = 1264

Data collection top

Rigaku R-axis rapid IP area-detector diffractometer	3906 independent reflections
Radiation source: rotating anode	2348 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
oscillation scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	h = −16→18
T_min = 0.945, T_max = 0.995	k = −27→27
29524 measured reflections	l = −12→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0861P)²] where P = (F_o² + 2F_c²)/3
3906 reflections	(Δ/σ)_max = 0.001
416 parameters	Δρ_max = 0.17 e Å⁻³
45 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₂₀O₃	V = 3048.7 (11) Å³
M_r = 296.35	Z = 8
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 14.458 (3) Å	µ = 0.09 mm⁻¹
b = 21.356 (4) Å	T = 293 K
c = 9.874 (2) Å	0.67 × 0.23 × 0.06 mm

Data collection top

Rigaku R-axis rapid IP area-detector diffractometer	3906 independent reflections
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	2348 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.995	R_int = 0.050
29524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	45 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 0.91	Δρ_max = 0.17 e Å⁻³
3906 reflections	Δρ_min = −0.17 e Å⁻³
416 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	Occ. (<1)
O1	0.87137 (19)	1.00832 (10)	0.2624 (2)	0.0803 (7)
O2	0.90714 (18)	1.08203 (9)	0.7756 (2)	0.0778 (7)
O3	0.8790 (2)	1.16690 (9)	0.5785 (3)	0.0920 (8)
O4	0.89413 (15)	0.36548 (8)	0.4585 (2)	0.0660 (6)
O5	0.85608 (18)	0.58846 (10)	0.6978 (2)	0.0824 (7)
O6	0.8791 (2)	0.48509 (11)	0.8459 (2)	0.0984 (9)
C1	0.7585 (3)	0.79976 (16)	0.7912 (5)	0.1037 (14)
H1A	0.7478	0.7857	0.7002	0.155*
H1B	0.7114	0.8292	0.8166	0.155*
H1C	0.7569	0.7646	0.8517	0.155*
C2	0.9283 (3)	0.78243 (15)	0.7692 (5)	0.0988 (13)
H2A	0.9188	0.7652	0.6805	0.148*
H2B	0.9256	0.7495	0.8353	0.148*
H2C	0.9878	0.8023	0.7730	0.148*
C3	0.8525 (2)	0.83106 (13)	0.7995 (4)	0.0652 (8)
C4	0.8728 (3)	0.85530 (16)	0.9435 (4)	0.0942 (12)
H4A	0.8523	0.8243	1.0086	0.113*
H4B	0.9391	0.8602	0.9541	0.113*
C5	0.8274 (3)	0.91526 (16)	0.9738 (4)	0.0973 (13)
H5A	0.8384	0.9262	1.0678	0.117*
H5B	0.7612	0.9111	0.9608	0.117*
C6	0.8640 (3)	0.96649 (14)	0.8836 (3)	0.0685 (8)
H6A	0.9260	0.9774	0.9125	0.082*
H6B	0.8254	1.0034	0.8942	0.082*
C7	0.86645 (18)	0.94856 (12)	0.7356 (3)	0.0502 (6)
C8	0.85864 (19)	0.88477 (12)	0.6973 (3)	0.0563 (7)
