Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034348/cv6438sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034348/cv6438Isup2.hkl |
CCDC reference: 263671
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.043
- wR factor = 0.079
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT128_ALERT_4_C Non-standard setting of Space group Pbca .... Pcab PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17A PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13B PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C18 -C23 1.36 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H4 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
C23H16N2O3·CH4O | F(000) = 1680 |
Mr = 400.42 | Dx = 1.265 Mg m−3 |
Orthorhombic, Pcab | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2bc 2ac | Cell parameters from 8043 reflections |
a = 10.8731 (9) Å | θ = 2.0–24.5° |
b = 18.7861 (14) Å | µ = 0.09 mm−1 |
c = 20.5836 (19) Å | T = 293 K |
V = 4204.5 (6) Å3 | Prism, colorless |
Z = 8 | 0.50 × 0.33 × 0.21 mm |
Stoe IPDS-II diffractometer | 3914 independent reflections |
Radiation source: sealed X-ray tube | 1743 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.099 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.5°, θmin = 2.0° |
ω scans | h = −13→13 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −22→22 |
Tmin = 0.965, Tmax = 0.984 | l = −24→24 |
27164 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0154P)2] where P = (Fo2 + 2Fc2)/3 |
3914 reflections | (Δ/σ)max < 0.001 |
327 parameters | Δρmax = 0.11 e Å−3 |
417 restraints | Δρmin = −0.20 e Å−3 |
Experimental. Experiments were followed by thin layer chromatography using a DC Alufolien Kieselgel 60 F254 Merck and Camag TLC lamp (254/366 nm). After completion of the reactions, solvents were evaporated with a rotary evaporator (Buchi RE model 111). The melting point was determined on an Electrothermal 9200 apparatus and is uncorrected. Microanalysis was performed with a Carlo Erba Elemental Analyser Model 1108. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.31931 (15) | 0.16088 (9) | 0.01148 (6) | 0.0829 (5) | |
O2A | 0.4548 (13) | 0.0740 (7) | 0.0159 (5) | 0.081 (3) | 0.509 (11) |
H2A | 0.4347 | 0.0681 | −0.0222 | 0.122* | 0.509 (11) |
O2B | 0.4315 (16) | 0.0629 (8) | 0.0219 (6) | 0.115 (5) | 0.491 (11) |
H2B | 0.4129 | 0.0564 | −0.0163 | 0.173* | 0.491 (11) |
O3 | 0.21399 (15) | 0.26963 (10) | 0.16199 (6) | 0.0878 (6) | |
O4 | 0.39288 (18) | 0.03190 (9) | −0.09865 (7) | 0.0975 (6) | |
H4 | 0.4297 | −0.0041 | −0.1100 | 0.146* | |
N1 | 0.48907 (16) | 0.11614 (10) | 0.20537 (7) | 0.0573 (5) | |
