Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001473/na6289sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001473/na6289Isup2.hkl |
CCDC reference: 234913
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).
C20H14N2O2 | F(000) = 1312 |
Mr = 314.34 | Dx = 1.298 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1166 (9) Å | Cell parameters from 8964 reflections |
b = 12.0736 (12) Å | θ = 1.6–22.9° |
c = 20.9806 (15) Å | µ = 0.09 mm−1 |
β = 104.454 (5)° | T = 293 K |
V = 3217.4 (5) Å3 | Plate, yellow |
Z = 8 | 0.30 × 0.23 × 0.12 mm |
Stoe IPDS-2 diffractometer | 6304 independent reflections |
Radiation source: fine-focus sealed tube | 2114 reflections with I > 2σI) |
Graphite monochromator | Rint = 0.101 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω rotation scans | h = −15→16 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.976, Tmax = 0.990 | l = −25→25 |
37155 measured reflections |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0334P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.68 | (Δ/σ)max = 0.001 |
6304 reflections | Δρmax = 0.11 e Å−3 |
436 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0031 (2) |
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. |
x | y | z | Uiso*/Ueq | ||
O2A | 0.79217 (15) | 0.60047 (15) | 0.35243 (9) | 0.1002 (6) | |
O2B | 0.28933 (14) | 0.49637 (15) | 0.36589 (9) | 0.0964 (6) | |
C20A | 0.8122 (3) | 0.6545 (3) | 0.41376 (15) | 0.1379 (13) | |
H20A | 0.8184 | 0.6006 | 0.4481 | 0.207* | |
H20B | 0.7553 | 0.7042 | 0.4144 | 0.207* | |
H20C | 0.8766 | 0.6958 | 0.4206 | 0.207* | |
C20B | 0.3034 (2) | 0.5600 (2) | 0.42438 (15) | 0.1255 (11) | |
H20D | 0.3287 | 0.5130 | 0.4619 | 0.188* | |
H20E | 0.2373 | 0.5921 | 0.4264 | 0.188* | |
H20F | 0.3536 | 0.6178 | 0.4243 | 0.188* | |
O1A | 0.71751 (11) | 0.54223 (12) | 0.19595 (8) | 0.0702 (4) | |
C4A | 0.63498 (18) | 0.63352 (18) | 0.10015 (11) | 0.0625 (6) | |
H4A | 0.6985 | 0.6696 | 0.1024 | 0.075* | |
C5A | 0.62727 (18) | 0.55817 (18) | 0.14823 (12) | 0.0595 (6) | |
C6A | 0.53261 (18) | 0.50528 (18) | 0.14552 (12) | 0.0676 (6) | |
H6A | 0.5267 | 0.4556 | 0.1783 | 0.081* | |
C8A | 0.45350 (18) | 0.60184 (19) | 0.04519 (12) | 0.0637 (6) | |
C9A | 0.71283 (17) | 0.46603 (19) | 0.24807 (11) | 0.0707 (7) | |
