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A disordered tartrate ion of the title compound, 2C20H25N2O2·C4H4O6·H2O, is located on the crystallographic twofold axis. Hydrogen bonds are formed between the carboxylate group and the quinuclidine group of the protonated quinine ion.
Supporting information
CCDC reference: 231843
Key indicators
- Single-crystal X-ray study
- T = 122 K
- H-atom completeness 90%
- R factor = 0.057
- wR factor = 0.154
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O6 .. O70 = 2.54 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.01 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.99
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O3
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O4
PLAT707_ALERT_1_C D...A Calc 2.675(7), Rep 2.662(9), Dev.. 1.86 Sigma
N2 -O2 1.555 2.555
PLAT707_ALERT_1_C D...A Calc 2.611(6), Rep 2.618(7), Dev.. 1.17 Sigma
O18 -O70 1.555 1.565
PLAT726_ALERT_1_C H...A Calc 1.79046, Rep 1.78000, Dev.. 0.01 Ang.
H2 -O2 1.555 2.555
PLAT726_ALERT_1_C H...A Calc 2.33854, Rep 2.32000, Dev.. 0.02 Ang.
H180 -O1 1.555 2.555
PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd) . 1.31 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 41.30 Deg.
O2 -O6 -C4 2.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.60 Deg.
O2 -O6 -C1 2.555 1.555 2.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.50 Deg.
C4 -O6 -C1 1.555 1.555 2.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.50 Deg.
C2 -O4 -C3 2.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.60 Deg.
O2 -C1 -O6 1.555 1.555 2.555
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C44 H56 N4 O11
Atom count from the _atom_site data: C44 H50 N4 O11
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_sum C44 H56 N4 O11
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 88.00 88.00 0.00
H 112.00 100.00 12.00
N 8.00 8.00 0.00
O 22.00 22.00 0.00
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 30.00
From the CIF: _reflns_number_total 3165
Count of symmetry unique reflns 3167
Completeness (_total/calc) 99.94%
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
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
20 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: DREADD (Blessing 1989); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2003).
Quininium (
R,
R)-tartrate hydrate
top
Crystal data top
2C20H25N2O2+·C4H4O62−·H2O | F(000) = 872 |
