The title compound, C45H60N8, is a symmetric molecule with four chemically identical substituents bonded to a central C atom. In the crystal structure, the 4-phenylpiperazin-1-yl groups exhibit four different conformations, with no obvious pseudosymmetry.
Supporting information
CCDC reference: 236100
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.061
- wR factor = 0.156
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C5 = 7.32 su
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C11
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C12
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C7
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C18
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 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
6 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
Crystal data top
C45H60N8 | Z = 2 |
Mr = 713.01 | F(000) = 772 |
Triclinic, P1 | Dx = 1.165 Mg m−3 |
a = 11.712 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.708 (4) Å | Cell parameters from 976 reflections |
c = 15.354 (5) Å | θ = 2.8–22.3° |
α = 80.869 (4)° | µ = 0.07 mm−1 |
β = 68.461 (4)° | T = 293 K |
γ = 73.281 (4)° | Prismatic, colourless |
V = 2032.2 (12) Å3 | 0.15 × 0.10 × 0.05 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4019 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
φ and ω scans | h = −11→13 |
8572 measured reflections | k = −15→13 |
7066 independent reflections | l = −15→18 |
Refinement top
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0635P)2 + 0.3853P] where P = (Fo2 + 2Fc2)/3 |
7066 reflections | (Δ/σ)max < 0.001 |
478 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | |
N1 | 0.45831 (19) | 0.21059 (16) | 0.36959 (14) | 0.0534 (6) | |
N2 | 0.4975 (2) | 0.26294 (17) | 0.52993 (14) | 0.0587 (6) | |
N3 | 0.30044 (19) | 0.37906 (16) | 0.15126 (14) | 0.0519 (5) | |
N4 | 0.1578 (2) | 0.56333 (17) | 0.06695 (15) | 0.0572 (6) | |
N5 | 0.5585 (2) | 0.14802 (17) | 0.07772 (14) | 0.0549 (6) | |
N6 | 0.7879 (2) | 0.11149 (17) | −0.07990 (14) | 0.0565 (6) | |
N7 | 0.25978 (19) | 0.07168 (15) | 0.34073 (14) | 0.0496 (5) | |
N8 | 0.16026 (19) | −0.11260 (17) | 0.43885 (14) | 0.0550 (6) | |
C1 | 0.3895 (2) | 0.20049 (19) | 0.23336 (17) | 0.0498 (6) | |
C2 | 0.4882 (2) | 0.1579 (2) | 0.28277 (18) | 0.0541 (7) | |
H2A | 0.4976 | 0.0794 | 0.2972 | 0.065* | |
H2B | 0.5692 | 0.1683 | 0.2395 | 0.065* | |
C3 | 0.5390 (3) | 0.2823 (2) | 0.36079 (18) | 0.0605 (7) | |
H3A | 0.5355 | 0.3364 | 0.3090 | 0.073* | |
H3B | 0.6260 | 0.2393 | 0.3472 | 0.073* | |
C4 | 0.4974 (3) | 0.3403 (2) | 0.44969 (18) | 0.0657 (8) | |
