In the title compound, C
23H
25NO
10, the five-membered rings adopt envelope conformations and the dihedral angle between the two benzene rings is 67.1 (7)°. The crystal structure is stabilized by intramolecular N—H
O and intermolecular O—H
O hydrogen-bond interactions.
Supporting information
CCDC reference: 604949
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.009 Å
- R factor = 0.056
- wR factor = 0.166
- Data-to-parameter ratio = 6.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.10 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.40 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for C4 - C9 .. 7.96 su
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C20
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.654
Test value = 0.600
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.64
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.22
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.65 e/A 3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C4 - C9 ... 1.54 Ang.
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 25.01
From the CIF: _reflns_number_total 2099
Count of symmetry unique reflns 2098
Completeness (_total/calc) 100.05%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Ethyl
4-{5-[1-(hydroxymethyl)ethylaminocarbonyl]-1,3-benzodioxol-4-yl}-7-methoxy-
3-benzodioxole-5-carboxylate
top
Crystal data top
C23H25NO10 | F(000) = 500 |
Mr = 475.44 | Dx = 1.384 Mg m−3 |
Monoclinic, P21 | Melting point: 412 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0277 (15) Å | Cell parameters from 2246 reflections |
b = 14.185 (2) Å | θ = 2.6–23.4° |
c = 9.7695 (17) Å | µ = 0.11 mm−1 |
β = 114.266 (3)° | T = 294 K |
V = 1140.5 (3) Å3 | Block, white |
Z = 2 | 0.24 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2099 independent reflections |
Radiation source: fine-focus sealed tube | 1699 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.974, Tmax = 0.987 | k = −16→16 |
5834 measured reflections | l = −11→9 |
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)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.1001P)2 + 0.5453P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
2099 reflections | Δρmax = 0.65 e Å−3 |
316 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Friedel Pairs merged |
Primary atom site location: structure-invariant direct methods | |