N2 | 0.48245 (16) | 0.08894 (10) | 0.14406 (7) | 0.0609 (5) | |
C1 | 0.42035 (18) | 0.13814 (12) | 0.11104 (8) | 0.0530 (5) | |
C2 | 0.38444 (18) | 0.19565 (11) | 0.14977 (8) | 0.0526 (5) | |
C3 | 0.43055 (19) | 0.17899 (12) | 0.21078 (8) | 0.0537 (5) | |
C4 | 0.3884 (2) | 0.12443 (14) | 0.04116 (9) | 0.0606 (6) | |
C5 | 0.3098 (2) | 0.25859 (12) | 0.13308 (9) | 0.0574 (6) | |
C6 | 0.3535 (2) | 0.30809 (12) | 0.08170 (9) | 0.0542 (5) | |
C7 | 0.2708 (2) | 0.35376 (14) | 0.05310 (10) | 0.0796 (7) | |
H7 | 0.1886 | 0.3531 | 0.0657 | 0.096* | |
C8 | 0.3097 (3) | 0.40072 (16) | 0.00547 (12) | 0.1021 (9) | |
H8 | 0.2537 | 0.4311 | −0.0144 | 0.123* | |
C9 | 0.4299 (3) | 0.40219 (16) | −0.01208 (12) | 0.1001 (9) | |
H9 | 0.4555 | 0.4339 | −0.0440 | 0.120* | |
C10 | 0.5141 (2) | 0.35795 (14) | 0.01620 (11) | 0.0860 (8) | |
H10 | 0.5966 | 0.3601 | 0.0044 | 0.103* | |
C11 | 0.4743 (2) | 0.30956 (13) | 0.06292 (9) | 0.0658 (6) | |
H11 | 0.5301 | 0.2780 | 0.0815 | 0.079* | |
C12 | 0.4252 (2) | 0.21998 (13) | 0.27227 (9) | 0.0596 (6) | |
C13A | 0.4835 (7) | 0.2870 (4) | 0.2712 (4) | 0.078 (2) | 0.509 (11) |
H13A | 0.5222 | 0.3034 | 0.2338 | 0.093* | 0.509 (11) |
C14A | 0.4815 (7) | 0.3278 (5) | 0.3275 (4) | 0.096 (3) | 0.509 (11) |
H14A | 0.5224 | 0.3713 | 0.3289 | 0.115* | 0.509 (11) |
C15A | 0.4201 (13) | 0.3042 (7) | 0.3804 (5) | 0.096 (3) | 0.509 (11) |
H15A | 0.4200 | 0.3313 | 0.4182 | 0.115* | 0.509 (11) |
C16A | 0.3584 (12) | 0.2413 (7) | 0.3788 (5) | 0.100 (4) | 0.509 (11) |
H16A | 0.3146 | 0.2265 | 0.4152 | 0.120* | 0.509 (11) |
C17A | 0.3598 (11) | 0.1992 (7) | 0.3237 (5) | 0.096 (4) | 0.509 (11) |
H17A | 0.3156 | 0.1568 | 0.3225 | 0.115* | 0.509 (11) |
C13B | 0.5215 (8) | 0.2546 (6) | 0.2994 (4) | 0.111 (3) | 0.491 (11) |
H13B | 0.5965 | 0.2558 | 0.2777 | 0.133* | 0.491 (11) |
C14B | 0.5100 (9) | 0.2885 (7) | 0.3595 (5) | 0.129 (4) | 0.491 (11) |
H14B | 0.5750 | 0.3152 | 0.3760 | 0.154* | 0.491 (11) |
C15B | 0.4043 (15) | 0.2824 (9) | 0.3934 (6) | 0.104 (4) | 0.491 (11) |
H15B | 0.3992 | 0.3027 | 0.4346 | 0.124* | 0.491 (11) |
C16B | 0.3050 (11) | 0.2474 (8) | 0.3689 (6) | 0.104 (4) | 0.491 (11) |
H16B | 0.2305 | 0.2463 | 0.3911 | 0.125* | 0.491 (11) |
C17B | 0.3196 (10) | 0.2132 (7) | 0.3092 (5) | 0.075 (3) | 0.491 (11) |
H17B | 0.2559 | 0.1848 | 0.2936 | 0.090* | 0.491 (11) |
C18 | 0.5503 (2) | 0.07337 (13) | 0.25426 (8) | 0.0567 (6) | |
C19 | 0.6554 (2) | 0.09568 (15) | 0.28198 (10) | 0.0820 (8) | |
H19 | 0.6893 | 0.1395 | 0.2711 | 0.098* | |
C20 | 0.7120 (3) | 0.0518 (2) | 0.32709 (11) | 0.0998 (10) | |
