The title compound, C
33H
24N
4O
4, is a symmetric molecule with four chemically identical substituents bonded to a central C atom. In the crystal structure, there are C—H
N, C—H
O, C—H
C, C—H
π(C
N) and edge-to-face aromatic interactions. The four chemically identical substituents have different conformations.
Supporting information
CCDC reference: 210725
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.145
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.83 Sigma
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O4
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C31
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C27
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C30
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C9 - C12 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C16 - C19 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C23 - C26 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C30 - C33 ... 1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H32 .. N2 .. 2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. N1 .. 2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28 .. O1 .. 2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. N2 .. 2.79 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. N2 .. 2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. N3 .. 2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. N3 .. 2.77 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3 .. N3 .. 3.79 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
18 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 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
10 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXTL (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C33H24N4O4 | F(000) = 1128 |
Mr = 540.56 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2069 (17) Å | Cell parameters from 2967 reflections |
b = 12.703 (2) Å | θ = 2.5–22.2° |
c = 20.750 (3) Å | µ = 0.08 mm−1 |
β = 101.003 (2)° | T = 293 K |
V = 2899.7 (8) Å3 | Parallelepiped, colourless |
Z = 4 | 0.60 × 0.50 × 0.30 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5683 independent reflections |
Radiation source: fine-focus sealed tube | 3685 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SABABS; Sheldrick, 1997a) | h = −13→13 |
Tmin = 0.952, Tmax = 0.976 | k = −14→15 |
13056 measured reflections | l = −15→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.3945P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5683 reflections | Δρmax = 0.16 e Å−3 |
