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In the asymmetric unit of the title compound, C20H24N2O2·1.5H2O, there are two independent quinidine [systematic name: (1S,3R,4S,8R,9S)-4-[hydr­oxy(5-vinyl-1-aza­bicyclo­[2.2.2]oct-2-yl)meth­yl]-6-methoxy­quinoline] mol­ecules and three water mol­ecules. Inter­molecular O—H...O and O—H...N hydrogen bonds stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006368/is2114sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006368/is2114Isup2.hkl
Contains datablock I

CCDC reference: 640396

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.116
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O7 - H7B ... ?
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
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 26.00 From the CIF: _reflns_number_total 4098 Count of symmetry unique reflns 4099 Completeness (_total/calc) 99.98% 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 C11 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 9 ALERT level G = General alerts; check 12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

(1S,3R,4S,8R,9S)-4-[hydroxy(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methyl]- 6-methoxyquinoline sesquihydrate top
Crystal data top
C20H24N2O2·1.5H2ODx = 1.247 Mg m3
Mr = 351.44Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P212121Cell parameters from 9358 reflections
a = 12.0742 (10) Åθ = 1.6–27.8°
b = 17.5445 (15) ŵ = 0.09 mm1
c = 17.6675 (16) ÅT = 113 K
V = 3742.6 (6) Å3Block, colorless
Z = 80.10 × 0.08 × 0.04 mm
F(000) = 1512
Data collection top
Rigaku Saturn CCD
diffractometer
4098 independent reflections
Radiation source: rotating anode3735 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.055
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.6°
ω scansh = 1414
Absorption correction: multi-scan
(Jacobson, 1998)
k = 2118
Tmin = 0.992, Tmax = 0.997l = 1721
27584 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)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.7488P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4098 reflectionsΔρmax = 0.21 e Å3
488 parametersΔρmin = 0.24 e Å3
6 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0148 (12)
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
C10.3133 (2)0.90446 (17)0.69057 (17)0.0236 (6)
H10.29480.93750.64990.028*
C20.3996 (2)0.85114 (16)0.67905 (17)0.0233 (6)
H20.43730.84920.63190.028*
C30.4287 (2)0.80224 (15)0.73644 (16)0.0199 (6)
C40.3714 (2)0.80806 (15)0.80687 (16)0.0195 (6)
C50.2862 (2)0.86372 (15)0.81329 (16)0.0214 (6)