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 | 1.0924 (4) | 1.0120 (4) | 0.4642 (5) | 0.0673 (13) | |
O2 | 0.8341 (5) | 1.0749 (3) | 0.3868 (5) | 0.0583 (11) | |
O3 | 1.1641 (5) | 0.8358 (3) | 0.3639 (5) | 0.0631 (12) | |
O4 | 0.4622 (6) | 0.7808 (4) | 0.1297 (7) | 0.0844 (16) | |
O5 | 0.5568 (6) | 0.7747 (4) | −0.0499 (6) | 0.0743 (14) | |
O6 | 0.5152 (5) | 1.0155 (3) | −0.0797 (4) | 0.0558 (11) | |
O7 | 0.2555 (5) | 1.0802 (4) | −0.1849 (4) | 0.0592 (12) | |
O8 | 0.0492 (5) | 1.0999 (4) | −0.0306 (4) | 0.0596 (12) | |
O9 | 0.4848 (6) | 1.0301 (3) | 0.5102 (4) | 0.0540 (10) | |
N1 | 0.5726 (6) | 0.8920 (3) | 0.4615 (5) | 0.0421 (11) | |
O10 | 0.6699 (9) | 0.7063 (4) | 0.5278 (7) | 0.0888 (17) | |
H10 | 0.6251 | 0.6546 | 0.5104 | 0.133* | |
C1 | 0.9995 (8) | 1.0861 (6) | 0.4889 (9) | 0.071 (2) | |
H1A | 1.0090 | 1.0838 | 0.5914 | 0.085* | |
H1B | 1.0398 | 1.1467 | 0.4731 | 0.085* | |
C2 | 0.8258 (6) | 0.9872 (4) | 0.3222 (5) | 0.0374 (11) | |
C3 | 0.6884 (6) | 0.9426 (4) | 0.2233 (5) | 0.0355 (11) | |
C4 | 0.7151 (6) | 0.8562 (4) | 0.1681 (6) | 0.0431 (12) | |
C5 | 0.8702 (7) | 0.8184 (4) | 0.2117 (6) | 0.0474 (13) | |
H5 | 0.8830 | 0.7609 | 0.1720 | 0.057* | |
C6 | 1.0066 (6) | 0.8653 (4) | 0.3139 (6) | 0.0445 (13) | |
C7 | 0.9792 (6) | 0.9502 (4) | 0.3681 (6) | 0.0433 (12) | |
C8 | 1.1942 (9) | 0.7570 (6) | 0.2892 (11) | 0.084 (3) | |
H8A | 1.1500 | 0.7689 | 0.1831 | 0.126* | |
H8B | 1.1437 | 0.7020 | 0.3083 | 0.126* | |
H8C | 1.3092 | 0.7469 | 0.3256 | 0.126* | |
C9 | 0.5586 (10) | 0.7998 (4) | 0.0785 (8) | 0.0655 (18) | |
C10 | 0.3985 (9) | 0.7297 (6) | −0.1453 (9) | 0.080 (2) | |
H10A | 0.3628 | 0.6910 | −0.0828 | 0.096* | |
H10B | 0.4129 | 0.6890 | −0.2187 | 0.096* | |
C11 | 0.2692 (10) | 0.8030 (7) | −0.2260 (10) | 0.095 (3) | |
H11A | 0.3067 | 0.8435 | −0.2838 | 0.143* | |
H11B | 0.2479 | 0.8398 | −0.1536 | 0.143* | |
H11C | 0.1712 | 0.7719 | −0.2916 | 0.143* | |
C12 | 0.5237 (6) | 0.9853 (3) | 0.1708 (5) | 0.0351 (11) | |
C13 | 0.4475 (6) | 1.0164 (4) | 0.0225 (6) | 0.0376 (11) | |
C14 | 0.3948 (7) | 1.0579 (5) | −0.2138 (6) | 0.0520 (14) | |
H14A | 0.4381 | 1.1147 | −0.2390 | 0.062* | |
H14B | 0.3650 | 1.0143 | −0.2975 | 0.062* | |
C15 | 0.2970 (6) | 1.0549 (4) | −0.0387 (5) | 0.0377 (11) | |
C16 | 0.2023 (6) | 1.0635 (4) | 0.0427 (6) | 0.0409 (12) | |
C17 | 0.2742 (6) | 1.0353 (4) | 0.1914 (6) | 0.0400 (12) | |
H17 | 0.2163 | 1.0417 | 0.2506 | 0.048* | |