H20 | 0.7853 | 0.0661 | 0.3463 | 0.120* | |
C21 | 0.6621 (3) | −0.0111 (2) | 0.34331 (12) | 0.1005 (10) | |
H21 | 0.7011 | −0.0400 | 0.3736 | 0.121* | |
C22 | 0.5557 (3) | −0.03254 (16) | 0.31578 (13) | 0.1071 (10) | |
H22 | 0.5217 | −0.0762 | 0.3272 | 0.129* | |
C23 | 0.4968 (2) | 0.01023 (15) | 0.27060 (10) | 0.0836 (8) | |
H23 | 0.4228 | −0.0038 | 0.2519 | 0.100* | |
C24 | 0.2783 (3) | 0.03358 (17) | −0.12805 (13) | 0.1319 (12) | |
H24A | 0.2240 | 0.0632 | −0.1032 | 0.158* | |
H24B | 0.2455 | −0.0138 | −0.1302 | 0.158* | |
H24C | 0.2861 | 0.0525 | −0.1712 | 0.158* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0996 (13) | 0.0888 (14) | 0.0604 (9) | 0.0237 (10) | −0.0226 (9) | −0.0088 (8) |
O2A | 0.107 (4) | 0.096 (6) | 0.041 (3) | 0.048 (4) | −0.019 (3) | −0.011 (3) |
O2B | 0.227 (14) | 0.070 (4) | 0.050 (4) | 0.032 (6) | −0.024 (5) | −0.021 (3) |
O3 | 0.0782 (12) | 0.1154 (15) | 0.0699 (9) | 0.0314 (11) | 0.0202 (9) | 0.0148 (9) |
O4 | 0.1532 (17) | 0.0812 (14) | 0.0583 (9) | 0.0352 (12) | −0.0283 (10) | −0.0170 (9) |
N1 | 0.0821 (13) | 0.0504 (12) | 0.0393 (8) | 0.0045 (11) | 0.0006 (8) | 0.0001 (8) |
N2 | 0.0861 (13) | 0.0552 (12) | 0.0414 (9) | 0.0037 (11) | 0.0020 (9) | −0.0068 (8) |
C1 | 0.0639 (15) | 0.0535 (15) | 0.0414 (10) | 0.0017 (12) | −0.0005 (10) | −0.0003 (10) |
C2 | 0.0590 (14) | 0.0529 (15) | 0.0458 (11) | 0.0036 (12) | 0.0016 (10) | −0.0009 (10) |
C3 | 0.0644 (14) | 0.0513 (15) | 0.0454 (11) | 0.0025 (13) | 0.0057 (10) | 0.0002 (10) |
C4 | 0.0742 (17) | 0.0600 (18) | 0.0475 (12) | −0.0002 (14) | 0.0016 (12) | −0.0046 (12) |
C5 | 0.0584 (15) | 0.0668 (17) | 0.0469 (11) | 0.0088 (13) | 0.0003 (11) | −0.0096 (11) |
C6 | 0.0576 (14) | 0.0561 (15) | 0.0490 (11) | 0.0079 (12) | −0.0011 (10) | −0.0058 (10) |
C7 | 0.0772 (17) | 0.088 (2) | 0.0735 (15) | 0.0194 (15) | 0.0024 (13) | 0.0127 (14) |
C8 | 0.112 (2) | 0.102 (2) | 0.0921 (18) | 0.019 (2) | −0.0043 (18) | 0.0299 (17) |
C9 | 0.110 (2) | 0.105 (2) | 0.0859 (17) | 0.001 (2) | 0.0052 (17) | 0.0340 (16) |
C10 | 0.0803 (19) | 0.092 (2) | 0.0861 (16) | −0.0110 (16) | 0.0051 (14) | 0.0147 (15) |
C11 | 0.0663 (16) | 0.0659 (17) | 0.0653 (13) | 0.0042 (13) | −0.0022 (12) | −0.0004 (12) |
C12 | 0.0681 (16) | 0.0618 (17) | 0.0487 (12) | 0.0052 (13) | 0.0032 (11) | −0.0066 (11) |
C13A | 0.093 (5) | 0.081 (5) | 0.060 (4) | −0.012 (4) | 0.010 (3) | −0.021 (3) |
C14A | 0.099 (5) | 0.098 (6) | 0.091 (5) | −0.009 (4) | 0.006 (4) | −0.045 (4) |
C15A | 0.117 (8) | 0.110 (7) | 0.059 (6) | 0.032 (5) | −0.006 (4) | −0.033 (5) |
C16A | 0.150 (10) | 0.114 (7) | 0.036 (4) | 0.008 (7) | 0.014 (6) | 0.002 (4) |
