Paxdaphnine B: a 1,19-bis­nor-daphniphyllum alkaloid

Lu, Y.-B.; Kong, N.-C.; Feng, Y.-Y.; Hao, X.-J.; Lu, Y.

doi:10.1107/S1600536806055826

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

Paxdaphnine B: a 1,19-bisnor-daphniphyllum alkaloid

Y.-B. Lu, N.-C. Kong, Y.-Y. Feng, X.-J. Hao and Y. Lu

The title compound, methyl 5-ethyl-2-methoxy-6-azapentacyclo[9.5.1.0^1,5.0^2,8.0^14,17]heptadec-11 (17)-ene-15-carboxylate, C₂₁H₃₁NO₃, obtained from the fruits of Daphniphyllum macropodum, is a newly identified alkaloid with a complex polycyclic skeleton. It crystallizes with two unique molecules in the asymmetric unit that differ in the orientation of the hydroxyl group. The molecules are linked into chains along the a axis by intermolecular O—H

N hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055826/sj2204sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055826/sj2204Isup2.hkl Contains datablock I

CCDC reference: 636807

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.052
wR factor = 0.137
Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.39
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1'    -   H1'B   ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

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           25.44
           From the CIF: _reflns_number_total               3431
           Count of symmetry unique reflns         3484
           Completeness (_total/calc)             98.48%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6'    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14'   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15'   = .          R

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

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

methyl 5-ethyl-2-methoxy-6-azapentacyclo[9.5.1.0^1,5.0^2,8.0^14,17]heptadec- 11 (17)-ene-15-carboxylate top

Crystal data top

C₂₁H₃₁NO₃	F(000) = 752
M_r = 345.47	D_x = 1.251 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3431 reflections
a = 7.7500 (15) Å	θ = 2.1–25.4°
b = 24.717 (3) Å	µ = 0.08 mm⁻¹
c = 9.605 (2) Å	T = 295 K
β = 94.619 (7)°	Prism, colorless
V = 1833.9 (5) Å³	0.50 × 0.20 × 0.20 mm
Z = 4

Data collection top

MAC DIP 2030K diffractometer	3019 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.035
Graphite monochromator	θ_max = 25.4°, θ_min = 2.1°
Detector resolution: 0 pixels mm^-1	h = −9→9
ω scans	k = −29→29
10725 measured reflections	l = −11→11
3431 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0864P)² + 0.2863P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.004
3431 reflections	Δρ_max = 0.16 e Å⁻³
464 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.134 (8)