H9A1 | 0.6839 | 0.3958 | 0.2294 | 0.085* | |
H9A2 | 0.6672 | 0.4956 | 0.2739 | 0.085* | |
C7A | 0.44716 (18) | 0.52719 (19) | 0.09353 (12) | 0.0696 (7) | |
H7A | 0.3839 | 0.4906 | 0.0912 | 0.083* | |
C10A | 0.82130 (18) | 0.4487 (2) | 0.29133 (12) | 0.0639 (6) | |
C3A | 0.54940 (19) | 0.65534 (17) | 0.04914 (11) | 0.0598 (6) | |
C14A | 0.9852 (2) | 0.3427 (2) | 0.32354 (13) | 0.0710 (7) | |
C15A | 0.88563 (19) | 0.35924 (19) | 0.27935 (12) | 0.0650 (6) | |
C1A | 0.3634 (2) | 0.6260 (2) | −0.00820 (15) | 0.0791 (8) | |
C16A | 0.8541 (2) | 0.2850 (2) | 0.22620 (13) | 0.0796 (7) | |
H16A | 0.7901 | 0.2959 | 0.1956 | 0.096* | |
C2A | 0.55921 (19) | 0.7335 (2) | −0.00033 (14) | 0.0749 (7) | |
C12A | 0.9584 (2) | 0.5019 (2) | 0.38668 (12) | 0.0864 (8) | |
H12A | 0.9827 | 0.5501 | 0.4217 | 0.104* | |
C11A | 0.8581 (2) | 0.5162 (2) | 0.34407 (13) | 0.0752 (7) | |
N1A | 0.29324 (19) | 0.6453 (2) | −0.05126 (13) | 0.1109 (8) | |
N2A | 0.56653 (19) | 0.7966 (2) | −0.03955 (12) | 0.1042 (8) | |
C18A | 1.0129 (3) | 0.1806 (2) | 0.26351 (18) | 0.1022 (10) | |
H18A | 1.0542 | 0.1202 | 0.2584 | 0.123* | |
C17A | 0.9155 (3) | 0.1976 (2) | 0.21893 (16) | 0.0970 (9) | |
H17A | 0.8926 | 0.1488 | 0.1840 | 0.116* | |
C13A | 1.0191 (2) | 0.4164 (2) | 0.37576 (13) | 0.0828 (8) | |
H13A | 1.0854 | 0.4066 | 0.4040 | 0.099* | |
C19A | 1.0470 (2) | 0.2514 (3) | 0.31384 (16) | 0.0892 (8) | |
H19A | 1.1124 | 0.2400 | 0.3428 | 0.107* | |
O1B | 0.24615 (12) | 0.44710 (13) | 0.20037 (8) | 0.0801 (5) | |
C10B | 0.35431 (18) | 0.37472 (19) | 0.29918 (12) | 0.0635 (6) | |
C5B | 0.15199 (19) | 0.4758 (2) | 0.16018 (11) | 0.0659 (6) | |
C3B | 0.0655 (2) | 0.60241 (19) | 0.07626 (11) | 0.0651 (6) | |
C14B | 0.5394 (2) | 0.31830 (19) | 0.32883 (13) | 0.0670 (6) | |
C6B | 0.05794 (18) | 0.42360 (19) | 0.15835 (11) | 0.0717 (7) | |
H6B | 0.0554 | 0.3641 | 0.1860 | 0.086* | |
C15B | 0.4382 (2) | 0.31334 (18) | 0.28512 (12) | 0.0642 (6) | |
C4B | 0.15612 (18) | 0.5646 (2) | 0.11894 (11) | 0.0690 (7) | |
H4B | 0.2202 | 0.5986 | 0.1202 | 0.083* | |
C7B | −0.03295 (19) | 0.4613 (2) | 0.11452 (12) | 0.0730 (7) | |
H7B | −0.0967 | 0.4260 | 0.1126 | 0.088* | |
C8B | −0.03024 (19) | 0.5500 (2) | 0.07397 (11) | 0.0669 (6) | |
C13B | 0.5541 (2) | 0.3862 (2) | 0.38433 (13) | 0.0766 (7) | |