C17A | 0.155 (9) | 0.086 (6) | 0.047 (4) | −0.010 (6) | 0.020 (5) | 0.012 (4) |
C13B | 0.096 (5) | 0.152 (9) | 0.085 (5) | −0.024 (5) | 0.009 (4) | −0.057 (5) |
C14B | 0.124 (6) | 0.171 (10) | 0.091 (6) | −0.007 (7) | −0.001 (5) | −0.072 (6) |
C15B | 0.140 (7) | 0.129 (12) | 0.041 (4) | 0.011 (8) | −0.003 (4) | −0.016 (6) |
C16B | 0.122 (7) | 0.129 (7) | 0.062 (5) | 0.017 (7) | 0.017 (5) | −0.012 (4) |
C17B | 0.099 (5) | 0.082 (6) | 0.045 (4) | 0.001 (5) | 0.009 (4) | −0.001 (4) |
C18 | 0.0705 (16) | 0.0587 (16) | 0.0409 (10) | 0.0073 (13) | 0.0028 (11) | 0.0025 (11) |
C19 | 0.089 (2) | 0.100 (2) | 0.0569 (13) | −0.0157 (17) | −0.0140 (13) | 0.0052 (14) |
C20 | 0.098 (2) | 0.138 (3) | 0.0636 (16) | 0.012 (2) | −0.0204 (15) | −0.0026 (18) |
C21 | 0.122 (3) | 0.114 (3) | 0.0654 (17) | 0.045 (2) | −0.0066 (17) | 0.0112 (18) |
C22 | 0.143 (3) | 0.080 (2) | 0.0984 (19) | 0.005 (2) | −0.0070 (19) | 0.0362 (17) |
C23 | 0.103 (2) | 0.071 (2) | 0.0767 (15) | −0.0042 (17) | −0.0151 (14) | 0.0182 (13) |
C24 | 0.169 (3) | 0.128 (3) | 0.100 (2) | 0.052 (3) | −0.027 (2) | 0.0036 (19) |
O1—C4 | 1.186 (2) | C13A—C14A | 1.390 (7) |
O2A—C4 | 1.300 (6) | C13A—H13A | 0.9300 |
O2A—H2A | 0.8200 | C14A—C15A | 1.351 (9) |
O2B—C4 | 1.308 (8) | C14A—H14A | 0.9300 |
O2B—H2B | 0.8200 | C15A—C16A | 1.359 (11) |
O3—C5 | 1.218 (2) | C15A—H15A | 0.9300 |
O4—C24 | 1.385 (3) | C16A—C17A | 1.383 (9) |
O4—H4 | 0.8200 | C16A—H16A | 0.9300 |
N1—C3 | 1.346 (2) | C17A—H17A | 0.9300 |
N1—N2 | 1.3634 (18) | C13B—C14B | 1.397 (8) |
N1—C18 | 1.449 (2) | C13B—H13B | 0.9300 |
N2—C1 | 1.331 (2) | C14B—C15B | 1.350 (11) |
C1—C2 | 1.398 (3) | C14B—H14B | 0.9300 |
C1—C4 | 1.502 (3) | C15B—C16B | 1.361 (12) |
C2—C3 | 1.388 (2) | C15B—H15B | 0.9300 |
C2—C5 | 1.475 (3) | C16B—C17B | 1.397 (10) |
C3—C12 | 1.483 (3) | C16B—H16B | 0.9300 |
C5—C6 | 1.486 (3) | C17B—H17B | 0.9300 |
C6—C11 | 1.369 (3) | C18—C19 | 1.345 (3) |
C6—C7 | 1.376 (3) | C18—C23 | 1.363 (3) |
C7—C8 | 1.385 (3) | C19—C20 | 1.386 (3) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—C9 | 1.356 (3) | C20—C21 | 1.342 (4) |
C8—H8 | 0.9300 | C20—H20 | 0.9300 |
C9—C10 | 1.367 (3) | C21—C22 | 1.350 (4) |
C9—H9 | 0.9300 | C21—H21 | 0.9300 |
C10—C11 | 1.392 (3) | C22—C23 | 1.385 (3) |
C10—H10 | 0.9300 | C22—H22 | 0.9300 |
C11—H11 | 0.9300 | C23—H23 | 0.9300 |
C12—C17A | 1.333 (9) | C24—H24A | 0.9600 |
C12—C13B | 1.353 (7) | C24—H24B | 0.9600 |
C12—C17B | 1.383 (9) | C24—H24C | 0.9600 |
C12—C13A | 1.410 (6) | ||
C4—O2A—H2A | 109.5 | C12—C13A—H13A | 120.9 |
C4—O2B—H2B | 109.5 | C15A—C14A—C13A | 119.8 (6) |
C24—O4—H4 | 109.5 | C15A—C14A—H14A | 120.1 |
