Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020082/lh6259sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020082/lh6259Isup2.hkl |
CCDC reference: 251733
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.146
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.75 Deg.
Author Response: The data set is lacking 31 expected reflections below a resolution of 0.6, this is out of a data set of 6005(4887 observed). The data set includes reflections out to a 2theta value of 28.23 degrees. |
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O5A - C5A .. 6.96 su
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997-2000); cell refinement: SAINT-Plus (Bruker, 1997-1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1995).
C16H12N2O3 | Z = 4 |
Mr = 280.28 | F(000) = 584 |
Triclinic, P1 | Dx = 1.382 Mg m−3 |
Hall symbol: -P 1 | Melting point: 426 K |
a = 9.502 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.906 (3) Å | Cell parameters from 6477 reflections |
c = 13.676 (3) Å | θ = 2.3–28.1° |
α = 105.712 (17)° | µ = 0.10 mm−1 |
β = 108.29 (2)° | T = 298 K |
γ = 101.13 (2)° | Rectangular, colorless |
V = 1347.1 (7) Å3 | 0.40 × 0.30 × 0.25 mm |
Bruker AXS SMART APEX CCD diffractometer | 6005 independent reflections |
Radiation source: fine-focus sealed tube | 4886 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 28.2°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1997-1999) | h = −12→12 |
Tmin = 0.901, Tmax = 0.976 | k = −15→15 |
11422 measured reflections | l = −17→18 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
6005 reflections | (Δ/σ)max < 0.001 |
381 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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. Mean-plane data from final SHELX refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 8.1127 (0.0046) x + 7.8485 (0.0066) y - 0.2533 (0.0094) z = 3.1676 (0.0041) * 0.0038 (0.0010) C14A * 0.0010 (0.0011) C15A * -0.0046 (0.0012) C16A * 0.0033 (0.0013) C17A * 0.0016 (0.0012) C18A * -0.0051 (0.0011) C19A Rms deviation of fitted atoms = 0.0035 - 2.6464 (0.0056) x + 10.8309 (0.0051) y + 2.0412 (0.0082) z = 10.1654 (0.0041) Angle to previous plane (with approximate e.s.d.) = 51.34 (0.06) * -0.0122 (0.0007) N3A * -0.0104 (0.0007) C6A * 0.0256 (0.0008) C7A * -0.0296 (0.0007) C12A * 0.0266 (0.0007) C4A Rms deviation of fitted atoms = 0.0224 - 2.4963 (0.0051) x + 11.1286 (0.0049) y + 1.1567 (0.0078) z = 9.9972 (0.0045) Angle to previous plane (with approximate e.s.d.) = 3.74 (0.07) * 0.0051 (0.0009) C6A * -0.0063 (0.0009) C7A * 0.0011 (0.0010) C8A * 0.0055 (0.0010) C9A * -0.0069 (0.0010) C10A * 0.0015 (0.0010) C11A Rms deviation of fitted atoms = 0.0050 - 2.8753 (0.0060) x + 10.7764 (0.0051) y + 2.2230 (0.0082) z = 10.1658 (0.0040) Angle to previous plane (with approximate e.s.d.) = 4.64 (0.07) * 0.0024 (0.0007) O1A * 0.0000 (0.0007) N2A * -0.0026 (0.0008) N3A * 0.0038 (0.0007) C4A * -0.0037 (0.0007) C5A Rms deviation of fitted atoms = 0.0029 - 3.4270 (0.0061) x + 7.5076 (0.0061) y - 10.0366 (0.0072) z = 5.8654 (0.0058) Angle to previous plane (with approximate e.s.d.) = 72.28 (0.05) * -0.0077 (0.0009) C14B * 0.0040 (0.0010) C15B * 0.0019 (0.0011) C16B * -0.0042 (0.0012) C17B * 0.0004 (0.0012) C18B * 0.0056 (0.0010) C19B Rms deviation of fitted atoms = 0.0046 1.4271 (0.0056) x + 3.7764 (0.0069) y + 8.9339 (0.0072) z = 4.1664 (0.0060) Angle to previous plane (with approximate e.s.d.) = 57.79 (0.05) * -0.0050 (0.0007) N3B * 0.0073 (0.0007) C6B * -0.0065 (0.0008) C7B * 0.0033 (0.0007) C12B * 0.0010 (0.0008) C4B Rms deviation of fitted atoms = 0.0051 1.3977 (0.0059) x + 3.9600 (0.0072) y + 8.8117 (0.0073) z = 4.2825 (0.0051) Angle to previous plane (with approximate e.s.d.) = 0.94 (0.11) * -0.0053 (0.0009) C6B * 0.0018 (0.0009) C7B * 0.0031 (0.0010) C8B * -0.0045 (0.0012) C9B * 0.0011 (0.0012) C10B * 0.0038 (0.0011) C11B Rms deviation of fitted atoms = 0.0036 1.7641 (0.0058) x + 3.6965 (0.0079) y + 8.7020 (0.0078) z = 4.3642 (0.0068) Angle to previous plane (with approximate e.s.d.) = 2.37 (0.12) * 0.0095 (0.0008) O1B * -0.0036 (0.0007) N2B * -0.0042 (0.0008) N3B * 0.0095 (0.0007) C4B * -0.0112 (0.0008) C5B Rms deviation of fitted atoms = 0.0082 |
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 | ||
O1A | 0.06381 (11) | 0.91184 (9) | 0.23631 (7) | 0.0514 (3) | |
O3A | 0.38874 (11) | 1.02465 (9) | 0.58549 (8) | 0.0510 (3) | |
H3A | 0.4699 | 1.0164 | 0.6225 | 0.077* | |
N3A | 0.04449 (12) | 0.87778 (9) | 0.37416 (8) | 0.0398 (2) | |
O5A | 0.32522 (12) | 0.97072 (11) | 0.28399 (8) | 0.0571 (3) | |
C14A | 0.25884 (15) | 0.68517 (12) | 0.41996 (11) | 0.0422 (3) | |
C4A | 0.19893 (14) | 0.91401 (11) | 0.40119 (10) | 0.0390 (3) | |
C5A | 0.21751 (15) | 0.93699 (12) | 0.31043 (10) | 0.0427 (3) | |
C7A | 0.14545 (15) | 0.87376 (11) | 0.54491 (10) | 0.0409 (3) | |
N2A | −0.04404 (14) | 0.87417 (12) | 0.27835 (9) | 0.0521 (3) | |
C13A | 0.36584 (15) | 0.80779 (13) | 0.50322 (11) | 0.0456 (3) | |
H13A | 0.4523 | 0.8328 | 0.4826 | 0.055* | |
H13B | 0.4077 | 0.7999 | 0.5746 | 0.055* | |
C12A | 0.28376 (14) | 0.90847 (11) | 0.51301 (10) | 0.0397 (3) | |