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	0.9069 (4)	0.21141 (18)	0.3615 (4)	0.0817 (11)
H1A	1.0036	0.1983	0.3583	0.123*
O2	0.9294 (4)	0.15803 (19)	0.7967 (4)	0.0882 (12)
O3	0.8505 (4)	0.12301 (13)	0.9931 (3)	0.0691 (8)
N1	0.2678 (4)	0.17681 (15)	0.4208 (4)	0.0512 (8)
H1B	0.251 (6)	0.1936 (19)	0.494 (5)	0.061*
C2	0.3733 (4)	0.12989 (16)	0.4737 (4)	0.0454 (8)
C3	0.4488 (5)	0.10087 (19)	0.3518 (4)	0.0560 (9)
H3A	0.3699	0.1035	0.2684	0.067*
H3B	0.4677	0.0629	0.3739	0.067*
C4	0.6227 (5)	0.1290 (2)	0.3282 (4)	0.0582 (10)
H4A	0.6212	0.1431	0.2339	0.070*
H4B	0.7183	0.1037	0.3433	0.070*
C5	0.6400 (4)	0.17582 (16)	0.4373 (4)	0.0442 (8)
C6	0.5427 (5)	0.22602 (17)	0.3719 (4)	0.0529 (9)
H6A	0.5989	0.2341	0.2865	0.063*
C7	0.3561 (5)	0.21161 (18)	0.3235 (4)	0.0564 (10)
H7A	0.2905	0.2448	0.3092	0.068*
H7B	0.3551	0.1934	0.2340	0.068*
C8	0.5426 (4)	0.15135 (14)	0.5579 (4)	0.0425 (8)
C9	0.5024 (5)	0.18855 (15)	0.6758 (4)	0.0452 (8)
C10	0.4663 (5)	0.24074 (17)	0.6902 (4)	0.0554 (9)
C11	0.4453 (6)	0.28359 (18)	0.5813 (5)	0.0667 (12)
H11A	0.4701	0.3182	0.6260	0.080*
H11D	0.3248	0.2842	0.5450	0.080*
C12	0.5556 (6)	0.27866 (18)	0.4589 (5)	0.0636 (11)
H12A	0.6756	0.2832	0.4942	0.076*
H12D	0.5268	0.3086	0.3961	0.076*
C13	0.6457 (5)	0.10440 (15)	0.6382 (4)	0.0493 (8)
H13A	0.5896	0.0700	0.6161	0.059*
H13B	0.7649	0.1017	0.6150	0.059*
C14	0.6518 (5)	0.11470 (16)	0.7981 (4)	0.0528 (9)
H14A	0.6203	0.0815	0.8459	0.063*
C15	0.5108 (5)	0.15819 (17)	0.8117 (4)	0.0501 (8)
H15A	0.3998	0.1398	0.8186	0.060*
C16	0.5265 (6)	0.2042 (2)	0.9219 (5)	0.0684 (12)
H16A	0.4661	0.1949	1.0033	0.082*
H16B	0.6467	0.2119	0.9510	0.082*
C17	0.4399 (7)	0.2523 (2)	0.8426 (6)	0.0753 (13)
H17A	0.3177	0.2541	0.8572	0.090*
H17B	0.4945	0.2861	0.8725	0.090*
C18	0.2536 (5)	0.09474 (18)	0.5560 (4)	0.0546 (9)
H18A	0.1960	0.1175	0.6201	0.066*
H18B	0.3230	0.0685	0.6109	0.066*
C20	0.1160 (6)	0.06455 (19)	0.4607 (5)	0.0676 (12)
H20A	0.0345	0.0475	0.5169	0.101*
H20B	0.1713	0.0375	0.4080	0.101*
H20C	0.0564	0.0898	0.3979	0.101*
C21	0.8288 (4)	0.19042 (19)	0.4795 (4)	0.0546 (9)
H21A	0.8341	0.2172	0.5535	0.066*
H21B	0.8911	0.1585	0.5143	0.066*
C22	0.8251 (5)	0.13440 (17)	0.8590 (4)	0.0548 (9)
C23	1.0104 (7)	0.1436 (2)	1.0657 (5)	0.0768 (14)
H23A	1.0178	0.1318	1.1612	0.115*
H23B	1.0101	0.1824	1.0625	0.115*
H23C	1.1080	0.1301	1.0210	0.115*
O1'	0.5459 (4)	0.93016 (18)	−0.1833 (4)	0.0811 (11)
H1'A	0.4518	0.9244	−0.1528	0.122*
O2'	0.5479 (4)	0.91780 (15)	0.2038 (4)	0.0737 (9)
O3'	0.6255 (4)	0.96447 (12)	0.3971 (3)	0.0649 (8)
N1'	1.2233 (4)	0.91365 (15)	−0.0858 (4)	0.0529 (8)
H1'B	1.246 (6)	0.8976 (19)	0.003 (5)	0.063*
C2'	1.1023 (4)	0.95842 (16)	−0.0550 (4)	0.0479 (8)
C3'	1.0353 (5)	0.9858 (2)	−0.1916 (5)	0.0624 (11)
H3'A	1.1227	0.9849	−0.2584	0.075*