H4A | 0.5540 | 0.3862 | 0.4426 | 0.079* | |
H4B | 0.4128 | 0.3877 | 0.4605 | 0.079* | |
C5 | 0.4255 (3) | 0.1849 (2) | 0.53651 (19) | 0.0717 (8) | |
H5A | 0.3364 | 0.2227 | 0.5520 | 0.086* | |
H5B | 0.4343 | 0.1294 | 0.5865 | 0.086* | |
C6 | 0.4701 (3) | 0.1302 (2) | 0.44599 (19) | 0.0655 (8) | |
H6A | 0.5580 | 0.0895 | 0.4320 | 0.079* | |
H6B | 0.4203 | 0.0785 | 0.4524 | 0.079* | |
C7 | 0.4835 (3) | 0.3062 (3) | 0.61305 (19) | 0.0665 (8) | |
C8 | 0.5556 (3) | 0.3763 (2) | 0.6114 (2) | 0.0725 (9) | |
H8 | 0.6081 | 0.3992 | 0.5538 | 0.087* | |
C9 | 0.5523 (4) | 0.4132 (3) | 0.6917 (2) | 0.0870 (10) | |
H9 | 0.6026 | 0.4598 | 0.6878 | 0.104* | |
C10 | 0.4768 (4) | 0.3825 (4) | 0.7764 (3) | 0.1176 (14) | |
H10 | 0.4740 | 0.4080 | 0.8309 | 0.141* | |
C11 | 0.4048 (5) | 0.3138 (5) | 0.7806 (3) | 0.154 (2) | |
H11 | 0.3520 | 0.2925 | 0.8387 | 0.185* | |
C12 | 0.4085 (4) | 0.2743 (4) | 0.6992 (2) | 0.1300 (17) | |
H12 | 0.3597 | 0.2261 | 0.7038 | 0.156* | |
C13 | 0.3808 (3) | 0.32371 (19) | 0.20767 (18) | 0.0555 (7) | |
H13A | 0.3493 | 0.3612 | 0.2654 | 0.067* | |
H13B | 0.4658 | 0.3326 | 0.1737 | 0.067* | |
C14 | 0.1780 (3) | 0.4441 (2) | 0.20611 (19) | 0.0676 (8) | |
H14A | 0.1903 | 0.5011 | 0.2344 | 0.081* | |
H14B | 0.1352 | 0.3973 | 0.2563 | 0.081* | |
C15 | 0.0959 (3) | 0.4965 (2) | 0.1473 (2) | 0.0713 (8) | |
H15A | 0.0754 | 0.4394 | 0.1251 | 0.086* | |
H15B | 0.0172 | 0.5425 | 0.1859 | 0.086* | |
C16 | 0.2845 (3) | 0.5029 (2) | 0.01602 (19) | 0.0649 (8) | |
H16A | 0.3273 | 0.5520 | −0.0315 | 0.078* | |
H16B | 0.2794 | 0.4449 | −0.0156 | 0.078* | |
C17 | 0.3604 (3) | 0.4531 (2) | 0.07868 (18) | 0.0593 (7) | |
H17A | 0.4442 | 0.4131 | 0.0416 | 0.071* | |
H17B | 0.3700 | 0.5112 | 0.1074 | 0.071* | |
C18 | 0.0835 (3) | 0.6282 (2) | 0.0147 (2) | 0.0644 (8) | |
C19 | −0.0436 (4) | 0.6746 (3) | 0.0558 (3) | 0.0953 (11) | |
H19 | −0.0824 | 0.6596 | 0.1196 | 0.114* | |
C20 | −0.1148 (4) | 0.7425 (3) | 0.0056 (4) | 0.1159 (14) | |
H20 | −0.2006 | 0.7726 | 0.0361 | 0.139* | |
C21 | −0.0633 (5) | 0.7663 (3) | −0.0868 (4) | 0.1161 (15) | |
H21 | −0.1126 | 0.8115 | −0.1205 | 0.139* | |
C22 | 0.0617 (5) | 0.7229 (3) | −0.1294 (3) | 0.1083 (13) | |
H22 | 0.0989 | 0.7399 | −0.1930 | 0.130* | |
C23 | 0.1359 (4) | 0.6535 (3) | −0.0805 (2) | 0.0887 (10) | |
H23 | 0.2215 | 0.6237 | −0.1118 | 0.106* | |
C24 | 0.4348 (3) | 0.1372 (2) | 0.14461 (18) | 0.0588 (7) | |
H24A | 0.4395 | 0.0598 | 0.1629 | 0.071* | |
H24B | 0.3723 | 0.1633 | 0.1135 | 0.071* | |
C25 | 0.5593 (3) | 0.1805 (2) | −0.01717 (18) | 0.0636 (8) | |
H25A | 0.4900 | 0.2447 | −0.0166 | 0.076* | |
H25B | 0.5469 | 0.1214 | −0.0429 | 0.076* | |