C6A | 0.00500 (15) | 0.85209 (11) | 0.46019 (10) | 0.0410 (3) | |
C8A | 0.14229 (18) | 0.86358 (13) | 0.64249 (12) | 0.0521 (3) | |
H8A | 0.2339 | 0.8782 | 0.7016 | 0.063* | |
C11A | −0.13872 (17) | 0.81907 (13) | 0.46460 (13) | 0.0514 (3) | |
H11A | −0.2302 | 0.8050 | 0.4056 | 0.062* | |
C15A | 0.17663 (18) | 0.60081 (14) | 0.44962 (13) | 0.0545 (4) | |
H15A | 0.1908 | 0.6181 | 0.5232 | 0.065* | |
C19A | 0.23467 (19) | 0.65548 (14) | 0.30891 (12) | 0.0540 (4) | |
H19A | 0.2900 | 0.7106 | 0.2873 | 0.065* | |
C9A | −0.0013 (2) | 0.83097 (14) | 0.65003 (13) | 0.0583 (4) | |
H9A | −0.0052 | 0.8243 | 0.7154 | 0.070* | |
C10A | −0.1384 (2) | 0.80816 (13) | 0.56291 (14) | 0.0584 (4) | |
H10A | −0.2326 | 0.7850 | 0.5704 | 0.070* | |
C18A | 0.1313 (2) | 0.54699 (16) | 0.23084 (14) | 0.0675 (4) | |
H18A | 0.1163 | 0.5295 | 0.1571 | 0.081* | |
C16A | 0.0734 (2) | 0.49084 (15) | 0.37131 (18) | 0.0713 (5) | |
H16A | 0.0194 | 0.4346 | 0.3927 | 0.086* | |
C17A | 0.0497 (2) | 0.46379 (16) | 0.26182 (17) | 0.0726 (5) | |
H17A | −0.0208 | 0.3901 | 0.2093 | 0.087* | |
N3B | 0.78504 (12) | 0.72564 (10) | 0.03365 (8) | 0.0442 (3) | |
O3B | 0.72381 (11) | 0.99693 (9) | 0.06274 (8) | 0.0538 (3) | |
H3B | 0.8027 | 1.0342 | 0.0588 | 0.081* | |
O1B | 0.98113 (12) | 0.72160 (11) | −0.00281 (9) | 0.0643 (3) | |
C12B | 0.67248 (14) | 0.87303 (11) | −0.00974 (10) | 0.0407 (3) | |
C7B | 0.58262 (14) | 0.79513 (11) | 0.03645 (10) | 0.0401 (3) | |
C14B | 0.52104 (15) | 0.73598 (12) | −0.21101 (10) | 0.0418 (3) | |
C13B | 0.57398 (16) | 0.86318 (12) | −0.12691 (11) | 0.0452 (3) | |
H13C | 0.4833 | 0.8886 | −0.1257 | 0.054* | |
H13D | 0.6347 | 0.9192 | −0.1492 | 0.054* | |
C6B | 0.65269 (15) | 0.70994 (12) | 0.06281 (10) | 0.0425 (3) | |
O5B | 0.99882 (13) | 0.87069 (11) | −0.07826 (10) | 0.0713 (4) | |
C4B | 0.80143 (14) | 0.81551 (12) | −0.00627 (10) | 0.0425 (3) | |
C19B | 0.61095 (17) | 0.70102 (15) | −0.26917 (11) | 0.0531 (3) | |
H19B | 0.7014 | 0.7580 | −0.2587 | 0.064* | |
N2B | 0.88544 (15) | 0.66495 (13) | 0.03915 (11) | 0.0609 (3) | |
C5B | 0.93047 (16) | 0.81594 (14) | −0.03500 (12) | 0.0522 (4) | |
C8B | 0.44961 (16) | 0.80003 (14) | 0.05550 (12) | 0.0508 (3) | |
H8B | 0.3995 | 0.8563 | 0.0388 | 0.061* | |
C15B | 0.38509 (16) | 0.64930 (14) | −0.23059 (11) | 0.0516 (3) | |
H15B | 0.3216 | 0.6709 | −0.1937 | 0.062* | |
C11B | 0.59983 (19) | 0.62972 (14) | 0.10828 (12) | 0.0567 (4) | |
H11B | 0.6512 | 0.5744 | 0.1258 | 0.068* | |
C18B | 0.5683 (2) | 0.58295 (17) | −0.34242 (13) | 0.0652 (4) | |
H18B | 0.6305 | 0.5608 | −0.3802 | 0.078* | |