C9	0.8555 (2)	0.87038 (12)	0.5608 (3)	0.0673 (8)
H9A	0.8490	0.8286	0.5360	0.081*
C10	0.8614 (2)	0.91450 (12)	0.4600 (3)	0.0642 (8)
H10A	0.8589	0.9028	0.3693	0.077*
C11	0.8712 (2)	0.97691 (12)	0.4965 (3)	0.0501 (6)
C12	0.8749 (2)	1.02556 (13)	0.3934 (3)	0.0570 (7)
C13	0.87488 (18)	0.99414 (12)	0.6333 (3)	0.0475 (6)
C14	0.88794 (19)	1.06275 (12)	0.6644 (3)	0.0568 (7)
C15	0.8813 (2)	1.11134 (12)	0.5476 (3)	0.0625 (8)
C16	0.8785 (2)	1.08752 (12)	0.4132 (3)	0.0583 (7)
C17	0.8720 (3)	1.12087 (15)	0.2798 (4)	0.0752 (9)
H17A	0.8104	1.1397	0.2721	0.090*
C18	0.9440 (3)	1.17106 (18)	0.2544 (5)	0.1051 (14)
H18A	0.9360	1.2044	0.3186	0.158*
H18B	0.9368	1.1872	0.1642	0.158*
H18C	1.0046	1.1534	0.2642	0.158*
C19	0.8778 (4)	1.06611 (17)	0.1834 (4)	0.1090 (14)
H19A	0.8276	1.0681	0.1183	0.131*
H19B	0.9359	1.0673	0.1344	0.131*
C20	0.7971 (3)	0.6300 (2)	0.0532 (5)	0.1083 (15)
H20A	0.8064	0.5920	0.0030	0.162*
H20B	0.7985	0.6651	−0.0075	0.162*
H20C	0.7382	0.6285	0.0980	0.162*
C21	0.9633 (3)	0.6368 (2)	0.0785 (6)	0.141 (2)
H21A	0.9708	0.5971	0.0341	0.212*
H21B	1.0141	0.6436	0.1393	0.212*
H21C	0.9620	0.6696	0.0119	0.212*
C22	0.8731 (2)	0.63695 (13)	0.1577 (3)	0.0666 (8)
C23	0.8410 (6)	0.6974 (3)	0.2320 (8)	0.086 (2)	0.646 (13)
H23A	0.8505	0.7333	0.1736	0.104*	0.646 (13)
H23B	0.7755	0.6944	0.2519	0.104*	0.646 (13)
C24	0.8945 (7)	0.7062 (3)	0.3624 (6)	0.087 (2)	0.646 (13)
H24A	0.8815	0.7471	0.4009	0.105*	0.646 (13)
H24B	0.9604	0.7031	0.3455	0.105*	0.646 (13)
C23'	0.9006 (11)	0.6972 (5)	0.2264 (11)	0.084 (4)	0.354 (13)
H23C	0.8919	0.7322	0.1653	0.101*	0.354 (13)
H23D	0.9652	0.6956	0.2526	0.101*	0.354 (13)
C24'	0.8397 (10)	0.7050 (6)	0.3515 (13)	0.095 (5)	0.354 (13)
H24C	0.7751	0.7010	0.3260	0.114*	0.354 (13)
H24D	0.8488	0.7464	0.3896	0.114*	0.354 (13)
C25	0.8637 (3)	0.65498 (12)	0.4585 (3)	0.0707 (9)
H25A	0.9019	0.6566	0.5392	0.085*	0.646 (13)
H25B	0.8004	0.6631	0.4857	0.085*	0.646 (13)
H25C	0.8152	0.6552	0.5249	0.085*	0.354 (13)
H25D	0.9207	0.6635	0.5051	0.085*	0.354 (13)
C26	0.86932 (19)	0.59014 (11)	0.3991 (3)	0.0513 (6)
C27	0.87235 (19)	0.58157 (12)	0.2578 (3)	0.0537 (6)
C28	0.8763 (2)	0.52137 (12)	0.2052 (3)	0.0580 (7)
H28A	0.8766	0.5159	0.1117	0.070*
C29	0.8798 (2)	0.46961 (12)	0.2876 (3)	0.0564 (7)
H29A	0.8831	0.4298	0.2499	0.068*
C30	0.87851 (18)	0.47673 (11)	0.4262 (3)	0.0469 (6)
C31	0.88620 (18)	0.42247 (12)	0.5161 (3)	0.0520 (6)