Mr = 816.94 | Dx = 1.351 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 20.352 (3) Å | Cell parameters from 20 reflections |
b = 6.6070 (16) Å | θ = 17.8–20.9° |
c = 15.501 (2) Å | µ = 0.10 mm−1 |
β = 105.580 (12)° | T = 122 K |
V = 2007.8 (6) Å3 | Rod, colourless |
Z = 2 | 0.33 × 0.15 × 0.1 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.1° |
Graphite monochromator | h = −28→27 |
ω–2θ scans | k = 0→9 |
3165 measured reflections | l = 0→21 |
3165 independent reflections | 5 standard reflections every 167 min |
2533 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0783P)2 + 1.2182P] where P = (Fo2 + 2Fc2)/3 |
3165 reflections | (Δ/σ)max < 0.001 |
318 parameters | Δρmax = 0.53 e Å−3 |
1 restraint | Δρmin = −0.31 e Å−3 |
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 | Uiso*/Ueq | Occ. (<1) |
C9 | 0.18180 (13) | 0.9337 (5) | 0.33213 (18) | 0.0194 (6) | |
C10 | 0.14622 (13) | 0.7789 (5) | 0.36554 (18) | 0.0187 (5) | |
C11 | 0.11555 (13) | 0.6091 (5) | 0.3151 (2) | 0.0209 (6) | |
H11 | 0.1168 | 0.5949 | 0.2546 | 0.031* | |
C12 | 0.08387 (14) | 0.4644 (5) | 0.3537 (2) | 0.0241 (6) | |
O12 | 0.05138 (11) | 0.2980 (4) | 0.31149 (18) | 0.0327 (6) | |
C30 | 0.05027 (17) | 0.2728 (7) | 0.2204 (3) | 0.0356 (8) | |
H30A | 0.0276 | 0.1449 | 0.1981 | 0.053* | |
H30B | 0.0971 | 0.2705 | 0.2149 | 0.053* | |
H30C | 0.0253 | 0.3853 | 0.1852 | 0.053* | |
C13 | 0.08274 (16) | 0.4826 (6) | 0.4446 (2) | 0.0308 (8) | |
H13 | 0.0624 | 0.3791 | 0.4714 | 0.046* | |
C14 | 0.11048 (16) | 0.6469 (6) | 0.4933 (2) | 0.0291 (7) | |
H14 | 0.1082 | 0.6588 | 0.5535 | 0.044* | |
C15 | 0.14269 (14) | 0.8008 (5) | 0.45617 (19) | 0.0219 (6) | |
N1 | 0.16878 (13) | 0.9619 (5) | 0.50904 (17) | 0.0268 (6) | |
C16 | 0.19905 (15) | 1.1021 (6) | 0.4739 (2) | 0.0268 (7) | |
H16 | 0.2164 | 1.2172 | 0.5095 | 0.040* | |
C17 | 0.20764 (14) | 1.0934 (5) | 0.3865 (2) | 0.0229 (6) | |
H17 | 0.2313 | 1.1985 | 0.3656 | 0.034* | |
C18 | 0.19330 (14) | 0.9177 (5) | 0.23914 (18) | 0.0187 (5) | |
H18 | 0.1504 | 0.8696 | 0.1958 | 0.028* | |
O18 | 0.21139 (13) | 1.1092 (4) | 0.21086 (17) | 0.0310 (5) | |
H180 | 0.1866 | 1.1348 | 0.1593 | 0.047* | |
C19 | 0.25032 (13) | 0.7616 (5) | 0.24337 (17) | 0.0175 (5) | |
H19 | 0.2392 | 0.6387 | 0.2744 | 0.026* | |
C20 | 0.32169 (13) | 0.8335 (5) | 0.29603 (19) | 0.0204 (6) | |
H20A | 0.3206 | 0.9805 | 0.3080 | 0.031* | |
H20B | 0.3358 | 0.7620 | 0.3542 | 0.031* | |
C21 | 0.37298 (14) | 0.7903 (5) | 0.2417 (2) | 0.0222 (6) | |
H21 | 0.4199 | 0.8284 | 0.2777 | 0.033* | |
