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In the crystal structure of strychnidine succinate, C
21H
25N
2O
+·C
4H
5O
4−, strychnidinium bilayers are separated by layers composed of extended carboxylic acid O—H
O hydrogen-bonded chains. The significantly different C—O distances of the carboxylate groups of the succinate anion allow the negatively charged O atoms to be identified.
Supporting information
CCDC reference: 298716
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.077
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.82
| Author Response: The high c/a ratio and unfavorable crystal orientation
together with small crystal dimensions caused this problem.
|
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.91
PLAT353_ALERT_3_C Long N-H Bond (0.87A) N19 - H19 ... 1.03 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C21 H25 N2 O
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.20
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 68.79
From the CIF: _reflns_number_total 3073
From the CIF: _diffrn_reflns_limit_ max hkl 7. 9. 38.
From the CIF: _diffrn_reflns_limit_ min hkl -6. -9. -42.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 7. 10. 47.
Calculated minimum hkl -7. -10. -47.
REFLT03_ALERT_4_G WARNING: CuKa measured Friedel data can be used to
determine absolute structure in a light-atom
study only if the Friedel fraction is large.
From the CIF: _diffrn_reflns_theta_max 68.79
From the CIF: _reflns_number_total 3073
Count of symmetry unique reflns 2300
Completeness (_total/calc) 133.61%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 773
Fraction of Friedel pairs measured 0.336
Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
1 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1999); software used to prepare material for publication: SHELXL97.
strychnidinium hydrogen 1,2-ethanedicarboxylate
top
Crystal data top
C21H25N2O+·C4H5O4− | Dx = 1.379 Mg m−3 |
Mr = 438.51 | Melting point = 462–467 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 8322 reflections |
a = 6.487 (2) Å | θ = 4.5–74.8° |
b = 8.314 (2) Å | µ = 0.78 mm−1 |
c = 39.165 (6) Å | T = 100 K |
V = 2112.3 (9) Å3 | Plate, colourless |
Z = 4 | 0.18 × 0.10 × 0.02 mm |
F(000) = 936 | |
Data collection top
Xcalibur PX kappa-geometry diffractometer with CCD Onyx camera | 3073 independent reflections |