C32	0.87149 (18)	0.53666 (12)	0.4848 (3)	0.0465 (6)
C33	0.8676 (2)	0.53998 (12)	0.6358 (3)	0.0551 (7)
C34	0.8794 (2)	0.47976 (14)	0.7229 (3)	0.0634 (8)
C35	0.88841 (19)	0.42228 (13)	0.6515 (3)	0.0557 (7)
C36	0.9037 (2)	0.35655 (14)	0.7008 (4)	0.0688 (9)
H36A	0.9681	0.3522	0.7302	0.083*
C37	0.8407 (3)	0.33347 (18)	0.8133 (4)	0.0949 (12)
H37A	0.8514	0.3577	0.8937	0.142*
H37B	0.8536	0.2902	0.8315	0.142*
H37C	0.7774	0.3379	0.7858	0.142*
C38	0.8905 (3)	0.32022 (13)	0.5693 (4)	0.0748 (9)
H38A	0.9390	0.2892	0.5589	0.090*
H38B	0.8313	0.2989	0.5697	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1163 (19)	0.0702 (13)	0.0542 (14)	−0.0031 (14)	−0.0071 (14)	0.0004 (11)
O2	0.1061 (17)	0.0592 (11)	0.0681 (15)	−0.0132 (11)	−0.0104 (13)	−0.0148 (11)
O3	0.133 (2)	0.0405 (10)	0.1023 (18)	−0.0057 (13)	−0.0156 (19)	−0.0045 (11)
O4	0.0867 (14)	0.0445 (9)	0.0670 (13)	0.0036 (10)	0.0046 (12)	0.0030 (9)
O5	0.1092 (18)	0.0710 (13)	0.0669 (14)	0.0181 (13)	−0.0038 (14)	−0.0189 (11)
O6	0.158 (3)	0.0908 (17)	0.0465 (14)	−0.0002 (18)	−0.0037 (17)	−0.0029 (12)
C1	0.095 (3)	0.083 (2)	0.133 (4)	−0.019 (2)	0.000 (3)	0.035 (3)
C2	0.109 (3)	0.070 (2)	0.117 (3)	0.026 (2)	0.015 (3)	0.028 (2)
C3	0.0714 (19)	0.0483 (14)	0.076 (2)	0.0034 (14)	0.0042 (17)	0.0102 (15)
C4	0.130 (3)	0.078 (2)	0.075 (3)	0.009 (2)	0.006 (3)	0.0202 (19)
C5	0.150 (4)	0.080 (2)	0.063 (2)	−0.015 (2)	0.002 (2)	0.0052 (19)
C6	0.084 (2)	0.0634 (17)	0.0578 (19)	−0.0054 (18)	−0.0063 (17)	−0.0021 (14)
C7	0.0450 (13)	0.0491 (13)	0.0564 (17)	−0.0009 (12)	−0.0032 (13)	−0.0014 (12)
C8	0.0581 (16)	0.0465 (13)	0.064 (2)	0.0046 (13)	0.0000 (15)	0.0032 (13)
C9	0.089 (2)	0.0416 (13)	0.071 (2)	0.0001 (14)	0.0040 (19)	−0.0086 (14)
C10	0.084 (2)	0.0517 (15)	0.0565 (18)	−0.0027 (16)	0.0024 (17)	−0.0100 (14)
C11	0.0478 (14)	0.0486 (13)	0.0537 (17)	0.0031 (13)	−0.0037 (13)	−0.0020 (12)
C12	0.0510 (15)	0.0619 (16)	0.0582 (18)	0.0014 (14)	−0.0030 (14)	−0.0029 (13)
C13	0.0411 (14)	0.0437 (12)	0.0577 (17)	0.0020 (12)	−0.0041 (13)	−0.0042 (11)
C14	0.0539 (16)	0.0499 (14)	0.067 (2)	−0.0017 (12)	−0.0048 (15)	−0.0074 (13)
C15	0.0637 (17)	0.0456 (13)	0.078 (2)	−0.0006 (14)	−0.0039 (18)	0.0001 (14)
C16	0.0604 (17)	0.0502 (14)	0.0644 (18)	−0.0010 (14)	−0.0039 (16)	0.0041 (14)
C17	0.081 (2)	0.0687 (18)	0.075 (2)	−0.0035 (18)	−0.003 (2)	0.0175 (17)
