Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021842/xu2052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021842/xu2052Isup2.hkl |
CCDC reference: 613863
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.072
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N32 - C53 .. 7.65 su
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C43 - C44 .. 5.37 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C46 - C47 .. 5.92 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C25 H19 N2 O0.5 Atom count from _chemical_formula_moiety:C25 H20 N2 O1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.
C25H18N2·H2O | F(000) = 1496 |
Mr = 355.44 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 23571 reflections |
a = 14.883 (3) Å | θ = 3.0–27.5° |
b = 22.675 (5) Å | µ = 0.08 mm−1 |
c = 11.334 (2) Å | T = 296 K |
β = 105.817 (9)° | Block, yellow |
V = 3680.1 (13) Å3 | 0.32 × 0.28 × 0.17 mm |
Z = 8 |
Rigaku R-AXIS RAPID diffractometer | Rint = 0.041 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5° |
ω scans | h = −19→19 |
34544 measured reflections | k = −29→29 |
8316 independent reflections | l = −14→14 |
4200 reflections with F2 > 2σ(F2) |
Refinement on F2 | w = 1/[σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.040 | (Δ/σ)max < 0.001 |
wR(F2) = 0.072 | Δρmax = 0.33 e Å−3 |
S = 1.01 | Δρmin = −0.29 e Å−3 |
8316 reflections | Extinction correction: not measured |
497 parameters | Extinction coefficient: not measured |
H-atom parameters constrained |
Experimental. 1H NMR (500 MHz, δ in p.p.m., CDCl3): 1.86 (s, 4H), 7.31 (d, J = 1.0 Hz, 2H), 7.55 (dd, J1 = 1.5 Hz, J2 = 4.5 Hz, 4H), 7.65 (dd, J1 = 1.5 Hz, J2 = 8.0 Hz, 2H), 7.95 (d, J = 8.0 Hz, 2H), 8.67 (dd, J1 = 1.5 Hz, J2 = 4.5 Hz, 4H) p.p.m.; 13C NMR (125 MHz, δ in p.p.m., CDCl3): 19.09, 30.07, 117.50, 121.15, 121.88, 125.59, 137.53, 140.26, 148.76, 149.76, 150.49 p.p.m.; HRMS (MALDI-TOF): Calcd for C25H18N2: 346.2, found: 346.2(M+). |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O6 | −0.33015 (8) | 0.49929 (5) | 0.95868 (10) | 0.0731 (4) | |
N11 | −0.16589 (10) | 0.53648 (6) | 0.89262 (12) | 0.0707 (5) | |
N12 | 0.56745 (9) | 0.89276 (6) | 0.46406 (11) | 0.0573 (4) | |
N31 | 0.00484 (12) | 0.38626 (8) | 0.66003 (18) | 0.0901 (6) | |
N32 | 0.79506 (12) | 0.74747 (6) | 0.36696 (17) | 0.0831 (6) | |