Radiation source: fine-focus sealed tube | 2730 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω and φ scans | θmax = 68.8°, θmin = 4.5° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003) | h = −6→7 |
Tmin = 0.842, Tmax = 0.988 | k = −9→9 |
13198 measured reflections | l = −42→38 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.25 e Å−3 |
3073 reflections | Δρmin = −0.21 e Å−3 |
298 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0030 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1182 Friedels |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (2) |
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 | |
O1 | −0.4509 (2) | 0.99996 (18) | 0.41911 (4) | 0.0301 (4) | |
C1 | 0.1639 (3) | 0.3936 (3) | 0.41260 (6) | 0.0276 (5) | |
H1 | 0.2578 | 0.3850 | 0.3941 | 0.033* | |
C2 | 0.2003 (4) | 0.3099 (3) | 0.44331 (5) | 0.0313 (6) | |
H2 | 0.3188 | 0.2436 | 0.4456 | 0.038* | |
C3 | 0.0626 (3) | 0.3247 (3) | 0.47001 (6) | 0.0281 (6) | |
H3 | 0.0893 | 0.2688 | 0.4907 | 0.034* | |
C4 | −0.1138 (3) | 0.4188 (2) | 0.46759 (5) | 0.0209 (5) | |
H4 | −0.2072 | 0.4273 | 0.4862 | 0.025* | |
C5 | −0.1496 (3) | 0.5000 (2) | 0.43720 (5) | 0.0176 (5) | |
C6 | −0.0095 (3) | 0.4878 (3) | 0.40986 (5) | 0.0187 (5) | |
C7 | −0.0912 (3) | 0.5874 (3) | 0.38033 (5) | 0.0175 (5) | |
C8 | −0.2388 (3) | 0.7014 (2) | 0.40006 (5) | 0.0158 (5) | |
H8 | −0.3557 | 0.7357 | 0.3851 | 0.019* | |
N9 | −0.3142 (2) | 0.5987 (2) | 0.42815 (4) | 0.0167 (4) | |
C10 | −0.4418 (3) | 0.6816 (3) | 0.45332 (5) | 0.0219 (5) | |
H10A | −0.4652 | 0.6091 | 0.4730 | 0.026* | |
H10B | −0.5776 | 0.7059 | 0.4430 | 0.026* | |
C11 | −0.3448 (4) | 0.8383 (3) | 0.46614 (5) | 0.0257 (5) | |
H11A | −0.4473 | 0.8977 | 0.4800 | 0.031* | |
H11B | −0.2262 | 0.8124 | 0.4811 | 0.031* | |
C12 | −0.2714 (4) | 0.9457 (3) | 0.43693 (5) | 0.0256 (5) | |
H12 | −0.1963 | 1.0405 | 0.4465 | 0.031* | |
C13 | −0.1249 (3) | 0.8485 (2) | 0.41422 (5) | 0.0198 (5) | |
H13 | −0.0141 | 0.8062 | 0.4295 | 0.024* | |
C14 | −0.0155 (3) | 0.9364 (3) | 0.38501 (5) | 0.0222 (5) | |
H14 | 0.0422 | 1.0407 | 0.3934 | 0.027* | |
C15 | 0.1590 (3) | 0.8276 (3) | 0.37260 (5) | 0.0248 (5) | |
H15A | 0.2409 | 0.8838 | 0.3549 | 0.030* | |
H15B | 0.2515 | 0.8006 | 0.3919 | 0.030* | |
C16 | 0.0672 (3) | 0.6763 (3) | 0.35798 (5) | 0.0205 (5) | |
H16 | 0.1814 | 0.6004 | 0.3521 | 0.025* | |
C17 | −0.2121 (3) | 0.4880 (3) | 0.35370 (5) | 0.0221 (5) | |