C26 | 0.6824 (3) | 0.2065 (2) | −0.07768 (19) | 0.0660 (8) | |
H26A | 0.6812 | 0.2283 | −0.1409 | 0.079* | |
H26B | 0.6932 | 0.2676 | −0.0534 | 0.079* | |
C27 | 0.7854 (3) | 0.0711 (2) | 0.01470 (18) | 0.0635 (8) | |
H27A | 0.8021 | 0.1253 | 0.0433 | 0.076* | |
H27B | 0.8518 | 0.0039 | 0.0119 | 0.076* | |
C28 | 0.6600 (3) | 0.0489 (2) | 0.07380 (19) | 0.0640 (8) | |
H28A | 0.6456 | −0.0087 | 0.0476 | 0.077* | |
H28B | 0.6604 | 0.0237 | 0.1367 | 0.077* | |
C29 | 0.9079 (3) | 0.1151 (2) | −0.14595 (18) | 0.0599 (7) | |
C30 | 0.9319 (3) | 0.2068 (3) | −0.2029 (2) | 0.0802 (9) | |
H30 | 0.8690 | 0.2723 | −0.1959 | 0.096* | |
C31 | 1.0511 (4) | 0.2011 (4) | −0.2715 (2) | 0.1011 (12) | |
H31 | 1.0673 | 0.2636 | −0.3095 | 0.121* | |
C32 | 1.1442 (4) | 0.1054 (4) | −0.2838 (3) | 0.1005 (12) | |
H32 | 1.2225 | 0.1019 | −0.3308 | 0.121* | |
C33 | 1.1213 (3) | 0.0165 (3) | −0.2270 (2) | 0.0959 (11) | |
H33 | 1.1847 | −0.0487 | −0.2341 | 0.115* | |
C34 | 1.0057 (3) | 0.0208 (3) | −0.1591 (2) | 0.0810 (9) | |
H34 | 0.9923 | −0.0418 | −0.1204 | 0.097* | |
C35 | 0.2597 (2) | 0.18390 (19) | 0.29882 (18) | 0.0540 (7) | |
H35A | 0.2270 | 0.2338 | 0.3490 | 0.065* | |
H35B | 0.2018 | 0.2043 | 0.2637 | 0.065* | |
C36 | 0.2088 (3) | 0.0107 (2) | 0.29757 (19) | 0.0654 (8) | |
H36A | 0.2535 | 0.0115 | 0.2304 | 0.078* | |
H36B | 0.1200 | 0.0460 | 0.3082 | 0.078* | |
C37 | 0.2223 (3) | −0.1060 (2) | 0.33742 (18) | 0.0665 (8) | |
H37A | 0.1856 | −0.1442 | 0.3087 | 0.080* | |
H37B | 0.3116 | −0.1428 | 0.3222 | 0.080* | |
C38 | 0.1960 (3) | −0.0428 (2) | 0.48544 (18) | 0.0593 (7) | |
H38A | 0.2829 | −0.0743 | 0.4831 | 0.071* | |
H38B | 0.1421 | −0.0396 | 0.5508 | 0.071* | |
C39 | 0.1839 (3) | 0.0714 (2) | 0.43984 (17) | 0.0569 (7) | |
H39A | 0.0956 | 0.1050 | 0.4469 | 0.068* | |
H39B | 0.2106 | 0.1154 | 0.4713 | 0.068* | |
C40 | 0.1481 (2) | −0.2167 (2) | 0.48195 (19) | 0.0603 (7) | |
C41 | 0.1235 (3) | −0.2909 (3) | 0.4381 (2) | 0.0841 (10) | |
H41 | 0.1172 | −0.2718 | 0.3787 | 0.101* | |
C42 | 0.1083 (4) | −0.3919 (3) | 0.4806 (3) | 0.1064 (13) | |
H42 | 0.0914 | −0.4397 | 0.4496 | 0.128* | |
C43 | 0.1175 (4) | −0.4232 (3) | 0.5672 (3) | 0.1119 (14) | |
H43 | 0.1089 | −0.4923 | 0.5950 | 0.134* | |
C44 | 0.1395 (4) | −0.3512 (3) | 0.6122 (3) | 0.0987 (12) | |
H44 | 0.1443 | −0.3711 | 0.6720 | 0.118* | |
C45 | 0.1550 (3) | −0.2489 (2) | 0.5709 (2) | 0.0757 (9) | |
H45 | 0.1701 | −0.2012 | 0.6031 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0587 (14) | 0.0487 (12) | 0.0544 (13) | −0.0151 (11) | −0.0240 (11) | 0.0070 (11) |
N2 | 0.0657 (15) | 0.0638 (14) | 0.0482 (13) | −0.0231 (12) | −0.0199 (11) | 0.0062 (11) |