C60.2288 (2)0.87170 (16)0.88303 (17)0.0256 (7)
H60.17140.90840.88740.031*
C70.2551 (3)0.82734 (17)0.94388 (18)0.0256 (6)
H70.21710.83380.99050.031*
C80.3402 (2)0.77108 (16)0.93716 (16)0.0226 (6)
C90.3972 (2)0.76172 (16)0.87054 (16)0.0223 (6)
H90.45380.72430.86700.027*
C100.4395 (3)0.66997 (17)0.99760 (18)0.0303 (7)
H10A0.41840.63430.95740.045*
H10B0.44250.64291.04610.045*
H10C0.51240.69170.98630.045*
C110.5195 (2)0.74264 (15)0.72518 (16)0.0206 (6)
H110.56570.74050.77210.025*
C120.4661 (2)0.66379 (15)0.71280 (16)0.0207 (6)
H120.40500.65920.75070.025*
C130.4126 (2)0.65418 (15)0.63445 (16)0.0223 (6)
H13A0.45150.68630.59680.027*
H13B0.33400.67000.63620.027*
C140.4214 (2)0.56965 (16)0.61209 (17)0.0231 (6)
H140.37310.55870.56740.028*
C150.3863 (3)0.52067 (16)0.67986 (18)0.0255 (7)
H15A0.38170.46640.66480.031*
H15B0.31260.53700.69840.031*
C160.4743 (3)0.53113 (16)0.74259 (19)0.0278 (7)
H16A0.43690.53670.79220.033*
H16B0.52200.48530.74490.033*
C170.6130 (2)0.58427 (17)0.65993 (19)0.0280 (7)
H17A0.67290.54810.67340.034*
H17B0.64800.63230.64290.034*
C180.5431 (2)0.55022 (16)0.59392 (18)0.0269 (7)
H180.55170.49350.59460.032*
C190.5790 (3)0.57895 (19)0.5178 (2)0.0361 (8)
H190.57950.63260.51040.043*
C200.6097 (3)0.5362 (2)0.4605 (2)0.0466 (10)
H20A0.61050.48230.46540.056*
H20B0.63130.55930.41410.056*
C210.7018 (3)1.12505 (16)0.27480 (18)0.0258 (7)
H210.71711.16180.31290.031*
C220.6136 (2)1.07376 (16)0.28666 (18)0.0246 (6)
H220.57081.07700.33170.029*
C230.5893 (2)1.01922 (15)0.23361 (16)0.0207 (6)
C240.6567 (2)1.01572 (15)0.16698 (17)0.0211 (6)
C250.7432 (2)1.07017 (16)0.15967 (17)0.0234 (6)
C260.8126 (3)1.06797 (17)0.09418 (18)0.0269 (7)
H260.87081.10410.08910.032*
C270.7967 (3)1.01506 (17)0.03915 (18)0.0273 (7)
H270.84401.01400.00380.033*
C280.7089 (3)0.96090 (17)0.04590 (17)0.0245 (6)
C290.6405 (2)0.96107 (16)0.10787 (17)0.0237 (6)
H290.58220.92490.11160.028*
C300.6149 (3)0.85639 (18)0.0115 (2)0.0327 (7)
H30A0.62370.82540.03420.049*
H30B0.61960.82360.05630.049*
H30C0.54250.88170.01050.049*
C310.4956 (2)0.96273 (15)0.24632 (18)0.0214 (6)
H310.45610.95440.19730.026*
C320.5464 (2)0.88563 (15)0.27278 (16)0.0216 (6)
H320.61820.87950.24530.026*
C330.5729 (2)0.88168 (16)0.35828 (16)0.0233 (6)
H33A0.52340.91630.38680.028*
H33B0.65050.89730.36750.028*
C340.5551 (2)0.79824 (16)0.38432 (18)0.0261 (7)
H340.58650.79020.43610.031*
C350.6105 (3)0.74444 (17)0.32684 (18)0.0291 (7)
H35A0.68900.75900.31950.035*
H35B0.60790.69130.34550.035*
C360.5468 (2)0.75133 (15)0.25187 (18)0.0260 (7)
H36A0.60030.75400.20950.031*
H36B0.50060.70530.24460.031*