H17A | −0.1325 | 0.3926 | 0.3463 | 0.027* | |
H17B | −0.3467 | 0.4525 | 0.3629 | 0.027* | |
C18 | −0.2405 (3) | 0.6068 (3) | 0.32434 (5) | 0.0243 (5) | |
H18A | −0.2482 | 0.5491 | 0.3023 | 0.029* | |
H18B | −0.3687 | 0.6697 | 0.3274 | 0.029* | |
N19 | −0.0540 (2) | 0.7161 (2) | 0.32521 (4) | 0.0204 (4) | |
H19 | 0.024 (3) | 0.697 (3) | 0.3028 (6) | 0.031 (6)* | |
C20 | −0.1055 (3) | 0.8934 (2) | 0.32199 (5) | 0.0221 (5) | |
H20A | 0.0153 | 0.9512 | 0.3126 | 0.027* | |
H20B | −0.2212 | 0.9067 | 0.3057 | 0.027* | |
C21 | −0.1639 (3) | 0.9670 (3) | 0.35575 (5) | 0.0207 (5) | |
C22 | −0.3398 (3) | 1.0473 (3) | 0.35961 (6) | 0.0263 (5) | |
H22 | −0.4270 | 1.0600 | 0.3403 | 0.032* | |
C23 | −0.4068 (4) | 1.1187 (3) | 0.39297 (6) | 0.0367 (6) | |
H23A | −0.2971 | 1.1914 | 0.4014 | 0.044* | |
H23B | −0.5319 | 1.1844 | 0.3891 | 0.044* | |
O1A | 0.1232 (2) | 0.69047 (19) | 0.26306 (4) | 0.0290 (4) | |
O2A | 0.3800 (2) | 0.8121 (2) | 0.29060 (4) | 0.0307 (4) | |
O3A | 0.9663 (2) | 0.7518 (2) | 0.20343 (4) | 0.0279 (4) | |
H3A | 1.015 (4) | 0.729 (3) | 0.2265 (6) | 0.041 (7)* | |
O4A | 0.6893 (2) | 0.8273 (2) | 0.17503 (4) | 0.0326 (4) | |
C1A | 0.3070 (3) | 0.7517 (3) | 0.26460 (5) | 0.0232 (5) | |
C2A | 0.4307 (3) | 0.7412 (4) | 0.23190 (6) | 0.0360 (7) | |
H2AA | 0.4141 | 0.6316 | 0.2224 | 0.043* | |
H2AB | 0.3705 | 0.8174 | 0.2152 | 0.043* | |
C3A | 0.6510 (3) | 0.7752 (4) | 0.23477 (5) | 0.0402 (7) | |
H3AA | 0.7149 | 0.6896 | 0.2488 | 0.048* | |
H3AB | 0.6680 | 0.8779 | 0.2473 | 0.048* | |
C4A | 0.7675 (3) | 0.7870 (3) | 0.20181 (5) | 0.0233 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0378 (9) | 0.0264 (9) | 0.0260 (8) | 0.0124 (8) | 0.0110 (7) | 0.0061 (8) |
C1 | 0.0301 (12) | 0.0298 (13) | 0.0229 (12) | 0.0108 (11) | 0.0053 (11) | 0.0026 (11) |
C2 | 0.0341 (12) | 0.0332 (14) | 0.0267 (13) | 0.0160 (12) | 0.0006 (11) | 0.0056 (12) |
C3 | 0.0417 (13) | 0.0226 (12) | 0.0201 (12) | 0.0084 (12) | −0.0042 (11) | 0.0064 (11) |
C4 | 0.0296 (11) | 0.0169 (11) | 0.0164 (11) | −0.0011 (10) | 0.0005 (10) | 0.0012 (10) |
C5 | 0.0192 (10) | 0.0176 (11) | 0.0160 (11) | 0.0006 (10) | −0.0013 (9) | −0.0016 (10) |
C6 | 0.0232 (11) | 0.0176 (11) | 0.0155 (11) | 0.0060 (10) | 0.0005 (9) | 0.0014 (10) |
C7 | 0.0185 (10) | 0.0188 (11) | 0.0153 (11) | 0.0061 (9) | 0.0018 (9) | 0.0013 (10) |