H3'B	1.0053	1.0233	−0.1749	0.075*
C4'	0.8744 (5)	0.9537 (2)	−0.2468 (5)	0.0656 (11)
H4'A	0.8897	0.9394	−0.3390	0.079*
H4'B	0.7729	0.9768	−0.2527	0.079*
C5'	0.8532 (4)	0.90690 (18)	−0.1416 (4)	0.0527 (9)
C6'	0.9650 (5)	0.85839 (19)	−0.1843 (5)	0.0621 (11)
H6'A	0.9204	0.8489	−0.2795	0.075*
C7'	1.1521 (5)	0.8764 (2)	−0.1954 (5)	0.0680 (12)
H7'A	1.2248	0.8444	−0.1938	0.082*
H7'B	1.1594	0.8937	−0.2853	0.082*
C8'	0.9327 (4)	0.93272 (15)	−0.0014 (4)	0.0432 (8)
C9'	0.9743 (4)	0.89697 (14)	0.1233 (4)	0.0443 (8)
C10'	1.0187 (5)	0.84529 (16)	0.1468 (5)	0.0564 (10)
C11'	1.0539 (6)	0.80220 (18)	0.0429 (6)	0.0697 (12)
H11B	1.0294	0.7673	0.0831	0.084*
H11C	1.1763	0.8029	0.0284	0.084*
C12'	0.9523 (6)	0.80648 (18)	−0.0981 (6)	0.0714 (13)
H12B	0.8312	0.8009	−0.0836	0.086*
H12C	0.9874	0.7766	−0.1549	0.086*
C13'	0.8101 (5)	0.97558 (15)	0.0586 (4)	0.0498 (8)
H13C	0.8472	1.0117	0.0355	0.060*
H13D	0.6927	0.9704	0.0175	0.060*
C14'	0.8152 (5)	0.96904 (15)	0.2194 (4)	0.0508 (9)
H14B	0.8442	1.0037	0.2652	0.061*
C15'	0.9604 (5)	0.92774 (16)	0.2553 (4)	0.0509 (9)
H15B	1.0687	0.9477	0.2760	0.061*
C16'	0.9515 (6)	0.8826 (2)	0.3648 (5)	0.0684 (12)
H16C	1.0107	0.8934	0.4534	0.082*
H16D	0.8323	0.8737	0.3792	0.082*
C17'	1.0411 (6)	0.8356 (2)	0.3030 (5)	0.0711 (13)
H17C	0.9880	0.8017	0.3272	0.085*
H17D	1.1628	0.8348	0.3359	0.085*
C18'	1.2026 (5)	0.99628 (18)	0.0480 (5)	0.0593 (10)
H18C	1.2615	0.9747	0.1216	0.071*
H18D	1.1208	1.0195	0.0906	0.071*
C20'	1.3362 (6)	1.0318 (2)	−0.0171 (6)	0.0709 (12)
H20D	1.4049	1.0505	0.0554	0.106*
H20E	1.2778	1.0577	−0.0787	0.106*
H20F	1.4099	1.0095	−0.0689	0.106*
C21'	0.6628 (5)	0.8881 (2)	−0.1400 (5)	0.0642 (11)
H21C	0.6433	0.8573	−0.2017	0.077*
H21D	0.6413	0.8767	−0.0463	0.077*
C22'	0.6463 (5)	0.94773 (17)	0.2668 (4)	0.0539 (9)
C23'	0.4792 (7)	0.9427 (2)	0.4631 (6)	0.0769 (14)
H23D	0.4889	0.9522	0.5603	0.115*
H23E	0.4776	0.9040	0.4537	0.115*
H23F	0.3740	0.9575	0.4191	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0546 (16)	0.124 (3)	0.068 (2)	−0.0006 (18)	0.0124 (14)	0.030 (2)
O2	0.0727 (19)	0.137 (3)	0.0534 (19)	−0.034 (2)	−0.0059 (15)	0.009 (2)
O3	0.0844 (19)	0.0698 (19)	0.0502 (18)	−0.0038 (16)	−0.0127 (14)	0.0090 (14)
N1	0.0454 (15)	0.063 (2)	0.0452 (18)	0.0019 (14)	0.0035 (13)	0.0049 (15)
C2	0.0400 (15)	0.054 (2)	0.0420 (19)	−0.0003 (14)	0.0022 (13)	−0.0032 (16)
C3	0.0503 (18)	0.070 (2)	0.047 (2)	0.0015 (17)	−0.0044 (15)	−0.0125 (19)
C4	0.055 (2)	0.077 (3)	0.043 (2)	0.0065 (19)	0.0034 (16)	−0.0117 (19)
C5	0.0394 (15)	0.060 (2)	0.0335 (17)	0.0024 (14)	0.0040 (12)	0.0023 (15)
C6	0.0456 (18)	0.067 (2)	0.046 (2)	0.0001 (17)	0.0023 (15)	0.0114 (18)
C7	0.0452 (18)	0.071 (3)	0.052 (2)	0.0031 (17)	0.0010 (16)	0.013 (2)
C8	0.0405 (15)	0.0469 (19)	0.0400 (19)	0.0022 (14)	0.0034 (13)	0.0018 (14)