C370.3850 (2)0.80971 (17)0.30706 (16)0.0247 (6)
H37A0.32980.77320.28700.030*
H37B0.34730.85910.31520.030*
C380.4297 (3)0.78004 (17)0.38329 (17)0.0266 (7)
H380.42100.72340.38390.032*
C390.3665 (3)0.81176 (19)0.44905 (19)0.0335 (7)
H390.37550.86440.46000.040*
C400.2990 (3)0.7722 (2)0.49307 (19)0.0366 (8)
H40A0.28780.71940.48400.044*
H40B0.26180.79660.53380.044*
N10.2567 (2)0.91133 (13)0.75442 (14)0.0242 (5)
N20.7645 (2)1.12477 (13)0.21345 (15)0.0259 (6)
N30.5442 (2)0.59964 (13)0.72793 (14)0.0242 (6)
N40.47507 (19)0.81985 (12)0.25053 (14)0.0207 (5)
O10.35914 (18)0.73010 (11)1.00211 (11)0.0280 (5)
O20.58971 (17)0.76096 (12)0.66289 (12)0.0251 (5)
H2A0.632 (3)0.799 (2)0.6835 (19)0.038*
O30.70048 (18)0.91247 (12)0.01442 (12)0.0302 (5)
O40.41797 (18)0.98959 (11)0.30112 (13)0.0263 (5)
H40.374 (3)1.018 (2)0.281 (2)0.039*
O50.3701 (2)0.84591 (13)0.11638 (13)0.0353 (6)
H5A0.404 (3)0.830 (2)0.1591 (18)0.053*
H5B0.378 (4)0.8066 (18)0.087 (2)0.053*
O60.1419 (2)0.87830 (17)0.12935 (14)0.0432 (6)
H6A0.117 (4)0.887 (2)0.1757 (17)0.065*
H6B0.215 (2)0.869 (2)0.130 (2)0.065*
O70.0922 (3)0.98855 (19)0.0197 (2)0.0662 (9)
H7A0.106 (5)0.951 (2)0.061 (2)0.099*
H7B0.161 (3)1.003 (3)0.000 (3)0.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0224 (15)0.0219 (14)0.0264 (16)0.0026 (12)0.0050 (12)0.0015 (12)
C20.0194 (15)0.0226 (14)0.0279 (16)0.0022 (12)0.0002 (12)0.0005 (12)
C30.0162 (13)0.0174 (13)0.0262 (15)0.0052 (11)0.0001 (11)0.0023 (11)
C40.0161 (13)0.0174 (13)0.0250 (15)0.0012 (11)0.0013 (11)0.0025 (11)
C50.0190 (14)0.0171 (14)0.0281 (16)0.0007 (11)0.0029 (12)0.0035 (11)
C60.0192 (14)0.0240 (15)0.0334 (17)0.0022 (12)0.0005 (12)0.0055 (13)
C70.0228 (15)0.0275 (15)0.0265 (15)0.0005 (12)0.0025 (13)0.0062 (13)
C80.0206 (14)0.0211 (14)0.0260 (16)0.0013 (12)0.0013 (12)0.0012 (12)
C90.0195 (14)0.0211 (14)0.0263 (15)0.0022 (11)0.0017 (12)0.0024 (12)
C100.0279 (16)0.0305 (16)0.0326 (17)0.0083 (13)0.0004 (13)0.0060 (13)
C110.0167 (13)0.0226 (14)0.0224 (15)0.0017 (11)0.0030 (11)0.0004 (11)
C120.0164 (13)0.0213 (14)0.0245 (15)0.0015 (11)0.0003 (12)0.0006 (12)
C130.0176 (14)0.0219 (14)0.0273 (15)0.0013 (11)0.0012 (12)0.0004 (12)
C140.0200 (14)0.0231 (14)0.0263 (15)0.0035 (12)0.0005 (12)0.0009 (12)
C150.0213 (15)0.0203 (14)0.0349 (17)0.0049 (12)0.0022 (13)0.0028 (12)
C160.0250 (15)0.0220 (15)0.0365 (18)0.0037 (12)0.0036 (14)0.0052 (13)
C170.0168 (14)0.0235 (15)0.0439 (19)0.0017 (12)0.0012 (13)0.0000 (13)
C180.0228 (15)0.0200 (14)0.0380 (18)0.0006 (12)0.0069 (13)0.0051 (13)
C190.0325 (18)0.0319 (17)0.044 (2)0.0070 (15)0.0113 (16)0.0022 (15)