N3 | 0.0478 (13) | 0.0482 (12) | 0.0551 (13) | −0.0103 (10) | −0.0170 (11) | 0.0052 (10) |
N4 | 0.0576 (15) | 0.0526 (13) | 0.0565 (14) | −0.0090 (11) | −0.0203 (12) | 0.0038 (11) |
N5 | 0.0508 (14) | 0.0597 (13) | 0.0517 (13) | −0.0113 (11) | −0.0161 (11) | −0.0046 (11) |
N6 | 0.0604 (15) | 0.0560 (13) | 0.0484 (13) | −0.0132 (11) | −0.0151 (11) | −0.0012 (10) |
N7 | 0.0505 (13) | 0.0490 (12) | 0.0485 (12) | −0.0148 (10) | −0.0142 (10) | −0.0023 (10) |
N8 | 0.0544 (14) | 0.0617 (14) | 0.0499 (13) | −0.0221 (11) | −0.0129 (11) | −0.0040 (11) |
C1 | 0.0496 (16) | 0.0465 (14) | 0.0539 (15) | −0.0115 (12) | −0.0185 (12) | −0.0029 (12) |
C2 | 0.0542 (17) | 0.0484 (14) | 0.0611 (17) | −0.0105 (12) | −0.0238 (13) | −0.0015 (13) |
C3 | 0.074 (2) | 0.0594 (16) | 0.0521 (16) | −0.0260 (15) | −0.0228 (14) | 0.0073 (13) |
C4 | 0.082 (2) | 0.0643 (17) | 0.0543 (17) | −0.0240 (15) | −0.0250 (15) | 0.0026 (15) |
C5 | 0.074 (2) | 0.084 (2) | 0.0555 (18) | −0.0289 (17) | −0.0218 (15) | 0.0165 (16) |
C6 | 0.073 (2) | 0.0627 (17) | 0.0703 (19) | −0.0309 (15) | −0.0325 (16) | 0.0152 (15) |
C7 | 0.0602 (19) | 0.083 (2) | 0.0477 (17) | −0.0107 (16) | −0.0152 (14) | −0.0017 (15) |
C8 | 0.096 (2) | 0.0585 (17) | 0.0598 (19) | −0.0153 (17) | −0.0243 (17) | −0.0069 (15) |
C9 | 0.112 (3) | 0.076 (2) | 0.072 (2) | −0.007 (2) | −0.037 (2) | −0.0212 (18) |
C10 | 0.103 (3) | 0.174 (4) | 0.069 (3) | −0.021 (3) | −0.018 (2) | −0.039 (3) |
C11 | 0.122 (4) | 0.298 (7) | 0.056 (2) | −0.107 (4) | −0.001 (2) | −0.020 (3) |
C12 | 0.116 (3) | 0.239 (5) | 0.057 (2) | −0.100 (4) | −0.013 (2) | −0.009 (3) |
C13 | 0.0574 (17) | 0.0492 (15) | 0.0620 (17) | −0.0152 (13) | −0.0232 (14) | 0.0012 (13) |
C14 | 0.0575 (19) | 0.0650 (17) | 0.0609 (18) | −0.0074 (15) | −0.0102 (15) | 0.0112 (14) |
C15 | 0.0562 (19) | 0.0622 (17) | 0.079 (2) | −0.0073 (15) | −0.0160 (16) | 0.0108 (16) |
C16 | 0.068 (2) | 0.0663 (18) | 0.0531 (16) | −0.0158 (15) | −0.0169 (15) | 0.0048 (14) |
C17 | 0.0551 (17) | 0.0567 (16) | 0.0589 (17) | −0.0147 (13) | −0.0133 (14) | 0.0032 (14) |
C18 | 0.079 (2) | 0.0471 (16) | 0.077 (2) | −0.0173 (15) | −0.0397 (18) | 0.0036 (15) |
C19 | 0.082 (3) | 0.087 (2) | 0.110 (3) | −0.010 (2) | −0.044 (2) | 0.024 (2) |
C20 | 0.094 (3) | 0.100 (3) | 0.160 (4) | −0.020 (2) | −0.071 (3) | 0.035 (3) |
C21 | 0.144 (4) | 0.090 (3) | 0.157 (5) | −0.039 (3) | −0.108 (4) | 0.030 (3) |
C22 | 0.161 (4) | 0.093 (3) | 0.094 (3) | −0.035 (3) | −0.079 (3) | 0.022 (2) |
C23 | 0.115 (3) | 0.079 (2) | 0.078 (2) | −0.020 (2) | −0.049 (2) | 0.0079 (19) |