C1 | 0.14077 (10) | 0.68774 (6) | 0.70295 (12) | 0.0406 (4) | |
C2 | 0.22586 (10) | 0.65765 (6) | 0.74020 (12) | 0.0401 (4) | |
C3 | 0.29590 (10) | 0.69115 (6) | 0.69944 (12) | 0.0402 (4) | |
C4 | 0.39010 (10) | 0.68080 (6) | 0.71395 (12) | 0.0455 (4) | |
C5 | 0.44041 (10) | 0.72017 (6) | 0.66476 (12) | 0.0466 (4) | |
C6 | 0.39914 (10) | 0.77026 (6) | 0.60129 (12) | 0.0428 (4) | |
C7 | 0.30408 (10) | 0.78042 (6) | 0.58677 (12) | 0.0462 (4) | |
C8 | 0.25312 (10) | 0.74126 (6) | 0.63610 (12) | 0.0427 (4) | |
C9 | 0.15263 (10) | 0.74116 (6) | 0.63298 (12) | 0.0457 (4) | |
C10 | 0.07849 (11) | 0.76099 (8) | 0.52138 (16) | 0.0704 (6) | |
C11 | 0.09773 (12) | 0.79697 (8) | 0.63327 (18) | 0.0741 (6) | |
C12 | 0.06232 (10) | 0.66557 (6) | 0.73103 (12) | 0.0445 (4) | |
C13 | 0.06868 (10) | 0.61293 (6) | 0.79601 (12) | 0.0430 (4) | |
C14 | 0.15400 (10) | 0.58354 (6) | 0.83188 (12) | 0.0480 (4) | |
C15 | 0.23251 (10) | 0.60513 (6) | 0.80434 (12) | 0.0465 (4) | |
C16 | −0.01395 (10) | 0.58740 (6) | 0.82705 (12) | 0.0457 (4) | |
C17 | −0.08213 (11) | 0.62163 (6) | 0.85540 (12) | 0.0544 (5) | |
C18 | −0.15515 (11) | 0.59426 (9) | 0.88731 (14) | 0.0641 (6) | |
C19 | −0.10055 (12) | 0.50404 (8) | 0.86377 (16) | 0.0698 (6) | |
C20 | −0.02548 (11) | 0.52703 (6) | 0.83051 (13) | 0.0601 (5) | |
C21 | 0.45564 (10) | 0.81235 (6) | 0.55137 (12) | 0.0425 (4) | |
C22 | 0.53338 (10) | 0.79429 (6) | 0.51431 (12) | 0.0506 (5) | |
C23 | 0.58614 (11) | 0.83521 (8) | 0.47352 (13) | 0.0572 (5) | |
C24 | 0.49156 (11) | 0.90944 (6) | 0.49676 (12) | 0.0535 (5) | |
C25 | 0.43515 (10) | 0.87193 (6) | 0.54029 (12) | 0.0464 (4) | |
C31 | 0.33735 (11) | 0.54373 (6) | 0.53883 (12) | 0.0470 (4) | |
C32 | 0.42147 (11) | 0.52958 (6) | 0.62515 (12) | 0.0468 (4) | |
C33 | 0.49728 (11) | 0.56238 (6) | 0.59639 (12) | 0.0467 (4) | |
C34 | 0.59179 (11) | 0.56352 (6) | 0.65283 (13) | 0.0544 (5) | |
C35 | 0.64846 (11) | 0.59915 (6) | 0.60540 (13) | 0.0544 (5) | |
C36 | 0.61243 (11) | 0.63380 (6) | 0.50189 (12) | 0.0455 (4) | |
C37 | 0.51689 (11) | 0.63224 (6) | 0.44458 (12) | 0.0476 (4) | |
C38 | 0.45929 (10) | 0.59694 (6) | 0.49200 (12) | 0.0447 (4) | |
C39 | 0.35681 (11) | 0.58736 (6) | 0.45057 (12) | 0.0493 (4) | |
C40 | 0.30401 (12) | 0.58672 (8) | 0.31593 (13) | 0.0674 (6) | |
C41 | 0.28905 (12) | 0.63574 (8) | 0.39395 (13) | 0.0646 (5) | |