C9	0.0538 (18)	0.049 (2)	0.0336 (18)	0.0003 (15)	0.0075 (14)	−0.0005 (14)
C10	0.057 (2)	0.063 (3)	0.047 (2)	0.0101 (18)	0.0098 (17)	−0.0049 (18)
C11	0.074 (3)	0.051 (2)	0.075 (3)	0.012 (2)	0.000 (2)	0.001 (2)
C12	0.065 (2)	0.054 (2)	0.072 (3)	0.0001 (18)	0.002 (2)	0.014 (2)
C13	0.0523 (18)	0.0447 (19)	0.049 (2)	0.0047 (15)	−0.0060 (15)	0.0012 (16)
C14	0.062 (2)	0.054 (2)	0.042 (2)	−0.0059 (17)	0.0027 (16)	0.0121 (16)
C15	0.0519 (18)	0.063 (2)	0.0358 (18)	−0.0053 (17)	0.0052 (15)	0.0015 (16)
C16	0.078 (3)	0.084 (3)	0.044 (2)	0.004 (2)	0.010 (2)	−0.012 (2)
C17	0.080 (3)	0.078 (3)	0.069 (3)	0.013 (2)	0.012 (2)	−0.018 (3)
C18	0.0509 (19)	0.060 (2)	0.052 (2)	−0.0057 (17)	0.0012 (16)	0.0015 (18)
C20	0.062 (2)	0.061 (3)	0.079 (3)	−0.0119 (19)	−0.003 (2)	−0.001 (2)
C21	0.0411 (16)	0.075 (3)	0.048 (2)	−0.0004 (17)	0.0033 (15)	0.0086 (19)
C22	0.059 (2)	0.054 (2)	0.050 (2)	0.0033 (17)	−0.0032 (17)	0.0017 (18)
C23	0.091 (3)	0.077 (3)	0.058 (3)	0.011 (3)	−0.025 (2)	−0.007 (2)
O1'	0.0449 (14)	0.131 (3)	0.068 (2)	0.0002 (17)	0.0111 (13)	0.016 (2)
O2'	0.0679 (17)	0.086 (2)	0.068 (2)	−0.0164 (17)	0.0115 (15)	−0.0041 (17)
O3'	0.0754 (18)	0.0676 (18)	0.0547 (17)	0.0003 (15)	0.0235 (14)	−0.0044 (15)
N1'	0.0394 (13)	0.068 (2)	0.053 (2)	0.0040 (13)	0.0109 (12)	−0.0023 (16)
C2'	0.0413 (16)	0.054 (2)	0.049 (2)	−0.0031 (15)	0.0093 (14)	0.0032 (16)
C3'	0.0514 (19)	0.081 (3)	0.055 (3)	−0.0002 (19)	0.0080 (17)	0.018 (2)
C4'	0.054 (2)	0.088 (3)	0.056 (3)	0.002 (2)	0.0094 (18)	0.006 (2)
C5'	0.0408 (17)	0.072 (2)	0.045 (2)	−0.0016 (16)	0.0025 (14)	−0.0050 (18)
C6'	0.053 (2)	0.074 (3)	0.060 (3)	−0.0062 (19)	0.0076 (18)	−0.020 (2)
C7'	0.058 (2)	0.077 (3)	0.071 (3)	0.001 (2)	0.020 (2)	−0.014 (2)
C8'	0.0400 (15)	0.0456 (18)	0.045 (2)	0.0003 (13)	0.0096 (14)	0.0016 (15)
C9'	0.0380 (15)	0.046 (2)	0.049 (2)	−0.0022 (13)	0.0005 (14)	0.0019 (15)
C10'	0.0523 (19)	0.048 (2)	0.070 (3)	0.0064 (16)	0.0096 (18)	0.0078 (19)
C11'	0.072 (3)	0.047 (2)	0.091 (4)	0.0097 (19)	0.014 (2)	−0.004 (2)
C12'	0.066 (2)	0.059 (3)	0.092 (4)	−0.006 (2)	0.018 (2)	−0.029 (2)
C13'	0.0476 (17)	0.050 (2)	0.053 (2)	0.0049 (15)	0.0075 (15)	0.0041 (17)
C14'	0.0551 (19)	0.0454 (19)	0.053 (2)	−0.0048 (16)	0.0100 (16)	−0.0042 (17)
C15'	0.0505 (18)	0.057 (2)	0.045 (2)	−0.0039 (16)	0.0016 (15)	−0.0002 (17)
C16'	0.074 (3)	0.082 (3)	0.049 (3)	0.006 (2)	0.003 (2)	0.018 (2)
C17'	0.068 (3)	0.072 (3)	0.072 (3)	0.013 (2)	0.002 (2)	0.024 (2)
C18'	0.056 (2)	0.057 (2)	0.067 (3)	−0.0083 (17)	0.0129 (19)	0.003 (2)
C20'	0.070 (2)	0.062 (3)	0.083 (3)	−0.019 (2)	0.023 (2)	−0.006 (2)
C21'	0.0467 (19)	0.085 (3)	0.061 (3)	−0.0082 (19)	0.0047 (17)	−0.008 (2)
C22'	0.061 (2)	0.052 (2)	0.050 (2)	0.0068 (17)	0.0128 (17)	0.0021 (18)
C23'	0.085 (3)	0.086 (3)	0.064 (3)	0.008 (3)	0.032 (2)	0.008 (3)

