Download citation
Download citation
link to html
The title compound (C25H39NO6), a polycyclic diterpenoid alkaloid, has been isolated from Delphinium roylei Munz. Two cis-fused ring junctions are observed between cyclo­hexane A and piperidine E rings and between cyclo­hexane B and cyclo­pentane C rings. Two trans-fused ring junctions involve cyclo­hexane A and cyclo­pentane B rings and also piperidine E and cyclo­pentane F rings. Cyclo­pentane ring F is in a twist conformation, while the other cyclo­pentane ring, C, forms an envelope conformation. Piperidine ring E is in a chair conformation, the two cyclo­hexane rings A and B adopt twist–boat conformations and cyclo­hexane ring D is in a screw-boat conformation. Of the five substituents, only one is α-oriented. The mol­ecules are packed along the c axis in layers parallel to the ab plane and stabilized by weak inter- and intra­molecular O—H...O and O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008944/ac2007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008944/ac2007Isup2.hkl
Contains datablock I

CCDC reference: 604945

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.085
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.25 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? 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) ... 2.53 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C25 H39 N O6 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
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 25.00 From the CIF: _reflns_number_total 2152 Count of symmetry unique reflns 2161 Completeness (_total/calc) 99.58% 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 0 ALERT level B = Potentially serious problem 12 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 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 6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

14-Acetyl-20-ethyl-1,8-dihydroxy-16–18-dimethoxylycoctonine top
Crystal data top
C25H39NO6F(000) = 488
Mr = 449.57Dx = 1.279 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.9484 (12) ÅCell parameters from 3947 reflections
b = 13.2080 (17) Åθ = 2.1–25.0°
c = 9.8945 (13) ŵ = 0.09 mm1
β = 93.553 (2)°T = 293 K
V = 1167.2 (3) Å3Block, colorless
Z = 20.45 × 0.20 × 0.19 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2152 independent reflections
Radiation source: fine-focus sealed tube2103 reflections with I > 2s(I)
Graphite monochromatorRint = 0.018
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.1°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1515
Tmin = 0.961, Tmax = 0.983l = 115
5883 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1886P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
2152 reflectionsΔρmax = 0.16 e Å3
297 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (10)