C8 | 0.0161 (10) | 0.0168 (11) | 0.0146 (10) | 0.0006 (9) | 0.0027 (8) | −0.0001 (9) |
N9 | 0.0181 (8) | 0.0174 (9) | 0.0146 (9) | 0.0022 (8) | 0.0046 (7) | 0.0015 (8) |
C10 | 0.0235 (11) | 0.0265 (12) | 0.0159 (11) | 0.0046 (11) | 0.0067 (9) | 0.0023 (11) |
C11 | 0.0364 (12) | 0.0243 (12) | 0.0165 (11) | 0.0051 (11) | 0.0062 (10) | −0.0011 (10) |
C12 | 0.0347 (13) | 0.0220 (12) | 0.0203 (12) | 0.0019 (10) | 0.0021 (11) | −0.0039 (10) |
C13 | 0.0219 (10) | 0.0200 (12) | 0.0176 (11) | −0.0016 (10) | 0.0028 (10) | −0.0025 (10) |
C14 | 0.0235 (11) | 0.0223 (12) | 0.0207 (12) | −0.0058 (10) | −0.0001 (10) | 0.0009 (10) |
C15 | 0.0166 (10) | 0.0342 (13) | 0.0235 (12) | −0.0034 (10) | 0.0018 (9) | 0.0084 (11) |
C16 | 0.0172 (10) | 0.0270 (12) | 0.0173 (11) | 0.0042 (10) | 0.0043 (9) | 0.0030 (10) |
C17 | 0.0326 (12) | 0.0195 (11) | 0.0143 (11) | −0.0003 (11) | 0.0015 (10) | −0.0002 (10) |
C18 | 0.0304 (11) | 0.0249 (12) | 0.0176 (11) | −0.0041 (11) | −0.0012 (10) | 0.0000 (10) |
N19 | 0.0234 (9) | 0.0221 (11) | 0.0158 (10) | 0.0044 (8) | 0.0040 (8) | 0.0031 (8) |
C20 | 0.0264 (11) | 0.0181 (11) | 0.0218 (12) | 0.0041 (10) | 0.0068 (10) | 0.0053 (10) |
C21 | 0.0251 (11) | 0.0169 (12) | 0.0201 (12) | 0.0005 (10) | 0.0037 (10) | 0.0035 (9) |
C22 | 0.0325 (12) | 0.0218 (13) | 0.0244 (12) | 0.0045 (11) | 0.0053 (11) | 0.0073 (10) |
C23 | 0.0554 (16) | 0.0222 (13) | 0.0325 (14) | 0.0158 (13) | 0.0165 (13) | 0.0118 (12) |
O1A | 0.0207 (7) | 0.0440 (10) | 0.0222 (8) | −0.0028 (8) | 0.0047 (7) | −0.0008 (8) |
O2A | 0.0224 (8) | 0.0522 (11) | 0.0173 (8) | 0.0025 (8) | 0.0019 (7) | −0.0043 (8) |
O3A | 0.0195 (8) | 0.0436 (10) | 0.0205 (9) | 0.0005 (7) | 0.0041 (6) | 0.0014 (8) |
O4A | 0.0257 (8) | 0.0514 (11) | 0.0208 (8) | −0.0051 (8) | −0.0014 (7) | 0.0072 (8) |
C1A | 0.0191 (10) | 0.0334 (13) | 0.0172 (12) | 0.0052 (10) | 0.0022 (10) | 0.0039 (11) |
C2A | 0.0222 (11) | 0.0648 (19) | 0.0210 (13) | −0.0056 (12) | 0.0051 (10) | 0.0006 (13) |
C3A | 0.0212 (11) | 0.081 (2) | 0.0184 (12) | −0.0003 (13) | 0.0041 (10) | 0.0022 (14) |
C4A | 0.0191 (11) | 0.0310 (13) | 0.0197 (12) | −0.0058 (10) | 0.0028 (10) | 0.0006 (11) |
Geometric parameters (Å, º) top
O1—C12 | 1.431 (3) | C15—C16 | 1.505 (3) |
O1—C23 | 1.451 (3) | C15—H15A | 0.9900 |
C1—C6 | 1.375 (3) | C15—H15B | 0.9900 |
C1—C2 | 1.410 (3) | C16—N19 | 1.541 (3) |
C1—H1 | 0.9500 | C16—H16 | 1.0000 |
C2—C3 | 1.381 (3) | C17—C18 | 1.527 (3) |