C16B | 0.3427 (2) | 0.53138 (15) | −0.30412 (13) | 0.0636 (4) | |
H16B | 0.2515 | 0.4740 | −0.3162 | 0.076* | |
C9B | 0.3922 (2) | 0.71922 (17) | 0.10006 (14) | 0.0620 (4) | |
H9B | 0.3018 | 0.7210 | 0.1125 | 0.074* | |
C10B | 0.4663 (2) | 0.63578 (16) | 0.12644 (14) | 0.0647 (4) | |
H10B | 0.4254 | 0.5831 | 0.1568 | 0.078* | |
C17B | 0.4351 (2) | 0.49881 (16) | −0.35943 (14) | 0.0678 (5) | |
H17B | 0.4068 | 0.4192 | −0.4086 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0469 (5) | 0.0629 (6) | 0.0357 (5) | 0.0116 (5) | 0.0085 (4) | 0.0168 (4) |
O3A | 0.0425 (5) | 0.0487 (5) | 0.0467 (5) | 0.0078 (4) | 0.0069 (4) | 0.0107 (4) |
N3A | 0.0378 (5) | 0.0372 (5) | 0.0371 (5) | 0.0095 (4) | 0.0095 (4) | 0.0094 (4) |
O5A | 0.0495 (6) | 0.0779 (7) | 0.0472 (5) | 0.0130 (5) | 0.0195 (5) | 0.0307 (5) |
C14A | 0.0463 (7) | 0.0464 (7) | 0.0487 (7) | 0.0242 (6) | 0.0254 (6) | 0.0238 (6) |
C4A | 0.0378 (6) | 0.0381 (6) | 0.0386 (6) | 0.0112 (5) | 0.0125 (5) | 0.0129 (5) |
C5A | 0.0443 (7) | 0.0427 (7) | 0.0349 (6) | 0.0112 (5) | 0.0095 (5) | 0.0127 (5) |
C7A | 0.0460 (7) | 0.0364 (6) | 0.0406 (6) | 0.0131 (5) | 0.0179 (6) | 0.0124 (5) |
N2A | 0.0430 (6) | 0.0613 (7) | 0.0393 (6) | 0.0101 (5) | 0.0069 (5) | 0.0136 (5) |
C13A | 0.0419 (7) | 0.0551 (8) | 0.0453 (7) | 0.0193 (6) | 0.0165 (6) | 0.0237 (6) |
C12A | 0.0383 (6) | 0.0430 (7) | 0.0357 (6) | 0.0109 (5) | 0.0122 (5) | 0.0144 (5) |
C6A | 0.0444 (7) | 0.0341 (6) | 0.0430 (7) | 0.0110 (5) | 0.0185 (6) | 0.0102 (5) |
C8A | 0.0613 (9) | 0.0545 (8) | 0.0456 (7) | 0.0192 (7) | 0.0240 (7) | 0.0203 (6) |
C11A | 0.0445 (7) | 0.0434 (7) | 0.0607 (9) | 0.0089 (6) | 0.0223 (7) | 0.0110 (6) |
C15A | 0.0708 (10) | 0.0533 (8) | 0.0639 (9) | 0.0291 (7) | 0.0429 (8) | 0.0309 (7) |
C19A | 0.0722 (10) | 0.0498 (8) | 0.0521 (8) | 0.0228 (7) | 0.0332 (7) | 0.0228 (7) |
C9A | 0.0784 (11) | 0.0498 (8) | 0.0583 (9) | 0.0177 (7) | 0.0421 (9) | 0.0197 (7) |
C10A | 0.0623 (9) | 0.0436 (7) | 0.0736 (10) | 0.0091 (7) | 0.0421 (8) | 0.0138 (7) |
C18A | 0.0848 (12) | 0.0614 (10) | 0.0535 (9) | 0.0277 (9) | 0.0272 (9) | 0.0120 (8) |
C16A | 0.0777 (12) | 0.0507 (9) | 0.1077 (14) | 0.0206 (8) | 0.0620 (11) | 0.0301 (9) |
C17A | 0.0628 (10) | 0.0533 (9) | 0.0873 (13) | 0.0132 (8) | 0.0308 (10) | 0.0047 (9) |
N3B | 0.0394 (6) | 0.0493 (6) | 0.0365 (5) | 0.0142 (5) | 0.0099 (5) | 0.0094 (5) |
O3B | 0.0517 (6) | 0.0442 (5) | 0.0586 (6) | 0.0054 (4) | 0.0289 (5) | 0.0053 (5) |
O1B | 0.0462 (6) | 0.0707 (7) | 0.0671 (7) | 0.0224 (5) | 0.0228 (5) | 0.0069 (6) |
C12B | 0.0386 (6) | 0.0414 (7) | 0.0416 (7) | 0.0088 (5) | 0.0190 (5) | 0.0125 (5) |