C200.041 (2)0.053 (2)0.046 (2)0.0120 (18)0.0160 (18)0.0079 (18)
C210.0247 (15)0.0176 (14)0.0350 (17)0.0009 (12)0.0057 (13)0.0009 (12)
C220.0213 (14)0.0214 (14)0.0310 (16)0.0044 (12)0.0023 (12)0.0000 (13)
C230.0188 (14)0.0141 (13)0.0292 (16)0.0027 (11)0.0039 (12)0.0028 (11)
C240.0164 (13)0.0184 (13)0.0285 (16)0.0037 (11)0.0028 (12)0.0034 (12)
C250.0212 (14)0.0201 (14)0.0288 (16)0.0009 (11)0.0034 (12)0.0057 (12)
C260.0218 (15)0.0263 (15)0.0327 (17)0.0052 (12)0.0017 (13)0.0068 (13)
C270.0217 (15)0.0305 (16)0.0297 (17)0.0023 (13)0.0024 (13)0.0064 (13)
C280.0227 (15)0.0245 (15)0.0262 (16)0.0010 (12)0.0015 (12)0.0008 (12)
C290.0212 (14)0.0212 (14)0.0286 (16)0.0026 (12)0.0005 (12)0.0034 (12)
C300.0281 (17)0.0313 (17)0.0386 (18)0.0052 (13)0.0030 (15)0.0070 (14)
C310.0158 (13)0.0206 (14)0.0279 (15)0.0018 (11)0.0015 (11)0.0009 (12)
C320.0156 (13)0.0189 (14)0.0303 (16)0.0001 (11)0.0022 (12)0.0039 (12)
C330.0176 (13)0.0222 (14)0.0300 (16)0.0008 (12)0.0016 (12)0.0022 (12)
C340.0245 (16)0.0235 (15)0.0302 (16)0.0020 (12)0.0044 (13)0.0020 (12)
C350.0231 (15)0.0221 (15)0.0422 (18)0.0045 (12)0.0037 (14)0.0001 (13)
C360.0239 (15)0.0170 (14)0.0373 (17)0.0014 (12)0.0019 (13)0.0056 (12)
C370.0163 (14)0.0261 (15)0.0318 (17)0.0002 (12)0.0001 (12)0.0008 (12)
C380.0263 (15)0.0206 (14)0.0329 (17)0.0001 (12)0.0041 (13)0.0026 (12)
C390.0312 (18)0.0336 (17)0.0356 (18)0.0006 (15)0.0064 (14)0.0010 (15)
C400.0281 (17)0.047 (2)0.0347 (19)0.0006 (15)0.0005 (15)0.0076 (16)
N10.0197 (12)0.0217 (12)0.0311 (14)0.0004 (10)0.0052 (11)0.0002 (10)
N20.0208 (12)0.0205 (12)0.0364 (15)0.0009 (10)0.0054 (11)0.0018 (11)
N30.0188 (12)0.0210 (12)0.0329 (14)0.0004 (10)0.0040 (10)0.0036 (10)
N40.0174 (12)0.0166 (11)0.0282 (13)0.0006 (9)0.0013 (10)0.0012 (10)
O10.0286 (12)0.0291 (12)0.0264 (11)0.0050 (9)0.0003 (9)0.0026 (9)
O20.0210 (10)0.0242 (10)0.0301 (12)0.0068 (9)0.0052 (9)0.0022 (9)
O30.0284 (11)0.0301 (12)0.0322 (12)0.0035 (10)0.0036 (10)0.0027 (9)
O40.0189 (10)0.0248 (11)0.0351 (12)0.0065 (9)0.0049 (9)0.0000 (9)
O50.0364 (14)0.0376 (13)0.0318 (13)0.0054 (11)0.0062 (11)0.0056 (10)
O60.0302 (13)0.0678 (17)0.0317 (13)0.0037 (13)0.0029 (11)0.0005 (13)
O70.067 (2)0.0631 (19)0.069 (2)0.0049 (17)0.0096 (18)0.0123 (16)
Geometric parameters (Å, º) top
C1—N11.324 (4)C22—H220.9500
C1—C21.415 (4)C23—C241.433 (4)
C1—H10.9500C23—C311.520 (4)
C2—C31.374 (4)C24—C251.421 (4)
C2—H20.9500C24—C291.431 (4)
C3—C41.427 (4)C25—N21.374 (4)
C3—C111.529 (4)C25—C261.430 (4)
C4—C91.423 (4)C26—C271.358 (4)
C4—C51.423 (4)C26—H260.9500
C5—N11.380 (4)C27—C281.429 (4)
C5—C61.420 (4)C27—H270.9500