C18 | 0.4313 (6) | 0.9975 (3) | 0.2555 (5) | 0.0343 (11) | |
C19 | 0.4981 (6) | 0.9744 (4) | 0.4196 (5) | 0.0369 (11) | |
C20 | 0.6503 (7) | 0.8599 (4) | 0.6173 (6) | 0.0475 (13) | |
H20 | 0.5958 | 0.8922 | 0.6724 | 0.057* | |
C21 | 0.8252 (13) | 0.8891 (10) | 0.6875 (11) | 0.141 (5) | |
H21A | 0.8322 | 0.9566 | 0.6866 | 0.211* | |
H21B | 0.8812 | 0.8626 | 0.6316 | 0.211* | |
H21C | 0.8742 | 0.8669 | 0.7892 | 0.211* | |
C22 | 0.6215 (12) | 0.7566 (5) | 0.6253 (9) | 0.081 (2) | |
H22A | 0.6819 | 0.7346 | 0.7272 | 0.097* | |
H22B | 0.5070 | 0.7456 | 0.5988 | 0.097* | |
C23 | −0.0570 (9) | 1.0909 (9) | 0.0405 (10) | 0.100 (3) | |
H23A | −0.0179 | 1.1283 | 0.1303 | 0.150* | |
H23B | −0.0625 | 1.0260 | 0.0658 | 0.150* | |
H23C | −0.1632 | 1.1122 | −0.0260 | 0.150* | |
H1 | 0.558 (7) | 0.855 (5) | 0.381 (7) | 0.050 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.031 (2) | 0.077 (3) | 0.073 (3) | −0.001 (2) | 0.001 (2) | −0.028 (3) |
O2 | 0.039 (2) | 0.060 (3) | 0.058 (2) | 0.0051 (19) | 0.0029 (18) | −0.023 (2) |
O3 | 0.031 (2) | 0.078 (3) | 0.074 (3) | 0.012 (2) | 0.015 (2) | −0.012 (2) |
O4 | 0.062 (3) | 0.082 (4) | 0.119 (4) | −0.022 (3) | 0.047 (3) | −0.023 (3) |
O5 | 0.076 (3) | 0.075 (3) | 0.064 (3) | −0.013 (3) | 0.020 (3) | −0.008 (3) |
O6 | 0.050 (2) | 0.088 (3) | 0.0361 (19) | 0.018 (2) | 0.0245 (17) | 0.015 (2) |
O7 | 0.048 (2) | 0.095 (3) | 0.0323 (18) | 0.022 (2) | 0.0137 (16) | 0.017 (2) |
O8 | 0.038 (2) | 0.088 (3) | 0.052 (2) | 0.020 (2) | 0.0187 (18) | 0.021 (2) |
O9 | 0.074 (3) | 0.057 (2) | 0.0339 (18) | 0.019 (2) | 0.0252 (18) | 0.0032 (18) |
N1 | 0.052 (3) | 0.042 (2) | 0.033 (2) | 0.008 (2) | 0.018 (2) | 0.004 (2) |
O10 | 0.139 (5) | 0.052 (3) | 0.107 (4) | 0.005 (3) | 0.082 (4) | 0.007 (3) |
C1 | 0.039 (3) | 0.073 (5) | 0.075 (4) | 0.003 (3) | −0.003 (3) | −0.031 (4) |
C2 | 0.035 (3) | 0.045 (3) | 0.030 (2) | 0.003 (2) | 0.011 (2) | −0.003 (2) |
C3 | 0.031 (3) | 0.047 (3) | 0.028 (2) | 0.000 (2) | 0.011 (2) | 0.003 (2) |
C4 | 0.035 (3) | 0.047 (3) | 0.042 (3) | −0.001 (2) | 0.010 (2) | 0.001 (2) |
C5 | 0.044 (3) | 0.048 (3) | 0.048 (3) | 0.002 (3) | 0.016 (3) | −0.008 (3) |
C6 | 0.027 (3) | 0.058 (3) | 0.046 (3) | 0.005 (2) | 0.013 (2) | 0.003 (3) |
C7 | 0.030 (3) | 0.056 (3) | 0.040 (3) | −0.006 (2) | 0.011 (2) | −0.008 (3) |
C8 | 0.051 (4) | 0.086 (6) | 0.115 (7) | 0.017 (4) | 0.035 (4) | −0.016 (5) |
C9 | 0.092 (5) | 0.037 (3) | 0.073 (4) | 0.001 (3) | 0.038 (4) | −0.004 (3) |