371 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0011 (6) |
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 | 0.4130 (2) | 0.3972 (2) | 0.21734 (14) | 0.0981 (9) | |
N2 | 0.3690 (2) | 1.4301 (2) | 0.02001 (12) | 0.0840 (7) | |
N3 | 1.5697 (2) | 0.8890 (2) | 0.04384 (12) | 0.0899 (8) | |
N4 | 1.0622 (3) | 1.2920 (3) | 0.59841 (16) | 0.1324 (12) | |
O1 | 0.79809 (14) | 0.78618 (13) | 0.18395 (7) | 0.0610 (4) | |
O2 | 0.80940 (14) | 1.10969 (13) | 0.17182 (9) | 0.0716 (5) | |
O3 | 1.07757 (15) | 0.87828 (14) | 0.18272 (9) | 0.0716 (5) | |
O4 | 0.90275 (15) | 1.01077 (15) | 0.32340 (9) | 0.0771 (6) | |
C1 | 0.90065 (19) | 0.94781 (18) | 0.21588 (11) | 0.0535 (6) | |
C2 | 0.8690 (2) | 0.83932 (18) | 0.23879 (12) | 0.0565 (6) | |
H2A | 0.9426 | 0.7999 | 0.2553 | 0.068* | |
H2B | 0.8231 | 0.8459 | 0.2738 | 0.068* | |
C3 | 0.7813 (2) | 1.00549 (19) | 0.19072 (12) | 0.0621 (7) | |
H3A | 0.7348 | 0.9684 | 0.1534 | 0.074* | |
H3B | 0.7333 | 1.0087 | 0.2249 | 0.074* | |
C4 | 0.9734 (2) | 0.9424 (2) | 0.16099 (12) | 0.0620 (6) | |
H4A | 0.9240 | 0.9124 | 0.1218 | 0.074* | |
H4B | 0.9982 | 1.0126 | 0.1506 | 0.074* | |
C5 | 0.9749 (2) | 1.0063 (2) | 0.27423 (11) | 0.0608 (7) | |
H5A | 1.0503 | 0.9693 | 0.2905 | 0.073* | |
H5B | 0.9941 | 1.0768 | 0.2614 | 0.073* | |
C6 | 0.72602 (18) | 0.70444 (17) | 0.19523 (11) | 0.0477 (5) | |
C7 | 0.6477 (2) | 0.66758 (19) | 0.14035 (11) | 0.0553 (6) | |
H7 | 0.6488 | 0.6971 | 0.0995 | 0.066* | |
C8 | 0.5685 (2) | 0.58779 (19) | 0.14596 (13) | 0.0602 (6) | |
H8 | 0.5155 | 0.5634 | 0.1089 | 0.072* | |
C9 | 0.56725 (19) | 0.54330 (19) | 0.20661 (12) | 0.0551 (6) | |
C10 | 0.6481 (2) | 0.57877 (18) | 0.26084 (12) | 0.0588 (6) | |
H10 | 0.6484 | 0.5481 | 0.3016 | 0.071* | |
C11 | 0.72813 (19) | 0.65876 (18) | 0.25555 (11) | 0.0525 (6) | |
H11 | 0.7830 | 0.6817 | 0.2923 | 0.063* | |
C12 | 0.4818 (2) | 0.4612 (2) | 0.21275 (13) | 0.0694 (7) | |
C13 | 0.7147 (2) | 1.1710 (2) | 0.14337 (12) | 0.0610 (6) | |
C14 | 0.5944 (2) | 1.1447 (2) | 0.13769 (13) | 0.0695 (7) | |
H14 | 0.5729 | 1.0813 | 0.1547 | 0.083* | |
C15 | 0.5056 (2) | 1.2124 (2) | 0.10670 (13) | 0.0740 (8) | |
H15 | 0.4242 | 1.1943 | 0.1033 | 0.089* | |
C16 | 0.5353 (2) | 1.3058 (2) | 0.08090 (12) | 0.0614 (6) | |
C17 | 0.6561 (3) | 1.3337 (2) | 0.08850 (15) | 0.0823 (9) | |
H17 | 0.6775 | 1.3977 | 0.0721 | 0.099* | |