C18	0.111 (3)	0.098 (3)	0.107 (3)	−0.028 (2)	0.009 (3)	0.031 (3)
C19	0.177 (4)	0.079 (2)	0.071 (2)	−0.001 (3)	−0.005 (3)	0.0157 (19)
C20	0.112 (3)	0.113 (3)	0.100 (3)	−0.013 (2)	−0.034 (3)	0.050 (3)
C21	0.106 (3)	0.155 (4)	0.163 (5)	0.012 (3)	0.031 (3)	0.101 (4)
C22	0.0753 (19)	0.0524 (14)	0.072 (2)	−0.0007 (16)	−0.0065 (19)	0.0109 (14)
C23	0.106 (5)	0.057 (3)	0.096 (5)	0.003 (4)	−0.016 (4)	0.020 (3)
C24	0.127 (6)	0.047 (3)	0.087 (4)	−0.006 (4)	−0.003 (4)	−0.005 (3)
C23'	0.113 (8)	0.050 (5)	0.089 (7)	−0.018 (6)	−0.013 (6)	0.018 (5)
C24'	0.103 (8)	0.066 (6)	0.115 (9)	−0.004 (7)	0.000 (7)	−0.003 (6)
C25	0.087 (2)	0.0517 (15)	0.074 (2)	0.0005 (17)	−0.006 (2)	−0.0079 (15)
C26	0.0453 (14)	0.0453 (13)	0.0632 (18)	0.0011 (13)	−0.0035 (13)	−0.0039 (12)
C27	0.0541 (15)	0.0523 (13)	0.0547 (17)	−0.0041 (14)	−0.0042 (14)	0.0040 (13)
C28	0.0704 (18)	0.0544 (15)	0.0492 (16)	−0.0021 (15)	−0.0022 (16)	−0.0080 (12)
C29	0.0639 (17)	0.0476 (13)	0.0578 (17)	−0.0018 (14)	0.0033 (15)	−0.0078 (12)
C30	0.0443 (14)	0.0452 (13)	0.0513 (15)	0.0015 (12)	−0.0003 (13)	−0.0032 (12)
C31	0.0467 (14)	0.0467 (13)	0.0628 (18)	−0.0002 (13)	0.0012 (13)	−0.0003 (12)
C32	0.0390 (12)	0.0509 (14)	0.0497 (16)	0.0005 (12)	0.0002 (12)	−0.0044 (11)
C33	0.0527 (16)	0.0580 (16)	0.0545 (17)	0.0051 (15)	−0.0007 (14)	−0.0084 (13)
C34	0.0671 (19)	0.0698 (18)	0.0531 (19)	−0.0019 (16)	0.0013 (16)	0.0003 (15)
C35	0.0574 (17)	0.0566 (15)	0.0530 (18)	0.0010 (13)	0.0004 (14)	0.0060 (13)
C36	0.0674 (19)	0.0671 (18)	0.072 (2)	0.0037 (15)	0.0031 (17)	0.0165 (16)
C37	0.108 (3)	0.088 (2)	0.089 (3)	0.002 (2)	0.030 (2)	0.020 (2)
C38	0.092 (2)	0.0521 (15)	0.081 (2)	0.0017 (16)	0.005 (2)	0.0134 (16)

Geometric parameters (Å, º) top

O1—C12	1.346 (4)	C20—H20A	0.96
O1—C19	1.463 (4)	C20—H20B	0.96
O2—C14	1.205 (3)	C20—H20C	0.96
O3—C15	1.226 (3)	C21—C22	1.521 (6)
O4—C31	1.348 (3)	C21—H21A	0.96
O4—C38	1.461 (4)	C21—H21B	0.96
O5—C33	1.214 (3)	C21—H21C	0.96
O6—C34	1.219 (4)	C22—C23'	1.507 (8)
C1—C3	1.516 (5)	C22—C27	1.541 (4)
C1—H1A	0.96	C22—C23	1.555 (6)
C1—H1B	0.96	C23—C24	1.514 (7)
C1—H1C	0.96	C23—H23A	0.97
C2—C3	1.539 (4)	C23—H23B	0.97
C2—H2A	0.96	C24—C25	1.515 (6)
C2—H2B	0.96	C24—H24A	0.97
C2—H2C	0.96	C24—H24B	0.97
C3—C8	1.530 (4)	C23'—C24'	1.526 (9)
C3—C4	1.541 (5)	C23'—H23C	0.97
C4—C5	1.469 (5)	C23'—H23D	0.97
C4—H4A	0.97	C24'—C25	1.542 (8)
C4—H4B	0.97	C24'—H24C	0.97