C7B | 0.0409 (6) | 0.0431 (7) | 0.0325 (6) | 0.0084 (5) | 0.0136 (5) | 0.0117 (5) |
C14B | 0.0420 (7) | 0.0503 (7) | 0.0358 (6) | 0.0154 (6) | 0.0126 (5) | 0.0214 (6) |
C13B | 0.0504 (7) | 0.0474 (7) | 0.0466 (7) | 0.0162 (6) | 0.0234 (6) | 0.0235 (6) |
C6B | 0.0423 (7) | 0.0467 (7) | 0.0332 (6) | 0.0099 (5) | 0.0126 (5) | 0.0110 (5) |
O5B | 0.0558 (6) | 0.0720 (7) | 0.0754 (8) | −0.0002 (5) | 0.0413 (6) | 0.0054 (6) |
C4B | 0.0377 (6) | 0.0461 (7) | 0.0354 (6) | 0.0073 (5) | 0.0119 (5) | 0.0082 (5) |
C19B | 0.0479 (8) | 0.0660 (9) | 0.0415 (7) | 0.0131 (7) | 0.0170 (6) | 0.0164 (7) |
N2B | 0.0555 (7) | 0.0660 (8) | 0.0615 (8) | 0.0294 (6) | 0.0210 (6) | 0.0175 (6) |
C5B | 0.0397 (7) | 0.0520 (8) | 0.0477 (8) | 0.0043 (6) | 0.0174 (6) | −0.0018 (6) |
C8B | 0.0495 (8) | 0.0615 (9) | 0.0521 (8) | 0.0192 (7) | 0.0278 (6) | 0.0249 (7) |
C15B | 0.0457 (7) | 0.0630 (9) | 0.0453 (7) | 0.0133 (6) | 0.0152 (6) | 0.0232 (7) |
C11B | 0.0684 (10) | 0.0548 (8) | 0.0510 (8) | 0.0187 (7) | 0.0228 (7) | 0.0256 (7) |
C18B | 0.0635 (10) | 0.0788 (11) | 0.0479 (8) | 0.0311 (9) | 0.0186 (7) | 0.0115 (8) |
C16B | 0.0580 (9) | 0.0592 (9) | 0.0552 (9) | 0.0026 (7) | 0.0071 (7) | 0.0211 (7) |
C9B | 0.0608 (9) | 0.0759 (11) | 0.0640 (9) | 0.0182 (8) | 0.0398 (8) | 0.0304 (8) |
C10B | 0.0752 (11) | 0.0681 (10) | 0.0630 (10) | 0.0123 (8) | 0.0385 (9) | 0.0343 (8) |
C17B | 0.0739 (11) | 0.0567 (9) | 0.0535 (9) | 0.0210 (8) | 0.0081 (8) | 0.0095 (7) |
O1A—N2A | 1.3835 (16) | N3B—N2B | 1.2994 (16) |
O1A—C5A | 1.4098 (16) | N3B—C4B | 1.3313 (18) |
O3A—C12A | 1.4124 (16) | N3B—C6B | 1.4282 (17) |
O3A—H3A | 0.8200 | O3B—C12B | 1.4224 (16) |
N3A—N2A | 1.3000 (16) | O3B—H3B | 0.8200 |
N3A—C4A | 1.3435 (17) | O1B—N2B | 1.3826 (18) |
N3A—C6A | 1.4305 (17) | O1B—C5B | 1.425 (2) |
O5A—C5A | 1.2214 (16) | C12B—C4B | 1.5092 (19) |
C14A—C15A | 1.3784 (19) | C12B—C7B | 1.5290 (17) |
C14A—C19A | 1.3940 (19) | C12B—C13B | 1.5402 (19) |
C14A—C13A | 1.504 (2) | C7B—C8B | 1.3767 (19) |
C4A—C5A | 1.3962 (18) | C7B—C6B | 1.3821 (19) |
C4A—C12A | 1.5147 (18) | C14B—C19B | 1.3858 (19) |
C7A—C8A | 1.3813 (18) | C14B—C15B | 1.387 (2) |
C7A—C6A | 1.3873 (19) | C14B—C13B | 1.5062 (19) |
C7A—C12A | 1.5284 (17) | C13B—H13C | 0.9700 |
C13A—C12A | 1.5500 (18) | C13B—H13D | 0.9700 |
C13A—H13A | 0.9700 | C6B—C11B | 1.372 (2) |
C13A—H13B | 0.9700 | O5B—C5B | 1.2179 (18) |
C6A—C11A | 1.3712 (19) | C4B—C5B | 1.3995 (18) |
C8A—C9A | 1.389 (2) | C19B—C18B | 1.381 (2) |
C8A—H8A | 0.9300 | C19B—H19B | 0.9300 |
C11A—C10A | 1.385 (2) | C8B—C9B | 1.385 (2) |
C11A—H11A | 0.9300 | C8B—H8B | 0.9300 |