C22 | 0.35293 (18) | 0.9177 (6) | 0.1562 (2) | 0.0332 (8) | |
H22A | 0.3525 | 1.0629 | 0.1718 | 0.050* | |
H22B | 0.3866 | 0.8981 | 0.1213 | 0.050* | |
C23 | 0.28226 (18) | 0.8535 (6) | 0.1005 (2) | 0.0295 (7) | |
H23A | 0.2516 | 0.9725 | 0.0881 | 0.044* | |
H23B | 0.2854 | 0.7971 | 0.0426 | 0.044* | |
N2 | 0.25376 (13) | 0.6965 (5) | 0.15074 (16) | 0.0221 (5) | |
H2 | 0.2115 | 0.6636 | 0.1181 | 0.033* | |
C24 | 0.29815 (16) | 0.5108 (5) | 0.1616 (2) | 0.0246 (6) | |
H24A | 0.2987 | 0.4581 | 0.1020 | 0.037* | |
H24B | 0.2796 | 0.4040 | 0.1932 | 0.037* | |
C25 | 0.37159 (15) | 0.5663 (5) | 0.2159 (2) | 0.0211 (6) | |
H25 | 0.4024 | 0.5481 | 0.1759 | 0.032* | |
C26 | 0.39698 (16) | 0.4332 (6) | 0.2957 (2) | 0.0270 (7) | |
H26 | 0.3694 | 0.4189 | 0.3360 | 0.040* | |
C27 | 0.4555 (2) | 0.3341 (8) | 0.3139 (3) | 0.0529 (13) | |
H27A | 0.4843 | 0.3454 | 0.2749 | 0.079* | |
H27B | 0.4689 | 0.2517 | 0.3658 | 0.079* | |
C4 | 0.0914 (4) | 0.6847 (13) | 0.0115 (4) | 0.0207 (13) | 0.50 |
O5 | 0.1234 (2) | 0.7866 (10) | −0.0298 (3) | 0.0365 (12) | 0.50 |
O6 | 0.1169 (2) | 0.5887 (8) | 0.0840 (3) | 0.0275 (10) | 0.50 |
C3 | 0.0142 (3) | 0.6753 (13) | −0.0274 (4) | 0.0212 (12) | 0.50 |
O4 | −0.0045 (2) | 0.7580 (9) | −0.1140 (3) | 0.0299 (11) | 0.50 |
C2 | −0.0219 (4) | 0.794 (2) | 0.0308 (5) | 0.038 (2) | 0.50 |
O3 | 0.0046 (3) | 0.9953 (13) | 0.0461 (5) | 0.066 (2) | 0.50 |
C1 | −0.0991 (4) | 0.806 (2) | −0.0136 (5) | 0.037 (2) | 0.50 |
O2 | −0.1308 (3) | 0.6413 (12) | −0.0364 (5) | 0.0445 (17) | 0.50 |
O1 | −0.1235 (3) | 0.9845 (13) | −0.0262 (5) | 0.057 (2) | 0.50 |
O70 | 0.1341 (3) | 0.2168 (9) | 0.0543 (3) | 0.0344 (12) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C9 | 0.0141 (11) | 0.0231 (15) | 0.0213 (12) | 0.0039 (11) | 0.0054 (9) | 0.0067 (12) |
C10 | 0.0129 (10) | 0.0222 (14) | 0.0214 (12) | 0.0026 (11) | 0.0052 (9) | 0.0039 (12) |
C11 | 0.0138 (11) | 0.0227 (15) | 0.0272 (14) | −0.0001 (11) | 0.0074 (10) | 0.0029 (13) |
C12 | 0.0144 (11) | 0.0217 (16) | 0.0373 (16) | 0.0019 (12) | 0.0086 (11) | 0.0075 (13) |
O12 | 0.0223 (10) | 0.0266 (13) | 0.0494 (14) | −0.0038 (11) | 0.0097 (10) | 0.0034 (12) |
C30 | 0.0247 (14) | 0.0289 (18) | 0.052 (2) | −0.0070 (15) | 0.0076 (14) | −0.0070 (17) |
C13 | 0.0256 (14) | 0.0322 (19) | 0.0397 (18) | 0.0076 (14) | 0.0176 (13) | 0.0197 (16) |
C14 | 0.0255 (14) | 0.036 (2) | 0.0289 (15) | 0.0098 (15) | 0.0125 (12) | 0.0103 (15) |
C15 | 0.0185 (12) | 0.0267 (17) | 0.0205 (12) | 0.0081 (13) | 0.0053 (10) | 0.0054 (12) |