C42 | 0.25450 (11) | 0.51758 (6) | 0.54432 (12) | 0.0535 (5) | |
C43 | 0.25514 (12) | 0.47658 (6) | 0.63721 (13) | 0.0517 (5) | |
C44 | 0.33958 (12) | 0.46396 (6) | 0.72310 (14) | 0.0579 (5) | |
C45 | 0.42256 (11) | 0.48970 (6) | 0.71780 (13) | 0.0549 (5) | |
C46 | 0.16860 (12) | 0.44605 (6) | 0.64447 (14) | 0.0567 (5) | |
C47 | 0.09223 (13) | 0.43926 (8) | 0.54490 (17) | 0.0762 (6) | |
C48 | 0.01291 (13) | 0.41008 (9) | 0.55651 (19) | 0.0893 (8) | |
C49 | 0.07856 (16) | 0.39290 (9) | 0.7554 (2) | 0.0867 (8) | |
C50 | 0.15944 (12) | 0.42175 (8) | 0.75340 (17) | 0.0727 (6) | |
C51 | 0.67614 (11) | 0.67218 (6) | 0.45574 (13) | 0.0485 (4) | |
C52 | 0.75715 (11) | 0.69574 (8) | 0.53229 (14) | 0.0609 (5) | |
C53 | 0.81229 (12) | 0.73277 (8) | 0.4843 (2) | 0.0767 (7) | |
C54 | 0.71784 (14) | 0.72422 (9) | 0.29466 (18) | 0.0822 (7) | |
C55 | 0.65745 (12) | 0.68761 (6) | 0.33334 (14) | 0.0648 (5) | |
H4 | 0.4184 | 0.6474 | 0.7556 | 0.054* | |
H5 | 0.5038 | 0.7136 | 0.6751 | 0.056* | |
H7 | 0.2748 | 0.8131 | 0.5434 | 0.056* | |
H102 | 0.0205 | 0.7391 | 0.4944 | 0.083* | |
H101 | 0.0965 | 0.7753 | 0.4505 | 0.083* | |
H111 | 0.1281 | 0.8350 | 0.6362 | 0.089* | |
H112 | 0.0521 | 0.7988 | 0.6801 | 0.089* | |
H12 | 0.0059 | 0.6858 | 0.7066 | 0.053* | |
H14 | 0.1576 | 0.5484 | 0.8751 | 0.057* | |
H15 | 0.2890 | 0.5850 | 0.8283 | 0.055* | |
H17 | −0.0784 | 0.6625 | 0.8528 | 0.065* | |
H18 | −0.2002 | 0.6179 | 0.9066 | 0.078* | |
H19 | −0.1066 | 0.4633 | 0.8659 | 0.082* | |
H20 | 0.0181 | 0.5023 | 0.8107 | 0.073* | |
H22 | 0.5493 | 0.7545 | 0.5184 | 0.062* | |
H23 | 0.6374 | 0.8219 | 0.4490 | 0.070* | |
H24 | 0.4757 | 0.9492 | 0.4882 | 0.065* | |
H25 | 0.3838 | 0.8863 | 0.5630 | 0.056* | |
H34 | 0.6167 | 0.5405 | 0.7219 | 0.064* | |
H35 | 0.7123 | 0.6004 | 0.6430 | 0.065* | |
H37 | 0.4923 | 0.6552 | 0.3753 | 0.056* | |
H402 | 0.2555 | 0.5576 | 0.2855 | 0.079* | |
H401 | 0.3372 | 0.5938 | 0.2546 | 0.079* | |
H411 | 0.3117 | 0.6750 | 0.3834 | 0.076* | |
H412 | 0.2300 | 0.6387 | 0.4143 | 0.076* | |
H42 | 0.1987 | 0.5275 | 0.4874 | 0.064* | |
H44 | 0.3395 | 0.4374 | 0.7856 | 0.072* | |
H45 | 0.4785 | 0.4804 | 0.7751 | 0.066* | |
H47 | 0.0940 | 0.4545 | 0.4693 | 0.094* | |
H48 | −0.0381 | 0.4068 | 0.4879 | 0.107* | |
H49 | 0.0755 | 0.3768 | 0.8297 | 0.104* | |
H50 | 0.2086 | 0.4256 | 0.8240 | 0.091* | |