C18 | 0.7452 (2) | 1.2673 (2) | 0.12022 (15) | 0.0833 (9) | |
H18 | 0.8264 | 1.2873 | 0.1261 | 0.100* | |
C19 | 0.4421 (3) | 1.3746 (2) | 0.04689 (13) | 0.0675 (7) | |
C20 | 1.1692 (2) | 0.8795 (2) | 0.14816 (13) | 0.0623 (7) | |
C21 | 1.1685 (2) | 0.9361 (2) | 0.09165 (13) | 0.0709 (7) | |
H21 | 1.0998 | 0.9740 | 0.0726 | 0.085* | |
C22 | 1.2710 (2) | 0.9363 (2) | 0.06322 (13) | 0.0754 (8) | |
H22 | 1.2708 | 0.9748 | 0.0251 | 0.090* | |
C23 | 1.3728 (2) | 0.8802 (2) | 0.09079 (13) | 0.0667 (7) | |
C24 | 1.3714 (2) | 0.8215 (2) | 0.14676 (14) | 0.0749 (8) | |
H24 | 1.4393 | 0.7821 | 0.1653 | 0.090* | |
C25 | 1.2702 (2) | 0.8210 (2) | 0.17512 (14) | 0.0747 (8) | |
H25 | 1.2698 | 0.7810 | 0.2126 | 0.090* | |
C26 | 1.4814 (3) | 0.8848 (2) | 0.06359 (13) | 0.0737 (8) | |
C27 | 0.9426 (2) | 1.06740 (19) | 0.37853 (12) | 0.0592 (6) | |
C28 | 1.0519 (2) | 1.1176 (2) | 0.39282 (14) | 0.0726 (8) | |
H28 | 1.1058 | 1.1133 | 0.3639 | 0.087* | |
C29 | 1.0825 (2) | 1.1743 (2) | 0.44966 (14) | 0.0788 (8) | |
H29 | 1.1576 | 1.2078 | 0.4592 | 0.095* | |
C30 | 1.0049 (3) | 1.1824 (2) | 0.49252 (13) | 0.0715 (7) | |
C31 | 0.8950 (3) | 1.1300 (3) | 0.47787 (15) | 0.1010 (11) | |
H31 | 0.8413 | 1.1337 | 0.5069 | 0.121* | |
C32 | 0.8642 (3) | 1.0732 (3) | 0.42182 (15) | 0.0914 (10) | |
H32 | 0.7901 | 1.0381 | 0.4127 | 0.110* | |
C33 | 1.0367 (3) | 1.2433 (3) | 0.55169 (17) | 0.0967 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0839 (17) | 0.0927 (19) | 0.129 (2) | −0.0343 (15) | 0.0492 (16) | −0.0232 (16) |
N2 | 0.0760 (16) | 0.0890 (19) | 0.0812 (17) | 0.0057 (14) | 0.0006 (13) | 0.0005 (14) |
N3 | 0.0764 (16) | 0.116 (2) | 0.0834 (18) | 0.0108 (15) | 0.0309 (14) | 0.0067 (15) |
N4 | 0.131 (3) | 0.166 (3) | 0.096 (2) | −0.026 (2) | 0.0123 (19) | −0.053 (2) |
O1 | 0.0707 (10) | 0.0596 (11) | 0.0555 (10) | −0.0155 (8) | 0.0192 (8) | −0.0062 (8) |
O2 | 0.0550 (10) | 0.0572 (11) | 0.1064 (15) | 0.0003 (8) | 0.0251 (10) | 0.0144 (10) |
O3 | 0.0702 (11) | 0.0732 (12) | 0.0798 (13) | 0.0139 (9) | 0.0356 (10) | 0.0118 (9) |
O4 | 0.0687 (11) | 0.0942 (14) | 0.0773 (12) | −0.0395 (10) | 0.0365 (10) | −0.0279 (11) |
C1 | 0.0473 (13) | 0.0551 (14) | 0.0603 (15) | −0.0061 (11) | 0.0160 (11) | −0.0008 (11) |
C2 | 0.0512 (13) | 0.0572 (15) | 0.0611 (16) | −0.0057 (11) | 0.0108 (11) | −0.0010 (12) |
C3 | 0.0563 (14) | 0.0547 (15) | 0.0769 (17) | −0.0087 (12) | 0.0168 (12) | 0.0069 (13) |
C4 | 0.0579 (14) | 0.0644 (16) | 0.0664 (17) | 0.0000 (13) | 0.0185 (12) | 0.0019 (13) |