C6—C71.365 (4)C28—O31.367 (4)
C6—H60.9500C28—C291.371 (4)
C7—C81.429 (4)C29—H290.9500
C7—H70.9500C30—O31.428 (4)
C8—C91.373 (4)C30—H30A0.9800
C8—O11.373 (3)C30—H30B0.9800
C9—H90.9500C30—H30C0.9800
C10—O11.436 (4)C31—O41.428 (3)
C10—H10A0.9800C31—C321.557 (4)
C10—H10B0.9800C31—H311.0000
C10—H10C0.9800C32—N41.493 (3)
C11—O21.426 (3)C32—C331.546 (4)
C11—C121.542 (4)C32—H321.0000
C11—H111.0000C33—C341.550 (4)
C12—N31.493 (4)C33—H33A0.9900
C12—C131.536 (4)C33—H33B0.9900
C12—H121.0000C34—C351.539 (4)
C13—C141.538 (4)C34—C381.547 (4)
C13—H13A0.9900C34—H341.0000
C13—H13B0.9900C35—C361.536 (4)
C14—C151.534 (4)C35—H35A0.9900
C14—C181.542 (4)C35—H35B0.9900
C14—H141.0000C36—N41.482 (3)
C15—C161.546 (4)C36—H36A0.9900
C15—H15A0.9900C36—H36B0.9900
C15—H15B0.9900C37—N41.487 (4)
C16—N31.492 (4)C37—C381.541 (4)
C16—H16A0.9900C37—H37A0.9900
C16—H16B0.9900C37—H37B0.9900
C17—N31.485 (4)C38—C391.498 (4)
C17—C181.559 (4)C38—H381.0000
C17—H17A0.9900C39—C401.323 (5)
C17—H17B0.9900C39—H390.9500
C18—C191.501 (5)C40—H40A0.9500
C18—H181.0000C40—H40B0.9500
C19—C201.313 (5)O2—H2A0.91 (4)
C19—H190.9500O4—H40.81 (4)
C20—H20A0.9500O5—H5A0.90 (3)
C20—H20B0.9500O5—H5B0.87 (3)
C21—N21.322 (4)O6—H6A0.89 (3)
C21—C221.410 (4)O6—H6B0.90 (3)
C21—H210.9500O7—H7A0.99 (3)
C22—C231.371 (4)O7—H7B0.93 (3)
N1—C1—C2124.2 (3)C24—C23—C31121.1 (2)
N1—C1—H1117.9C25—C24—C29119.0 (3)
C2—C1—H1117.9C25—C24—C23117.6 (3)
C3—C2—C1119.7 (3)C29—C24—C23123.4 (3)
C3—C2—H2120.2N2—C25—C24122.9 (3)
C1—C2—H2120.2N2—C25—C26118.0 (3)
C2—C3—C4118.3 (3)C24—C25—C26119.1 (3)
C2—C3—C11121.0 (3)C27—C26—C25121.0 (3)
C4—C3—C11120.7 (2)C27—C26—H26119.5
C9—C4—C5119.2 (3)C25—C26—H26119.5
C9—C4—C3122.8 (3)C26—C27—C28120.0 (3)
C5—C4—C3118.0 (2)C26—C27—H27120.0
N1—C5—C6117.9 (2)C28—C27—H27120.0
N1—C5—C4122.8 (3)O3—C28—C29125.4 (3)
C6—C5—C4119.3 (3)O3—C28—C27113.8 (3)
C7—C6—C5120.9 (3)C29—C28—C27120.8 (3)
C7—C6—H6119.5C28—C29—C24120.1 (3)
C5—C6—H6119.5C28—C29—H29120.0
C6—C7—C8119.7 (3)C24—C29—H29120.0
C6—C7—H7120.1O3—C30—H30A109.5
C8—C7—H7120.1O3—C30—H30B109.5
C9—C8—O1124.7 (3)H30A—C30—H30B109.5
C9—C8—C7120.9 (3)O3—C30—H30C109.5
O1—C8—C7114.3 (3)H30A—C30—H30C109.5
C8—C9—C4120.0 (3)H30B—C30—H30C109.5
C8—C9—H9120.0O4—C31—C23111.9 (2)
C4—C9—H9120.0O4—C31—C32110.0 (2)
O1—C10—H10A109.5C23—C31—C32108.6 (2)
O1—C10—H10B109.5O4—C31—H31108.8
H10A—C10—H10B109.5C23—C31—H31108.8
O1—C10—H10C109.5C32—C31—H31108.8
H10A—C10—H10C109.5N4—C32—C33110.0 (2)
H10B—C10—H10C109.5N4—C32—C31111.5 (2)
O2—C11—C3111.9 (2)C33—C32—C31114.5 (2)
O2—C11—C12110.0 (2)N4—C32—H32106.8
C3—C11—C12109.4 (2)C33—C32—H32106.8