H52 | 0.7737 | 0.6865 | 0.6153 | 0.073* | |
H53 | 0.8656 | 0.7487 | 0.5377 | 0.092* | |
H54 | 0.7041 | 0.7329 | 0.2115 | 0.099* | |
H55 | 0.6043 | 0.6728 | 0.2776 | 0.079* | |
H601 | −0.2821 | 0.5023 | 0.9290 | 0.088* | |
H602 | −0.3581 | 0.5323 | 0.9520 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O6 | 0.0693 (8) | 0.0582 (7) | 0.1052 (9) | 0.0066 (6) | 0.0467 (7) | 0.0166 (6) |
N11 | 0.0486 (9) | 0.0784 (11) | 0.0861 (10) | −0.0093 (8) | 0.0203 (8) | 0.0140 (9) |
N12 | 0.0575 (9) | 0.0564 (9) | 0.0631 (8) | −0.0120 (7) | 0.0252 (7) | −0.0056 (7) |
N31 | 0.0979 (14) | 0.0895 (13) | 0.0970 (13) | −0.0379 (11) | 0.0507 (12) | −0.0217 (11) |
N32 | 0.0703 (12) | 0.0824 (12) | 0.1011 (13) | −0.0189 (9) | 0.0313 (10) | 0.0088 (10) |
C1 | 0.0415 (9) | 0.0421 (9) | 0.0385 (7) | 0.0022 (7) | 0.0115 (7) | 0.0008 (7) |
C2 | 0.0410 (9) | 0.0401 (9) | 0.0402 (8) | 0.0016 (7) | 0.0127 (7) | 0.0007 (7) |
C3 | 0.0395 (9) | 0.0402 (9) | 0.0419 (8) | 0.0015 (7) | 0.0128 (7) | 0.0006 (7) |
C4 | 0.0443 (9) | 0.0435 (9) | 0.0486 (8) | 0.0056 (7) | 0.0123 (7) | 0.0077 (7) |
C5 | 0.0389 (9) | 0.0504 (10) | 0.0530 (9) | 0.0034 (7) | 0.0165 (7) | 0.0033 (8) |
C6 | 0.0445 (9) | 0.0415 (9) | 0.0454 (8) | −0.0006 (7) | 0.0173 (7) | −0.0000 (7) |
C7 | 0.0481 (9) | 0.0415 (9) | 0.0515 (8) | 0.0051 (7) | 0.0179 (7) | 0.0065 (7) |
C8 | 0.0435 (9) | 0.0408 (9) | 0.0466 (8) | 0.0019 (7) | 0.0169 (7) | 0.0021 (7) |
C9 | 0.0409 (9) | 0.0436 (9) | 0.0551 (9) | 0.0072 (7) | 0.0174 (7) | 0.0101 (7) |
C10 | 0.0449 (11) | 0.0867 (14) | 0.0758 (12) | 0.0082 (10) | 0.0102 (9) | 0.0356 (11) |
C11 | 0.0617 (12) | 0.0512 (11) | 0.1192 (16) | 0.0172 (9) | 0.0415 (11) | 0.0188 (11) |
C12 | 0.0394 (9) | 0.0476 (9) | 0.0473 (8) | 0.0045 (7) | 0.0133 (7) | 0.0026 (7) |
C13 | 0.0433 (9) | 0.0442 (9) | 0.0415 (8) | −0.0016 (7) | 0.0117 (7) | 0.0004 (7) |
C14 | 0.0493 (10) | 0.0423 (9) | 0.0520 (9) | −0.0004 (7) | 0.0131 (7) | 0.0091 (7) |
C15 | 0.0403 (9) | 0.0458 (9) | 0.0532 (9) | 0.0053 (7) | 0.0124 (7) | 0.0058 (7) |
C16 | 0.0441 (9) | 0.0494 (10) | 0.0431 (8) | −0.0026 (7) | 0.0110 (7) | 0.0030 (7) |
C17 | 0.0493 (10) | 0.0570 (11) | 0.0591 (9) | −0.0055 (8) | 0.0188 (8) | −0.0004 (8) |
C18 | 0.0494 (11) | 0.0745 (13) | 0.0725 (11) | −0.0007 (10) | 0.0236 (9) | 0.0006 (10) |
C19 | 0.0530 (11) | 0.0602 (12) | 0.0924 (13) | −0.0118 (9) | 0.0134 (10) | 0.0125 (10) |