C3—N1—N2 | 112.36 (15) | C13A—C14A—H14A | 120.1 |
C3—N1—C18 | 130.22 (16) | C14A—C15A—C16A | 120.7 (7) |
N2—N1—C18 | 117.33 (18) | C14A—C15A—H15A | 119.7 |
C1—N2—N1 | 103.84 (16) | C16A—C15A—H15A | 119.7 |
N2—C1—C2 | 112.77 (15) | C15A—C16A—C17A | 120.8 (8) |
N2—C1—C4 | 119.16 (19) | C15A—C16A—H16A | 119.6 |
C2—C1—C4 | 127.9 (2) | C17A—C16A—H16A | 119.6 |
C3—C2—C1 | 103.93 (18) | C12—C17A—C16A | 119.3 (9) |
C3—C2—C5 | 126.19 (18) | C12—C17A—H17A | 120.4 |
C1—C2—C5 | 129.81 (17) | C16A—C17A—H17A | 120.4 |
N1—C3—C2 | 107.07 (17) | C12—C13B—C14B | 121.0 (6) |
N1—C3—C12 | 123.02 (17) | C12—C13B—H13B | 119.5 |
C2—C3—C12 | 129.9 (2) | C14B—C13B—H13B | 119.5 |
O1—C4—O2A | 124.5 (4) | C15B—C14B—C13B | 119.7 (8) |
O1—C4—O2B | 125.5 (5) | C15B—C14B—H14B | 120.1 |
O1—C4—C1 | 122.7 (2) | C13B—C14B—H14B | 120.1 |
O2A—C4—C1 | 112.3 (4) | C14B—C15B—C16B | 121.6 (8) |
O2B—C4—C1 | 111.0 (5) | C14B—C15B—H15B | 119.2 |
O3—C5—C2 | 119.6 (2) | C16B—C15B—H15B | 119.2 |
O3—C5—C6 | 121.0 (2) | C15B—C16B—C17B | 117.3 (9) |
C2—C5—C6 | 119.45 (19) | C15B—C16B—H16B | 121.3 |
C11—C6—C7 | 119.6 (2) | C17B—C16B—H16B | 121.3 |
C11—C6—C5 | 121.3 (2) | C12—C17B—C16B | 122.4 (8) |
C7—C6—C5 | 119.1 (2) | C12—C17B—H17B | 118.8 |
C6—C7—C8 | 120.0 (2) | C16B—C17B—H17B | 118.8 |
C6—C7—H7 | 120.0 | C19—C18—C23 | 121.9 (2) |
C8—C7—H7 | 120.0 | C19—C18—N1 | 120.8 (2) |
C9—C8—C7 | 119.8 (3) | C23—C18—N1 | 117.3 (2) |
C9—C8—H8 | 120.1 | C18—C19—C20 | 118.4 (3) |
C7—C8—H8 | 120.1 | C18—C19—H19 | 120.8 |
C8—C9—C10 | 121.3 (3) | C20—C19—H19 | 120.8 |
C8—C9—H9 | 119.3 | C21—C20—C19 | 120.7 (3) |
C10—C9—H9 | 119.3 | C21—C20—H20 | 119.6 |
C9—C10—C11 | 118.9 (2) | C19—C20—H20 | 119.6 |
C9—C10—H10 | 120.6 | C20—C21—C22 | 120.3 (3) |
C11—C10—H10 | 120.6 | C20—C21—H21 | 119.8 |
C6—C11—C10 | 120.4 (2) | C22—C21—H21 | 119.8 |
C6—C11—H11 | 119.8 | C21—C22—C23 | 120.3 (3) |
C10—C11—H11 | 119.8 | C21—C22—H22 | 119.9 |
C17A—C12—C13B | 103.0 (5) | C23—C22—H22 | 119.9 |
C13B—C12—C17B | 117.4 (6) | C18—C23—C22 | 118.3 (3) |
C17A—C12—C13A | 120.9 (6) | C18—C23—H23 | 120.9 |
C17B—C12—C13A | 117.7 (6) | C22—C23—H23 | 120.9 |
C17A—C12—C3 | 123.1 (6) | O4—C24—H24A | 109.5 |
C13B—C12—C3 | 124.8 (4) | O4—C24—H24B | 109.5 |
C17B—C12—C3 | 117.0 (5) | H24A—C24—H24B | 109.5 |
C13A—C12—C3 | 115.7 (3) | O4—C24—H24C | 109.5 |
C14A—C13A—C12 | 118.2 (5) | H24A—C24—H24C | 109.5 |
C14A—C13A—H13A | 120.9 | H24B—C24—H24C | 109.5 |
C3—N1—N2—C1 | 1.6 (2) | C2—C3—C12—C13B | −106.5 (8) |
C18—N1—N2—C1 | 178.68 (18) | N1—C3—C12—C17B | −98.5 (6) |
N1—N2—C1—C2 | −1.3 (2) | C2—C3—C12—C17B | 83.9 (6) |