O2—C11—H11108.5C31—C32—H32106.8
C3—C11—H11108.5C32—C33—C34107.7 (2)
C12—C11—H11108.5C32—C33—H33A110.2
N3—C12—C13110.1 (2)C34—C33—H33A110.2
N3—C12—C11112.7 (2)C32—C33—H33B110.2
C13—C12—C11113.7 (2)C34—C33—H33B110.2
N3—C12—H12106.6H33A—C33—H33B108.5
C13—C12—H12106.6C35—C34—C38106.9 (2)
C11—C12—H12106.6C35—C34—C33108.8 (2)
C12—C13—C14108.0 (2)C38—C34—C33109.1 (2)
C12—C13—H13A110.1C35—C34—H34110.6
C14—C13—H13A110.1C38—C34—H34110.6
C12—C13—H13B110.1C33—C34—H34110.6
C14—C13—H13B110.1C36—C35—C34107.6 (2)
H13A—C13—H13B108.4C36—C35—H35A110.2
C15—C14—C13108.7 (2)C34—C35—H35A110.2
C15—C14—C18107.6 (2)C36—C35—H35B110.2
C13—C14—C18109.4 (2)C34—C35—H35B110.2
C15—C14—H14110.4H35A—C35—H35B108.5
C13—C14—H14110.4N4—C36—C35111.7 (2)
C18—C14—H14110.4N4—C36—H36A109.3
C14—C15—C16107.6 (2)C35—C36—H36A109.3
C14—C15—H15A110.2N4—C36—H36B109.3
C16—C15—H15A110.2C35—C36—H36B109.3
C14—C15—H15B110.2H36A—C36—H36B107.9
C16—C15—H15B110.2N4—C37—C38111.8 (2)
H15A—C15—H15B108.5N4—C37—H37A109.3
N3—C16—C15111.1 (2)C38—C37—H37A109.3
N3—C16—H16A109.4N4—C37—H37B109.3
C15—C16—H16A109.4C38—C37—H37B109.3
N3—C16—H16B109.4H37A—C37—H37B107.9
C15—C16—H16B109.4C39—C38—C37112.0 (3)
H16A—C16—H16B108.0C39—C38—C34114.4 (3)
N3—C17—C18111.8 (2)C37—C38—C34106.4 (2)
N3—C17—H17A109.3C39—C38—H38107.9
C18—C17—H17A109.3C37—C38—H38107.9
N3—C17—H17B109.3C34—C38—H38107.9
C18—C17—H17B109.3C40—C39—C38125.1 (3)
H17A—C17—H17B107.9C40—C39—H39117.4
C19—C18—C14112.8 (3)C38—C39—H39117.4
C19—C18—C17112.7 (2)C39—C40—H40A120.0
C14—C18—C17106.0 (2)C39—C40—H40B120.0
C19—C18—H18108.4H40A—C40—H40B120.0
C14—C18—H18108.4C1—N1—C5117.0 (2)
C17—C18—H18108.4C21—N2—C25117.6 (2)
C20—C19—C18125.5 (3)C17—N3—C16108.1 (2)
C20—C19—H19117.2C17—N3—C12110.2 (2)
C18—C19—H19117.2C16—N3—C12106.3 (2)
C19—C20—H20A120.0C36—N4—C37108.6 (2)
C19—C20—H20B120.0C36—N4—C32106.6 (2)
H20A—C20—H20B120.0C37—N4—C32109.7 (2)
N2—C21—C22123.5 (3)C8—O1—C10116.8 (2)
N2—C21—H21118.3C11—O2—H2A101 (2)
C22—C21—H21118.3C28—O3—C30117.0 (2)
C23—C22—C21120.4 (3)C31—O4—H4109 (3)
C23—C22—H22119.8H5A—O5—H5B102 (4)
C21—C22—H22119.8H6A—O6—H6B111 (4)
C22—C23—C24118.0 (3)H7A—O7—H7B108 (5)
C22—C23—C31120.9 (3)
N1—C1—C2—C30.2 (4)C25—C26—C27—C280.6 (4)
C1—C2—C3—C41.1 (4)C26—C27—C28—O3178.3 (3)
C1—C2—C3—C11178.5 (3)C26—C27—C28—C290.6 (5)
C2—C3—C4—C9178.1 (3)O3—C28—C29—C24178.9 (3)
C11—C3—C4—C92.3 (4)C27—C28—C29—C240.2 (4)
C2—C3—C4—C50.8 (4)C25—C24—C29—C281.1 (4)
C11—C3—C4—C5178.8 (2)C23—C24—C29—C28179.6 (3)
C9—C4—C5—N1179.5 (3)C22—C23—C31—O420.7 (4)
C3—C4—C5—N10.5 (4)C24—C23—C31—O4161.1 (2)
C9—C4—C5—C60.1 (4)C22—C23—C31—C32100.8 (3)
C3—C4—C5—C6179.0 (3)C24—C23—C31—C3277.3 (3)