C20 | 0.0498 (10) | 0.0535 (11) | 0.0795 (11) | −0.0042 (8) | 0.0216 (9) | 0.0042 (9) |
C21 | 0.0437 (9) | 0.0430 (9) | 0.0424 (8) | −0.0012 (7) | 0.0145 (7) | −0.0028 (7) |
C22 | 0.0516 (10) | 0.0446 (9) | 0.0597 (9) | 0.0009 (8) | 0.0220 (8) | 0.0016 (7) |
C23 | 0.0492 (10) | 0.0635 (12) | 0.0654 (10) | −0.0042 (9) | 0.0263 (8) | −0.0041 (9) |
C24 | 0.0640 (11) | 0.0415 (9) | 0.0574 (9) | −0.0092 (8) | 0.0205 (9) | −0.0056 (7) |
C25 | 0.0509 (10) | 0.0443 (9) | 0.0469 (8) | −0.0022 (7) | 0.0183 (7) | −0.0051 (7) |
C31 | 0.0531 (10) | 0.0463 (9) | 0.0439 (8) | −0.0025 (8) | 0.0170 (8) | −0.0024 (7) |
C32 | 0.0541 (10) | 0.0447 (9) | 0.0448 (8) | 0.0013 (8) | 0.0187 (8) | −0.0009 (7) |
C33 | 0.0521 (10) | 0.0458 (9) | 0.0435 (8) | 0.0026 (8) | 0.0155 (8) | −0.0019 (7) |
C34 | 0.0516 (10) | 0.0621 (11) | 0.0478 (9) | 0.0075 (9) | 0.0105 (8) | 0.0083 (8) |
C35 | 0.0452 (10) | 0.0630 (11) | 0.0542 (9) | 0.0023 (8) | 0.0123 (8) | 0.0022 (8) |
C36 | 0.0458 (10) | 0.0459 (9) | 0.0460 (8) | 0.0011 (7) | 0.0147 (7) | −0.0028 (7) |
C37 | 0.0513 (10) | 0.0496 (10) | 0.0423 (8) | −0.0006 (8) | 0.0135 (8) | 0.0012 (7) |
C38 | 0.0476 (9) | 0.0466 (9) | 0.0409 (8) | −0.0012 (7) | 0.0139 (7) | −0.0043 (7) |
C39 | 0.0505 (10) | 0.0532 (10) | 0.0436 (8) | −0.0043 (8) | 0.0119 (7) | 0.0033 (7) |
C40 | 0.0669 (12) | 0.0855 (14) | 0.0451 (9) | −0.0171 (10) | 0.0074 (8) | 0.0019 (9) |
C41 | 0.0554 (11) | 0.0682 (12) | 0.0659 (11) | 0.0014 (9) | 0.0093 (9) | 0.0136 (9) |
C42 | 0.0544 (11) | 0.0557 (11) | 0.0518 (9) | −0.0046 (8) | 0.0168 (8) | −0.0033 (8) |
C43 | 0.0602 (11) | 0.0488 (10) | 0.0515 (9) | −0.0049 (8) | 0.0245 (9) | −0.0057 (8) |
C44 | 0.0734 (12) | 0.0526 (10) | 0.0542 (10) | −0.0026 (9) | 0.0284 (9) | 0.0043 (8) |
C45 | 0.0593 (11) | 0.0561 (11) | 0.0506 (9) | 0.0052 (8) | 0.0171 (9) | 0.0072 (8) |
C46 | 0.0651 (12) | 0.0500 (10) | 0.0621 (10) | −0.0070 (9) | 0.0296 (9) | −0.0095 (9) |
C47 | 0.0801 (14) | 0.0862 (14) | 0.0705 (12) | −0.0271 (11) | 0.0347 (11) | −0.0141 (11) |
C48 | 0.0875 (16) | 0.0994 (16) | 0.0885 (15) | −0.0354 (13) | 0.0367 (13) | −0.0299 (13) |
C49 | 0.0991 (17) | 0.0826 (15) | 0.0926 (16) | −0.0237 (13) | 0.0502 (14) | −0.0005 (13) |
C50 | 0.0788 (14) | 0.0715 (13) | 0.0762 (12) | −0.0163 (10) | 0.0355 (11) | 0.0014 (10) |