C10 | 0.065 (5) | 0.069 (5) | 0.074 (5) | −0.020 (4) | −0.004 (4) | −0.008 (4) |
C11 | 0.063 (5) | 0.092 (6) | 0.093 (6) | −0.006 (4) | −0.007 (4) | −0.008 (5) |
C12 | 0.034 (3) | 0.037 (3) | 0.032 (2) | 0.001 (2) | 0.010 (2) | 0.001 (2) |
C13 | 0.037 (3) | 0.045 (3) | 0.034 (2) | 0.001 (2) | 0.018 (2) | −0.002 (2) |
C14 | 0.053 (3) | 0.068 (4) | 0.034 (3) | 0.005 (3) | 0.018 (2) | 0.007 (3) |
C15 | 0.033 (3) | 0.047 (3) | 0.026 (2) | 0.001 (2) | 0.005 (2) | 0.003 (2) |
C16 | 0.040 (3) | 0.042 (3) | 0.038 (3) | 0.005 (2) | 0.013 (2) | 0.002 (2) |
C17 | 0.039 (3) | 0.042 (3) | 0.039 (3) | 0.007 (2) | 0.016 (2) | 0.005 (2) |
C18 | 0.037 (3) | 0.033 (2) | 0.032 (2) | 0.000 (2) | 0.013 (2) | 0.001 (2) |
C19 | 0.037 (3) | 0.042 (3) | 0.032 (2) | 0.003 (2) | 0.014 (2) | 0.005 (2) |
C20 | 0.057 (3) | 0.049 (3) | 0.034 (3) | 0.013 (3) | 0.016 (3) | 0.012 (2) |
C21 | 0.105 (8) | 0.161 (11) | 0.088 (7) | −0.048 (7) | −0.030 (6) | 0.058 (7) |
C22 | 0.119 (7) | 0.061 (4) | 0.061 (4) | 0.012 (4) | 0.036 (4) | 0.016 (3) |
C23 | 0.046 (4) | 0.166 (10) | 0.093 (6) | 0.040 (5) | 0.033 (4) | 0.057 (6) |
Geometric parameters (Å, º) top
O1—C7 | 1.380 (7) | C6—C7 | 1.378 (8) |
O1—C1 | 1.426 (8) | C8—H8A | 0.9600 |
O2—C2 | 1.382 (7) | C8—H8B | 0.9600 |
O2—C1 | 1.424 (7) | C8—H8C | 0.9600 |
O3—C6 | 1.365 (6) | C10—C11 | 1.519 (12) |
O3—C8 | 1.421 (9) | C10—H10A | 0.9700 |
O4—C9 | 1.199 (9) | C10—H10B | 0.9700 |
O5—C9 | 1.298 (8) | C11—H11A | 0.9600 |
O5—C10 | 1.491 (8) | C11—H11B | 0.9600 |
O6—C13 | 1.369 (6) | C11—H11C | 0.9600 |
O6—C14 | 1.445 (7) | C12—C13 | 1.396 (7) |
O7—C15 | 1.367 (6) | C12—C18 | 1.406 (7) |
O7—C14 | 1.433 (7) | C13—C15 | 1.355 (7) |
O8—C16 | 1.369 (6) | C14—H14A | 0.9700 |
O8—C23 | 1.401 (7) | C14—H14B | 0.9700 |
O9—C19 | 1.228 (6) | C15—C16 | 1.392 (7) |
N1—C19 | 1.327 (7) | C16—C17 | 1.384 (7) |
N1—C20 | 1.463 (7) | C17—C18 | 1.401 (7) |
N1—H1 | 0.91 (7) | C17—H17 | 0.9300 |
O10—C22 | 1.396 (9) | C18—C19 | 1.500 (7) |
O10—H10 | 0.8200 | C20—C22 | 1.495 (10) |
C1—H1A | 0.9700 | C20—C21 | 1.498 (11) |
C1—H1B | 0.9700 | C20—H20 | 0.9800 |
C2—C7 | 1.373 (7) | C21—H21A | 0.9600 |
C2—C3 | 1.374 (7) | C21—H21B | 0.9600 |
C3—C4 | 1.399 (8) | C21—H21C | 0.9600 |
C3—C12 | 1.488 (7) | C22—H22A | 0.9700 |
C4—C5 | 1.393 (8) | C22—H22B | 0.9700 |
C4—C9 | 1.545 (9) | C23—H23A | 0.9600 |
C5—C6 | 1.395 (8) | C23—H23B | 0.9600 |
C5—H5 | 0.9300 | C23—H23C | 0.9600 |