C2—H2 | 0.9500 | C17—H17A | 0.9900 |
C3—C4 | 1.390 (3) | C17—H17B | 0.9900 |
C3—H3 | 0.9500 | C18—N19 | 1.514 (3) |
C4—C5 | 1.388 (3) | C18—H18A | 0.9900 |
C4—H4 | 0.9500 | C18—H18B | 0.9900 |
C5—N9 | 1.393 (3) | N19—C20 | 1.517 (3) |
C5—C6 | 1.408 (3) | N19—H19 | 1.02 (2) |
C6—C7 | 1.518 (3) | C20—C21 | 1.505 (3) |
C7—C16 | 1.539 (3) | C20—H20A | 0.9900 |
C7—C17 | 1.545 (3) | C20—H20B | 0.9900 |
C7—C8 | 1.552 (3) | C21—C22 | 1.330 (3) |
C8—N9 | 1.476 (2) | C22—C23 | 1.499 (3) |
C8—C13 | 1.533 (3) | C22—H22 | 0.9500 |
C8—H8 | 1.0000 | C23—H23A | 0.9900 |
N9—C10 | 1.460 (2) | C23—H23B | 0.9900 |
C10—C11 | 1.532 (3) | O1A—C1A | 1.298 (2) |
C10—H10A | 0.9900 | O2A—C1A | 1.230 (2) |
C10—H10B | 0.9900 | O3A—C4A | 1.324 (2) |
C11—C12 | 1.527 (3) | O3A—H3A | 0.98 (3) |
C11—H11A | 0.9900 | O4A—C4A | 1.213 (2) |
C11—H11B | 0.9900 | C1A—C2A | 1.513 (3) |
C12—C13 | 1.532 (3) | C2A—C3A | 1.461 (3) |
C12—H12 | 1.0000 | C2A—H2AA | 0.9900 |
C13—C14 | 1.532 (3) | C2A—H2AB | 0.9900 |
C13—H13 | 1.0000 | C3A—C4A | 1.499 (3) |
C14—C21 | 1.518 (3) | C3A—H3AA | 0.9900 |
C14—C15 | 1.528 (3) | C3A—H3AB | 0.9900 |
C14—H14 | 1.0000 | | |
| | | |
C12—O1—C23 | 113.49 (17) | C14—C15—H15A | 109.9 |
C6—C1—C2 | 119.0 (2) | C16—C15—H15B | 109.9 |
C6—C1—H1 | 120.5 | C14—C15—H15B | 109.9 |
C2—C1—H1 | 120.5 | H15A—C15—H15B | 108.3 |
C3—C2—C1 | 119.6 (2) | C15—C16—C7 | 116.68 (17) |
C3—C2—H2 | 120.2 | C15—C16—N19 | 109.86 (17) |
C1—C2—H2 | 120.2 | C7—C16—N19 | 103.66 (15) |
C2—C3—C4 | 122.1 (2) | C15—C16—H16 | 108.8 |
C2—C3—H3 | 119.0 | C7—C16—H16 | 108.8 |
C4—C3—H3 | 119.0 | N19—C16—H16 | 108.8 |
C5—C4—C3 | 118.05 (19) | C18—C17—C7 | 102.94 (17) |
C5—C4—H4 | 121.0 | C18—C17—H17A | 111.2 |
C3—C4—H4 | 121.0 | C7—C17—H17A | 111.2 |
C4—C5—N9 | 129.28 (18) | C18—C17—H17B | 111.2 |
C4—C5—C6 | 120.60 (18) | C7—C17—H17B | 111.2 |
N9—C5—C6 | 110.12 (16) | H17A—C17—H17B | 109.1 |
C1—C6—C5 | 120.66 (19) | N19—C18—C17 | 105.96 (16) |
C1—C6—C7 | 131.00 (19) | N19—C18—H18A | 110.5 |
C5—C6—C7 | 108.32 (16) | C17—C18—H18A | 110.5 |
C6—C7—C16 | 117.53 (16) | N19—C18—H18B | 110.5 |
C6—C7—C17 | 113.55 (17) | C17—C18—H18B | 110.5 |
C16—C7—C17 | 102.24 (16) | H18A—C18—H18B | 108.7 |
C6—C7—C8 | 99.74 (15) | C18—N19—C20 | 113.94 (16) |
C16—C7—C8 | 113.69 (17) | C18—N19—C16 | 107.32 (15) |
C17—C7—C8 | 110.46 (16) | C20—N19—C16 | 112.96 (17) |
N9—C8—C13 | 110.57 (15) | C18—N19—H19 | 106.5 (13) |