C51 | 0.0476 (10) | 0.0436 (9) | 0.0568 (9) | 0.0024 (8) | 0.0187 (8) | −0.0032 (8) |
C52 | 0.0476 (10) | 0.0674 (12) | 0.0676 (11) | 0.0011 (9) | 0.0155 (9) | −0.0027 (9) |
C53 | 0.0483 (12) | 0.0740 (14) | 0.1075 (16) | −0.0114 (10) | 0.0211 (11) | −0.0053 (12) |
C54 | 0.0869 (16) | 0.0854 (15) | 0.0797 (13) | −0.0229 (12) | 0.0320 (12) | 0.0102 (11) |
C55 | 0.0661 (12) | 0.0673 (12) | 0.0624 (11) | −0.0158 (9) | 0.0197 (10) | 0.0023 (9) |
N11—C18 | 1.323 (2) | C40—C41 | 1.475 (2) |
N11—C19 | 1.329 (2) | C42—C43 | 1.403 (2) |
N12—C23 | 1.332 (2) | C43—C44 | 1.394 (2) |
N12—C24 | 1.336 (2) | C43—C46 | 1.484 (2) |
N31—C48 | 1.327 (3) | C44—C45 | 1.382 (2) |
N31—C49 | 1.323 (2) | C46—C47 | 1.375 (2) |
N32—C53 | 1.327 (2) | C46—C50 | 1.392 (2) |
N32—C54 | 1.325 (2) | C47—C48 | 1.390 (3) |
C1—C2 | 1.3986 (19) | C49—C50 | 1.376 (3) |
C1—C9 | 1.484 (2) | C51—C52 | 1.386 (2) |
C1—C12 | 1.386 (2) | C51—C55 | 1.384 (2) |
C2—C3 | 1.463 (2) | C52—C53 | 1.385 (2) |
C2—C15 | 1.3846 (19) | C54—C55 | 1.380 (2) |
C3—C4 | 1.386 (2) | O6—H601 | 0.872 |
C3—C8 | 1.4009 (18) | O6—H602 | 0.849 |
C4—C5 | 1.377 (2) | C4—H4 | 0.930 |
C5—C6 | 1.3942 (18) | C5—H5 | 0.930 |
C6—C7 | 1.398 (2) | C7—H7 | 0.930 |
C6—C21 | 1.482 (2) | C10—H102 | 0.970 |
C7—C8 | 1.381 (2) | C10—H101 | 0.970 |
C8—C9 | 1.486 (2) | C11—H111 | 0.970 |
C9—C10 | 1.5030 (19) | C11—H112 | 0.970 |
C9—C11 | 1.507 (2) | C12—H12 | 0.930 |
C10—C11 | 1.469 (2) | C14—H14 | 0.930 |
C12—C13 | 1.392 (2) | C15—H15 | 0.930 |
C13—C14 | 1.393 (2) | C17—H17 | 0.930 |
C13—C16 | 1.486 (2) | C18—H18 | 0.930 |
C14—C15 | 1.379 (2) | C19—H19 | 0.930 |
C16—C17 | 1.383 (2) | C20—H20 | 0.930 |
C16—C20 | 1.381 (2) | C22—H22 | 0.930 |
C17—C18 | 1.383 (2) | C23—H23 | 0.930 |
C19—C20 | 1.375 (2) | C24—H24 | 0.930 |
C21—C22 | 1.396 (2) | C25—H25 | 0.930 |
C21—C25 | 1.383 (2) | C34—H34 | 0.930 |
C22—C23 | 1.374 (2) | C35—H35 | 0.930 |
C24—C25 | 1.377 (2) | C37—H37 | 0.930 |
C31—C32 | 1.4000 (19) | C40—H402 | 0.970 |
C31—C39 | 1.490 (2) | C40—H401 | 0.970 |
C31—C42 | 1.385 (2) | C41—H411 | 0.970 |
C32—C33 | 1.460 (2) | C41—H412 | 0.970 |
C32—C45 | 1.383 (2) | C42—H42 | 0.930 |
C33—C34 | 1.378 (2) | C44—H44 | 0.930 |
C33—C38 | 1.403 (2) | C45—H45 | 0.930 |
C34—C35 | 1.378 (2) | C47—H47 | 0.930 |
C35—C36 | 1.392 (2) | C48—H48 | 0.930 |
C36—C37 | 1.393 (2) | C49—H49 | 0.930 |
C36—C51 | 1.483 (2) | C50—H50 | 0.930 |