H13B | 0.6207 | 0.3907 | 0.4130 | 0.092* | |
C1B | −0.1257 (2) | 0.5897 (2) | 0.03059 (13) | 0.0776 (7) | |
C12B | 0.4743 (2) | 0.4459 (2) | 0.39766 (12) | 0.0760 (7) | |
H12B | 0.4861 | 0.4909 | 0.4348 | 0.091* | |
C9B | 0.24603 (18) | 0.37158 (19) | 0.25419 (11) | 0.0728 (7) | |
H9B1 | 0.2289 | 0.2971 | 0.2376 | 0.087* | |
H9B2 | 0.1943 | 0.3946 | 0.2775 | 0.087* | |
C11B | 0.3733 (2) | 0.43881 (19) | 0.35466 (13) | 0.0714 (6) | |
C16B | 0.4258 (2) | 0.2459 (2) | 0.22859 (13) | 0.0782 (7) | |
H16B | 0.3604 | 0.2423 | 0.1985 | 0.094* | |
C2B | 0.0708 (2) | 0.6961 (2) | 0.03488 (14) | 0.0801 (8) | |
C19B | 0.6223 (2) | 0.2553 (2) | 0.31557 (15) | 0.0830 (8) | |
H19B | 0.6887 | 0.2585 | 0.3444 | 0.100* | |
C18B | 0.6065 (3) | 0.1903 (2) | 0.26153 (17) | 0.0930 (9) | |
H18B | 0.6617 | 0.1482 | 0.2539 | 0.112* | |
C17B | 0.5078 (3) | 0.1861 (2) | 0.21721 (14) | 0.0918 (8) | |
H17B | 0.4978 | 0.1424 | 0.1797 | 0.110* | |
N1B | −0.20274 (19) | 0.6199 (2) | −0.00397 (12) | 0.1038 (8) | |
N2B | 0.0767 (2) | 0.7709 (2) | 0.00272 (13) | 0.1107 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2A | 0.1071 (15) | 0.1006 (14) | 0.0838 (14) | 0.0269 (12) | 0.0070 (11) | −0.0155 (11) |
O2B | 0.0789 (12) | 0.1067 (14) | 0.0945 (14) | 0.0170 (11) | 0.0046 (11) | −0.0212 (11) |
C20A | 0.139 (3) | 0.170 (3) | 0.098 (2) | 0.025 (2) | 0.016 (2) | −0.054 (2) |
C20B | 0.113 (2) | 0.134 (3) | 0.125 (3) | 0.012 (2) | 0.020 (2) | −0.059 (2) |
O1A | 0.0603 (10) | 0.0758 (10) | 0.0689 (11) | −0.0078 (8) | 0.0058 (9) | 0.0159 (9) |
C4A | 0.0563 (16) | 0.0660 (15) | 0.0641 (16) | −0.0023 (12) | 0.0128 (14) | 0.0002 (13) |
C5A | 0.0538 (15) | 0.0626 (15) | 0.0590 (15) | 0.0003 (13) | 0.0082 (13) | −0.0009 (13) |
C6A | 0.0608 (16) | 0.0670 (15) | 0.0736 (17) | −0.0027 (13) | 0.0142 (15) | 0.0068 (13) |
C8A | 0.0553 (16) | 0.0668 (16) | 0.0631 (16) | 0.0077 (13) | 0.0039 (14) | −0.0084 (13) |
C9A | 0.0684 (17) | 0.0737 (16) | 0.0692 (17) | 0.0021 (13) | 0.0157 (14) | 0.0179 (14) |
C7A | 0.0567 (16) | 0.0706 (17) | 0.0796 (18) | −0.0012 (13) | 0.0137 (15) | −0.0094 (15) |
C10A | 0.0597 (16) | 0.0673 (15) | 0.0614 (16) | 0.0016 (14) | 0.0091 (13) | 0.0116 (13) |
C3A | 0.0641 (17) | 0.0590 (14) | 0.0554 (15) | 0.0080 (13) | 0.0132 (14) | −0.0009 (12) |