Geometric parameters (Å, º) top

O1—C21	1.425 (5)	O1'—C21'	1.419 (6)
O1—H1A	0.8200	O1'—H1'A	0.8200
O2—C22	1.196 (5)	O2'—C22'	1.192 (5)
O3—C22	1.318 (5)	O3'—C22'	1.340 (5)
O3—C23	1.463 (6)	O3'—C23'	1.447 (6)
N1—C7	1.478 (5)	N1'—C7'	1.473 (6)
N1—C2	1.485 (5)	N1'—C2'	1.495 (5)
N1—H1B	0.83 (5)	N1'—H1'B	0.95 (5)
C2—C3	1.528 (5)	C2'—C18'	1.528 (6)
C2—C18	1.536 (5)	C2'—C3'	1.530 (6)
C2—C8	1.577 (5)	C2'—C8'	1.582 (4)
C3—C4	1.549 (6)	C3'—C4'	1.536 (6)
C3—H3A	0.9700	C3'—H3'A	0.9700
C3—H3B	0.9700	C3'—H3'B	0.9700
C4—C5	1.560 (6)	C4'—C5'	1.554 (6)
C4—H4A	0.9700	C4'—H4'A	0.9700
C4—H4B	0.9700	C4'—H4'B	0.9700
C5—C21	1.530 (5)	C5'—C21'	1.548 (5)
C5—C8	1.555 (5)	C5'—C6'	1.554 (6)
C5—C6	1.558 (5)	C5'—C8'	1.570 (5)
C6—C7	1.525 (5)	C6'—C7'	1.529 (6)
C6—C12	1.546 (6)	C6'—C12'	1.534 (7)
C6—H6A	0.9800	C6'—H6'A	0.9800
C7—H7A	0.9700	C7'—H7'A	0.9700
C7—H7B	0.9700	C7'—H7'B	0.9700
C8—C9	1.510 (5)	C8'—C9'	1.503 (5)
C8—C13	1.575 (5)	C8'—C13'	1.564 (5)
C9—C10	1.330 (6)	C9'—C10'	1.337 (5)
C9—C15	1.503 (5)	C9'—C15'	1.489 (5)
C10—C11	1.488 (6)	C10'—C11'	1.499 (6)
C10—C17	1.521 (6)	C10'—C17'	1.516 (7)
C11—C12	1.513 (7)	C11'—C12'	1.515 (7)
C11—H11A	0.9700	C11'—H11B	0.9700
C11—H11D	0.9700	C11'—H11C	0.9700
C12—H12A	0.9700	C12'—H12B	0.9700
C12—H12D	0.9700	C12'—H12C	0.9700
C13—C14	1.554 (5)	C13'—C14'	1.551 (6)
C13—H13A	0.9700	C13'—H13C	0.9700
C13—H13B	0.9700	C13'—H13D	0.9700
C14—C22	1.502 (5)	C14'—C22'	1.514 (5)
C14—C15	1.546 (6)	C14'—C15'	1.538 (5)
C14—H14A	0.9800	C14'—H14B	0.9800
C15—C16	1.551 (6)	C15'—C16'	1.539 (6)
C15—H15A	0.9800	C15'—H15B	0.9800
C16—C17	1.537 (7)	C16'—C17'	1.501 (7)
C16—H16A	0.9700	C16'—H16C	0.9700
C16—H16B	0.9700	C16'—H16D	0.9700
C17—H17A	0.9700	C17'—H17C	0.9700
C17—H17B	0.9700	C17'—H17D	0.9700
C18—C20	1.541 (6)	C18'—C20'	1.529 (6)
C18—H18A	0.9700	C18'—H18C	0.9700
C18—H18B	0.9700	C18'—H18D	0.9700
C20—H20A	0.9600	C20'—H20D	0.9600
C20—H20B	0.9600	C20'—H20E	0.9600
C20—H20C	0.9600	C20'—H20F	0.9600
C21—H21A	0.9700	C21'—H21C	0.9700
C21—H21B	0.9700	C21'—H21D	0.9700
C23—H23A	0.9600	C23'—H23D	0.9600
C23—H23B	0.9600	C23'—H23E	0.9600
C23—H23C	0.9600	C23'—H23F	0.9600