| | | |
C7—O1—C1 | 105.1 (4) | H11A—C11—H11C | 109.5 |
C2—O2—C1 | 105.4 (4) | H11B—C11—H11C | 109.5 |
C6—O3—C8 | 116.6 (5) | C13—C12—C18 | 114.4 (4) |
C9—O5—C10 | 110.4 (6) | C13—C12—C3 | 118.8 (4) |
C13—O6—C14 | 105.2 (4) | C18—C12—C3 | 126.7 (4) |
C15—O7—C14 | 105.2 (4) | C15—C13—O6 | 110.4 (4) |
C16—O8—C23 | 117.1 (5) | C15—C13—C12 | 124.3 (4) |
C19—N1—C20 | 124.1 (5) | O6—C13—C12 | 125.3 (4) |
C19—N1—H1 | 111 (4) | O7—C14—O6 | 107.9 (4) |
C20—N1—H1 | 124 (4) | O7—C14—H14A | 110.1 |
C22—O10—H10 | 109.5 | O6—C14—H14A | 110.1 |
O2—C1—O1 | 108.6 (5) | O7—C14—H14B | 110.1 |
O2—C1—H1A | 110.0 | O6—C14—H14B | 110.1 |
O1—C1—H1A | 110.0 | H14A—C14—H14B | 108.4 |
O2—C1—H1B | 110.0 | C13—C15—O7 | 111.2 (4) |
O1—C1—H1B | 110.0 | C13—C15—C16 | 121.5 (4) |
H1A—C1—H1B | 108.3 | O7—C15—C16 | 127.3 (4) |
C7—C2—C3 | 123.5 (5) | O8—C16—C17 | 126.5 (5) |
C7—C2—O2 | 109.7 (4) | O8—C16—C15 | 117.3 (4) |
C3—C2—O2 | 126.8 (5) | C17—C16—C15 | 116.2 (4) |
C2—C3—C4 | 115.2 (5) | C16—C17—C18 | 122.1 (5) |
C2—C3—C12 | 122.7 (5) | C16—C17—H17 | 118.9 |
C4—C3—C12 | 122.0 (4) | C18—C17—H17 | 118.9 |
C5—C4—C3 | 122.0 (5) | C17—C18—C12 | 121.4 (4) |
C5—C4—C9 | 122.9 (5) | C17—C18—C19 | 116.7 (4) |
C3—C4—C9 | 114.2 (5) | C12—C18—C19 | 121.8 (4) |
C4—C5—C6 | 121.0 (5) | O9—C19—N1 | 122.2 (5) |
C4—C5—H5 | 119.5 | O9—C19—C18 | 120.9 (5) |
C6—C5—H5 | 119.5 | N1—C19—C18 | 116.9 (4) |
O3—C6—C7 | 117.1 (5) | N1—C20—C22 | 109.9 (6) |
O3—C6—C5 | 126.4 (5) | N1—C20—C21 | 110.8 (5) |
C7—C6—C5 | 116.5 (5) | C22—C20—C21 | 114.9 (8) |
C2—C7—C6 | 121.7 (5) | N1—C20—H20 | 107.0 |
C2—C7—O1 | 110.1 (5) | C22—C20—H20 | 107.0 |
C6—C7—O1 | 128.1 (5) | C21—C20—H20 | 107.0 |
O3—C8—H8A | 109.5 | C20—C21—H21A | 109.5 |
O3—C8—H8B | 109.5 | C20—C21—H21B | 109.5 |
H8A—C8—H8B | 109.5 | H21A—C21—H21B | 109.5 |
O3—C8—H8C | 109.5 | C20—C21—H21C | 109.5 |
H8A—C8—H8C | 109.5 | H21A—C21—H21C | 109.5 |
H8B—C8—H8C | 109.5 | H21B—C21—H21C | 109.5 |
O4—C9—O5 | 128.2 (7) | O10—C22—C20 | 110.8 (6) |
O4—C9—C4 | 122.1 (6) | O10—C22—H22A | 109.5 |
O5—C9—C4 | 109.6 (6) | C20—C22—H22A | 109.5 |
O5—C10—C11 | 111.5 (6) | O10—C22—H22B | 109.5 |
O5—C10—H10A | 109.3 | C20—C22—H22B | 109.5 |
C11—C10—H10A | 109.3 | H22A—C22—H22B | 108.1 |
O5—C10—H10B | 109.3 | O8—C23—H23A | 109.5 |
C11—C10—H10B | 109.3 | O8—C23—H23B | 109.5 |
H10A—C10—H10B | 108.0 | H23A—C23—H23B | 109.5 |
C10—C11—H11A | 109.5 | O8—C23—H23C | 109.5 |