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
xyzUiso*/Ueq
N10.3639 (2)0.48219 (15)0.27905 (19)0.0341 (4)
O10.2970 (3)0.81512 (16)0.4893 (2)0.0576 (5)
O20.1244 (3)0.6113 (3)0.3640 (2)0.0817 (8)
O30.0185 (2)0.38135 (16)0.22029 (18)0.0524 (5)
O40.55491 (17)0.55829 (14)0.08037 (18)0.0439 (5)
H1O40.52870.52440.14630.058 (10)*
O50.15078 (18)0.53292 (16)0.16063 (18)0.0459 (5)
H1O50.21060.54580.11050.039 (8)*
O60.14475 (18)0.58007 (14)0.14183 (16)0.0419 (4)
C10.4650 (3)0.64769 (19)0.0919 (2)0.0364 (5)
H10.46790.67850.00170.044*
C20.5291 (3)0.7251 (2)0.1858 (3)0.0466 (6)
H2A0.47850.78940.17590.056*
H2B0.63460.73510.16040.056*
C30.5113 (3)0.6916 (2)0.3326 (3)0.0463 (6)
H3A0.58010.63630.34630.056*
H3B0.53860.74730.39000.056*
C40.3496 (3)0.65655 (19)0.3770 (2)0.0370 (5)
C50.2377 (3)0.67786 (18)0.2659 (2)0.0321 (5)
H50.22400.75070.25240.039*
C60.0863 (2)0.62416 (19)0.3004 (2)0.0353 (5)
H6A0.00370.66510.27240.042*
H6B0.07220.61160.39700.042*
C70.0959 (2)0.52348 (18)0.2210 (2)0.0321 (5)
H70.06550.46660.28000.038*
C80.0021 (2)0.52910 (19)0.0995 (2)0.0326 (5)
C90.0354 (2)0.62819 (19)0.0211 (2)0.0331 (5)
H90.02100.68500.06260.040*
C100.2052 (2)0.65248 (17)0.0109 (2)0.0311 (5)
H100.21580.72550.00400.037*
C110.2965 (2)0.62503 (17)0.1333 (2)0.0294 (5)
C120.2649 (3)0.59827 (19)0.1223 (2)0.0353 (5)
H12A0.33900.54760.10280.042*
H12B0.31050.64690.18570.042*
C130.1286 (2)0.54858 (18)0.1813 (2)0.0332 (5)
H130.13820.54980.28040.040*
C140.0044 (3)0.61904 (19)0.1284 (2)0.0369 (5)
H140.01520.68520.17260.044*
C150.0121 (3)0.4334 (2)0.0075 (3)0.0388 (5)
H15A0.08840.41170.00990.055 (9)*
H15B0.05630.38010.05950.040 (7)*
C160.1019 (3)0.44004 (19)0.1295 (2)0.0372 (5)
H160.19930.40750.12090.045*
C170.2625 (2)0.51501 (17)0.1739 (2)0.0290 (5)
H170.27480.47080.09450.035*
C180.2986 (3)0.7095 (2)0.5092 (3)0.0441 (6)
H18A0.36610.69280.57880.053*
H18B0.19910.68640.53910.053*
C190.3468 (3)0.5422 (2)0.4042 (2)0.0386 (6)
H19A0.25270.52450.45250.046*
H19B0.42700.52510.46180.046*
C200.3509 (3)0.3739 (2)0.3107 (3)0.0445 (6)
H20A0.40980.35900.38740.053*
H20B0.24720.35840.33700.053*
C210.4027 (4)0.3064 (2)0.1936 (3)0.0612 (8)
H21A0.41580.23860.22570.092*
H21B0.32910.30660.12700.092*
H21C0.49620.33110.15360.092*
C220.2325 (4)0.8685 (3)0.6025 (3)0.0688 (9)
H22A0.23090.93950.58240.103*
H22B0.13200.84500.62260.103*
H22C0.29070.85710.67930.103*
C230.1917 (3)0.5753 (3)0.2680 (3)0.0520 (7)
C240.3351 (3)0.5177 (3)0.2694 (3)0.0674 (9)
H24A0.39610.54610.33630.101*
H24B0.31410.44810.29080.101*
H24C0.38730.52200.18180.101*
C250.0966 (5)0.3594 (3)0.3456 (3)0.0738 (10)
H25A0.04360.30810.39210.111*
H25B0.10370.41960.40000.111*
H25C0.19530.33560.32980.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0343 (10)0.0366 (10)0.0317 (10)0.0065 (8)0.0047 (8)0.0033 (8)
O10.0828 (15)0.0459 (11)0.0428 (11)0.0013 (10)0.0073 (9)0.0110 (9)