C21—O1—H1A	109.5	C21'—O1'—H1'A	109.5
C22—O3—C23	116.5 (4)	C22'—O3'—C23'	116.9 (4)
C7—N1—C2	113.6 (3)	C7'—N1'—C2'	113.6 (3)
C7—N1—H1B	111 (3)	C7'—N1'—H1'B	114 (3)
C2—N1—H1B	103 (3)	C2'—N1'—H1'B	102 (3)
N1—C2—C3	109.8 (3)	N1'—C2'—C18'	106.7 (3)
N1—C2—C18	106.2 (3)	N1'—C2'—C3'	109.5 (3)
C3—C2—C18	114.4 (3)	C18'—C2'—C3'	113.8 (3)
N1—C2—C8	109.0 (3)	N1'—C2'—C8'	108.5 (3)
C3—C2—C8	101.4 (3)	C18'—C2'—C8'	115.3 (3)
C18—C2—C8	116.0 (3)	C3'—C2'—C8'	102.9 (3)
C2—C3—C4	107.0 (3)	C2'—C3'—C4'	106.1 (3)
C2—C3—H3A	110.3	C2'—C3'—H3'A	110.5
C4—C3—H3A	110.3	C4'—C3'—H3'A	110.5
C2—C3—H3B	110.3	C2'—C3'—H3'B	110.5
C4—C3—H3B	110.3	C4'—C3'—H3'B	110.5
H3A—C3—H3B	108.6	H3'A—C3'—H3'B	108.7
C3—C4—C5	105.3 (3)	C3'—C4'—C5'	106.6 (3)
C3—C4—H4A	110.7	C3'—C4'—H4'A	110.4
C5—C4—H4A	110.7	C5'—C4'—H4'A	110.4
C3—C4—H4B	110.7	C3'—C4'—H4'B	110.4
C5—C4—H4B	110.7	C5'—C4'—H4'B	110.4
H4A—C4—H4B	108.8	H4'A—C4'—H4'B	108.6
C21—C5—C8	113.9 (3)	C21'—C5'—C6'	108.9 (4)
C21—C5—C6	109.9 (3)	C21'—C5'—C4'	112.4 (3)
C8—C5—C6	111.2 (3)	C6'—C5'—C4'	108.2 (3)
C21—C5—C4	112.5 (3)	C21'—C5'—C8'	114.9 (3)
C8—C5—C4	101.0 (3)	C6'—C5'—C8'	110.6 (3)
C6—C5—C4	107.9 (3)	C4'—C5'—C8'	101.5 (3)
C7—C6—C12	112.4 (3)	C7'—C6'—C12'	112.5 (4)
C7—C6—C5	110.7 (3)	C7'—C6'—C5'	110.3 (4)
C12—C6—C5	116.4 (3)	C12'—C6'—C5'	116.2 (4)
C7—C6—H6A	105.5	C7'—C6'—H6'A	105.6
C12—C6—H6A	105.5	C12'—C6'—H6'A	105.6
C5—C6—H6A	105.5	C5'—C6'—H6'A	105.6
N1—C7—C6	114.8 (3)	N1'—C7'—C6'	115.8 (4)
N1—C7—H7A	108.6	N1'—C7'—H7'A	108.3
C6—C7—H7A	108.6	C6'—C7'—H7'A	108.3
N1—C7—H7B	108.6	N1'—C7'—H7'B	108.3
C6—C7—H7B	108.6	C6'—C7'—H7'B	108.3
H7A—C7—H7B	107.6	H7'A—C7'—H7'B	107.4
C9—C8—C5	117.6 (3)	C9'—C8'—C13'	101.7 (3)
C9—C8—C13	102.1 (3)	C9'—C8'—C5'	119.3 (3)
C5—C8—C13	113.2 (3)	C13'—C8'—C5'	112.5 (3)
C9—C8—C2	112.1 (3)	C9'—C8'—C2'	111.4 (3)
C5—C8—C2	100.5 (3)	C13'—C8'—C2'	113.2 (3)
C13—C8—C2	111.8 (3)	C5'—C8'—C2'	99.4 (3)
C10—C9—C15	112.9 (3)	C10'—C9'—C15'	112.3 (3)
C10—C9—C8	136.6 (4)	C10'—C9'—C8'	137.0 (4)
C15—C9—C8	110.5 (3)	C15'—C9'—C8'	110.7 (3)
C9—C10—C11	129.0 (4)	C9'—C10'—C11'	128.7 (4)
C9—C10—C17	109.1 (4)	C9'—C10'—C17'	109.0 (4)
C11—C10—C17	121.8 (4)	C11'—C10'—C17'	122.3 (4)
C10—C11—C12	116.9 (4)	C10'—C11'—C12'	115.9 (4)
C10—C11—H11A	108.1	C10'—C11'—H11B	108.3
C12—C11—H11A	108.1	C12'—C11'—H11B	108.3
C10—C11—H11D	108.1	C10'—C11'—H11C	108.3
C12—C11—H11D	108.1	C12'—C11'—H11C	108.3
H11A—C11—H11D	107.3	H11B—C11'—H11C	107.4
C11—C12—C6	118.1 (4)	C11'—C12'—C6'	119.3 (4)
C11—C12—H12A	107.8	C11'—C12'—H12B	107.5