N1 | 0.0232 (12) | 0.0362 (17) | 0.0213 (11) | 0.0087 (12) | 0.0066 (9) | −0.0012 (12) |
C16 | 0.0221 (13) | 0.0322 (18) | 0.0243 (14) | 0.0066 (14) | 0.0029 (11) | −0.0080 (14) |
C17 | 0.0175 (12) | 0.0245 (16) | 0.0270 (14) | 0.0028 (12) | 0.0067 (11) | −0.0005 (13) |
C18 | 0.0166 (11) | 0.0206 (14) | 0.0195 (12) | 0.0002 (11) | 0.0058 (9) | 0.0034 (12) |
O18 | 0.0369 (12) | 0.0225 (12) | 0.0398 (13) | 0.0056 (11) | 0.0209 (11) | 0.0116 (11) |
C19 | 0.0162 (11) | 0.0202 (14) | 0.0158 (11) | 0.0028 (11) | 0.0038 (9) | 0.0011 (11) |
C20 | 0.0152 (11) | 0.0250 (15) | 0.0193 (12) | −0.0008 (11) | 0.0017 (9) | −0.0027 (12) |
C21 | 0.0156 (11) | 0.0251 (16) | 0.0263 (14) | −0.0001 (12) | 0.0066 (10) | −0.0007 (13) |
C22 | 0.0386 (17) | 0.0271 (18) | 0.0399 (18) | −0.0003 (16) | 0.0213 (14) | 0.0076 (16) |
C23 | 0.0398 (17) | 0.0303 (18) | 0.0211 (14) | 0.0113 (15) | 0.0131 (13) | 0.0060 (14) |
N2 | 0.0195 (11) | 0.0267 (14) | 0.0169 (11) | 0.0047 (11) | −0.0007 (9) | −0.0040 (10) |
C24 | 0.0264 (14) | 0.0213 (15) | 0.0244 (14) | 0.0034 (13) | 0.0036 (11) | −0.0036 (12) |
C25 | 0.0192 (12) | 0.0230 (15) | 0.0243 (13) | 0.0047 (12) | 0.0111 (11) | 0.0032 (12) |
C26 | 0.0234 (13) | 0.0293 (17) | 0.0277 (14) | 0.0033 (14) | 0.0058 (11) | 0.0005 (14) |
C27 | 0.0367 (19) | 0.062 (3) | 0.062 (3) | 0.023 (2) | 0.0178 (19) | 0.031 (3) |
C4 | 0.021 (3) | 0.019 (3) | 0.020 (3) | −0.004 (3) | 0.002 (2) | −0.007 (3) |
O5 | 0.022 (2) | 0.053 (4) | 0.034 (2) | −0.009 (3) | 0.007 (2) | 0.012 (3) |
O6 | 0.026 (2) | 0.034 (3) | 0.017 (2) | −0.007 (2) | −0.0032 (18) | 0.004 (2) |
C3 | 0.021 (3) | 0.024 (3) | 0.015 (3) | −0.004 (3) | −0.002 (2) | −0.002 (3) |
O4 | 0.026 (2) | 0.043 (3) | 0.019 (2) | 0.000 (2) | 0.0036 (16) | 0.010 (2) |
C2 | 0.020 (3) | 0.069 (7) | 0.025 (3) | −0.006 (4) | 0.004 (3) | −0.011 (4) |
O3 | 0.025 (2) | 0.092 (6) | 0.078 (4) | −0.013 (3) | 0.007 (3) | −0.070 (4) |
C1 | 0.020 (3) | 0.071 (8) | 0.019 (3) | −0.008 (4) | 0.004 (3) | −0.003 (4) |
O2 | 0.022 (3) | 0.064 (5) | 0.038 (3) | −0.014 (3) | −0.008 (2) | 0.021 (3) |
O1 | 0.023 (3) | 0.081 (6) | 0.066 (4) | −0.001 (3) | 0.007 (3) | −0.042 (4) |
O70 | 0.041 (3) | 0.037 (3) | 0.024 (2) | −0.002 (2) | 0.006 (2) | 0.015 (2) |
Geometric parameters (Å, º) top
C9—C17 | 1.365 (5) | C22—H22A | 0.9900 |
C9—C10 | 1.428 (4) | C22—H22B | 0.9900 |
C9—C18 | 1.525 (4) | C23—N2 | 1.504 (5) |
C10—C11 | 1.413 (4) | C23—H23A | 0.9900 |
C10—C15 | 1.433 (4) | C23—H23B | 0.9900 |
C11—C12 | 1.377 (4) | N2—C24 | 1.506 (4) |