C15A—C16A | 1.382 (2) | C15B—C16B | 1.381 (2) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C19A—C18A | 1.370 (2) | C11B—C10B | 1.379 (2) |
C19A—H19A | 0.9300 | C11B—H11B | 0.9300 |
C9A—C10A | 1.380 (2) | C18B—C17B | 1.363 (3) |
C9A—H9A | 0.9300 | C18B—H18B | 0.9300 |
C10A—H10A | 0.9300 | C16B—C17B | 1.372 (3) |
C18A—C17A | 1.378 (3) | C16B—H16B | 0.9300 |
C18A—H18A | 0.9300 | C9B—C10B | 1.385 (3) |
C16A—C17A | 1.377 (3) | C9B—H9B | 0.9300 |
C16A—H16A | 0.9300 | C10B—H10B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
N2A···N3Bi | 3.040 (2) | H9A···O5Biv | 2.711 |
H3A···O5Aii | 1.914 | H3B···O5Bv | 1.899 |
O5A···H13Diii | 2.612 | O5B···H9Avi | 2.711 |
N2A—O1A—C5A | 111.76 (9) | N2B—N3B—C4B | 117.92 (12) |
C12A—O3A—H3A | 109.5 | N2B—N3B—C6B | 129.62 (12) |
N2A—N3A—C4A | 117.14 (11) | C4B—N3B—C6B | 112.45 (11) |
N2A—N3A—C6A | 130.36 (11) | C12B—O3B—H3B | 109.5 |
C4A—N3A—C6A | 112.47 (11) | N2B—O1B—C5B | 111.80 (10) |
C15A—C14A—C19A | 117.82 (14) | O3B—C12B—C4B | 114.01 (11) |
C15A—C14A—C13A | 121.47 (12) | O3B—C12B—C7B | 107.73 (10) |
C19A—C14A—C13A | 120.66 (12) | C4B—C12B—C7B | 99.37 (11) |
N3A—C4A—C5A | 105.29 (11) | O3B—C12B—C13B | 109.53 (11) |
N3A—C4A—C12A | 110.17 (11) | C4B—C12B—C13B | 112.89 (10) |
C5A—C4A—C12A | 144.44 (12) | C7B—C12B—C13B | 112.93 (11) |
O5A—C5A—C4A | 137.25 (12) | C8B—C7B—C6B | 118.48 (12) |
O5A—C5A—O1A | 119.01 (11) | C8B—C7B—C12B | 129.84 (12) |
C4A—C5A—O1A | 103.75 (11) | C6B—C7B—C12B | 111.67 (11) |
C8A—C7A—C6A | 118.16 (13) | C19B—C14B—C15B | 117.84 (13) |
C8A—C7A—C12A | 129.99 (12) | C19B—C14B—C13B | 120.26 (12) |
C6A—C7A—C12A | 111.84 (11) | C15B—C14B—C13B | 121.87 (12) |
N3A—N2A—O1A | 102.05 (10) | C14B—C13B—C12B | 113.42 (11) |
C14A—C13A—C12A | 112.91 (11) | C14B—C13B—H13C | 108.9 |
C14A—C13A—H13A | 109.0 | C12B—C13B—H13C | 108.9 |
C12A—C13A—H13A | 109.0 | C14B—C13B—H13D | 108.9 |
C14A—C13A—H13B | 109.0 | C12B—C13B—H13D | 108.9 |
C12A—C13A—H13B | 109.0 | H13C—C13B—H13D | 107.7 |
H13A—C13A—H13B | 107.8 | C11B—C6B—C7B | 124.48 (13) |
O3A—C12A—C4A | 110.28 (10) | C11B—C6B—N3B | 129.66 (13) |
O3A—C12A—C7A | 111.74 (10) | C7B—C6B—N3B | 105.86 (11) |
C4A—C12A—C7A | 99.50 (10) | N3B—C4B—C5B | 105.60 (13) |
O3A—C12A—C13A | 111.97 (10) | N3B—C4B—C12B | 110.63 (11) |
C4A—C12A—C13A | 111.31 (10) | C5B—C4B—C12B | 143.64 (13) |
C7A—C12A—C13A | 111.42 (10) | C18B—C19B—C14B | 121.05 (14) |
C11A—C6A—C7A | 125.12 (13) | C18B—C19B—H19B | 119.5 |
C11A—C6A—N3A | 129.06 (13) | C14B—C19B—H19B | 119.5 |
C7A—C6A—N3A | 105.75 (11) | N3B—N2B—O1B | 101.68 (12) |
C7A—C8A—C9A | 118.24 (15) | O5B—C5B—C4B | 137.41 (16) |