C37—C38 | 1.384 (2) | C52—H52 | 0.930 |
C38—C39 | 1.484 (2) | C53—H53 | 0.930 |
C39—C40 | 1.5142 (19) | C54—H54 | 0.930 |
C39—C41 | 1.510 (2) | C55—H55 | 0.930 |
C18—N11—C19 | 115.54 (16) | N31—C49—C50 | 125.1 (2) |
C23—N12—C24 | 115.39 (14) | C46—C50—C49 | 120.05 (16) |
C48—N31—C49 | 114.96 (19) | C36—C51—C52 | 122.40 (14) |
C53—N32—C54 | 114.71 (18) | C36—C51—C55 | 121.93 (13) |
C2—C1—C9 | 109.24 (13) | C52—C51—C55 | 115.66 (15) |
C2—C1—C12 | 120.27 (12) | C51—C52—C53 | 119.70 (15) |
C9—C1—C12 | 130.47 (12) | N32—C53—C52 | 124.94 (15) |
C1—C2—C3 | 108.42 (11) | N32—C54—C55 | 124.96 (18) |
C1—C2—C15 | 120.49 (14) | C51—C55—C54 | 120.03 (14) |
C3—C2—C15 | 131.10 (13) | H601—O6—H602 | 109.3 |
C2—C3—C4 | 131.25 (12) | C3—C4—H4 | 120.1 |
C2—C3—C8 | 108.64 (12) | C5—C4—H4 | 120.8 |
C4—C3—C8 | 120.12 (13) | C4—C5—H5 | 119.4 |
C3—C4—C5 | 119.09 (12) | C6—C5—H5 | 118.9 |
C4—C5—C6 | 121.69 (13) | C6—C7—H7 | 120.5 |
C5—C6—C7 | 118.97 (13) | C8—C7—H7 | 119.8 |
C5—C6—C21 | 120.36 (13) | C9—C10—H102 | 119.9 |
C7—C6—C21 | 120.67 (11) | C9—C10—H101 | 119.5 |
C6—C7—C8 | 119.75 (12) | C11—C10—H102 | 120.2 |
C3—C8—C7 | 120.39 (13) | C11—C10—H101 | 119.8 |
C3—C8—C9 | 108.95 (12) | H102—C10—H101 | 109.5 |
C7—C8—C9 | 130.65 (12) | C9—C11—H111 | 119.9 |
C1—C9—C8 | 104.71 (11) | C9—C11—H112 | 119.9 |
C1—C9—C10 | 121.79 (12) | C10—C11—H111 | 120.1 |
C1—C9—C11 | 122.72 (15) | C10—C11—H112 | 119.7 |
C8—C9—C10 | 121.52 (14) | H111—C11—H112 | 109.5 |
C8—C9—C11 | 122.78 (12) | C1—C12—H12 | 120.1 |
C10—C9—C11 | 58.43 (11) | C13—C12—H12 | 120.4 |
C9—C10—C11 | 60.92 (10) | C13—C14—H14 | 118.8 |
C9—C11—C10 | 60.65 (11) | C15—C14—H14 | 119.5 |
C1—C12—C13 | 119.51 (12) | C2—C15—H15 | 120.3 |
C12—C13—C14 | 119.32 (14) | C14—C15—H15 | 120.9 |
C12—C13—C16 | 121.20 (13) | C16—C17—H17 | 119.9 |
C14—C13—C16 | 119.48 (13) | C18—C17—H17 | 120.9 |
C13—C14—C15 | 121.70 (14) | N11—C18—H18 | 117.1 |
C2—C15—C14 | 118.72 (13) | C17—C18—H18 | 118.1 |
C13—C16—C17 | 122.92 (14) | N11—C19—H19 | 117.5 |
C13—C16—C20 | 120.67 (14) | C20—C19—H19 | 118.4 |
C17—C16—C20 | 116.41 (15) | C16—C20—H20 | 119.3 |
C16—C17—C18 | 119.19 (15) | C19—C20—H20 | 120.7 |
N11—C18—C17 | 124.73 (17) | C21—C22—H22 | 119.3 |
N11—C19—C20 | 124.13 (16) | C23—C22—H22 | 120.7 |
C16—C20—C19 | 119.99 (15) | N12—C23—H23 | 117.6 |
C6—C21—C22 | 121.94 (12) | C22—C23—H23 | 118.2 |