C14A | 0.0628 (17) | 0.0755 (18) | 0.0733 (18) | 0.0045 (15) | 0.0142 (16) | 0.0178 (15) |
C15A | 0.0671 (17) | 0.0662 (16) | 0.0623 (16) | −0.0041 (14) | 0.0173 (14) | 0.0131 (13) |
C1A | 0.0697 (18) | 0.0760 (18) | 0.0839 (19) | 0.0019 (15) | 0.0046 (17) | −0.0118 (15) |
C16A | 0.0728 (18) | 0.0775 (18) | 0.090 (2) | 0.0001 (16) | 0.0236 (16) | 0.0004 (16) |
C2A | 0.0705 (18) | 0.0797 (19) | 0.0720 (19) | 0.0134 (15) | 0.0132 (15) | 0.0040 (16) |
C12A | 0.087 (2) | 0.092 (2) | 0.0699 (19) | −0.0007 (17) | 0.0016 (17) | 0.0020 (15) |
C11A | 0.0775 (19) | 0.0774 (19) | 0.0663 (18) | 0.0076 (15) | 0.0093 (16) | 0.0081 (15) |
N1A | 0.0827 (17) | 0.1173 (19) | 0.112 (2) | 0.0042 (15) | −0.0144 (16) | 0.0028 (16) |
N2A | 0.1044 (19) | 0.1096 (19) | 0.099 (2) | 0.0213 (15) | 0.0262 (16) | 0.0297 (16) |
C18A | 0.108 (3) | 0.083 (2) | 0.129 (3) | 0.015 (2) | 0.054 (2) | 0.017 (2) |
C17A | 0.099 (2) | 0.087 (2) | 0.110 (2) | −0.0026 (19) | 0.036 (2) | −0.0098 (18) |
C13A | 0.0676 (18) | 0.101 (2) | 0.0723 (19) | 0.0012 (17) | 0.0026 (15) | 0.0223 (17) |
C19A | 0.0735 (19) | 0.095 (2) | 0.102 (2) | 0.0162 (19) | 0.0283 (18) | 0.0341 (19) |
O1B | 0.0620 (11) | 0.0962 (12) | 0.0734 (11) | −0.0102 (10) | 0.0003 (10) | 0.0165 (10) |
C10B | 0.0581 (16) | 0.0656 (15) | 0.0616 (16) | −0.0063 (13) | 0.0051 (13) | 0.0055 (13) |
C5B | 0.0576 (17) | 0.0737 (17) | 0.0604 (16) | −0.0033 (14) | 0.0031 (14) | −0.0012 (13) |
C3B | 0.0712 (18) | 0.0637 (16) | 0.0610 (16) | 0.0035 (14) | 0.0176 (14) | −0.0018 (13) |
C14B | 0.0667 (18) | 0.0596 (16) | 0.0731 (18) | −0.0034 (14) | 0.0141 (15) | 0.0154 (14) |
C6B | 0.0651 (17) | 0.0766 (17) | 0.0686 (17) | −0.0094 (14) | 0.0079 (15) | 0.0038 (13) |
C15B | 0.0702 (18) | 0.0605 (15) | 0.0613 (17) | −0.0104 (13) | 0.0156 (15) | 0.0064 (13) |
C4B | 0.0629 (17) | 0.0756 (17) | 0.0650 (16) | −0.0080 (14) | 0.0097 (14) | −0.0032 (14) |
C7B | 0.0626 (17) | 0.0821 (18) | 0.0696 (17) | −0.0070 (14) | 0.0077 (14) | −0.0006 (15) |
C8B | 0.0617 (17) | 0.0747 (16) | 0.0592 (16) | 0.0078 (15) | 0.0056 (13) | −0.0041 (14) |
C13B | 0.0700 (18) | 0.0758 (18) | 0.0734 (18) | −0.0039 (15) | −0.0018 (15) | 0.0101 (15) |
C1B | 0.0765 (19) | 0.0866 (19) | 0.0720 (19) | 0.0047 (16) | 0.0227 (17) | 0.0011 (15) |