C24 | 0.0580 (18) | 0.0614 (16) | 0.0604 (17) | −0.0158 (14) | −0.0219 (14) | −0.0072 (14) |
C25 | 0.067 (2) | 0.0637 (17) | 0.0579 (18) | −0.0054 (15) | −0.0246 (15) | −0.0084 (14) |
C26 | 0.077 (2) | 0.0611 (17) | 0.0559 (17) | −0.0122 (16) | −0.0236 (15) | 0.0023 (14) |
C27 | 0.0597 (19) | 0.0638 (17) | 0.0580 (17) | −0.0085 (14) | −0.0179 (14) | 0.0034 (14) |
C28 | 0.0633 (19) | 0.0622 (17) | 0.0575 (17) | −0.0104 (15) | −0.0174 (14) | 0.0039 (14) |
C29 | 0.069 (2) | 0.0690 (18) | 0.0500 (16) | −0.0297 (16) | −0.0209 (15) | −0.0033 (14) |
C30 | 0.095 (3) | 0.079 (2) | 0.071 (2) | −0.0393 (19) | −0.0224 (19) | 0.0018 (17) |
C31 | 0.113 (3) | 0.117 (3) | 0.078 (3) | −0.067 (3) | −0.020 (2) | 0.021 (2) |
C32 | 0.076 (3) | 0.143 (4) | 0.082 (3) | −0.048 (3) | −0.014 (2) | 0.001 (3) |
C33 | 0.067 (2) | 0.119 (3) | 0.081 (2) | −0.019 (2) | −0.0084 (19) | 0.002 (2) |
C34 | 0.066 (2) | 0.085 (2) | 0.075 (2) | −0.0182 (18) | −0.0080 (17) | 0.0017 (17) |
C35 | 0.0523 (17) | 0.0497 (15) | 0.0573 (16) | −0.0082 (12) | −0.0194 (13) | −0.0020 (13) |
C36 | 0.081 (2) | 0.0700 (18) | 0.0534 (16) | −0.0325 (16) | −0.0245 (15) | 0.0017 (14) |
C37 | 0.084 (2) | 0.0659 (18) | 0.0534 (17) | −0.0331 (16) | −0.0165 (15) | −0.0051 (14) |
C38 | 0.0648 (19) | 0.0653 (17) | 0.0491 (16) | −0.0228 (14) | −0.0159 (13) | −0.0032 (13) |
C39 | 0.0526 (17) | 0.0607 (17) | 0.0555 (17) | −0.0144 (13) | −0.0133 (13) | −0.0102 (13) |
C40 | 0.0508 (17) | 0.0656 (18) | 0.0592 (18) | −0.0223 (14) | −0.0078 (14) | −0.0018 (15) |
C41 | 0.101 (3) | 0.088 (2) | 0.078 (2) | −0.053 (2) | −0.0268 (19) | 0.0024 (18) |
C42 | 0.137 (4) | 0.094 (3) | 0.099 (3) | −0.071 (3) | −0.025 (3) | 0.006 (2) |
C43 | 0.138 (4) | 0.088 (3) | 0.099 (3) | −0.059 (3) | −0.012 (3) | 0.016 (2) |
C44 | 0.120 (3) | 0.092 (3) | 0.073 (2) | −0.044 (2) | −0.015 (2) | 0.016 (2) |
C45 | 0.085 (2) | 0.075 (2) | 0.065 (2) | −0.0313 (18) | −0.0180 (17) | 0.0032 (17) |
Geometric parameters (Å, º) top
N1—C6 | 1.448 (3) | C16—H16B | 0.9700 |
N1—C3 | 1.451 (3) | C17—H17A | 0.9700 |
N1—C2 | 1.468 (3) | C17—H17B | 0.9700 |
N2—C7 | 1.406 (3) | C18—C19 | 1.373 (4) |
N2—C5 | 1.446 (3) | C18—C23 | 1.386 (4) |
N2—C4 | 1.449 (3) | C19—C20 | 1.372 (5) |
N3—C17 | 1.447 (3) | C19—H19 | 0.9300 |
N3—C14 | 1.450 (3) | C20—C21 | 1.345 (6) |
N3—C13 | 1.468 (3) | C20—H20 | 0.9300 |
N4—C18 | 1.404 (3) | C21—C22 | 1.350 (6) |
N4—C16 | 1.444 (3) | C21—H21 | 0.9300 |
N4—C15 | 1.461 (3) | C22—C23 | 1.388 (5) |
N5—C25 | 1.447 (3) | C22—H22 | 0.9300 |
N5—C28 | 1.453 (3) | C23—H23 | 0.9300 |
N5—C24 | 1.467 (3) | C24—H24A | 0.9700 |
N6—C29 | 1.408 (3) | C24—H24B | 0.9700 |
N6—C26 | 1.452 (3) | C25—C26 | 1.498 (4) |