C5—C6	1.507 (5)	C24'—H24D	0.97
C5—H5A	0.97	C25—C26	1.506 (4)
C5—H5B	0.97	C25—H25A	0.97
C6—C7	1.511 (4)	C25—H25B	0.97
C6—H6A	0.97	C25—H25C	0.96
C6—H6B	0.97	C25—H25D	0.96
C7—C13	1.407 (4)	C26—C27	1.408 (4)
C7—C8	1.418 (4)	C26—C32	1.422 (4)
C8—C9	1.383 (4)	C27—C28	1.388 (4)
C9—C10	1.373 (4)	C28—C29	1.374 (4)
C9—H9A	0.93	C28—H28A	0.93
C10—C11	1.388 (4)	C29—C30	1.376 (4)
C10—H10A	0.93	C29—H29A	0.93
C11—C13	1.401 (4)	C30—C32	1.408 (3)
C11—C12	1.455 (4)	C30—C31	1.464 (4)
C12—C16	1.339 (4)	C31—C35	1.338 (4)
C13—C14	1.509 (4)	C32—C33	1.494 (4)
C14—C15	1.554 (4)	C33—C34	1.557 (4)
C15—C16	1.421 (4)	C34—C35	1.422 (4)
C16—C17	1.501 (4)	C35—C36	1.502 (4)
C17—C19	1.510 (5)	C36—C37	1.519 (5)
C17—C18	1.515 (5)	C36—C38	1.525 (5)
C17—H17A	0.98	C36—H36A	0.98
C18—H18A	0.96	C37—H37A	0.96
C18—H18B	0.96	C37—H37B	0.96
C18—H18C	0.96	C37—H37C	0.96
C19—H19A	0.97	C38—H38A	0.97
C19—H19B	0.97	C38—H38B	0.97
C20—C22	1.515 (5)

C12—O1—C19	106.2 (2)	C23'—C22—C21	90.4 (6)
C31—O4—C38	106.2 (2)	C20—C22—C21	105.8 (3)
C3—C1—H1A	109.5	C23'—C22—C27	111.6 (5)
C3—C1—H1B	109.5	C20—C22—C27	110.9 (3)
H1A—C1—H1B	109.5	C21—C22—C27	109.6 (3)
C3—C1—H1C	109.5	C20—C22—C23	100.7 (4)
H1A—C1—H1C	109.5	C21—C22—C23	120.0 (5)
H1B—C1—H1C	109.5	C27—C22—C23	109.4 (4)
C3—C2—H2A	109.5	C24—C23—C22	110.6 (6)
C3—C2—H2B	109.5	C24—C23—H23A	109.5
H2A—C2—H2B	109.5	C22—C23—H23A	109.5
C3—C2—H2C	109.5	C24—C23—H23B	109.5
H2A—C2—H2C	109.5	C22—C23—H23B	109.5
H2B—C2—H2C	109.5	H23A—C23—H23B	108.1
C1—C3—C8	110.3 (3)	C23—C24—C25	107.0 (6)
C1—C3—C2	109.3 (3)	C23—C24—H24A	110.3
C8—C3—C2	109.7 (3)	C25—C24—H24A	110.3
C1—C3—C4	111.6 (3)	C23—C24—H24B	110.3
C8—C3—C4	110.2 (2)	C25—C24—H24B	110.3
C2—C3—C4	105.7 (3)	H24A—C24—H24B	108.6
C5—C4—C3	113.4 (3)	C22—C23'—C24'	107.8 (11)
C5—C4—H4A	108.9	C22—C23'—H23C	110.1
C3—C4—H4A	108.9	C24'—C23'—H23C	110.1
C5—C4—H4B	108.9	C22—C23'—H23D	110.1
C3—C4—H4B	108.9	C24'—C23'—H23D	110.1
H4A—C4—H4B	107.7	H23C—C23'—H23D	108.5
C4—C5—C6	110.8 (3)	C23'—C24'—C25	110.4 (9)
C4—C5—H5A	109.5	C23'—C24'—H24C	109.6
C6—C5—H5A	109.5	C25—C24'—H24C	109.6
C4—C5—H5B	109.5	C23'—C24'—H24D	109.6
C6—C5—H5B	109.5	C25—C24'—H24D	109.6
H5A—C5—H5B	108.1	H24C—C24'—H24D	108.1
C5—C6—C7	113.4 (3)	C26—C25—C24	113.8 (4)
C5—C6—H6A	108.9	C26—C25—C24'	112.5 (7)
C7—C6—H6A	108.9	C26—C25—H25A	108.8
C5—C6—H6B	108.9	C24—C25—H25A	108.8
C7—C6—H6B	108.9	C24'—C25—H25A	131.8