C11—H11 | 0.9500 | N2—H2 | 0.9000 |
C12—O12 | 1.357 (4) | C24—C25 | 1.550 (4) |
C12—C13 | 1.420 (5) | C24—H24A | 0.9900 |
O12—C30 | 1.416 (5) | C24—H24B | 0.9900 |
C30—H30A | 0.9800 | C25—C26 | 1.493 (5) |
C30—H30B | 0.9800 | C25—H25 | 1.0000 |
C30—H30C | 0.9800 | C26—C27 | 1.322 (5) |
C13—C14 | 1.356 (6) | C26—H26 | 0.9500 |
C13—H13 | 0.9500 | C27—H27A | 0.9500 |
C14—C15 | 1.413 (5) | C27—H27B | 0.9500 |
C14—H14 | 0.9500 | C4—O5 | 1.229 (9) |
C15—N1 | 1.361 (5) | C4—O6 | 1.274 (9) |
N1—C16 | 1.309 (5) | C4—C3 | 1.526 (10) |
C16—C17 | 1.414 (4) | O6—O2i | 0.926 (8) |
C16—H16 | 0.9500 | O6—C1i | 1.783 (13) |
C17—H17 | 0.9500 | C3—O4 | 1.404 (8) |
C18—O18 | 1.420 (4) | C3—C2 | 1.524 (10) |
C18—C19 | 1.541 (4) | O4—C2i | 1.279 (9) |
C18—H18 | 1.0000 | C2—O4i | 1.279 (9) |
O18—H180 | 0.8400 | C2—O3 | 1.430 (15) |
C19—N2 | 1.518 (4) | C2—C1 | 1.539 (11) |
C19—C20 | 1.538 (4) | C2—O3i | 1.881 (13) |
C19—H19 | 1.0000 | O3—O3i | 1.390 (14) |
C20—C21 | 1.533 (4) | O3—C2i | 1.881 (13) |
C20—H20A | 0.9900 | C1—O2 | 1.268 (13) |
C20—H20B | 0.9900 | C1—O1 | 1.272 (16) |
C21—C22 | 1.530 (5) | C1—O6i | 1.783 (13) |
C21—C25 | 1.532 (5) | O2—O6i | 0.926 (8) |
C21—H21 | 1.0000 | O1—O70ii | 1.594 (11) |
C22—C23 | 1.526 (5) | O70—O1iii | 1.594 (11) |
| | | |
C17—C9—C10 | 118.6 (3) | C21—C22—H22B | 109.8 |
C17—C9—C18 | 120.4 (3) | H22A—C22—H22B | 108.3 |
C10—C9—C18 | 121.0 (3) | N2—C23—C22 | 109.6 (3) |
C11—C10—C9 | 124.0 (3) | N2—C23—H23A | 109.8 |
C11—C10—C15 | 119.4 (3) | C22—C23—H23A | 109.8 |
C9—C10—C15 | 116.6 (3) | N2—C23—H23B | 109.8 |
C12—C11—C10 | 120.0 (3) | C22—C23—H23B | 109.8 |
C12—C11—H11 | 120.0 | H23A—C23—H23B | 108.2 |
C10—C11—H11 | 120.0 | C23—N2—C24 | 108.4 (2) |
O12—C12—C11 | 125.3 (3) | C23—N2—C19 | 114.6 (3) |
O12—C12—C13 | 114.3 (3) | C24—N2—C19 | 107.7 (2) |
C11—C12—C13 | 120.4 (3) | C23—N2—H2 | 108.6 |
C12—O12—C30 | 116.9 (3) | C24—N2—H2 | 108.6 |
O12—C30—H30A | 109.5 | C19—N2—H2 | 108.6 |
O12—C30—H30B | 109.5 | N2—C24—C25 | 109.2 (3) |
H30A—C30—H30B | 109.5 | N2—C24—H24A | 109.8 |
O12—C30—H30C | 109.5 | C25—C24—H24A | 109.8 |
H30A—C30—H30C | 109.5 | N2—C24—H24B | 109.8 |
H30B—C30—H30C | 109.5 | C25—C24—H24B | 109.8 |
C14—C13—C12 | 120.3 (3) | H24A—C24—H24B | 108.3 |
C14—C13—H13 | 119.8 | C26—C25—C21 | 112.0 (3) |
C12—C13—H13 | 119.8 | C26—C25—C24 | 112.3 (3) |
C13—C14—C15 | 121.3 (3) | C21—C25—C24 | 108.6 (2) |
C13—C14—H14 | 119.4 | C26—C25—H25 | 107.9 |
C15—C14—H14 | 119.4 | C21—C25—H25 | 107.9 |