N1—N2—C1—C4 | −176.51 (17) | N1—C3—C12—C13A | 116.2 (5) |
N2—C1—C2—C3 | 0.6 (2) | C2—C3—C12—C13A | −61.5 (5) |
C4—C1—C2—C3 | 175.28 (19) | C17A—C12—C13A—C14A | 6.4 (8) |
N2—C1—C2—C5 | −176.6 (2) | C13B—C12—C13A—C14A | −65.5 (7) |
C4—C1—C2—C5 | −1.8 (4) | C17B—C12—C13A—C14A | 35.0 (7) |
N2—N1—C3—C2 | −1.3 (2) | C3—C12—C13A—C14A | −179.9 (4) |
C18—N1—C3—C2 | −177.9 (2) | C12—C13A—C14A—C15A | −2.9 (11) |
N2—N1—C3—C12 | −179.42 (19) | C13A—C14A—C15A—C16A | −1.0 (18) |
C18—N1—C3—C12 | 4.0 (4) | C14A—C15A—C16A—C17A | 2 (2) |
C1—C2—C3—N1 | 0.4 (2) | C13B—C12—C17A—C16A | 32.7 (10) |
C5—C2—C3—N1 | 177.7 (2) | C17B—C12—C17A—C16A | −96 (2) |
C1—C2—C3—C12 | 178.4 (2) | C13A—C12—C17A—C16A | −5.8 (11) |
C5—C2—C3—C12 | −4.3 (4) | C3—C12—C17A—C16A | −178.9 (7) |
N2—C1—C4—O1 | 169.3 (2) | C15A—C16A—C17A—C12 | 1.7 (17) |
C2—C1—C4—O1 | −5.1 (4) | C17A—C12—C13B—C14B | −28.6 (9) |
N2—C1—C4—O2A | −18.0 (9) | C17B—C12—C13B—C14B | −6.6 (9) |
C2—C1—C4—O2A | 167.6 (9) | C13A—C12—C13B—C14B | 94.5 (10) |
N2—C1—C4—O2B | −1.4 (11) | C3—C12—C13B—C14B | −176.2 (5) |
C2—C1—C4—O2B | −175.8 (10) | C12—C13B—C14B—C15B | 5.0 (13) |
C3—C2—C5—O3 | −56.6 (3) | C13B—C14B—C15B—C16B | −4 (2) |
C1—C2—C5—O3 | 119.9 (2) | C14B—C15B—C16B—C17B | 5 (2) |
C3—C2—C5—C6 | 122.6 (2) | C17A—C12—C17B—C16B | 67 (2) |
C1—C2—C5—C6 | −60.8 (3) | C13B—C12—C17B—C16B | 7.6 (12) |
O3—C5—C6—C11 | 159.9 (2) | C13A—C12—C17B—C16B | −37.3 (11) |
C2—C5—C6—C11 | −19.4 (3) | C3—C12—C17B—C16B | 178.1 (8) |
O3—C5—C6—C7 | −19.5 (3) | C15B—C16B—C17B—C12 | −6.6 (18) |
C2—C5—C6—C7 | 161.29 (19) | C3—N1—C18—C19 | −68.8 (3) |
C11—C6—C7—C8 | 0.2 (3) | N2—N1—C18—C19 | 114.7 (2) |
C5—C6—C7—C8 | 179.5 (2) | C3—N1—C18—C23 | 111.2 (3) |
C6—C7—C8—C9 | −1.0 (4) | N2—N1—C18—C23 | −65.3 (2) |
C7—C8—C9—C10 | 0.2 (4) | C23—C18—C19—C20 | 1.8 (3) |
C8—C9—C10—C11 | 1.4 (4) | N1—C18—C19—C20 | −178.2 (2) |
C7—C6—C11—C10 | 1.4 (3) | C18—C19—C20—C21 | −0.8 (4) |
C5—C6—C11—C10 | −177.90 (19) | C19—C20—C21—C22 | 0.0 (5) |
C9—C10—C11—C6 | −2.2 (3) | C20—C21—C22—C23 | −0.1 (4) |
N1—C3—C12—C17A | −70.3 (7) | C19—C18—C23—C22 | −1.9 (4) |
C2—C3—C12—C17A | 112.0 (7) | N1—C18—C23—C22 | 178.1 (2) |
N1—C3—C12—C13B | 71.2 (8) | C21—C22—C23—C18 | 1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···N2i | 0.82 | 1.99 | 2.804 (2) | 176 |
O2B—H2B···O4 | 0.82 | 1.77 | 2.583 (10) | 171 |
O2A—H2A···O4 | 0.82 | 1.77 | 2.576 (8) | 165 |
C10—H10···O1ii | 0.93 | 2.46 | 3.339 (3) | 158 |
C14A—H14A···O4iii | 0.93 | 2.53 | 3.334 (6) | 145 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1/2, −y+1/2, z; (iii) −x+1, −y+1/2, z+1/2. |
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