H6A—C6—H6B	107.7	C26—C25—H25B	108.8
C13—C7—C8	118.7 (3)	C24—C25—H25B	108.8
C13—C7—C6	121.4 (2)	C24'—C25—H25B	81.6
C8—C7—C6	120.0 (2)	H25A—C25—H25B	107.7
C9—C8—C7	118.4 (3)	C26—C25—H25C	108.0
C9—C8—C3	118.3 (2)	C24—C25—H25C	129.7
C7—C8—C3	123.3 (3)	C24'—C25—H25C	107.4
C10—C9—C8	123.5 (3)	H25A—C25—H25C	81.7
C10—C9—H9A	118.3	C26—C25—H25D	108.3
C8—C9—H9A	118.3	C24—C25—H25D	84.9
C9—C10—C11	118.5 (3)	C24'—C25—H25D	113.0
C9—C10—H10A	120.8	H25B—C25—H25D	130.0
C11—C10—H10A	120.8	H25C—C25—H25D	107.4
C10—C11—C13	120.4 (3)	C27—C26—C32	119.0 (2)
C10—C11—C12	120.5 (3)	C27—C26—C25	120.5 (2)
C13—C11—C12	119.0 (2)	C32—C26—C25	120.5 (3)
C16—C12—O1	114.4 (3)	C28—C27—C26	119.5 (2)
C16—C12—C11	127.2 (3)	C28—C27—C22	118.1 (3)
O1—C12—C11	118.4 (2)	C26—C27—C22	122.4 (2)
C11—C13—C7	120.4 (2)	C29—C28—C27	121.6 (3)
C11—C13—C14	117.1 (2)	C29—C28—H28A	119.2
C7—C13—C14	122.4 (2)	C27—C28—H28A	119.2
O2—C14—C13	123.1 (3)	C28—C29—C30	120.0 (2)
O2—C14—C15	117.5 (2)	C28—C29—H29A	120.0
C13—C14—C15	119.3 (3)	C30—C29—H29A	120.0
O3—C15—C16	125.3 (3)	C29—C30—C32	120.7 (2)
O3—C15—C14	117.6 (3)	C29—C30—C31	120.9 (2)
C16—C15—C14	117.1 (2)	C32—C30—C31	118.4 (2)
C12—C16—C15	119.4 (3)	C35—C31—O4	114.6 (3)
C12—C16—C17	109.8 (3)	C35—C31—C30	127.6 (3)
C15—C16—C17	130.6 (3)	O4—C31—C30	117.8 (2)
C16—C17—C19	100.5 (3)	C30—C32—C26	119.1 (2)
C16—C17—C18	116.0 (3)	C30—C32—C33	117.1 (2)
C19—C17—C18	113.9 (4)	C26—C32—C33	123.7 (2)
C16—C17—H17A	108.7	O5—C33—C32	123.3 (3)
C19—C17—H17A	108.7	O5—C33—C34	116.2 (3)
C18—C17—H17A	108.7	C32—C33—C34	120.5 (2)
C17—C18—H18A	109.5	O6—C34—C35	125.1 (3)
C17—C18—H18B	109.5	O6—C34—C33	118.2 (3)
H18A—C18—H18B	109.5	C35—C34—C33	116.7 (3)
C17—C18—H18C	109.5	C31—C35—C34	119.4 (3)
H18A—C18—H18C	109.5	C31—C35—C36	109.3 (3)
H18B—C18—H18C	109.5	C34—C35—C36	131.3 (3)
O1—C19—C17	108.3 (3)	C35—C36—C37	116.9 (3)
O1—C19—H19A	110.0	C35—C36—C38	100.4 (2)
C17—C19—H19A	110.0	C37—C36—C38	112.5 (3)
O1—C19—H19B	110.0	C35—C36—H36A	108.9
C17—C19—H19B	110.0	C37—C36—H36A	108.9
H19A—C19—H19B	108.4	C38—C36—H36A	108.9
C22—C20—H20A	109.5	C36—C37—H37A	109.5
C22—C20—H20B	109.5	C36—C37—H37B	109.5
H20A—C20—H20B	109.5	H37A—C37—H37B	109.5
C22—C20—H20C	109.5	C36—C37—H37C	109.5
H20A—C20—H20C	109.5	H37A—C37—H37C	109.5
H20B—C20—H20C	109.5	H37B—C37—H37C	109.5
C22—C21—H21A	109.5	O4—C38—C36	107.2 (2)
C22—C21—H21B	109.5	O4—C38—H38A	110.3
H21A—C21—H21B	109.5	C36—C38—H38A	110.3