N6—C27 | 1.454 (3) | C25—H25A | 0.9700 |
N7—C39 | 1.454 (3) | C25—H25B | 0.9700 |
N7—C36 | 1.454 (3) | C26—H26A | 0.9700 |
N7—C35 | 1.469 (3) | C26—H26B | 0.9700 |
N8—C40 | 1.403 (3) | C27—C28 | 1.496 (4) |
N8—C38 | 1.453 (3) | C27—H27A | 0.9700 |
N8—C37 | 1.457 (3) | C27—H27B | 0.9700 |
C1—C2 | 1.535 (3) | C28—H28A | 0.9700 |
C1—C24 | 1.536 (3) | C28—H28B | 0.9700 |
C1—C13 | 1.536 (3) | C29—C30 | 1.373 (4) |
C1—C35 | 1.537 (3) | C29—C34 | 1.381 (4) |
C2—H2A | 0.9700 | C30—C31 | 1.397 (5) |
C2—H2B | 0.9700 | C30—H30 | 0.9300 |
C3—C4 | 1.506 (4) | C31—C32 | 1.364 (5) |
C3—H3A | 0.9700 | C31—H31 | 0.9300 |
C3—H3B | 0.9700 | C32—C33 | 1.341 (5) |
C4—H4A | 0.9700 | C32—H32 | 0.9300 |
C4—H4B | 0.9700 | C33—C34 | 1.365 (4) |
C5—C6 | 1.500 (4) | C33—H33 | 0.9300 |
C5—H5A | 0.9700 | C34—H34 | 0.9300 |
C5—H5B | 0.9700 | C35—H35A | 0.9700 |
C6—H6A | 0.9700 | C35—H35B | 0.9700 |
C6—H6B | 0.9700 | C36—C37 | 1.499 (4) |
C7—C12 | 1.367 (4) | C36—H36A | 0.9700 |
C7—C8 | 1.384 (4) | C36—H36B | 0.9700 |
C8—C9 | 1.372 (4) | C37—H37A | 0.9700 |
C8—H8 | 0.9300 | C37—H37B | 0.9700 |
C9—C10 | 1.348 (5) | C38—C39 | 1.499 (3) |
C9—H9 | 0.9300 | C38—H38A | 0.9700 |
C10—C11 | 1.357 (6) | C38—H38B | 0.9700 |
C10—H10 | 0.9300 | C39—H39A | 0.9700 |
C11—C12 | 1.401 (5) | C39—H39B | 0.9700 |
C11—H11 | 0.9300 | C40—C45 | 1.386 (4) |
C12—H12 | 0.9300 | C40—C41 | 1.387 (4) |
C13—H13A | 0.9700 | C41—C42 | 1.373 (4) |
C13—H13B | 0.9700 | C41—H41 | 0.9300 |
C14—C15 | 1.503 (4) | C42—C43 | 1.360 (5) |
C14—H14A | 0.9700 | C42—H42 | 0.9300 |
C14—H14B | 0.9700 | C43—C44 | 1.360 (5) |
C15—H15A | 0.9700 | C43—H43 | 0.9300 |
C15—H15B | 0.9700 | C44—C45 | 1.384 (4) |
C16—C17 | 1.492 (4) | C44—H44 | 0.9300 |
C16—H16A | 0.9700 | C45—H45 | 0.9300 |
| | | |
C1—C2—N1 | 115.1 (2) | H17A—C17—H17B | 108.0 |
C1—C13—N3 | 116.5 (2) | C19—C18—C23 | 116.4 (3) |
C1—C24—N5 | 114.1 (2) | C19—C18—N4 | 121.9 (3) |
C1—C35—N7 | 115.2 (2) | C23—C18—N4 | 121.7 (3) |
C4—N2—C5 | 110.8 (2) | C20—C19—C18 | 121.9 (4) |
C15—N4—C16 | 111.0 (2) | C20—C19—H19 | 119.1 |
C26—N6—C27 | 110.7 (2) | C18—C19—H19 | 119.1 |
C37—N8—C38 | 112.2 (2) | C21—C20—C19 | 121.4 (4) |
C6—N1—C3 | 106.9 (2) | C21—C20—H20 | 119.3 |
C6—N1—C2 | 111.72 (19) | C19—C20—H20 | 119.3 |
C3—N1—C2 | 113.5 (2) | C20—C21—C22 | 118.4 (4) |
C7—N2—C5 | 118.1 (2) | C20—C21—H21 | 120.8 |
C7—N2—C4 | 116.6 (2) | C22—C21—H21 | 120.8 |
C5—N2—C4 | 110.8 (2) | C21—C22—C23 | 121.5 (4) |
C17—N3—C14 | 106.77 (19) | C21—C22—H22 | 119.2 |
C17—N3—C13 | 111.0 (2) | C23—C22—H22 | 119.2 |
C14—N3—C13 | 113.0 (2) | C18—C23—C22 | 120.5 (4) |
C18—N4—C16 | 117.7 (2) | C18—C23—H23 | 119.7 |