N1—C5—C6—C7178.9 (3)O4—C31—C32—N485.4 (3)
C4—C5—C6—C70.7 (4)C23—C31—C32—N4151.8 (2)
C5—C6—C7—C81.1 (4)O4—C31—C32—C3340.2 (3)
C6—C7—C8—C91.0 (4)C23—C31—C32—C3382.5 (3)
C6—C7—C8—O1180.0 (3)N4—C32—C33—C3420.9 (3)
O1—C8—C9—C4179.3 (3)C31—C32—C33—C34147.3 (2)
C7—C8—C9—C40.4 (4)C32—C33—C34—C3546.1 (3)
C5—C4—C9—C80.0 (4)C32—C33—C34—C3870.2 (3)
C3—C4—C9—C8178.8 (3)C38—C34—C35—C3651.2 (3)
C2—C3—C11—O219.4 (4)C33—C34—C35—C3666.6 (3)
C4—C3—C11—O2161.0 (2)C34—C35—C36—N415.5 (3)
C2—C3—C11—C12102.7 (3)N4—C37—C38—C39145.6 (3)
C4—C3—C11—C1276.9 (3)N4—C37—C38—C3419.9 (3)
O2—C11—C12—N376.7 (3)C35—C34—C38—C39164.9 (3)
C3—C11—C12—N3160.1 (2)C33—C34—C38—C3977.6 (3)
O2—C11—C12—C1349.5 (3)C35—C34—C38—C3770.9 (3)
C3—C11—C12—C1373.7 (3)C33—C34—C38—C3746.6 (3)
N3—C12—C13—C1421.7 (3)C37—C38—C39—C40110.1 (4)
C11—C12—C13—C14149.2 (2)C34—C38—C39—C40128.8 (4)
C12—C13—C14—C1546.1 (3)C2—C1—N1—C51.1 (4)
C12—C13—C14—C1871.1 (3)C6—C5—N1—C1178.1 (2)
C13—C14—C15—C1667.3 (3)C4—C5—N1—C11.4 (4)
C18—C14—C15—C1651.1 (3)C22—C21—N2—C251.6 (4)
C14—C15—C16—N316.4 (3)C24—C25—N2—C211.0 (4)
C15—C14—C18—C19165.5 (2)C26—C25—N2—C21178.1 (3)
C13—C14—C18—C1976.5 (3)C18—C17—N3—C1647.0 (3)
C15—C14—C18—C1770.7 (3)C18—C17—N3—C1268.7 (3)
C13—C14—C18—C1747.2 (3)C15—C16—N3—C1768.2 (3)
N3—C17—C18—C19142.8 (3)C15—C16—N3—C1250.1 (3)
N3—C17—C18—C1419.0 (3)C13—C12—N3—C1744.1 (3)
C14—C18—C19—C20116.2 (4)C11—C12—N3—C1784.0 (3)
C17—C18—C19—C20123.8 (4)C13—C12—N3—C1672.8 (3)
N2—C21—C22—C230.7 (4)C11—C12—N3—C16159.1 (2)
C21—C22—C23—C240.8 (4)C35—C36—N4—C3767.2 (3)
C21—C22—C23—C31178.9 (3)C35—C36—N4—C3251.0 (3)
C22—C23—C24—C251.3 (4)C38—C37—N4—C3646.0 (3)
C31—C23—C24—C25179.4 (2)C38—C37—N4—C3270.2 (3)
C22—C23—C24—C29179.4 (3)C33—C32—N4—C3672.5 (3)
C31—C23—C24—C291.2 (4)C31—C32—N4—C36159.4 (2)
C29—C24—C25—N2179.8 (3)C33—C32—N4—C3745.0 (3)
C23—C24—C25—N20.4 (4)C31—C32—N4—C3783.1 (3)
C29—C24—C25—C261.1 (4)C9—C8—O1—C104.4 (4)
C23—C24—C25—C26179.5 (3)C7—C8—O1—C10176.7 (2)
N2—C25—C26—C27179.4 (3)C29—C28—O3—C301.5 (4)
C24—C25—C26—C270.3 (4)C27—C28—O3—C30179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7A···O60.99 (3)1.81 (3)2.802 (4)174 (5)
O6—H6A···N3i0.89 (3)1.93 (3)2.810 (4)172 (4)
O6—H6B···O50.90 (3)1.93 (3)2.823 (4)171 (4)
O5—H5B···O1ii0.87 (3)2.02 (3)2.867 (3)163 (4)
O5—H5A···N40.90 (3)1.84 (3)2.727 (3)168 (4)
O4—H4···N1iii0.81 (4)2.06 (4)2.855 (3)166 (4)
O2—H2A···N2iv0.91 (4)1.91 (4)2.814 (3)171 (3)
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x, y, z1; (iii) x+1/2, y+2, z1/2; (iv) x+3/2, y+2, z+1/2.
 

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