N1—C15—C14 | 117.8 (3) | C24—C25—H25 | 107.9 |
N1—C15—C10 | 123.7 (3) | C27—C26—C25 | 124.0 (3) |
C14—C15—C10 | 118.5 (3) | C27—C26—H26 | 118.0 |
C16—N1—C15 | 117.0 (3) | C25—C26—H26 | 118.0 |
N1—C16—C17 | 124.3 (3) | C26—C27—H27A | 120.0 |
N1—C16—H16 | 117.9 | C26—C27—H27B | 120.0 |
C17—C16—H16 | 117.9 | H27A—C27—H27B | 120.0 |
C9—C17—C16 | 119.8 (3) | O5—C4—O6 | 125.8 (7) |
C9—C17—H17 | 120.1 | O5—C4—C3 | 116.7 (7) |
C16—C17—H17 | 120.1 | O6—C4—C3 | 117.4 (6) |
O18—C18—C9 | 110.4 (3) | O2i—O6—C4 | 41.3 (5) |
O18—C18—C19 | 110.8 (2) | O2i—O6—C1i | 42.6 (5) |
C9—C18—C19 | 108.1 (2) | C4—O6—C1i | 24.5 (4) |
O18—C18—H18 | 109.2 | O4—C3—C2 | 108.4 (6) |
C9—C18—H18 | 109.2 | O4—C3—C4 | 110.3 (6) |
C19—C18—H18 | 109.2 | C2—C3—C4 | 110.7 (5) |
C18—O18—H180 | 109.5 | C2i—O4—C3 | 34.5 (5) |
N2—C19—C20 | 108.2 (2) | O4i—C2—O3 | 88.2 (6) |
N2—C19—C18 | 112.0 (2) | O4i—C2—C3 | 111.3 (7) |
C20—C19—C18 | 114.1 (3) | O3—C2—C3 | 110.9 (6) |
N2—C19—H19 | 107.4 | O4i—C2—C1 | 124.2 (6) |
C20—C19—H19 | 107.4 | O3—C2—C1 | 108.5 (10) |
C18—C19—H19 | 107.4 | C3—C2—C1 | 111.0 (6) |
C21—C20—C19 | 109.7 (2) | O4i—C2—O3i | 132.1 (7) |
C21—C20—H20A | 109.7 | O3—C2—O3i | 47.2 (7) |
C19—C20—H20A | 109.7 | C3—C2—O3i | 77.7 (5) |
C21—C20—H20B | 109.7 | C1—C2—O3i | 91.3 (7) |
C19—C20—H20B | 109.7 | O3i—O3—C2 | 83.7 (5) |
H20A—C20—H20B | 108.2 | O3i—O3—C2i | 49.1 (4) |
C22—C21—C25 | 108.9 (3) | C2—O3—C2i | 50.5 (6) |
C22—C21—C20 | 108.1 (3) | O2—C1—O1 | 127.2 (7) |
C25—C21—C20 | 110.9 (3) | O2—C1—C2 | 117.4 (11) |
C22—C21—H21 | 109.7 | O1—C1—C2 | 115.4 (9) |
C25—C21—H21 | 109.7 | O2—C1—O6i | 29.6 (4) |
C20—C21—H21 | 109.7 | O1—C1—O6i | 130.2 (6) |
C23—C22—C21 | 109.2 (3) | C2—C1—O6i | 104.2 (8) |
C23—C22—H22A | 109.8 | O6i—O2—C1 | 107.7 (8) |
C21—C22—H22A | 109.8 | C1—O1—O70ii | 162.0 (7) |
C23—C22—H22B | 109.8 | | |
| | | |
C17—C9—C10—C11 | 178.2 (3) | C20—C21—C25—C26 | −66.6 (3) |
C18—C9—C10—C11 | −4.2 (4) | C22—C21—C25—C24 | −60.8 (3) |
C17—C9—C10—C15 | −2.3 (4) | C20—C21—C25—C24 | 57.9 (3) |
C18—C9—C10—C15 | 175.4 (2) | N2—C24—C25—C26 | 125.8 (3) |
C9—C10—C11—C12 | 178.2 (3) | N2—C24—C25—C21 | 1.4 (3) |
C15—C10—C11—C12 | −1.3 (4) | C21—C25—C26—C27 | −109.9 (5) |
C10—C11—C12—O12 | 178.3 (3) | C24—C25—C26—C27 | 127.7 (4) |
C10—C11—C12—C13 | −1.1 (4) | O5—C4—O6—O2i | −21.2 (9) |
C11—C12—O12—C30 | 0.0 (4) | C3—C4—O6—O2i | 159.6 (11) |
C13—C12—O12—C30 | 179.4 (3) | O5—C4—O6—C1i | 57.7 (10) |
O12—C12—C13—C14 | −176.8 (3) | C3—C4—O6—C1i | −121.4 (14) |
C11—C12—C13—C14 | 2.7 (4) | O5—C4—C3—O4 | 10.9 (10) |