C5 | 0.0538 (14) | 0.0657 (16) | 0.0678 (17) | −0.0105 (12) | 0.0234 (12) | −0.0030 (13) |
C6 | 0.0425 (12) | 0.0472 (13) | 0.0563 (15) | 0.0025 (10) | 0.0163 (11) | −0.0035 (11) |
C7 | 0.0607 (14) | 0.0572 (15) | 0.0485 (14) | 0.0020 (12) | 0.0116 (11) | −0.0037 (11) |
C8 | 0.0516 (14) | 0.0666 (16) | 0.0607 (17) | −0.0045 (12) | 0.0067 (12) | −0.0154 (13) |
C9 | 0.0475 (13) | 0.0567 (15) | 0.0654 (17) | −0.0028 (11) | 0.0218 (12) | −0.0108 (13) |
C10 | 0.0650 (15) | 0.0573 (15) | 0.0575 (16) | −0.0033 (12) | 0.0204 (13) | 0.0013 (12) |
C11 | 0.0519 (13) | 0.0547 (14) | 0.0495 (15) | −0.0029 (11) | 0.0062 (11) | −0.0038 (11) |
C12 | 0.0592 (15) | 0.0733 (18) | 0.0820 (19) | −0.0111 (14) | 0.0296 (14) | −0.0188 (15) |
C13 | 0.0586 (15) | 0.0564 (15) | 0.0729 (17) | 0.0006 (13) | 0.0246 (13) | 0.0021 (13) |
C14 | 0.0611 (16) | 0.0638 (17) | 0.085 (2) | −0.0056 (13) | 0.0179 (14) | 0.0132 (14) |
C15 | 0.0554 (16) | 0.077 (2) | 0.089 (2) | −0.0041 (14) | 0.0100 (14) | 0.0058 (16) |
C16 | 0.0635 (16) | 0.0635 (17) | 0.0581 (16) | 0.0054 (13) | 0.0138 (12) | −0.0048 (13) |
C17 | 0.0751 (19) | 0.0711 (19) | 0.109 (2) | 0.0077 (16) | 0.0377 (17) | 0.0214 (17) |
C18 | 0.0593 (16) | 0.0697 (19) | 0.127 (3) | 0.0032 (15) | 0.0320 (16) | 0.0213 (18) |
C19 | 0.0708 (18) | 0.0694 (18) | 0.0617 (17) | 0.0012 (15) | 0.0110 (14) | −0.0095 (14) |
C20 | 0.0658 (16) | 0.0602 (16) | 0.0659 (17) | 0.0028 (13) | 0.0251 (13) | −0.0031 (13) |
C21 | 0.0631 (16) | 0.092 (2) | 0.0600 (17) | 0.0131 (14) | 0.0180 (13) | 0.0068 (15) |
C22 | 0.0791 (19) | 0.096 (2) | 0.0566 (17) | 0.0080 (16) | 0.0255 (14) | 0.0041 (15) |
C23 | 0.0696 (17) | 0.0758 (18) | 0.0599 (17) | 0.0084 (14) | 0.0251 (14) | −0.0065 (14) |
C24 | 0.0731 (17) | 0.082 (2) | 0.0751 (19) | 0.0233 (15) | 0.0275 (15) | 0.0006 (15) |
C25 | 0.0864 (19) | 0.0682 (18) | 0.0776 (19) | 0.0211 (15) | 0.0363 (16) | 0.0118 (14) |
C26 | 0.0759 (19) | 0.087 (2) | 0.0623 (18) | 0.0072 (16) | 0.0234 (15) | −0.0059 (14) |
C27 | 0.0573 (14) | 0.0616 (16) | 0.0613 (16) | −0.0136 (12) | 0.0180 (12) | −0.0055 (12) |
C28 | 0.0568 (15) | 0.091 (2) | 0.0736 (19) | −0.0217 (14) | 0.0226 (13) | −0.0140 (15) |
C29 | 0.0592 (16) | 0.097 (2) | 0.080 (2) | −0.0229 (15) | 0.0117 (15) | −0.0134 (17) |
C30 | 0.0724 (17) | 0.080 (2) | 0.0616 (17) | −0.0084 (15) | 0.0118 (14) | −0.0099 (14) |
C31 | 0.093 (2) | 0.136 (3) | 0.085 (2) | −0.040 (2) | 0.0442 (18) | −0.037 (2) |