C12B | 0.0811 (19) | 0.0681 (16) | 0.0693 (17) | −0.0032 (15) | 0.0011 (16) | −0.0022 (14) |
C9B | 0.0660 (17) | 0.0772 (16) | 0.0713 (17) | −0.0076 (13) | 0.0101 (14) | 0.0125 (14) |
C11B | 0.0689 (17) | 0.0683 (16) | 0.0721 (17) | 0.0032 (14) | 0.0084 (15) | 0.0028 (14) |
C16B | 0.0821 (19) | 0.0759 (17) | 0.0755 (19) | −0.0105 (16) | 0.0174 (15) | 0.0012 (15) |
C2B | 0.0771 (19) | 0.083 (2) | 0.078 (2) | 0.0080 (16) | 0.0157 (16) | −0.0041 (17) |
C19B | 0.0756 (19) | 0.0751 (18) | 0.100 (2) | 0.0042 (16) | 0.0243 (17) | 0.0237 (17) |
C18B | 0.100 (3) | 0.081 (2) | 0.108 (3) | 0.0102 (18) | 0.044 (2) | 0.0180 (19) |
C17B | 0.113 (3) | 0.082 (2) | 0.085 (2) | −0.0041 (19) | 0.035 (2) | −0.0025 (16) |
N1B | 0.0808 (17) | 0.126 (2) | 0.1017 (19) | 0.0162 (15) | 0.0169 (15) | 0.0241 (16) |
N2B | 0.123 (2) | 0.102 (2) | 0.109 (2) | 0.0062 (17) | 0.0326 (17) | 0.0214 (16) |
O2A—C11A | 1.375 (3) | C18A—C17A | 1.397 (4) |
O2A—C20A | 1.408 (3) | C18A—H18A | 0.9300 |
O2B—C11B | 1.371 (3) | C17A—H17A | 0.9300 |
O2B—C20B | 1.420 (3) | C13A—H13A | 0.9300 |
C20A—H20A | 0.9600 | C19A—H19A | 0.9300 |
C20A—H20B | 0.9600 | O1B—C5B | 1.355 (2) |
C20A—H20C | 0.9600 | O1B—C9B | 1.452 (2) |
C20B—H20D | 0.9600 | C10B—C11B | 1.368 (3) |
C20B—H20E | 0.9600 | C10B—C15B | 1.417 (3) |
C20B—H20F | 0.9600 | C10B—C9B | 1.497 (3) |
O1A—C5A | 1.360 (2) | C5B—C6B | 1.377 (3) |
O1A—C9A | 1.442 (2) | C5B—C4B | 1.387 (3) |
C4A—C3A | 1.369 (3) | C3B—C4B | 1.376 (3) |
C4A—C5A | 1.381 (3) | C3B—C8B | 1.396 (3) |
C4A—H4A | 0.9300 | C3B—C2B | 1.438 (3) |
C5A—C6A | 1.385 (3) | C14B—C13B | 1.397 (3) |
C6A—C7A | 1.380 (3) | C14B—C19B | 1.410 (3) |
C6A—H6A | 0.9300 | C14B—C15B | 1.414 (3) |
C8A—C7A | 1.375 (3) | C6B—C7B | 1.388 (3) |
C8A—C3A | 1.398 (3) | C6B—H6B | 0.9300 |
C8A—C1A | 1.441 (3) | C15B—C16B | 1.414 (3) |
C9A—C10A | 1.499 (3) | C4B—H4B | 0.9300 |
C9A—H9A1 | 0.9700 | C7B—C8B | 1.374 (3) |
C9A—H9A2 | 0.9700 | C7B—H7B | 0.9300 |
C7A—H7A | 0.9300 | C8B—C1B | 1.434 (3) |
C10A—C11A | 1.362 (3) | C13B—C12B | 1.357 (3) |
C10A—C15A | 1.431 (3) | C13B—H13B | 0.9300 |
C3A—C2A | 1.432 (3) | C1B—N1B | 1.146 (3) |
C14A—C13A | 1.395 (3) | C12B—C11B | 1.407 (3) |
C14A—C19A | 1.412 (3) | C12B—H12B | 0.9300 |
C14A—C15A | 1.414 (3) | C9B—H9B1 | 0.9700 |
C15A—C16A | 1.410 (3) | C9B—H9B2 | 0.9700 |
C1A—N1A | 1.141 (3) | C16B—C17B | 1.365 (3) |