C22—C21—H21C	109.5	O4—C38—H38B	110.3
H21A—C21—H21C	109.5	C36—C38—H38B	110.3
H21B—C21—H21C	109.5	H38A—C38—H38B	108.5
C23'—C22—C20	125.5 (7)

C1—C3—C4—C5	−79.9 (4)	C27—C22—C23'—C24'	−51.4 (13)
C8—C3—C4—C5	43.0 (4)	C23—C22—C23'—C24'	41.1 (8)
C2—C3—C4—C5	161.5 (3)	C22—C23'—C24'—C25	68.3 (18)
C3—C4—C5—C6	−64.0 (5)	C23—C24—C25—C26	52.1 (8)
C4—C5—C6—C7	48.4 (5)	C23—C24—C25—C24'	−42.0 (12)
C5—C6—C7—C13	163.2 (3)	C23'—C24'—C25—C26	−48.0 (15)
C5—C6—C7—C8	−15.8 (5)	C23'—C24'—C25—C24	51.2 (9)
C13—C7—C8—C9	−2.9 (4)	C24—C25—C26—C27	−19.9 (6)
C6—C7—C8—C9	176.1 (3)	C24'—C25—C26—C27	13.1 (7)
C13—C7—C8—C3	177.8 (3)	C24—C25—C26—C32	160.2 (4)
C6—C7—C8—C3	−3.2 (4)	C24'—C25—C26—C32	−166.8 (6)
C1—C3—C8—C9	−65.3 (4)	C32—C26—C27—C28	0.7 (4)
C2—C3—C8—C9	55.0 (4)	C25—C26—C27—C28	−179.2 (3)
C4—C3—C8—C9	171.0 (3)	C32—C26—C27—C22	−178.2 (2)
C1—C3—C8—C7	114.0 (4)	C25—C26—C27—C22	1.9 (5)
C2—C3—C8—C7	−125.6 (3)	C23'—C22—C27—C28	−160.8 (7)
C4—C3—C8—C7	−9.7 (4)	C20—C22—C27—C28	54.1 (4)
C7—C8—C9—C10	1.4 (5)	C21—C22—C27—C28	−62.2 (4)
C3—C8—C9—C10	−179.3 (3)	C23—C22—C27—C28	164.3 (4)
C8—C9—C10—C11	0.1 (5)	C23'—C22—C27—C26	18.1 (8)
C9—C10—C11—C13	0.0 (5)	C20—C22—C27—C26	−127.0 (3)
C9—C10—C11—C12	−178.1 (3)	C21—C22—C27—C26	116.7 (4)
C19—O1—C12—C16	3.0 (5)	C23—C22—C27—C26	−16.8 (5)
C19—O1—C12—C11	−179.2 (3)	C26—C27—C28—C29	−1.7 (5)
C10—C11—C12—C16	175.6 (3)	C22—C27—C28—C29	177.2 (3)
C13—C11—C12—C16	−2.6 (5)	C27—C28—C29—C30	0.7 (5)
C10—C11—C12—O1	−1.9 (5)	C28—C29—C30—C32	1.4 (4)
C13—C11—C12—O1	179.9 (3)	C28—C29—C30—C31	−177.3 (3)
C10—C11—C13—C7	−1.6 (5)	C38—O4—C31—C35	7.3 (3)
C12—C11—C13—C7	176.6 (3)	C38—O4—C31—C30	−174.1 (2)
C10—C11—C13—C14	178.5 (3)	C29—C30—C31—C35	178.1 (3)
C12—C11—C13—C14	−3.3 (4)	C32—C30—C31—C35	−0.7 (4)
C8—C7—C13—C11	3.0 (4)	C29—C30—C31—O4	−0.3 (4)
C6—C7—C13—C11	−175.9 (3)	C32—C30—C31—O4	−179.1 (2)
C8—C7—C13—C14	−177.1 (2)	C29—C30—C32—C26	−2.4 (4)
C6—C7—C13—C14	3.9 (4)	C31—C30—C32—C26	176.4 (2)
C11—C13—C14—O2	−167.5 (3)	C29—C30—C32—C33	178.1 (3)
C7—C13—C14—O2	12.6 (4)	C31—C30—C32—C33	−3.0 (4)
C11—C13—C14—C15	9.4 (4)	C27—C26—C32—C30	1.3 (4)
C7—C13—C14—C15	−170.5 (3)	C25—C26—C32—C30	−178.8 (3)
O2—C14—C15—O3	−13.0 (4)	C27—C26—C32—C33	−179.3 (3)
C13—C14—C15—O3	169.8 (3)	C25—C26—C32—C33	0.6 (4)
O2—C14—C15—C16	166.8 (3)	C30—C32—C33—O5	−175.5 (3)
C13—C14—C15—C16	−10.3 (4)	C26—C32—C33—O5	5.0 (5)