C32 | 0.0716 (18) | 0.124 (3) | 0.089 (2) | −0.0450 (18) | 0.0413 (17) | −0.036 (2) |
C33 | 0.088 (2) | 0.119 (3) | 0.081 (2) | −0.018 (2) | 0.0133 (18) | −0.021 (2) |
Geometric parameters (Å, º) top
N1—C12 | 1.137 (3) | C11—H11 | 0.9300 |
N2—C19 | 1.143 (3) | C13—C14 | 1.371 (3) |
N3—C26 | 1.142 (3) | C13—C18 | 1.380 (3) |
N4—C33 | 1.139 (4) | C14—C15 | 1.378 (3) |
O1—C6 | 1.363 (2) | C14—H14 | 0.9300 |
O1—C2 | 1.427 (3) | C15—C16 | 1.369 (3) |
O2—C13 | 1.358 (3) | C15—H15 | 0.9300 |
O2—C3 | 1.432 (3) | C16—C17 | 1.380 (3) |
O3—C20 | 1.360 (3) | C16—C19 | 1.439 (4) |
O3—C4 | 1.425 (3) | C17—C18 | 1.376 (4) |
O4—C27 | 1.353 (3) | C17—H17 | 0.9300 |
O4—C5 | 1.419 (2) | C18—H18 | 0.9300 |
C1—C2 | 1.522 (3) | C20—C21 | 1.374 (3) |
C1—C4 | 1.523 (3) | C20—C25 | 1.381 (3) |
C1—C5 | 1.525 (3) | C21—C22 | 1.388 (3) |
C1—C3 | 1.527 (3) | C21—H21 | 0.9300 |
C2—H2A | 0.9700 | C22—C23 | 1.374 (3) |
C2—H2B | 0.9700 | C22—H22 | 0.9300 |
C3—H3A | 0.9700 | C23—C24 | 1.383 (4) |
C3—H3B | 0.9700 | C23—C26 | 1.437 (4) |
C4—H4A | 0.9700 | C24—C25 | 1.373 (3) |
C4—H4B | 0.9700 | C24—H24 | 0.9300 |
C5—H5A | 0.9700 | C25—H25 | 0.9300 |
C5—H5B | 0.9700 | C27—C28 | 1.363 (3) |
C6—C11 | 1.376 (3) | C27—C32 | 1.372 (3) |
C6—C7 | 1.380 (3) | C28—C29 | 1.368 (4) |
C7—C8 | 1.367 (3) | C28—H28 | 0.9300 |
C7—H7 | 0.9300 | C29—C30 | 1.361 (4) |
C8—C9 | 1.382 (3) | C29—H29 | 0.9300 |
C8—H8 | 0.9300 | C30—C31 | 1.383 (4) |
C9—C10 | 1.379 (3) | C30—C33 | 1.438 (4) |
C9—C12 | 1.438 (3) | C31—C32 | 1.356 (4) |
C10—C11 | 1.374 (3) | C31—H31 | 0.9300 |
C10—H10 | 0.9300 | C32—H32 | 0.9300 |
| | | |
C6—O1—C2 | 118.77 (17) | C14—C13—C18 | 119.4 (2) |
C13—O2—C3 | 117.07 (18) | C13—C14—C15 | 119.9 (2) |
C20—O3—C4 | 118.80 (19) | C13—C14—H14 | 120.0 |
C27—O4—C5 | 119.22 (18) | C15—C14—H14 | 120.0 |
C2—C1—C4 | 112.5 (2) | C16—C15—C14 | 121.0 (2) |
C2—C1—C5 | 108.51 (19) | C16—C15—H15 | 119.5 |
C4—C1—C5 | 109.08 (18) | C14—C15—H15 | 119.5 |
C2—C1—C3 | 107.47 (18) | C15—C16—C17 | 119.0 (2) |
C4—C1—C3 | 108.93 (19) | C15—C16—C19 | 120.7 (2) |
C5—C1—C3 | 110.3 (2) | C17—C16—C19 | 120.3 (2) |
O1—C2—C1 | 107.87 (19) | C18—C17—C16 | 120.3 (3) |
O1—C2—H2A | 110.1 | C18—C17—H17 | 119.9 |
C1—C2—H2A | 110.1 | C16—C17—H17 | 119.9 |
O1—C2—H2B | 110.1 | C17—C18—C13 | 120.3 (3) |
C1—C2—H2B | 110.1 | C17—C18—H18 | 119.9 |
H2A—C2—H2B | 108.4 | C13—C18—H18 | 119.9 |
O2—C3—C1 | 108.26 (18) | N2—C19—C16 | 179.2 (3) |
O2—C3—H3A | 110.0 | O3—C20—C21 | 125.1 (2) |
C1—C3—H3A | 110.0 | O3—C20—C25 | 115.0 (2) |