C16A—C17A | 1.359 (3) | C16B—H16B | 0.9300 |
C16A—H16A | 0.9300 | C2B—N2B | 1.141 (3) |
C2A—N2A | 1.143 (3) | C19B—C18B | 1.352 (3) |
C12A—C13A | 1.358 (3) | C19B—H19B | 0.9300 |
C12A—C11A | 1.404 (3) | C18B—C17B | 1.393 (4) |
C12A—H12A | 0.9300 | C18B—H18B | 0.9300 |
C18A—C19A | 1.346 (4) | C17B—H17B | 0.9300 |
C11A—O2A—C20A | 118.7 (2) | C18A—C17A—H17A | 119.7 |
C11B—O2B—C20B | 119.1 (2) | C12A—C13A—C14A | 122.1 (3) |
O2A—C20A—H20A | 109.5 | C12A—C13A—H13A | 118.9 |
O2A—C20A—H20B | 109.5 | C14A—C13A—H13A | 118.9 |
H20A—C20A—H20B | 109.5 | C18A—C19A—C14A | 121.3 (3) |
O2A—C20A—H20C | 109.5 | C18A—C19A—H19A | 119.4 |
H20A—C20A—H20C | 109.5 | C14A—C19A—H19A | 119.4 |
H20B—C20A—H20C | 109.5 | C5B—O1B—C9B | 117.81 (18) |
O2B—C20B—H20D | 109.5 | C11B—C10B—C15B | 119.2 (2) |
O2B—C20B—H20E | 109.5 | C11B—C10B—C9B | 119.6 (2) |
H20D—C20B—H20E | 109.5 | C15B—C10B—C9B | 121.3 (2) |
O2B—C20B—H20F | 109.5 | O1B—C5B—C6B | 124.9 (2) |
H20D—C20B—H20F | 109.5 | O1B—C5B—C4B | 114.5 (2) |
H20E—C20B—H20F | 109.5 | C6B—C5B—C4B | 120.7 (2) |
C5A—O1A—C9A | 117.04 (17) | C4B—C3B—C8B | 119.7 (2) |
C3A—C4A—C5A | 120.2 (2) | C4B—C3B—C2B | 119.3 (2) |
C3A—C4A—H4A | 119.9 | C8B—C3B—C2B | 121.0 (2) |
C5A—C4A—H4A | 119.9 | C13B—C14B—C19B | 121.9 (3) |
O1A—C5A—C4A | 115.0 (2) | C13B—C14B—C15B | 118.5 (2) |
O1A—C5A—C6A | 124.9 (2) | C19B—C14B—C15B | 119.6 (3) |
C4A—C5A—C6A | 120.2 (2) | C5B—C6B—C7B | 118.9 (2) |
C7A—C6A—C5A | 119.1 (2) | C5B—C6B—H6B | 120.5 |
C7A—C6A—H6A | 120.4 | C7B—C6B—H6B | 120.5 |
C5A—C6A—H6A | 120.4 | C16B—C15B—C14B | 117.5 (2) |
C7A—C8A—C3A | 118.6 (2) | C16B—C15B—C10B | 122.9 (2) |
C7A—C8A—C1A | 121.1 (2) | C14B—C15B—C10B | 119.7 (2) |
C3A—C8A—C1A | 120.3 (2) | C3B—C4B—C5B | 120.0 (2) |
O1A—C9A—C10A | 109.55 (18) | C3B—C4B—H4B | 120.0 |
O1A—C9A—H9A1 | 109.8 | C5B—C4B—H4B | 120.0 |
C10A—C9A—H9A1 | 109.8 | C8B—C7B—C6B | 121.0 (2) |
O1A—C9A—H9A2 | 109.8 | C8B—C7B—H7B | 119.5 |
C10A—C9A—H9A2 | 109.8 | C6B—C7B—H7B | 119.5 |
H9A1—C9A—H9A2 | 108.2 | C7B—C8B—C3B | 119.6 (2) |
C8A—C7A—C6A | 121.5 (2) | C7B—C8B—C1B | 120.0 (2) |
C8A—C7A—H7A | 119.3 | C3B—C8B—C1B | 120.4 (2) |
C6A—C7A—H7A | 119.3 | C12B—C13B—C14B | 122.0 (2) |
C11A—C10A—C15A | 119.3 (2) | C12B—C13B—H13B | 119.0 |
C11A—C10A—C9A | 119.9 (2) | C14B—C13B—H13B | 119.0 |
