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The asymmetric unit of the crystal structure of the title compound, C
25H
18N
2·0.5H
2O, contains two independent dipyridylspiro(cyclopropanefluorene) (CPF) molecules and one solvent water molecule. The two CPF molecules show significantly different dihedral angles between the pyridine rings and fluorene plane. The water molecule links with the CPF molecules
via O—H
N hydrogen bonding to form a one-dimensional supramolecular chain.
Supporting information
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.
2',7'-Di-4-pyridylspiro[cyclopropane-1,9'-fluorene] hemihydrate
top
Crystal data top
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 | |
Data collection top
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 top
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 | |
Special details top
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). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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. |
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