C7A—C8A—H8A | 120.9 | O5B—C5B—O1B | 119.61 (13) |
C9A—C8A—H8A | 120.9 | C4B—C5B—O1B | 102.95 (12) |
C6A—C11A—C10A | 115.44 (15) | C7B—C8B—C9B | 118.45 (14) |
C6A—C11A—H11A | 122.3 | C7B—C8B—H8B | 120.8 |
C10A—C11A—H11A | 122.3 | C9B—C8B—H8B | 120.8 |
C14A—C15A—C16A | 120.77 (15) | C16B—C15B—C14B | 120.89 (15) |
C14A—C15A—H15A | 119.6 | C16B—C15B—H15B | 119.6 |
C16A—C15A—H15A | 119.6 | C14B—C15B—H15B | 119.6 |
C18A—C19A—C14A | 121.61 (15) | C6B—C11B—C10B | 116.18 (15) |
C18A—C19A—H19A | 119.2 | C6B—C11B—H11B | 121.9 |
C14A—C19A—H19A | 119.2 | C10B—C11B—H11B | 121.9 |
C10A—C9A—C8A | 121.63 (14) | C17B—C18B—C19B | 120.11 (16) |
C10A—C9A—H9A | 119.2 | C17B—C18B—H18B | 119.9 |
C8A—C9A—H9A | 119.2 | C19B—C18B—H18B | 119.9 |
C9A—C10A—C11A | 121.40 (14) | C17B—C16B—C15B | 120.01 (16) |
C9A—C10A—H10A | 119.3 | C17B—C16B—H16B | 120.0 |
C11A—C10A—H10A | 119.3 | C15B—C16B—H16B | 120.0 |
C19A—C18A—C17A | 119.84 (16) | C10B—C9B—C8B | 121.51 (14) |
C19A—C18A—H18A | 120.1 | C10B—C9B—H9B | 119.2 |
C17A—C18A—H18A | 120.1 | C8B—C9B—H9B | 119.2 |
C17A—C16A—C15A | 120.56 (15) | C11B—C10B—C9B | 120.89 (14) |
C17A—C16A—H16A | 119.7 | C11B—C10B—H10B | 119.6 |
C15A—C16A—H16A | 119.7 | C9B—C10B—H10B | 119.6 |
C16A—C17A—C18A | 119.40 (17) | C18B—C17B—C16B | 120.08 (16) |
C16A—C17A—H17A | 120.3 | C18B—C17B—H17B | 120.0 |
C18A—C17A—H17A | 120.3 | C16B—C17B—H17B | 120.0 |
N2A—N3A—C4A—C5A | −0.67 (15) | O3B—C12B—C7B—C8B | 60.84 (17) |
C6A—N3A—C4A—C5A | −179.07 (10) | C4B—C12B—C7B—C8B | 179.90 (13) |
N2A—N3A—C4A—C12A | −177.95 (11) | C13B—C12B—C7B—C8B | −60.24 (18) |
C6A—N3A—C4A—C12A | 3.64 (14) | O3B—C12B—C7B—C6B | −118.16 (12) |
N3A—C4A—C5A—O5A | −179.62 (16) | C4B—C12B—C7B—C6B | 0.91 (13) |
C12A—C4A—C5A—O5A | −4.0 (3) | C13B—C12B—C7B—C6B | 120.76 (12) |
N3A—C4A—C5A—O1A | 0.70 (13) | C19B—C14B—C13B—C12B | −91.04 (15) |
C12A—C4A—C5A—O1A | 176.32 (16) | C15B—C14B—C13B—C12B | 86.92 (15) |
N2A—O1A—C5A—O5A | 179.66 (12) | O3B—C12B—C13B—C14B | 177.02 (10) |
N2A—O1A—C5A—C4A | −0.58 (14) | C4B—C12B—C13B—C14B | 48.82 (15) |
C4A—N3A—N2A—O1A | 0.29 (14) | C7B—C12B—C13B—C14B | −62.92 (15) |
C6A—N3A—N2A—O1A | 178.36 (11) | C8B—C7B—C6B—C11B | −0.8 (2) |
C5A—O1A—N2A—N3A | 0.21 (13) | C12B—C7B—C6B—C11B | 178.36 (12) |
C15A—C14A—C13A—C12A | −91.37 (15) | C8B—C7B—C6B—N3B | 179.58 (11) |
C19A—C14A—C13A—C12A | 85.83 (15) | C12B—C7B—C6B—N3B | −1.30 (14) |
N3A—C4A—C12A—O3A | −122.54 (11) | N2B—N3B—C6B—C11B | 2.8 (2) |
C5A—C4A—C12A—O3A | 62.0 (2) | C4B—N3B—C6B—C11B | −178.41 (13) |
N3A—C4A—C12A—C7A | −5.01 (12) | N2B—N3B—C6B—C7B | −177.57 (13) |