C6—C12—H12A	107.8	C6'—C12'—H12B	107.5
C11—C12—H12D	107.8	C11'—C12'—H12C	107.5
C6—C12—H12D	107.8	C6'—C12'—H12C	107.5
H12A—C12—H12D	107.1	H12B—C12'—H12C	107.0
C14—C13—C8	109.7 (3)	C14'—C13'—C8'	109.2 (3)
C14—C13—H13A	109.7	C14'—C13'—H13C	109.8
C8—C13—H13A	109.7	C8'—C13'—H13C	109.8
C14—C13—H13B	106.5	C14'—C13'—H13D	109.8
C8—C13—H13B	113.2	C8'—C13'—H13D	109.8
H13A—C13—H13B	108.0	H13C—C13'—H13D	108.3
C22—C14—C15	110.9 (3)	C22'—C14'—C15'	109.7 (3)
C22—C14—C13	113.1 (3)	C22'—C14'—C13'	112.4 (3)
C15—C14—C13	103.4 (3)	C15'—C14'—C13'	104.6 (3)
C22—C14—H14A	109.7	C22'—C14'—H14B	110.0
C15—C14—H14A	109.7	C15'—C14'—H14B	110.0
C13—C14—H14A	109.7	C13'—C14'—H14B	110.0
C9—C15—C14	104.8 (3)	C9'—C15'—C14'	104.5 (3)
C9—C15—C16	102.9 (3)	C9'—C15'—C16'	102.8 (3)
C14—C15—C16	123.4 (3)	C14'—C15'—C16'	124.2 (3)
C9—C15—H15A	108.3	C9'—C15'—H15B	108.1
C14—C15—H15A	108.3	C14'—C15'—H15B	108.1
C16—C15—H15A	108.3	C16'—C15'—H15B	108.1
C17—C16—C15	102.8 (3)	C17'—C16'—C15'	104.1 (4)
C17—C16—H16A	111.2	C17'—C16'—H16C	110.9
C15—C16—H16A	111.2	C15'—C16'—H16C	110.9
C17—C16—H16B	111.2	C17'—C16'—H16D	110.9
C15—C16—H16B	111.2	C15'—C16'—H16D	110.9
H16A—C16—H16B	109.1	H16C—C16'—H16D	109.0
C10—C17—C16	104.2 (4)	C16'—C17'—C10'	104.4 (3)
C10—C17—H17A	110.9	C16'—C17'—H17C	110.9
C16—C17—H17A	110.9	C10'—C17'—H17C	110.9
C10—C17—H17B	110.9	C16'—C17'—H17D	110.9
C16—C17—H17B	110.9	C10'—C17'—H17D	110.9
H17A—C17—H17B	108.9	H17C—C17'—H17D	108.9
C2—C18—C20	112.7 (3)	C2'—C18'—C20'	114.4 (4)
C2—C18—H18A	109.0	C2'—C18'—H18C	108.7
C20—C18—H18A	109.0	C20'—C18'—H18C	108.7
C2—C18—H18B	109.0	C2'—C18'—H18D	108.7
C20—C18—H18B	109.0	C20'—C18'—H18D	108.7
H18A—C18—H18B	107.8	H18C—C18'—H18D	107.6
C18—C20—H20A	109.5	C18'—C20'—H20D	109.5
C18—C20—H20B	109.5	C18'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C18—C20—H20C	109.5	C18'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
O1—C21—C5	109.5 (3)	O1'—C21'—C5'	111.3 (4)
O1—C21—H21A	109.8	O1'—C21'—H21C	109.4
C5—C21—H21A	109.8	C5'—C21'—H21C	109.4
O1—C21—H21B	109.8	O1'—C21'—H21D	109.4
C5—C21—H21B	109.8	C5'—C21'—H21D	109.4
H21A—C21—H21B	108.2	H21C—C21'—H21D	108.0
O2—C22—O3	122.6 (4)	O2'—C22'—O3'	123.1 (4)
O2—C22—C14	125.7 (4)	O2'—C22'—C14'	126.6 (4)
O3—C22—C14	111.7 (4)	O3'—C22'—C14'	110.2 (4)
O3—C23—H23A	109.5	O3'—C23'—H23D	109.5
O3—C23—H23B	109.5	O3'—C23'—H23E	109.5
H23A—C23—H23B	109.5	H23D—C23'—H23E	109.5
O3—C23—H23C	109.5	O3'—C23'—H23F	109.5
H23A—C23—H23C	109.5	H23D—C23'—H23F	109.5
H23B—C23—H23C	109.5	H23E—C23'—H23F	109.5