C15A—C10A—C9A | 120.8 (2) | N1B—C1B—C8B | 179.0 (3) |
C4A—C3A—C8A | 120.5 (2) | C13B—C12B—C11B | 119.2 (2) |
C4A—C3A—C2A | 119.3 (2) | C13B—C12B—H12B | 120.4 |
C8A—C3A—C2A | 120.3 (2) | C11B—C12B—H12B | 120.4 |
C13A—C14A—C19A | 121.9 (3) | O1B—C9B—C10B | 106.83 (18) |
C13A—C14A—C15A | 119.1 (2) | O1B—C9B—H9B1 | 110.4 |
C19A—C14A—C15A | 119.0 (3) | C10B—C9B—H9B1 | 110.4 |
C16A—C15A—C14A | 118.0 (2) | O1B—C9B—H9B2 | 110.4 |
C16A—C15A—C10A | 123.3 (2) | C10B—C9B—H9B2 | 110.4 |
C14A—C15A—C10A | 118.7 (2) | H9B1—C9B—H9B2 | 108.6 |
N1A—C1A—C8A | 178.7 (3) | C10B—C11B—O2B | 116.7 (2) |
C17A—C16A—C15A | 121.1 (3) | C10B—C11B—C12B | 121.5 (2) |
C17A—C16A—H16A | 119.4 | O2B—C11B—C12B | 121.8 (2) |
C15A—C16A—H16A | 119.4 | C17B—C16B—C15B | 121.4 (3) |
N2A—C2A—C3A | 179.4 (3) | C17B—C16B—H16B | 119.3 |
C13A—C12A—C11A | 118.8 (3) | C15B—C16B—H16B | 119.3 |
C13A—C12A—H12A | 120.6 | N2B—C2B—C3B | 178.8 (3) |
C11A—C12A—H12A | 120.6 | C18B—C19B—C14B | 121.0 (3) |
C10A—C11A—O2A | 116.1 (2) | C18B—C19B—H19B | 119.5 |
C10A—C11A—C12A | 121.9 (3) | C14B—C19B—H19B | 119.5 |
O2A—C11A—C12A | 121.9 (3) | C19B—C18B—C17B | 120.2 (3) |
C19A—C18A—C17A | 120.0 (3) | C19B—C18B—H18B | 119.9 |
C19A—C18A—H18A | 120.0 | C17B—C18B—H18B | 119.9 |
C17A—C18A—H18A | 120.0 | C16B—C17B—C18B | 120.4 (3) |
C16A—C17A—C18A | 120.6 (3) | C16B—C17B—H17B | 119.8 |
C16A—C17A—H17A | 119.7 | C18B—C17B—H17B | 119.8 |
C9A—O1A—C5A—C4A | 178.69 (18) | C9B—O1B—C5B—C6B | −13.0 (3) |
C9A—O1A—C5A—C6A | −1.3 (3) | C9B—O1B—C5B—C4B | 167.22 (19) |
C3A—C4A—C5A—O1A | 179.2 (2) | O1B—C5B—C6B—C7B | −179.8 (2) |
C3A—C4A—C5A—C6A | −0.8 (3) | C4B—C5B—C6B—C7B | 0.0 (3) |
O1A—C5A—C6A—C7A | −178.7 (2) | C13B—C14B—C15B—C16B | 178.7 (2) |
C4A—C5A—C6A—C7A | 1.4 (3) | C19B—C14B—C15B—C16B | −1.3 (3) |
C5A—O1A—C9A—C10A | 173.32 (19) | C13B—C14B—C15B—C10B | −1.4 (3) |
C3A—C8A—C7A—C6A | 0.6 (3) | C19B—C14B—C15B—C10B | 178.58 (19) |
C1A—C8A—C7A—C6A | −178.7 (2) | C11B—C10B—C15B—C16B | −179.4 (2) |
C5A—C6A—C7A—C8A | −1.3 (3) | C9B—C10B—C15B—C16B | 0.0 (3) |
O1A—C9A—C10A—C11A | 89.6 (2) | C11B—C10B—C15B—C14B | 0.7 (3) |
O1A—C9A—C10A—C15A | −92.7 (2) | C9B—C10B—C15B—C14B | −179.9 (2) |
C5A—C4A—C3A—C8A | 0.1 (3) | C8B—C3B—C4B—C5B | −0.9 (3) |
C5A—C4A—C3A—C2A | −179.8 (2) | C2B—C3B—C4B—C5B | 178.6 (2) |