C5A—C4A—C12A—C7A | 179.50 (18) | C4B—N3B—C6B—C7B | 1.22 (14) |
N3A—C4A—C12A—C13A | 112.56 (12) | N2B—N3B—C4B—C5B | 1.39 (16) |
C5A—C4A—C12A—C13A | −62.9 (2) | C6B—N3B—C4B—C5B | −177.56 (10) |
C8A—C7A—C12A—O3A | −57.53 (18) | N2B—N3B—C4B—C12B | 178.29 (11) |
C6A—C7A—C12A—O3A | 121.37 (12) | C6B—N3B—C4B—C12B | −0.65 (14) |
C8A—C7A—C12A—C4A | −173.96 (13) | O3B—C12B—C4B—N3B | 114.15 (12) |
C6A—C7A—C12A—C4A | 4.94 (13) | C7B—C12B—C4B—N3B | −0.14 (13) |
C8A—C7A—C12A—C13A | 68.56 (17) | C13B—C12B—C4B—N3B | −120.02 (12) |
C6A—C7A—C12A—C13A | −112.54 (12) | O3B—C12B—C4B—C5B | −70.9 (2) |
C14A—C13A—C12A—O3A | −175.62 (10) | C7B—C12B—C4B—C5B | 174.83 (17) |
C14A—C13A—C12A—C4A | −51.66 (14) | C13B—C12B—C4B—C5B | 54.9 (2) |
C14A—C13A—C12A—C7A | 58.41 (14) | C15B—C14B—C19B—C18B | −1.4 (2) |
C8A—C7A—C6A—C11A | −1.1 (2) | C13B—C14B—C19B—C18B | 176.63 (13) |
C12A—C7A—C6A—C11A | 179.84 (12) | C4B—N3B—N2B—O1B | −0.13 (15) |
C8A—C7A—C6A—N3A | 175.87 (11) | C6B—N3B—N2B—O1B | 178.60 (11) |
C12A—C7A—C6A—N3A | −3.17 (14) | C5B—O1B—N2B—N3B | −1.20 (14) |
N2A—N3A—C6A—C11A | −1.6 (2) | N3B—C4B—C5B—O5B | 176.36 (17) |
C4A—N3A—C6A—C11A | 176.53 (12) | C12B—C4B—C5B—O5B | 1.2 (3) |
N2A—N3A—C6A—C7A | −178.44 (12) | N3B—C4B—C5B—O1B | −1.90 (13) |
C4A—N3A—C6A—C7A | −0.30 (14) | C12B—C4B—C5B—O1B | −177.01 (16) |
C6A—C7A—C8A—C9A | 0.7 (2) | N2B—O1B—C5B—O5B | −176.66 (12) |
C12A—C7A—C8A—C9A | 179.50 (12) | N2B—O1B—C5B—C4B | 1.98 (14) |
C7A—C6A—C11A—C10A | 0.4 (2) | C6B—C7B—C8B—C9B | −0.1 (2) |
N3A—C6A—C11A—C10A | −175.90 (12) | C12B—C7B—C8B—C9B | −179.02 (13) |
C19A—C14A—C15A—C16A | −0.3 (2) | C19B—C14B—C15B—C16B | 1.3 (2) |
C13A—C14A—C15A—C16A | 177.00 (13) | C13B—C14B—C15B—C16B | −176.75 (13) |
C15A—C14A—C19A—C18A | 0.9 (2) | C7B—C6B—C11B—C10B | 0.9 (2) |
C13A—C14A—C19A—C18A | −176.42 (14) | N3B—C6B—C11B—C10B | −179.50 (14) |
C7A—C8A—C9A—C10A | 0.5 (2) | C14B—C19B—C18B—C17B | 0.7 (2) |
C8A—C9A—C10A—C11A | −1.3 (2) | C14B—C15B—C16B—C17B | −0.4 (2) |
C6A—C11A—C10A—C9A | 0.8 (2) | C7B—C8B—C9B—C10B | 0.7 (2) |
C14A—C19A—C18A—C17A | −0.7 (3) | C6B—C11B—C10B—C9B | −0.3 (2) |
C14A—C15A—C16A—C17A | −0.5 (3) | C8B—C9B—C10B—C11B | −0.5 (3) |
C15A—C16A—C17A—C18A | 0.7 (3) | C19B—C18B—C17B—C16B | 0.3 (3) |
C19A—C18A—C17A—C16A | −0.1 (3) | C15B—C16B—C17B—C18B | −0.4 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+2, −z; (iv) x−1, y, z+1; (v) −x+2, −y+2, −z; (vi) x+1, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···O5Aii | 0.82 | 1.91 | 2.7240 (18) | 169 |
O3B—H3B···O5Bv | 0.82 | 1.90 | 2.7091 (19) | 169 |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (v) −x+2, −y+2, −z. |