O20.0679 (14)0.136 (2)0.0426 (11)0.0125 (16)0.0150 (10)0.0190 (15)
O30.0632 (12)0.0532 (11)0.0403 (10)0.0214 (10)0.0004 (8)0.0054 (9)
O40.0284 (8)0.0597 (12)0.0430 (10)0.0003 (8)0.0039 (7)0.0021 (9)
O50.0234 (8)0.0722 (13)0.0416 (9)0.0000 (8)0.0009 (7)0.0104 (9)
O60.0314 (8)0.0577 (11)0.0374 (9)0.0013 (8)0.0079 (7)0.0025 (8)
C10.0319 (12)0.0465 (14)0.0305 (11)0.0079 (10)0.0010 (9)0.0027 (10)
C20.0406 (13)0.0551 (16)0.0438 (14)0.0182 (12)0.0009 (11)0.0030 (12)
C30.0410 (14)0.0583 (17)0.0403 (13)0.0077 (12)0.0063 (10)0.0106 (12)
C40.0382 (13)0.0426 (13)0.0304 (12)0.0011 (10)0.0038 (10)0.0030 (10)
C50.0353 (12)0.0318 (11)0.0290 (11)0.0024 (9)0.0000 (9)0.0006 (9)
C60.0324 (11)0.0445 (13)0.0284 (11)0.0041 (10)0.0020 (9)0.0013 (10)
C70.0296 (11)0.0368 (12)0.0292 (11)0.0001 (10)0.0026 (9)0.0072 (10)
C80.0224 (10)0.0425 (12)0.0326 (11)0.0014 (9)0.0011 (8)0.0048 (11)
C90.0287 (11)0.0390 (13)0.0317 (11)0.0033 (10)0.0037 (9)0.0026 (10)
C100.0318 (11)0.0306 (11)0.0309 (11)0.0025 (9)0.0015 (9)0.0054 (9)
C110.0270 (11)0.0341 (11)0.0270 (10)0.0013 (9)0.0021 (8)0.0007 (9)
C120.0347 (11)0.0413 (13)0.0295 (11)0.0071 (10)0.0009 (9)0.0054 (10)
C130.0353 (12)0.0378 (13)0.0264 (11)0.0041 (10)0.0015 (9)0.0032 (9)
C140.0363 (12)0.0397 (13)0.0352 (12)0.0015 (10)0.0060 (10)0.0089 (10)
C150.0384 (12)0.0405 (13)0.0377 (13)0.0101 (11)0.0044 (10)0.0070 (11)
C160.0354 (12)0.0375 (12)0.0389 (13)0.0050 (10)0.0040 (10)0.0007 (10)
C170.0271 (10)0.0336 (12)0.0263 (10)0.0009 (9)0.0003 (8)0.0024 (9)
C180.0521 (15)0.0485 (16)0.0319 (13)0.0013 (12)0.0036 (11)0.0016 (11)
C190.0428 (13)0.0449 (14)0.0288 (11)0.0045 (11)0.0071 (9)0.0020 (11)
C200.0495 (14)0.0417 (14)0.0424 (14)0.0085 (12)0.0056 (11)0.0068 (12)
C210.082 (2)0.0407 (15)0.0615 (19)0.0156 (15)0.0057 (15)0.0028 (14)
C220.081 (2)0.067 (2)0.0578 (18)0.0142 (18)0.0002 (16)0.0212 (17)
C230.0418 (14)0.0720 (19)0.0433 (15)0.0085 (14)0.0130 (12)0.0039 (14)
C240.0497 (16)0.088 (3)0.067 (2)0.0017 (17)0.0184 (15)0.0215 (19)
C250.111 (3)0.059 (2)0.0485 (17)0.0249 (19)0.0163 (17)0.0134 (15)
Geometric parameters (Å, º) top
N1—C201.468 (3)C9—C101.550 (3)
N1—C191.470 (3)C9—H90.9800
N1—C171.487 (3)C10—C111.545 (3)
O1—C181.408 (4)C10—C121.564 (3)
O1—C221.416 (4)C10—H100.9800
O2—C231.191 (4)C11—C171.533 (3)
O3—C251.415 (4)C12—C131.532 (3)
O3—C161.432 (3)C12—H12A0.9700
O4—C11.429 (3)C12—H12B0.9700
O4—H1O40.8140C13—C141.518 (3)
O5—C81.428 (3)C13—C161.536 (3)
O5—H1O50.7709C13—H130.9800
O6—C231.344 (3)C14—H140.9800
O6—C141.444 (3)C15—C161.535 (3)
C1—C21.518 (4)C15—H15A0.9700
C1—C111.567 (3)C15—H15B0.9700
C1—H10.9800C16—H160.9800
C2—C31.517 (4)C17—H170.9800
C2—H2A0.9700C18—H18A0.9700
C2—H2B0.9700C18—H18B0.9700
C3—C41.556 (3)C19—H19A0.9700
C3—H3A0.9700C19—H19B0.9700
C3—H3B0.9700C20—C211.512 (4)
C4—C181.528 (3)C20—H20A0.9700
C4—C191.534 (4)C20—H20B0.9700
C4—C51.557 (3)C21—H21A0.9600