C7A—C8A—C3A—C4A | 0.0 (3) | O1B—C5B—C4B—C3B | −179.3 (2) |
C1A—C8A—C3A—C4A | 179.3 (2) | C6B—C5B—C4B—C3B | 0.9 (3) |
C7A—C8A—C3A—C2A | 179.9 (2) | C5B—C6B—C7B—C8B | −0.8 (4) |
C1A—C8A—C3A—C2A | −0.8 (3) | C6B—C7B—C8B—C3B | 0.7 (3) |
C13A—C14A—C15A—C16A | 178.7 (2) | C6B—C7B—C8B—C1B | −178.0 (2) |
C19A—C14A—C15A—C16A | −1.9 (3) | C4B—C3B—C8B—C7B | 0.2 (3) |
C13A—C14A—C15A—C10A | −2.5 (3) | C2B—C3B—C8B—C7B | −179.4 (2) |
C19A—C14A—C15A—C10A | 177.0 (2) | C4B—C3B—C8B—C1B | 178.9 (2) |
C11A—C10A—C15A—C16A | 179.8 (2) | C2B—C3B—C8B—C1B | −0.7 (3) |
C9A—C10A—C15A—C16A | 2.1 (3) | C19B—C14B—C13B—C12B | −179.1 (2) |
C11A—C10A—C15A—C14A | 1.0 (3) | C15B—C14B—C13B—C12B | 0.8 (3) |
C9A—C10A—C15A—C14A | −176.7 (2) | C7B—C8B—C1B—N1B | −18 (17) |
C7A—C8A—C1A—N1A | −144 (13) | C3B—C8B—C1B—N1B | 163 (100) |
C3A—C8A—C1A—N1A | 37 (13) | C14B—C13B—C12B—C11B | 0.4 (4) |
C14A—C15A—C16A—C17A | 2.4 (3) | C5B—O1B—C9B—C10B | −167.0 (2) |
C10A—C15A—C16A—C17A | −176.4 (2) | C11B—C10B—C9B—O1B | 98.9 (2) |
C4A—C3A—C2A—N2A | −104 (34) | C15B—C10B—C9B—O1B | −80.5 (2) |
C8A—C3A—C2A—N2A | 76 (34) | C15B—C10B—C11B—O2B | −179.96 (19) |
C15A—C10A—C11A—O2A | 179.86 (19) | C9B—C10B—C11B—O2B | 0.7 (3) |
C9A—C10A—C11A—O2A | −2.4 (3) | C15B—C10B—C11B—C12B | 0.6 (3) |
C15A—C10A—C11A—C12A | 1.1 (3) | C9B—C10B—C11B—C12B | −178.8 (2) |
C9A—C10A—C11A—C12A | 178.8 (2) | C20B—O2B—C11B—C10B | 177.0 (2) |
C20A—O2A—C11A—C10A | 163.7 (2) | C20B—O2B—C11B—C12B | −3.5 (4) |
C20A—O2A—C11A—C12A | −17.5 (4) | C13B—C12B—C11B—C10B | −1.2 (4) |
C13A—C12A—C11A—C10A | −1.7 (4) | C13B—C12B—C11B—O2B | 179.4 (2) |
C13A—C12A—C11A—O2A | 179.6 (2) | C14B—C15B—C16B—C17B | 1.3 (3) |
C15A—C16A—C17A—C18A | −1.2 (4) | C10B—C15B—C16B—C17B | −178.7 (2) |
C19A—C18A—C17A—C16A | −0.6 (4) | C4B—C3B—C2B—N2B | −14 (15) |
C11A—C12A—C13A—C14A | 0.2 (4) | C8B—C3B—C2B—N2B | 165 (100) |
C19A—C14A—C13A—C12A | −177.5 (2) | C13B—C14B—C19B—C18B | −179.8 (2) |
C15A—C14A—C13A—C12A | 1.8 (4) | C15B—C14B—C19B—C18B | 0.2 (3) |
C17A—C18A—C19A—C14A | 1.1 (4) | C14B—C19B—C18B—C17B | 1.2 (4) |
C13A—C14A—C19A—C18A | 179.5 (2) | C15B—C16B—C17B—C18B | 0.0 (4) |
C15A—C14A—C19A—C18A | 0.1 (4) | C19B—C18B—C17B—C16B | −1.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H9A2···O2A | 0.97 | 2.38 | 2.716 (3) | 100 |
C9B—H9B2···O2B | 0.97 | 2.31 | 2.724 (3) | 105 |