N9—C8—C7 | 102.87 (16) | C20—N19—H19 | 100.6 (13) |
C13—C8—C7 | 111.71 (16) | C16—N19—H19 | 115.4 (12) |
N9—C8—H8 | 110.5 | C21—C20—N19 | 112.18 (17) |
C13—C8—H8 | 110.5 | C21—C20—H20A | 109.2 |
C7—C8—H8 | 110.5 | N19—C20—H20A | 109.2 |
C5—N9—C10 | 122.75 (16) | C21—C20—H20B | 109.2 |
C5—N9—C8 | 106.03 (14) | N19—C20—H20B | 109.2 |
C10—N9—C8 | 114.75 (16) | H20A—C20—H20B | 107.9 |
N9—C10—C11 | 112.94 (17) | C22—C21—C20 | 121.3 (2) |
N9—C10—H10A | 109.0 | C22—C21—C14 | 122.8 (2) |
C11—C10—H10A | 109.0 | C20—C21—C14 | 115.80 (18) |
N9—C10—H10B | 109.0 | C21—C22—C23 | 123.1 (2) |
C11—C10—H10B | 109.0 | C21—C22—H22 | 118.4 |
H10A—C10—H10B | 107.8 | C23—C22—H22 | 118.4 |
C12—C11—C10 | 112.31 (17) | O1—C23—C22 | 113.74 (18) |
C12—C11—H11A | 109.1 | O1—C23—H23A | 108.8 |
C10—C11—H11A | 109.1 | C22—C23—H23A | 108.8 |
C12—C11—H11B | 109.1 | O1—C23—H23B | 108.8 |
C10—C11—H11B | 109.1 | C22—C23—H23B | 108.8 |
H11A—C11—H11B | 107.9 | H23A—C23—H23B | 107.7 |
O1—C12—C11 | 107.24 (18) | C4A—O3A—H3A | 113.7 (14) |
O1—C12—C13 | 112.82 (17) | O2A—C1A—O1A | 123.51 (19) |
C11—C12—C13 | 108.63 (18) | O2A—C1A—C2A | 121.31 (19) |
O1—C12—H12 | 109.4 | O1A—C1A—C2A | 115.17 (19) |
C11—C12—H12 | 109.4 | C3A—C2A—C1A | 116.3 (2) |
C13—C12—H12 | 109.4 | C3A—C2A—H2AA | 108.2 |
C14—C13—C12 | 117.96 (17) | C1A—C2A—H2AA | 108.2 |
C14—C13—C8 | 109.50 (16) | C3A—C2A—H2AB | 108.2 |
C12—C13—C8 | 109.41 (16) | C1A—C2A—H2AB | 108.2 |
C14—C13—H13 | 106.4 | H2AA—C2A—H2AB | 107.4 |
C12—C13—H13 | 106.4 | C2A—C3A—C4A | 116.1 (2) |
C8—C13—H13 | 106.4 | C2A—C3A—H3AA | 108.3 |
C21—C14—C15 | 109.20 (17) | C4A—C3A—H3AA | 108.3 |
C21—C14—C13 | 110.48 (17) | C2A—C3A—H3AB | 108.3 |
C15—C14—C13 | 107.33 (17) | C4A—C3A—H3AB | 108.3 |
C21—C14—H14 | 109.9 | H3AA—C3A—H3AB | 107.4 |
C15—C14—H14 | 109.9 | O4A—C4A—O3A | 120.68 (19) |
C13—C14—H14 | 109.9 | O4A—C4A—C3A | 123.50 (19) |
C16—C15—C14 | 108.83 (17) | O3A—C4A—C3A | 115.82 (19) |
C16—C15—H15A | 109.9 | | |
| | | |
C6—C1—C2—C3 | −0.4 (4) | N9—C8—C13—C12 | −59.4 (2) |
C1—C2—C3—C4 | 0.7 (4) | C7—C8—C13—C12 | −173.28 (16) |
C2—C3—C4—C5 | −0.2 (3) | C12—C13—C14—C21 | −75.5 (2) |
C3—C4—C5—N9 | 178.9 (2) | C8—C13—C14—C21 | 50.5 (2) |
C3—C4—C5—C6 | −0.5 (3) | C12—C13—C14—C15 | 165.57 (18) |
C2—C1—C6—C5 | −0.4 (3) | C8—C13—C14—C15 | −68.5 (2) |
C2—C1—C6—C7 | −178.5 (2) | C21—C14—C15—C16 | −55.6 (2) |
C4—C5—C6—C1 | 0.8 (3) | C13—C14—C15—C16 | 64.1 (2) |