C5—C61.548 (3)C21—H21B0.9600
C5—C111.549 (3)C21—H21C0.9600
C5—H50.9800C22—H22A0.9600
C6—C71.544 (3)C22—H22B0.9600
C6—H6A0.9700C22—H22C0.9600
C6—H6B0.9700C23—C241.492 (4)
C7—C81.534 (3)C24—H24A0.9600
C7—C171.539 (3)C24—H24B0.9600
C7—H70.9800C24—H24C0.9600
C8—C91.547 (3)C25—H25A0.9600
C8—C151.558 (4)C25—H25B0.9600
C9—C141.527 (3)C25—H25C0.9600
C20—N1—C19110.04 (19)C10—C12—H12B110.5
C20—N1—C17113.0 (2)H12A—C12—H12B108.7
C19—N1—C17113.34 (18)C14—C13—C12100.91 (19)
C18—O1—C22112.9 (2)C14—C13—C16111.22 (18)
C25—O3—C16114.4 (2)C12—C13—C16112.55 (19)
C1—O4—H1O4104.9C14—C13—H13110.6
C8—O5—H1O5113.6C12—C13—H13110.6
C23—O6—C14116.5 (2)C16—C13—H13110.6
O4—C1—C2111.9 (2)O6—C14—C13114.3 (2)
O4—C1—C11113.00 (19)O6—C14—C9110.02 (18)
C2—C1—C11111.27 (19)C13—C14—C9102.07 (18)
O4—C1—H1106.7O6—C14—H14110.1
C2—C1—H1106.7C13—C14—H14110.1
C11—C1—H1106.7C9—C14—H14110.1
C3—C2—C1111.6 (2)C16—C15—C8119.2 (2)
C3—C2—H2A109.3C16—C15—H15A107.5
C1—C2—H2A109.3C8—C15—H15A107.5
C3—C2—H2B109.3C16—C15—H15B107.5
C1—C2—H2B109.3C8—C15—H15B107.5
H2A—C2—H2B108.0H15A—C15—H15B107.0
C2—C3—C4113.4 (2)O3—C16—C15104.98 (19)
C2—C3—H3A108.9O3—C16—C13111.8 (2)
C4—C3—H3A108.9C15—C16—C13114.2 (2)
C2—C3—H3B108.9O3—C16—H16108.5
C4—C3—H3B108.9C15—C16—H16108.5
H3A—C3—H3B107.7C13—C16—H16108.5
C18—C4—C19107.4 (2)N1—C17—C11109.88 (18)
C18—C4—C3109.2 (2)N1—C17—C7115.51 (17)
C19—C4—C3110.3 (2)C11—C17—C7100.56 (17)
C18—C4—C5110.5 (2)N1—C17—H17110.2
C19—C4—C5107.32 (19)C11—C17—H17110.2
C3—C4—C5112.0 (2)C7—C17—H17110.2
C6—C5—C11103.12 (18)O1—C18—C4109.8 (2)
C6—C5—C4110.72 (18)O1—C18—H18A109.7
C11—C5—C4108.46 (18)C4—C18—H18A109.7
C6—C5—H5111.4O1—C18—H18B109.7
C11—C5—H5111.4C4—C18—H18B109.7
C4—C5—H5111.4H18A—C18—H18B108.2
C7—C6—C5105.19 (17)N1—C19—C4112.51 (19)
C7—C6—H6A110.7N1—C19—H19A109.1
C5—C6—H6A110.7C4—C19—H19A109.1
C7—C6—H6B110.7N1—C19—H19B109.1
C5—C6—H6B110.7C4—C19—H19B109.1
H6A—C6—H6B108.8H19A—C19—H19B107.8
C8—C7—C17110.87 (17)N1—C20—C21113.2 (2)
C8—C7—C6109.92 (19)N1—C20—H20A108.9
C17—C7—C6103.83 (18)C21—C20—H20A108.9
C8—C7—H7110.7N1—C20—H20B108.9
C17—C7—H7110.7C21—C20—H20B108.9
C6—C7—H7110.7H20A—C20—H20B107.7
O5—C8—C7103.43 (17)C20—C21—H21A109.5
O5—C8—C9110.49 (19)C20—C21—H21B109.5
C7—C8—C9108.49 (18)H21A—C21—H21B109.5
O5—C8—C15108.44 (19)C20—C21—H21C109.5
C7—C8—C15112.87 (19)H21A—C21—H21C109.5
C9—C8—C15112.73 (18)H21B—C21—H21C109.5
C14—C9—C8111.82 (19)O1—C22—H22A109.5
C14—C9—C10100.95 (18)O1—C22—H22B109.5
C8—C9—C10112.90 (18)H22A—C22—H22B109.5
C14—C9—H9110.3O1—C22—H22C109.5
C8—C9—H9110.3H22A—C22—H22C109.5
C10—C9—H9110.3H22B—C22—H22C109.5
C11—C10—C9117.66 (17)O2—C23—O6123.4 (3)
C11—C10—C12112.54 (18)O2—C23—C24126.1 (3)
C9—C10—C12104.01 (18)O6—C23—C24110.5 (3)
C11—C10—H10107.4C23—C24—H24A109.5
C9—C10—H10107.4C23—C24—H24B109.5
C12—C10—H10107.4H24A—C24—H24B109.5
C17—C11—C10108.77 (18)C23—C24—H24C109.5
C17—C11—C598.84 (16)H24A—C24—H24C109.5