C18—N4—C15 | 117.0 (2) | C22—C23—H23 | 119.7 |
C16—N4—C15 | 111.0 (2) | N5—C24—C1 | 114.1 (2) |
C25—N5—C28 | 107.5 (2) | N5—C24—H24A | 108.7 |
C25—N5—C24 | 113.9 (2) | C1—C24—H24A | 108.7 |
C28—N5—C24 | 113.7 (2) | N5—C24—H24B | 108.7 |
C29—N6—C26 | 118.0 (2) | C1—C24—H24B | 108.7 |
C29—N6—C27 | 115.8 (2) | H24A—C24—H24B | 107.6 |
C26—N6—C27 | 110.7 (2) | N5—C25—C26 | 110.6 (2) |
C39—N7—C36 | 105.9 (2) | N5—C25—H25A | 109.5 |
C39—N7—C35 | 111.82 (19) | C26—C25—H25A | 109.5 |
C36—N7—C35 | 113.5 (2) | N5—C25—H25B | 109.5 |
C40—N8—C38 | 117.7 (2) | C26—C25—H25B | 109.5 |
C40—N8—C37 | 117.1 (2) | H25A—C25—H25B | 108.1 |
C38—N8—C37 | 112.2 (2) | N6—C26—C25 | 110.6 (2) |
C2—C1—C24 | 108.4 (2) | N6—C26—H26A | 109.5 |
C2—C1—C13 | 107.3 (2) | C25—C26—H26A | 109.5 |
C24—C1—C13 | 110.6 (2) | N6—C26—H26B | 109.5 |
C2—C1—C35 | 110.4 (2) | C25—C26—H26B | 109.5 |
C24—C1—C35 | 110.1 (2) | H26A—C26—H26B | 108.1 |
C13—C1—C35 | 109.9 (2) | N6—C27—C28 | 111.3 (2) |
N1—C2—C1 | 115.1 (2) | N6—C27—H27A | 109.4 |
N1—C2—H2A | 108.5 | C28—C27—H27A | 109.4 |
C1—C2—H2A | 108.5 | N6—C27—H27B | 109.4 |
N1—C2—H2B | 108.5 | C28—C27—H27B | 109.4 |
C1—C2—H2B | 108.5 | H27A—C27—H27B | 108.0 |
H2A—C2—H2B | 107.5 | N5—C28—C27 | 110.5 (2) |
N1—C3—C4 | 110.9 (2) | N5—C28—H28A | 109.6 |
N1—C3—H3A | 109.5 | C27—C28—H28A | 109.6 |
C4—C3—H3A | 109.5 | N5—C28—H28B | 109.6 |
N1—C3—H3B | 109.5 | C27—C28—H28B | 109.6 |
C4—C3—H3B | 109.5 | H28A—C28—H28B | 108.1 |
H3A—C3—H3B | 108.0 | C30—C29—C34 | 117.3 (3) |
N2—C4—C3 | 111.7 (2) | C30—C29—N6 | 123.3 (3) |
N2—C4—H4A | 109.3 | C34—C29—N6 | 119.3 (3) |
C3—C4—H4A | 109.3 | C29—C30—C31 | 119.7 (3) |
N2—C4—H4B | 109.3 | C29—C30—H30 | 120.1 |
C3—C4—H4B | 109.3 | C31—C30—H30 | 120.1 |
H4A—C4—H4B | 107.9 | C32—C31—C30 | 121.1 (3) |
N2—C5—C6 | 111.2 (2) | C32—C31—H31 | 119.5 |
N2—C5—H5A | 109.4 | C30—C31—H31 | 119.5 |
C6—C5—H5A | 109.4 | C33—C32—C31 | 119.1 (4) |
N2—C5—H5B | 109.4 | C33—C32—H32 | 120.4 |
C6—C5—H5B | 109.4 | C31—C32—H32 | 120.4 |
H5A—C5—H5B | 108.0 | C32—C33—C34 | 120.6 (4) |
N1—C6—C5 | 111.0 (2) | C32—C33—H33 | 119.7 |
N1—C6—H6A | 109.4 | C34—C33—H33 | 119.7 |
C5—C6—H6A | 109.4 | C33—C34—C29 | 122.2 (3) |
N1—C6—H6B | 109.4 | C33—C34—H34 | 118.9 |
C5—C6—H6B | 109.4 | C29—C34—H34 | 118.9 |
H6A—C6—H6B | 108.0 | N7—C35—C1 | 115.2 (2) |
C12—C7—C8 | 116.9 (3) | N7—C35—H35A | 108.5 |
C12—C7—N2 | 122.4 (3) | C1—C35—H35A | 108.5 |
C8—C7—N2 | 120.5 (2) | N7—C35—H35B | 108.5 |
C9—C8—C7 | 122.2 (3) | C1—C35—H35B | 108.5 |
C9—C8—H8 | 118.9 | H35A—C35—H35B | 107.5 |
C7—C8—H8 | 118.9 | N7—C36—C37 | 110.9 (2) |
C10—C9—C8 | 120.6 (4) | N7—C36—H36A | 109.5 |