O2—C3—H3B | 110.0 | C21—C20—C25 | 119.9 (2) |
C1—C3—H3B | 110.0 | C20—C21—C22 | 119.6 (2) |
H3A—C3—H3B | 108.4 | C20—C21—H21 | 120.2 |
O3—C4—C1 | 108.18 (19) | C22—C21—H21 | 120.2 |
O3—C4—H4A | 110.1 | C23—C22—C21 | 120.7 (3) |
C1—C4—H4A | 110.1 | C23—C22—H22 | 119.6 |
O3—C4—H4B | 110.1 | C21—C22—H22 | 119.6 |
C1—C4—H4B | 110.1 | C22—C23—C24 | 119.2 (2) |
H4A—C4—H4B | 108.4 | C22—C23—C26 | 120.9 (3) |
O4—C5—C1 | 106.92 (18) | C24—C23—C26 | 119.9 (3) |
O4—C5—H5A | 110.3 | C25—C24—C23 | 120.3 (3) |
C1—C5—H5A | 110.3 | C25—C24—H24 | 119.8 |
O4—C5—H5B | 110.3 | C23—C24—H24 | 119.8 |
C1—C5—H5B | 110.3 | C24—C25—C20 | 120.3 (3) |
H5A—C5—H5B | 108.6 | C24—C25—H25 | 119.9 |
O1—C6—C11 | 124.7 (2) | C20—C25—H25 | 119.9 |
O1—C6—C7 | 114.9 (2) | N3—C26—C23 | 177.9 (3) |
C11—C6—C7 | 120.4 (2) | O4—C27—C28 | 124.8 (2) |
C8—C7—C6 | 120.1 (2) | O4—C27—C32 | 115.6 (2) |
C8—C7—H7 | 119.9 | C28—C27—C32 | 119.6 (2) |
C6—C7—H7 | 119.9 | C27—C28—C29 | 120.0 (2) |
C7—C8—C9 | 120.0 (2) | C27—C28—H28 | 120.0 |
C7—C8—H8 | 120.0 | C29—C28—H28 | 120.0 |
C9—C8—H8 | 120.0 | C30—C29—C28 | 121.1 (3) |
C10—C9—C8 | 119.4 (2) | C30—C29—H29 | 119.4 |
C10—C9—C12 | 120.6 (2) | C28—C29—H29 | 119.4 |
C8—C9—C12 | 120.0 (2) | C29—C30—C31 | 118.3 (3) |
C11—C10—C9 | 120.9 (2) | C29—C30—C33 | 120.9 (3) |
C11—C10—H10 | 119.5 | C31—C30—C33 | 120.8 (3) |
C9—C10—H10 | 119.5 | C32—C31—C30 | 121.0 (3) |
C10—C11—C6 | 119.1 (2) | C32—C31—H31 | 119.5 |
C10—C11—H11 | 120.4 | C30—C31—H31 | 119.5 |
C6—C11—H11 | 120.4 | C31—C32—C27 | 120.0 (3) |
N1—C12—C9 | 179.1 (3) | C31—C32—H32 | 120.0 |
O2—C13—C14 | 124.9 (2) | C27—C32—H32 | 120.0 |
O2—C13—C18 | 115.7 (2) | N4—C33—C30 | 179.7 (5) |
| | | |
C1—C2—O1—C6 | −158.68 (18) | C1—C4—O3—C20 | −166.3 (2) |
C1—C3—O2—C13 | 175.16 (19) | C1—C5—O4—C27 | −173.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C32—H32···N2i | 0.93 | 2.82 | 3.577 (4) | 139 |
C2—H2B···N1ii | 0.97 | 2.77 | 3.529 (3) | 136 |
C11—H11···N4iii | 0.93 | 2.60 | 3.518 (4) | 169 |
C28—H28···O1iv | 0.93 | 2.72 | 3.312 (3) | 123 |
C28—H28···C6iv | 0.93 | 2.70 | 3.533 (4) | 150 |
C8—H8···N2v | 0.93 | 2.79 | 3.689 (3) | 162 |
C7—H7···N2vi | 0.93 | 2.93 | 3.523 (3) | 123 |
C3—H3A···N3vii | 0.97 | 2.83 | 3.788 (4) | 170 |
C7—H7···N3vii | 0.93 | 2.77 | 3.467 (4) | 133 |
C3—H3B···N1ii | 0.97 | 2.62 | 3.444 (3) | 143 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, −y+2, −z+1; (iv) −x+2, y+1/2, −z+1/2; (v) x, y−1, z; (vi) −x+1, −y+2, −z; (vii) x−1, y, z. |