C6—C21—C25 | 121.97 (14) | N12—C24—H24 | 117.1 |
C22—C21—C25 | 116.08 (14) | C25—C24—H24 | 118.3 |
C21—C22—C23 | 119.98 (14) | C21—C25—H25 | 119.7 |
N12—C23—C22 | 124.22 (16) | C24—C25—H25 | 120.7 |
N12—C24—C25 | 124.65 (14) | C33—C34—H34 | 120.2 |
C21—C25—C24 | 119.66 (14) | C35—C34—H34 | 120.8 |
C32—C31—C39 | 108.71 (14) | C34—C35—H35 | 119.8 |
C32—C31—C42 | 120.54 (14) | C36—C35—H35 | 118.7 |
C39—C31—C42 | 130.74 (12) | C36—C37—H37 | 119.8 |
C31—C32—C33 | 108.99 (13) | C38—C37—H37 | 120.5 |
C31—C32—C45 | 120.25 (15) | C39—C40—H402 | 119.8 |
C33—C32—C45 | 130.75 (13) | C39—C40—H401 | 119.7 |
C32—C33—C34 | 131.23 (13) | C41—C40—H402 | 120.5 |
C32—C33—C38 | 108.32 (12) | C41—C40—H401 | 119.7 |
C34—C33—C38 | 120.45 (15) | H402—C40—H401 | 109.5 |
C33—C34—C35 | 119.06 (13) | C39—C41—H411 | 120.3 |
C34—C35—C36 | 121.55 (14) | C39—C41—H412 | 119.5 |
C35—C36—C37 | 119.22 (15) | C40—C41—H411 | 120.2 |
C35—C36—C51 | 119.46 (13) | C40—C41—H412 | 119.4 |
C37—C36—C51 | 121.31 (13) | H411—C41—H412 | 109.5 |
C36—C37—C38 | 119.67 (13) | C31—C42—H42 | 120.2 |
C33—C38—C37 | 120.03 (13) | C43—C42—H42 | 120.2 |
C33—C38—C39 | 109.16 (13) | C43—C44—H44 | 118.5 |
C37—C38—C39 | 130.81 (12) | C45—C44—H44 | 119.5 |
C31—C39—C38 | 104.81 (11) | C32—C45—H45 | 120.1 |
C31—C39—C40 | 121.85 (13) | C44—C45—H45 | 121.0 |
C31—C39—C41 | 122.55 (15) | C46—C47—H47 | 119.4 |
C38—C39—C40 | 121.77 (14) | C48—C47—H47 | 120.1 |
C38—C39—C41 | 122.54 (14) | N31—C48—H48 | 117.1 |
C40—C39—C41 | 58.37 (10) | C47—C48—H48 | 118.7 |
C39—C40—C41 | 60.67 (10) | N31—C49—H49 | 117.5 |
C39—C41—C40 | 60.97 (10) | C50—C49—H49 | 117.4 |
C31—C42—C43 | 119.57 (13) | C46—C50—H50 | 118.8 |
C42—C43—C44 | 118.74 (16) | C49—C50—H50 | 121.1 |
C42—C43—C46 | 121.49 (13) | C51—C52—H52 | 119.4 |
C44—C43—C46 | 119.77 (14) | C53—C52—H52 | 120.9 |
C43—C44—C45 | 121.96 (15) | N32—C53—H53 | 116.9 |
C32—C45—C44 | 118.92 (13) | C52—C53—H53 | 118.1 |
C43—C46—C47 | 122.86 (16) | N32—C54—H54 | 117.1 |
C43—C46—C50 | 122.01 (13) | C55—C54—H54 | 117.9 |
C47—C46—C50 | 115.14 (17) | C51—C55—H55 | 119.4 |
C46—C47—C48 | 120.59 (18) | C54—C55—H55 | 120.6 |
N31—C48—C47 | 124.15 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H601···N11 | 0.87 | 2.04 | 2.872 (2) | 160 |
O6—H602···N12i | 0.85 | 2.05 | 2.8928 (17) | 170 |
Symmetry code: (i) x−1, −y+3/2, z+1/2. |