C10—C9—H9 | 119.7 | C37—C36—H36A | 109.5 |
C8—C9—H9 | 119.7 | N7—C36—H36B | 109.5 |
C9—C10—C11 | 118.7 (4) | C37—C36—H36B | 109.5 |
C9—C10—H10 | 120.6 | H36A—C36—H36B | 108.0 |
C11—C10—H10 | 120.6 | N8—C37—C36 | 112.1 (2) |
C10—C11—C12 | 121.3 (4) | N8—C37—H37A | 109.2 |
C10—C11—H11 | 119.3 | C36—C37—H37A | 109.2 |
C12—C11—H11 | 119.3 | N8—C37—H37B | 109.2 |
C7—C12—C11 | 120.3 (4) | C36—C37—H37B | 109.2 |
C7—C12—H12 | 119.9 | H37A—C37—H37B | 107.9 |
C11—C12—H12 | 119.9 | N8—C38—C39 | 111.2 (2) |
N3—C13—C1 | 116.5 (2) | N8—C38—H38A | 109.4 |
N3—C13—H13A | 108.2 | C39—C38—H38A | 109.4 |
C1—C13—H13A | 108.2 | N8—C38—H38B | 109.4 |
N3—C13—H13B | 108.2 | C39—C38—H38B | 109.4 |
C1—C13—H13B | 108.2 | H38A—C38—H38B | 108.0 |
H13A—C13—H13B | 107.3 | N7—C39—C38 | 112.0 (2) |
N3—C14—C15 | 111.9 (2) | N7—C39—H39A | 109.2 |
N3—C14—H14A | 109.2 | C38—C39—H39A | 109.2 |
C15—C14—H14A | 109.2 | N7—C39—H39B | 109.2 |
N3—C14—H14B | 109.2 | C38—C39—H39B | 109.2 |
C15—C14—H14B | 109.2 | H39A—C39—H39B | 107.9 |
H14A—C14—H14B | 107.9 | C45—C40—C41 | 116.9 (3) |
N4—C15—C14 | 112.2 (2) | C45—C40—N8 | 122.3 (3) |
N4—C15—H15A | 109.2 | C41—C40—N8 | 120.8 (3) |
C14—C15—H15A | 109.2 | C42—C41—C40 | 121.4 (3) |
N4—C15—H15B | 109.2 | C42—C41—H41 | 119.3 |
C14—C15—H15B | 109.2 | C40—C41—H41 | 119.3 |
H15A—C15—H15B | 107.9 | C43—C42—C41 | 121.1 (4) |
N4—C16—C17 | 112.2 (2) | C43—C42—H42 | 119.4 |
N4—C16—H16A | 109.2 | C41—C42—H42 | 119.4 |
C17—C16—H16A | 109.2 | C42—C43—C44 | 118.6 (3) |
N4—C16—H16B | 109.2 | C42—C43—H43 | 120.7 |
C17—C16—H16B | 109.2 | C44—C43—H43 | 120.7 |
H16A—C16—H16B | 107.9 | C43—C44—C45 | 121.3 (4) |
N3—C17—C16 | 111.5 (2) | C43—C44—H44 | 119.4 |
N3—C17—H17A | 109.3 | C45—C44—H44 | 119.4 |
C16—C17—H17A | 109.3 | C44—C45—C40 | 120.7 (3) |
N3—C17—H17B | 109.3 | C44—C45—H45 | 119.6 |
C16—C17—H17B | 109.3 | C40—C45—H45 | 119.6 |
| | | |
C1—C35—N7—C39 | 136.2 (2) | C1—C24—N5—N6 | 169.8 (4) |
C1—C35—N7—C36 | −104.0 (3) | C1—C35—N7—N8 | −167.1 (3) |
C1—C24—N5—C28 | 107.7 (3) | C4—C5—C8—C12 | 150.4 (2) |
C1—C24—N5—C25 | −128.7 (2) | C4—C5—C12—C8 | −22.92 (17) |
C1—C13—N3—C17 | −137.9 (2) | C15—C16—C19—C23 | −167.0 (2) |
C1—C13—N3—C14 | 102.1 (3) | C15—C16—C23—C19 | 10.03 (16) |
C1—C2—N1—C6 | 130.1 (2) | C26—C27—C30—C34 | −142.28 (18) |
C1—C2—N1—C3 | −109.0 (2) | C26—C27—C34—C30 | 29.15 (14) |
C1—C2—N1—N2 | −172.5 (3) | C37—C38—C41—C45 | 160.69 (19) |
C1—C13—N3—N4 | 165.7 (3) | C37—C38—C45—C41 | −14.84 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···C21i | 0.93 | 2.63 | 3.471 (6) | 151 |
C39—H39A···C40ii | 0.97 | 2.69 | 3.622 (4) | 162 |
Symmetry codes: (i) x+1, y−1, z; (ii) −x, −y, −z+1. |