C12—C13—C14—C15 | −1.7 (5) | O6—C4—C3—O4 | −169.8 (7) |
C13—C14—C15—N1 | 179.4 (3) | O5—C4—C3—C2 | −109.1 (8) |
C13—C14—C15—C10 | −0.7 (4) | O6—C4—C3—C2 | 70.1 (9) |
C11—C10—C15—N1 | −177.9 (3) | C2—C3—O4—C2i | 56.9 (10) |
C9—C10—C15—N1 | 2.5 (4) | C4—C3—O4—C2i | −64.5 (8) |
C11—C10—C15—C14 | 2.2 (4) | O4—C3—C2—O4i | −165.1 (8) |
C9—C10—C15—C14 | −177.4 (3) | C4—C3—C2—O4i | −43.9 (9) |
C14—C15—N1—C16 | 179.3 (3) | O4—C3—C2—O3 | −68.6 (7) |
C10—C15—N1—C16 | −0.6 (4) | C4—C3—C2—O3 | 52.6 (8) |
C15—N1—C16—C17 | −1.7 (4) | O4—C3—C2—C1 | 52.2 (9) |
C10—C9—C17—C16 | 0.3 (4) | C4—C3—C2—C1 | 173.3 (10) |
C18—C9—C17—C16 | −177.4 (3) | O4—C3—C2—O3i | −34.4 (5) |
N1—C16—C17—C9 | 1.9 (5) | C4—C3—C2—O3i | 86.7 (6) |
C17—C9—C18—O18 | −19.2 (4) | O4i—C2—O3—O3i | 160.5 (6) |
C10—C9—C18—O18 | 163.3 (2) | C3—C2—O3—O3i | 48.4 (6) |
C17—C9—C18—C19 | 102.2 (3) | C1—C2—O3—O3i | −73.8 (7) |
C10—C9—C18—C19 | −75.4 (3) | O4i—C2—O3—C2i | 120.2 (8) |
O18—C18—C19—N2 | −72.9 (3) | C3—C2—O3—C2i | 8.1 (4) |
C9—C18—C19—N2 | 166.0 (2) | C1—C2—O3—C2i | −114.2 (8) |
O18—C18—C19—C20 | 50.5 (3) | O3i—C2—O3—C2i | −40.3 (6) |
C9—C18—C19—C20 | −70.6 (3) | O4i—C2—C1—O2 | −82.7 (13) |
N2—C19—C20—C21 | −7.0 (4) | O3—C2—C1—O2 | 176.4 (7) |
C18—C19—C20—C21 | −132.4 (3) | C3—C2—C1—O2 | 54.3 (10) |
C19—C20—C21—C22 | 64.3 (4) | O3i—C2—C1—O2 | 131.6 (7) |
C19—C20—C21—C25 | −54.9 (3) | O4i—C2—C1—O1 | 99.8 (13) |
C25—C21—C22—C23 | 58.1 (3) | O3—C2—C1—O1 | −1.0 (9) |
C20—C21—C22—C23 | −62.3 (4) | C3—C2—C1—O1 | −123.2 (8) |
C21—C22—C23—N2 | 3.8 (4) | O3i—C2—C1—O1 | −45.9 (8) |
C22—C23—N2—C24 | −64.3 (3) | O4i—C2—C1—O6i | −111.2 (11) |
C22—C23—N2—C19 | 56.1 (3) | O3—C2—C1—O6i | 147.9 (6) |
C20—C19—N2—C23 | −53.9 (3) | C3—C2—C1—O6i | 25.8 (9) |
C18—C19—N2—C23 | 72.8 (3) | O3i—C2—C1—O6i | 103.1 (6) |
C20—C19—N2—C24 | 66.9 (3) | O1—C1—O2—O6i | 107.8 (10) |
C18—C19—N2—C24 | −166.4 (2) | C2—C1—O2—O6i | −69.4 (9) |
C23—N2—C24—C25 | 60.9 (3) | O2—C1—O1—O70ii | −129.3 (18) |
C19—N2—C24—C25 | −63.7 (3) | C2—C1—O1—O70ii | 48 (2) |
C22—C21—C25—C26 | 174.6 (2) | O6i—C1—O1—O70ii | −91 (2) |
Symmetry codes: (i) −x, y, −z; (ii) −x, y+1, −z; (iii) −x, y−1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O6 | 0.90 | 1.92 | 2.790 (7) | 163 |
N2—H2···O2i | 0.90 | 1.78 | 2.662 (9) | 167 |
O18—H180···O70iv | 0.84 | 1.78 | 2.618 (7) | 174 |
O18—H180···O1i | 0.84 | 2.32 | 3.053 (8) | 143 |
Symmetry codes: (i) −x, y, −z; (iv) x, y+1, z. |
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