C7—N1—C2—C3	−48.4 (4)	C7'—N1'—C2'—C18'	−173.9 (4)
C7—N1—C2—C18	−172.6 (3)	C7'—N1'—C2'—C3'	−50.4 (4)
C7—N1—C2—C8	61.8 (4)	C7'—N1'—C2'—C8'	61.2 (4)
N1—C2—C3—C4	87.6 (4)	N1'—C2'—C3'—C4'	87.6 (4)
C18—C2—C3—C4	−153.1 (3)	C18'—C2'—C3'—C4'	−153.2 (4)
C8—C2—C3—C4	−27.6 (4)	C8'—C2'—C3'—C4'	−27.7 (4)
C2—C3—C4—C5	−1.7 (4)	C2'—C3'—C4'—C5'	−1.3 (5)
C3—C4—C5—C21	152.6 (3)	C3'—C4'—C5'—C21'	153.1 (4)
C3—C4—C5—C8	30.7 (4)	C3'—C4'—C5'—C6'	−86.6 (4)
C3—C4—C5—C6	−86.0 (4)	C3'—C4'—C5'—C8'	29.8 (4)
C21—C5—C6—C7	177.6 (3)	C21'—C5'—C6'—C7'	176.6 (4)
C8—C5—C6—C7	−55.3 (4)	C4'—C5'—C6'—C7'	54.2 (5)
C4—C5—C6—C7	54.6 (4)	C8'—C5'—C6'—C7'	−56.2 (5)
C21—C5—C6—C12	−52.5 (4)	C21'—C5'—C6'—C12'	−53.8 (5)
C8—C5—C6—C12	74.6 (4)	C4'—C5'—C6'—C12'	−176.2 (3)
C4—C5—C6—C12	−175.5 (3)	C8'—C5'—C6'—C12'	73.4 (4)
C2—N1—C7—C6	−46.5 (5)	C2'—N1'—C7'—C6'	−44.8 (6)
C12—C6—C7—N1	−90.1 (4)	C12'—C6'—C7'—N1'	−90.5 (5)
C5—C6—C7—N1	41.9 (5)	C5'—C6'—C7'—N1'	41.0 (6)
C21—C5—C8—C9	69.8 (4)	C21'—C5'—C8'—C9'	71.8 (4)
C6—C5—C8—C9	−55.1 (4)	C6'—C5'—C8'—C9'	−52.0 (4)
C4—C5—C8—C9	−169.4 (3)	C4'—C5'—C8'—C9'	−166.6 (3)
C21—C5—C8—C13	−48.9 (4)	C21'—C5'—C8'—C13'	−47.1 (5)
C6—C5—C8—C13	−173.8 (3)	C6'—C5'—C8'—C13'	−170.8 (3)
C4—C5—C8—C13	71.9 (3)	C4'—C5'—C8'—C13'	74.5 (3)
C21—C5—C8—C2	−168.3 (3)	C21'—C5'—C8'—C2'	−167.1 (4)
C6—C5—C8—C2	66.8 (3)	C6'—C5'—C8'—C2'	69.1 (4)
C4—C5—C8—C2	−47.5 (3)	C4'—C5'—C8'—C2'	−45.5 (3)
N1—C2—C8—C9	56.6 (4)	N1'—C2'—C8'—C9'	56.2 (4)
C3—C2—C8—C9	172.3 (3)	C18'—C2'—C8'—C9'	−63.3 (4)
C18—C2—C8—C9	−63.2 (4)	C3'—C2'—C8'—C9'	172.1 (3)
N1—C2—C8—C5	−69.1 (3)	N1'—C2'—C8'—C13'	170.0 (3)
C3—C2—C8—C5	46.6 (3)	C18'—C2'—C8'—C13'	50.5 (4)
C18—C2—C8—C5	171.1 (3)	C3'—C2'—C8'—C13'	−74.0 (4)
N1—C2—C8—C13	170.5 (3)	N1'—C2'—C8'—C5'	−70.5 (3)
C3—C2—C8—C13	−73.7 (4)	C18'—C2'—C8'—C5'	170.0 (3)
C18—C2—C8—C13	50.7 (4)	C3'—C2'—C8'—C5'	45.5 (4)
C5—C8—C9—C10	31.8 (6)	C13'—C8'—C9'—C10'	152.7 (4)
C13—C8—C9—C10	156.3 (5)	C5'—C8'—C9'—C10'	28.3 (6)
C2—C8—C9—C10	−83.9 (5)	C2'—C8'—C9'—C10'	−86.5 (5)
C5—C8—C9—C15	−146.2 (3)	C13'—C8'—C9'—C15'	−26.7 (3)
C13—C8—C9—C15	−21.7 (4)	C5'—C8'—C9'—C15'	−151.1 (3)
C2—C8—C9—C15	98.1 (3)	C2'—C8'—C9'—C15'	94.1 (3)
C15—C9—C10—C11	−179.3 (4)	C15'—C9'—C10'—C11'	−176.8 (4)
C8—C9—C10—C11	2.8 (8)	C8'—C9'—C10'—C11'	3.8 (7)
C15—C9—C10—C17	−1.6 (5)	C15'—C9'—C10'—C17'	−0.3 (4)
C8—C9—C10—C17	−179.5 (4)	C8'—C9'—C10'—C17'	−179.7 (4)
C9—C10—C11—C12	−33.2 (7)	C9'—C10'—C11'—C12'	−31.7 (7)
C17—C10—C11—C12	149.4 (4)	C17'—C10'—C11'—C12'	152.3 (4)
C10—C11—C12—C6	56.6 (5)	C10'—C11'—C12'—C6'	57.1 (6)
C7—C6—C12—C11	51.7 (5)	C7'—C6'—C12'—C11'	48.6 (5)
C5—C6—C12—C11	−77.4 (5)	C5'—C6'—C12'—C11'	−79.9 (5)
C9—C8—C13—C14	3.2 (4)	C9'—C8'—C13'—C14'	10.7 (4)
C5—C8—C13—C14	130.5 (3)	C5'—C8'—C13'—C14'	139.4 (3)
C2—C8—C13—C14	−116.9 (3)	C2'—C8'—C13'—C14'	−108.9 (3)
C8—C13—C14—C22	−104.8 (4)	C8'—C13'—C14'—C22'	−111.2 (3)
C8—C13—C14—C15	15.3 (4)	C8'—C13'—C14'—C15'	7.8 (4)
C10—C9—C15—C14	−146.2 (3)	C10'—C9'—C15'—C14'	−146.9 (3)
C8—C9—C15—C14	32.3 (4)	C8'—C9'—C15'—C14'	32.6 (4)
C10—C9—C15—C16	−16.1 (4)	C10'—C9'—C15'—C16'	−16.1 (4)
C8—C9—C15—C16	162.4 (3)	C8'—C9'—C15'—C16'	163.5 (3)
C22—C14—C15—C9	93.8 (4)	C22'—C14'—C15'—C9'	97.4 (4)
C13—C14—C15—C9	−27.8 (4)	C13'—C14'—C15'—C9'	−23.4 (4)
C22—C14—C15—C16	−22.9 (5)	C22'—C14'—C15'—C16'	−19.6 (5)
C13—C14—C15—C16	−144.5 (4)	C13'—C14'—C15'—C16'	−140.4 (4)
C9—C15—C16—C17	26.2 (4)	C9'—C15'—C16'—C17'	25.5 (4)
C14—C15—C16—C17	143.9 (4)	C14'—C15'—C16'—C17'	143.2 (4)
C9—C10—C17—C16	18.9 (5)	C15'—C16'—C17'—C10'	−26.0 (5)
C11—C10—C17—C16	−163.2 (4)	C9'—C10'—C17'—C16'	17.1 (5)
C15—C16—C17—C10	−27.5 (5)	C11'—C10'—C17'—C16'	−166.2 (4)
N1—C2—C18—C20	72.3 (4)	N1'—C2'—C18'—C20'	74.7 (4)
C3—C2—C18—C20	−48.9 (4)	C3'—C2'—C18'—C20'	−46.1 (5)
C8—C2—C18—C20	−166.4 (3)	C8'—C2'—C18'—C20'	−164.7 (4)
C8—C5—C21—O1	178.9 (3)	C6'—C5'—C21'—O1'	−145.5 (4)
C6—C5—C21—O1	−55.5 (4)	C4'—C5'—C21'—O1'	−25.7 (5)
C4—C5—C21—O1	64.7 (5)	C8'—C5'—C21'—O1'	89.8 (4)
C23—O3—C22—O2	3.5 (7)	C23'—O3'—C22'—O2'	2.5 (6)
C23—O3—C22—C14	−175.9 (4)	C23'—O3'—C22'—C14'	−173.5 (4)
C15—C14—C22—O2	−90.4 (6)	C15'—C14'—C22'—O2'	−84.5 (5)
C13—C14—C22—O2	25.3 (6)	C13'—C14'—C22'—O2'	31.4 (6)
C15—C14—C22—O3	89.0 (4)	C15'—C14'—C22'—O3'	91.4 (4)
C13—C14—C22—O3	−155.3 (3)	C13'—C14'—C22'—O3'	−152.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.15	2.937 (4)	160
O1′—H1′A···N1′ⁱⁱ	0.82	1.95	2.770 (4)	177

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

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