C10—C11—H11B | 109.5 | H23A—C23—H23C | 109.5 |
H11A—C11—H11B | 109.5 | H23B—C23—H23C | 109.5 |
C10—C11—H11C | 109.5 | | |
| | | |
C2—O2—C1—O1 | 10.0 (8) | C14—O6—C13—C15 | 0.4 (6) |
C7—O1—C1—O2 | −9.9 (8) | C14—O6—C13—C12 | −177.5 (5) |
C1—O2—C2—C7 | −6.3 (7) | C18—C12—C13—C15 | −0.5 (8) |
C1—O2—C2—C3 | 175.5 (6) | C3—C12—C13—C15 | 178.9 (5) |
C7—C2—C3—C4 | −1.5 (7) | C18—C12—C13—O6 | 177.2 (5) |
O2—C2—C3—C4 | 176.5 (5) | C3—C12—C13—O6 | −3.5 (8) |
C7—C2—C3—C12 | −177.9 (5) | C15—O7—C14—O6 | 2.1 (7) |
O2—C2—C3—C12 | 0.1 (8) | C13—O6—C14—O7 | −1.6 (7) |
C2—C3—C4—C5 | 0.4 (7) | O6—C13—C15—O7 | 1.0 (7) |
C12—C3—C4—C5 | 176.8 (5) | C12—C13—C15—O7 | 178.9 (5) |
C2—C3—C4—C9 | 170.4 (5) | O6—C13—C15—C16 | 179.7 (5) |
C12—C3—C4—C9 | −13.2 (7) | C12—C13—C15—C16 | −2.4 (8) |
C3—C4—C5—C6 | 0.4 (9) | C14—O7—C15—C13 | −1.9 (6) |
C9—C4—C5—C6 | −168.7 (5) | C14—O7—C15—C16 | 179.5 (5) |
C8—O3—C6—C7 | −169.7 (6) | C23—O8—C16—C17 | −13.6 (10) |
C8—O3—C6—C5 | 9.6 (9) | C23—O8—C16—C15 | 167.4 (7) |
C4—C5—C6—O3 | −179.4 (6) | C13—C15—C16—O8 | −177.5 (5) |
C4—C5—C6—C7 | −0.2 (8) | O7—C15—C16—O8 | 1.0 (8) |
C3—C2—C7—C6 | 1.8 (8) | C13—C15—C16—C17 | 3.5 (8) |
O2—C2—C7—C6 | −176.5 (5) | O7—C15—C16—C17 | −178.0 (6) |
C3—C2—C7—O1 | 178.5 (5) | O8—C16—C17—C18 | 179.1 (5) |
O2—C2—C7—O1 | 0.2 (6) | C15—C16—C17—C18 | −2.0 (8) |
O3—C6—C7—C2 | 178.4 (5) | C16—C17—C18—C12 | −0.7 (8) |
C5—C6—C7—C2 | −0.9 (8) | C16—C17—C18—C19 | 177.0 (5) |
O3—C6—C7—O1 | 2.4 (9) | C13—C12—C18—C17 | 1.9 (7) |
C5—C6—C7—O1 | −176.9 (6) | C3—C12—C18—C17 | −177.4 (5) |
C1—O1—C7—C2 | 6.0 (7) | C13—C12—C18—C19 | −175.7 (5) |
C1—O1—C7—C6 | −177.6 (6) | C3—C12—C18—C19 | 5.0 (8) |
C10—O5—C9—O4 | 9.8 (10) | C20—N1—C19—O9 | −1.9 (8) |
C10—O5—C9—C4 | −173.6 (5) | C20—N1—C19—C18 | 177.5 (5) |
C5—C4—C9—O4 | 115.7 (8) | C17—C18—C19—O9 | −45.5 (7) |
C3—C4—C9—O4 | −54.2 (8) | C12—C18—C19—O9 | 132.2 (5) |
C5—C4—C9—O5 | −61.2 (8) | C17—C18—C19—N1 | 135.0 (5) |
C3—C4—C9—O5 | 128.9 (6) | C12—C18—C19—N1 | −47.2 (7) |
C9—O5—C10—C11 | 82.6 (8) | C19—N1—C20—C22 | 141.7 (6) |
C2—C3—C12—C13 | 109.0 (6) | C19—N1—C20—C21 | −90.3 (9) |
C4—C3—C12—C13 | −67.1 (7) | N1—C20—C22—O10 | 53.7 (8) |
C2—C3—C12—C18 | −71.7 (7) | C21—C20—C22—O10 | −72.0 (10) |
C4—C3—C12—C18 | 112.2 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.91 (7) | 2.48 (7) | 3.367 (8) | 166 (5) |
O10—H10···O9i | 0.82 | 1.99 | 2.811 (7) | 174 |
Symmetry code: (i) −x+1, y−1/2, −z+1. |