O1—C12—C16—C15	179.2 (3)	C30—C32—C33—C34	5.1 (4)
C11—C12—C16—C15	1.6 (5)	C26—C32—C33—C34	−174.3 (3)
O1—C12—C16—C17	3.2 (4)	O5—C33—C34—O6	−2.1 (5)
C11—C12—C16—C17	−174.4 (3)	C32—C33—C34—O6	177.3 (3)
O3—C15—C16—C12	−175.4 (3)	O5—C33—C34—C35	177.0 (3)
C14—C15—C16—C12	4.8 (5)	C32—C33—C34—C35	−3.6 (4)
O3—C15—C16—C17	−0.3 (6)	O4—C31—C35—C34	−179.2 (2)
C14—C15—C16—C17	179.8 (3)	C30—C31—C35—C34	2.4 (5)
C12—C16—C17—C19	−7.6 (4)	O4—C31—C35—C36	2.5 (4)
C15—C16—C17—C19	177.0 (4)	C30—C31—C35—C36	−176.0 (3)
C12—C16—C17—C18	−130.9 (3)	O6—C34—C35—C31	178.9 (4)
C15—C16—C17—C18	53.7 (5)	C33—C34—C35—C31	−0.1 (4)
C12—O1—C19—C17	−7.9 (5)	O6—C34—C35—C36	−3.2 (6)
C16—C17—C19—O1	9.1 (4)	C33—C34—C35—C36	177.8 (3)
C18—C17—C19—O1	133.9 (4)	C31—C35—C36—C37	−132.5 (3)
C23'—C22—C23—C24	−49.6 (9)	C34—C35—C36—C37	49.5 (5)
C20—C22—C23—C24	167.2 (7)	C31—C35—C36—C38	−10.5 (3)
C21—C22—C23—C24	−77.4 (8)	C34—C35—C36—C38	171.4 (3)
C27—C22—C23—C24	50.4 (8)	C31—O4—C38—C36	−13.9 (3)
C22—C23—C24—C25	−69.1 (10)	C35—C36—C38—O4	14.5 (3)
C20—C22—C23'—C24'	87.4 (11)	C37—C36—C38—O4	139.5 (3)
C21—C22—C23'—C24'	−162.7 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O2	0.97	2.36	2.760 (4)	104
C25—H25A···O5	0.97	2.24	2.759 (4)	113
C29—H29A···O4	0.93	2.48	2.799 (3)	100

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₃
M_r	296.35
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	14.458 (3), 21.356 (4), 9.874 (2)
V (Å³)	3048.7 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.67 × 0.23 × 0.06

Data collection
Diffractometer	Rigaku R-axis rapid IP area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (ABSCOR; Higashi, 1995)
T_min, T_max	0.945, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	29524, 3906, 2348
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 0.91
No. of reflections	3906
No. of parameters	416
No. of restraints	45
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected bond lengths (Å) top

O1—C12	1.346 (4)	O5—C33	1.214 (3)
O1—C19	1.463 (4)	O6—C34	1.219 (4)
O2—C14	1.205 (3)	C12—C16	1.339 (4)
O3—C15	1.226 (3)	C14—C15	1.554 (4)
O4—C31	1.348 (3)	C31—C35	1.338 (4)
O4—C38	1.461 (4)	C33—C34	1.557 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O2	0.97	2.36	2.760 (4)	104
C25—H25A···O5	0.97	2.24	2.759 (4)	113
C29—H29A···O4	0.93	2.48	2.799 (3)	100

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page