N9—C5—C6—C1 | −178.68 (19) | C14—C15—C16—C7 | −50.7 (2) |
C4—C5—C6—C7 | 179.35 (18) | C14—C15—C16—N19 | 66.9 (2) |
N9—C5—C6—C7 | −0.2 (2) | C6—C7—C16—C15 | −76.9 (2) |
C1—C6—C7—C16 | −37.4 (3) | C17—C7—C16—C15 | 158.07 (17) |
C5—C6—C7—C16 | 144.28 (18) | C8—C7—C16—C15 | 39.0 (2) |
C1—C6—C7—C17 | 81.8 (3) | C6—C7—C16—N19 | 162.21 (17) |
C5—C6—C7—C17 | −96.5 (2) | C17—C7—C16—N19 | 37.18 (19) |
C1—C6—C7—C8 | −160.7 (2) | C8—C7—C16—N19 | −81.88 (19) |
C5—C6—C7—C8 | 21.0 (2) | C6—C7—C17—C18 | −169.79 (17) |
C6—C7—C8—N9 | −33.06 (18) | C16—C7—C17—C18 | −42.17 (19) |
C16—C7—C8—N9 | −159.03 (16) | C8—C7—C17—C18 | 79.1 (2) |
C17—C7—C8—N9 | 86.72 (18) | C7—C17—C18—N19 | 30.9 (2) |
C6—C7—C8—C13 | 85.55 (18) | C17—C18—N19—C20 | −133.60 (18) |
C16—C7—C8—C13 | −40.4 (2) | C17—C18—N19—C16 | −7.8 (2) |
C17—C7—C8—C13 | −154.67 (17) | C15—C16—N19—C18 | −143.92 (17) |
C4—C5—N9—C10 | 23.4 (3) | C7—C16—N19—C18 | −18.5 (2) |
C6—C5—N9—C10 | −157.09 (19) | C15—C16—N19—C20 | −17.5 (2) |
C4—C5—N9—C8 | 158.1 (2) | C7—C16—N19—C20 | 107.89 (18) |
C6—C5—N9—C8 | −22.4 (2) | C18—N19—C20—C21 | 83.9 (2) |
C13—C8—N9—C5 | −84.37 (18) | C16—N19—C20—C21 | −38.9 (2) |
C7—C8—N9—C5 | 35.04 (19) | N19—C20—C21—C22 | −126.5 (2) |
C13—C8—N9—C10 | 54.4 (2) | N19—C20—C21—C14 | 50.6 (2) |
C7—C8—N9—C10 | 173.83 (16) | C15—C14—C21—C22 | 174.5 (2) |
C5—N9—C10—C11 | 82.0 (2) | C13—C14—C21—C22 | 56.7 (3) |
C8—N9—C10—C11 | −49.2 (2) | C15—C14—C21—C20 | −2.5 (2) |
N9—C10—C11—C12 | 49.4 (2) | C13—C14—C21—C20 | −120.35 (19) |
C23—O1—C12—C11 | 173.21 (16) | C20—C21—C22—C23 | 178.3 (2) |
C23—O1—C12—C13 | −67.2 (2) | C14—C21—C22—C23 | 1.4 (3) |
C10—C11—C12—O1 | 67.5 (2) | C12—O1—C23—C22 | 83.4 (2) |
C10—C11—C12—C13 | −54.8 (2) | C21—C22—C23—O1 | −66.0 (3) |
O1—C12—C13—C14 | 66.9 (2) | O2A—C1A—C2A—C3A | 12.2 (4) |
C11—C12—C13—C14 | −174.36 (18) | O1A—C1A—C2A—C3A | −166.7 (2) |
O1—C12—C13—C8 | −59.1 (2) | C1A—C2A—C3A—C4A | −171.9 (2) |
C11—C12—C13—C8 | 59.6 (2) | C2A—C3A—C4A—O4A | 27.4 (4) |
N9—C8—C13—C14 | 169.94 (16) | C2A—C3A—C4A—O3A | −153.3 (2) |
C7—C8—C13—C14 | 56.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N19—H19···O1A | 1.02 (2) | 1.69 (2) | 2.700 (2) | 170.0 (19) |
N19—H19···O2A | 1.02 (2) | 2.54 (2) | 3.225 (2) | 123.5 (16) |
O3A—H3A···O1Ai | 0.98 (3) | 1.63 (3) | 2.598 (2) | 173 (2) |
Symmetry code: (i) x+1, y, z. |
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