C10—C11—C5112.93 (18)H24B—C24—H24C109.5
C17—C11—C1114.93 (18)O3—C25—H25A109.5
C10—C11—C1107.30 (17)O3—C25—H25B109.5
C5—C11—C1113.97 (18)H25A—C25—H25B109.5
C13—C12—C10106.19 (18)O3—C25—H25C109.5
C13—C12—H12A110.5H25A—C25—H25C109.5
C10—C12—H12A110.5H25B—C25—H25C109.5
C13—C12—H12B110.5
O4—C1—C2—C371.3 (3)C9—C10—C12—C131.0 (2)
C11—C1—C2—C356.2 (3)C10—C12—C13—C1428.6 (2)
C1—C2—C3—C449.5 (3)C10—C12—C13—C1690.1 (2)
C2—C3—C4—C18130.5 (2)C23—O6—C14—C1370.8 (3)
C2—C3—C4—C19111.6 (3)C23—O6—C14—C9175.1 (2)
C2—C3—C4—C57.8 (3)C12—C13—C14—O6166.94 (18)
C18—C4—C5—C669.0 (3)C16—C13—C14—O647.3 (2)
C19—C4—C5—C647.8 (2)C12—C13—C14—C948.2 (2)
C3—C4—C5—C6169.0 (2)C16—C13—C14—C971.4 (2)
C18—C4—C5—C11178.5 (2)C8—C9—C14—O650.4 (3)
C19—C4—C5—C1164.6 (2)C10—C9—C14—O6170.73 (19)
C3—C4—C5—C1156.6 (3)C8—C9—C14—C1371.2 (2)
C11—C5—C6—C719.9 (2)C10—C9—C14—C1349.1 (2)
C4—C5—C6—C795.9 (2)O5—C8—C15—C16140.7 (2)
C5—C6—C7—C8106.04 (19)C7—C8—C15—C16105.3 (2)
C5—C6—C7—C1712.6 (2)C9—C8—C15—C1618.1 (3)
C17—C7—C8—O5178.02 (19)C25—O3—C16—C15167.4 (3)
C6—C7—C8—O567.8 (2)C25—O3—C16—C1368.3 (3)
C17—C7—C8—C964.6 (2)C8—C15—C16—O3140.8 (2)
C6—C7—C8—C949.6 (2)C8—C15—C16—C1317.9 (3)
C17—C7—C8—C1561.0 (2)C14—C13—C16—O391.0 (2)
C6—C7—C8—C15175.27 (18)C12—C13—C16—O3156.64 (19)
O5—C8—C9—C1494.1 (2)C14—C13—C16—C1528.1 (3)
C7—C8—C9—C14153.14 (18)C12—C13—C16—C1584.3 (2)
C15—C8—C9—C1427.4 (3)C20—N1—C17—C11172.81 (18)
O5—C8—C9—C10152.85 (19)C19—N1—C17—C1161.2 (2)
C7—C8—C9—C1040.1 (2)C20—N1—C17—C774.3 (3)
C15—C8—C9—C1085.6 (2)C19—N1—C17—C751.7 (3)
C14—C9—C10—C11155.2 (2)C10—C11—C17—N1172.40 (17)
C8—C9—C10—C1135.7 (3)C5—C11—C17—N169.61 (19)
C14—C9—C10—C1230.0 (2)C1—C11—C17—N152.1 (2)
C8—C9—C10—C1289.6 (2)C10—C11—C17—C765.37 (19)
C9—C10—C11—C1749.9 (2)C5—C11—C17—C752.63 (19)
C12—C10—C11—C1771.0 (2)C1—C11—C17—C7174.34 (17)
C9—C10—C11—C558.8 (3)C8—C7—C17—N1164.58 (19)
C12—C10—C11—C5179.66 (18)C6—C7—C17—N177.4 (2)
C9—C10—C11—C1174.79 (19)C8—C7—C17—C1177.2 (2)
C12—C10—C11—C153.9 (2)C6—C7—C17—C1140.8 (2)
C6—C5—C11—C1744.8 (2)C22—O1—C18—C4172.3 (2)
C4—C5—C11—C1772.7 (2)C19—C4—C18—O1179.2 (2)
C6—C5—C11—C1070.0 (2)C3—C4—C18—O161.2 (3)
C4—C5—C11—C10172.52 (18)C5—C4—C18—O162.4 (3)
C6—C5—C11—C1167.17 (19)C20—N1—C19—C4176.4 (2)
C4—C5—C11—C149.7 (2)C17—N1—C19—C448.9 (3)
O4—C1—C11—C178.5 (3)C18—C4—C19—N1168.33 (19)
C2—C1—C11—C17118.4 (2)C3—C4—C19—N172.8 (3)
O4—C1—C11—C10112.6 (2)C5—C4—C19—N149.5 (3)
C2—C1—C11—C10120.5 (2)C19—N1—C20—C21166.5 (2)
O4—C1—C11—C5121.6 (2)C17—N1—C20—C2165.8 (3)
C2—C1—C11—C55.3 (3)C14—O6—C23—O28.6 (4)
C11—C10—C12—C13129.41 (19)C14—O6—C23—C24170.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1O4···N10.811.992.7166 (19)148
O5—H1O5···O4i0.772.152.8184 (17)146
O5—H1O5···O60.772.573.0546 (18)123
C3—H3B···O10.972.492.895 (3)105
C6—H6A···O50.972.522.868 (2)101
Symmetry code: (i) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds