The title compound, C39H39N3O4, although having potential C2 molecular symmetry, crystallizes as an asymmetric conformer, due to a couple of strong intramolecular hydrogen bonds involving hydroxyl groups and a pyridine N atom. This geometrical feature explains why this compound behaves as a poor chiral inductor for asymmetric synthesis.
Supporting information
CCDC reference: 269399
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.097
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.53 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C14' - C15 .. 5.67 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C37
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 29.00
From the CIF: _reflns_number_total 4642
Count of symmetry unique reflns 4643
Completeness (_total/calc) 99.98%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.
N,
N'-Bis[(
R)-2-hydroxy-2-phenylethyl]-
N,
N'-bis[(
S)-1-phenylethyl]pyridine-2,6- dicarboxamide
top
Crystal data top
C39H39N3O4 | F(000) = 652 |
Mr = 613.73 | Dx = 1.215 Mg m−3 |
Monoclinic, P21 | Melting point: 475 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7976 (9) Å | Cell parameters from 49 reflections |
b = 14.3385 (13) Å | θ = 4.4–13.5° |
c = 11.9807 (10) Å | µ = 0.08 mm−1 |
β = 94.534 (4)° | T = 299 K |
V = 1677.8 (3) Å3 | Prism, colorless |
Z = 2 | 0.6 × 0.6 × 0.6 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 29.0°, θmin = 1.7° |
Graphite monochromator | h = −13→6 |
2θ/ω scans | k = −1→19 |
7926 measured reflections | l = −16→16 |
4642 independent reflections | 3 standard reflections every 97 reflections |
3939 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0436P)2 + 0.1246P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4642 reflections | Δρmax = 0.13 e Å−3 |
422 parameters | Δρmin = −0.10 e Å−3 |
1 restraint | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0140 (16) |
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 | 0.56887 (14) | 0.16974 (12) | 0.50422 (13) | 0.0506 (3) | |
C2 | 0.60834 (17) | 0.19986 (14) | 0.40545 (16) | 0.0518 (4) | |
C3 | 0.7402 (2) | 0.23066 (18) | 0.3929 (2) | 0.0651 (5) | |
H3A | 0.7649 | 0.2512 | 0.3237 | 0.078* | |
C4 | 0.8341 (2) | 0.2304 (2) | 0.4848 (2) | 0.0739 (6) | |
H4A | 0.9232 | 0.2509 | 0.4783 | 0.089* | |
C5 | 0.79470 (19) | 0.19945 (18) | 0.58675 (19) | 0.0652 (5) | |
H5A | 0.8568 | 0.1984 | 0.6496 | 0.078* | |
C6 | 0.66073 (18) | 0.17004 (15) | 0.59330 (16) | 0.0535 (4) | |
C7 | 0.61876 (18) | 0.12703 (16) | 0.70037 (17) | 0.0562 (4) | |
O8 | 0.69974 (16) | 0.07295 (16) | 0.74890 (15) | 0.0836 (6) | |
N9 | 0.49263 (15) | 0.14449 (11) | 0.73447 (12) | 0.0487 (3) | |
C10 | 0.45360 (19) | 0.09136 (15) | 0.83352 (15) | 0.0524 (4) | |
H10A | 0.5127 | 0.0362 | 0.8398 | 0.063* | |
C11 | 0.4836 (3) | 0.1474 (2) | 0.94068 (17) | 0.0744 (6) | |
H11A | 0.5776 | 0.1669 | 0.9463 | 0.112* | |
H11B | 0.4668 | 0.1093 | 1.0041 | 0.112* | |
H11C | 0.4252 | 0.2012 | 0.9392 | 0.112* | |
C12 | 0.3073 (2) | 0.05609 (14) | 0.81451 (16) | 0.0538 (4) | |
C13 | 0.2019 (2) | 0.0888 (2) | 0.8726 (2) | 0.0746 (6) | |
H13A | 0.2203 | 0.1309 | 0.9309 | 0.090* | |
C13' | 0.2763 (3) | −0.00903 (18) | 0.7312 (2) | 0.0767 (6) | |
H13B | 0.3462 | −0.0343 | 0.6925 | 0.092* | |
C14 | 0.0672 (3) | 0.0597 (3) | 0.8454 (3) | 0.1027 (11) | |
H14A | −0.0028 | 0.0822 | 0.8860 | 0.123* | |
C14' | 0.1409 (4) | −0.0373 (2) | 0.7046 (3) | 0.1069 (11) | |
H14B | 0.1212 | −0.0810 | 0.6484 | 0.128* | |
C15 | 0.0381 (3) | −0.0007 (3) | 0.7609 (4) | 0.1091 (11) | |
H15A | −0.0523 | −0.0175 | 0.7410 | 0.131* | |
C16 | 0.41494 (18) | 0.22931 (13) | 0.70310 (14) | 0.0486 (4) | |
H16A | 0.4722 | 0.2692 | 0.6610 | 0.058* | |
H16B | 0.3971 | 0.2623 | 0.7711 | 0.058* | |
C17 | 0.27764 (17) | 0.21506 (13) | 0.63343 (14) | 0.0461 (4) | |
H17A | 0.2184 | 0.1771 | 0.6774 | 0.055* | |
O18 | 0.29451 (13) | 0.16787 (11) | 0.53179 (11) | 0.0562 (3) | |
H18 | 0.385 (3) | 0.165 (2) | 0.521 (2) | 0.084* | |
C19 | 0.20986 (18) | 0.30871 (14) | 0.61257 (16) | 0.0507 (4) | |
C20 | 0.2443 (3) | 0.36618 (17) | 0.5266 (2) | 0.0704 (6) | |
H20A | 0.3106 | 0.3474 | 0.4799 | 0.084* | |
C20' | 0.1119 (2) | 0.33878 (18) | 0.6822 (2) | 0.0682 (6) | |
H20B | 0.0881 | 0.3011 | 0.7408 | 0.082* | |
C21 | 0.1796 (4) | 0.4524 (2) | 0.5099 (3) | 0.0949 (10) | |
H21A | 0.2024 | 0.4909 | 0.4517 | 0.114* | |
C21' | 0.0495 (3) | 0.4248 (2) | 0.6646 (3) | 0.0949 (10) | |
H21B | −0.0156 | 0.4447 | 0.7118 | 0.114* | |
C22 | 0.0826 (3) | 0.4803 (2) | 0.5790 (4) | 0.1086 (12) | |
H22A | 0.0391 | 0.5375 | 0.5673 | 0.130* | |
C23 | 0.49740 (18) | 0.20656 (15) | 0.31124 (16) | 0.0527 (4) | |
O24 | 0.48199 (17) | 0.28148 (13) | 0.26241 (16) | 0.0762 (5) | |
N25 | 0.41242 (15) | 0.13278 (12) | 0.28967 (12) | 0.0496 (3) | |
C26 | 0.4556 (2) | 0.03478 (14) | 0.31379 (16) | 0.0520 (4) | |
H26A | 0.5391 | 0.0379 | 0.3644 | 0.062* | |
C27 | 0.3505 (3) | −0.01898 (18) | 0.3750 (2) | 0.0712 (6) | |
H27A | 0.3306 | 0.0146 | 0.4411 | 0.107* | |
H27B | 0.3865 | −0.0794 | 0.3958 | 0.107* | |
H27C | 0.2681 | −0.0262 | 0.3269 | 0.107* | |
C28 | 0.49456 (18) | −0.01309 (14) | 0.20672 (15) | 0.0511 (4) | |
C29 | 0.6285 (2) | −0.00810 (17) | 0.17862 (18) | 0.0626 (5) | |
H29A | 0.6935 | 0.0228 | 0.2259 | 0.075* | |
C29' | 0.4016 (2) | −0.06145 (15) | 0.13495 (18) | 0.0620 (5) | |
H29B | 0.3115 | −0.0676 | 0.1532 | 0.074* | |
C30 | 0.6674 (3) | −0.0487 (2) | 0.0804 (2) | 0.0781 (7) | |
H30A | 0.7581 | −0.0449 | 0.0630 | 0.094* | |
C30' | 0.4404 (3) | −0.10074 (18) | 0.0365 (2) | 0.0721 (6) | |
H30B | 0.3761 | −0.1318 | −0.0112 | 0.086* | |
C31 | 0.5734 (3) | −0.09393 (19) | 0.0093 (2) | 0.0757 (6) | |
H31A | 0.5995 | −0.1199 | −0.0569 | 0.091* | |
C32 | 0.29440 (18) | 0.15013 (15) | 0.20849 (15) | 0.0529 (4) | |
H32A | 0.2568 | 0.0907 | 0.1823 | 0.064* | |
H32B | 0.3257 | 0.1828 | 0.1444 | 0.064* | |
C33 | 0.18113 (18) | 0.20724 (16) | 0.25637 (15) | 0.0540 (4) | |
H33A | 0.2193 | 0.2661 | 0.2863 | 0.065* | |
O34 | 0.12102 (14) | 0.15802 (15) | 0.34230 (12) | 0.0734 (5) | |
H34 | 0.179 (3) | 0.160 (3) | 0.403 (3) | 0.110* | |
C35 | 0.07235 (18) | 0.22747 (16) | 0.16262 (16) | 0.0557 (4) | |
C36 | −0.0398 (3) | 0.1713 (2) | 0.1441 (2) | 0.0869 (8) | |
H36A | −0.0522 | 0.1216 | 0.1923 | 0.104* | |
C36' | 0.0856 (3) | 0.3016 (2) | 0.0917 (2) | 0.0816 (7) | |
H36B | 0.1594 | 0.3420 | 0.1044 | 0.098* | |
C37 | −0.1351 (3) | 0.1873 (3) | 0.0548 (3) | 0.1164 (13) | |
H37A | −0.2106 | 0.1482 | 0.0431 | 0.140* | |
C37' | −0.0094 (3) | 0.3170 (3) | 0.0013 (3) | 0.0950 (9) | |
H37B | 0.0022 | 0.3666 | −0.0472 | 0.114* | |
C38 | −0.1189 (3) | 0.2599 (3) | −0.0163 (3) | 0.0985 (10) | |
H38A | −0.1829 | 0.2702 | −0.0765 | 0.118* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0379 (6) | 0.0601 (9) | 0.0543 (8) | −0.0028 (6) | 0.0074 (6) | −0.0018 (7) |
C2 | 0.0424 (8) | 0.0567 (10) | 0.0573 (9) | −0.0052 (8) | 0.0102 (7) | −0.0025 (8) |
C3 | 0.0494 (10) | 0.0784 (14) | 0.0694 (12) | −0.0140 (10) | 0.0161 (9) | 0.0017 (11) |
C4 | 0.0411 (9) | 0.0932 (17) | 0.0879 (15) | −0.0182 (11) | 0.0087 (9) | −0.0020 (13) |
C5 | 0.0427 (9) | 0.0809 (15) | 0.0715 (12) | −0.0078 (10) | 0.0009 (8) | −0.0068 (11) |
C6 | 0.0405 (8) | 0.0613 (11) | 0.0587 (10) | 0.0005 (8) | 0.0041 (7) | −0.0044 (9) |
C7 | 0.0416 (8) | 0.0685 (12) | 0.0576 (10) | 0.0039 (9) | −0.0023 (7) | 0.0000 (9) |
O8 | 0.0536 (8) | 0.1132 (15) | 0.0840 (10) | 0.0284 (9) | 0.0053 (7) | 0.0278 (10) |
N9 | 0.0430 (7) | 0.0564 (9) | 0.0466 (7) | 0.0057 (6) | 0.0021 (6) | 0.0028 (6) |
C10 | 0.0513 (9) | 0.0578 (10) | 0.0473 (8) | 0.0067 (8) | −0.0009 (7) | 0.0065 (8) |
C11 | 0.0863 (15) | 0.0870 (17) | 0.0476 (10) | −0.0111 (14) | −0.0083 (10) | 0.0021 (11) |
C12 | 0.0557 (10) | 0.0523 (10) | 0.0531 (9) | 0.0038 (8) | 0.0023 (8) | 0.0101 (8) |
C13 | 0.0651 (12) | 0.0966 (18) | 0.0632 (12) | 0.0066 (13) | 0.0117 (10) | 0.0095 (12) |
C13' | 0.0767 (14) | 0.0583 (12) | 0.0923 (16) | 0.0068 (11) | −0.0095 (12) | −0.0109 (12) |
C14 | 0.0634 (15) | 0.147 (3) | 0.100 (2) | 0.0057 (18) | 0.0205 (15) | 0.034 (2) |
C14' | 0.097 (2) | 0.0690 (16) | 0.146 (3) | −0.0080 (15) | −0.043 (2) | −0.0105 (18) |
C15 | 0.0685 (17) | 0.112 (3) | 0.144 (3) | −0.0175 (18) | −0.0101 (18) | 0.025 (3) |
C16 | 0.0495 (9) | 0.0520 (9) | 0.0438 (8) | 0.0064 (8) | 0.0011 (7) | −0.0017 (7) |
C17 | 0.0435 (8) | 0.0517 (9) | 0.0435 (8) | 0.0033 (7) | 0.0055 (6) | 0.0007 (7) |
O18 | 0.0447 (6) | 0.0724 (9) | 0.0512 (6) | 0.0049 (6) | 0.0025 (5) | −0.0142 (6) |
C19 | 0.0437 (8) | 0.0545 (10) | 0.0525 (9) | 0.0041 (8) | −0.0056 (7) | −0.0020 (8) |
C20 | 0.0821 (15) | 0.0603 (12) | 0.0669 (12) | 0.0024 (11) | −0.0058 (11) | 0.0077 (10) |
C20' | 0.0457 (10) | 0.0756 (14) | 0.0825 (14) | 0.0086 (10) | 0.0008 (9) | −0.0166 (12) |
C21 | 0.114 (2) | 0.0631 (14) | 0.102 (2) | −0.0015 (16) | −0.0312 (18) | 0.0198 (15) |
C21' | 0.0561 (13) | 0.090 (2) | 0.136 (3) | 0.0236 (13) | −0.0096 (15) | −0.039 (2) |
C22 | 0.088 (2) | 0.0682 (17) | 0.161 (3) | 0.0266 (16) | −0.048 (2) | −0.015 (2) |
C23 | 0.0452 (9) | 0.0624 (11) | 0.0517 (9) | −0.0018 (8) | 0.0128 (7) | 0.0033 (9) |
O24 | 0.0664 (9) | 0.0722 (10) | 0.0891 (11) | −0.0110 (8) | 0.0013 (8) | 0.0253 (9) |
N25 | 0.0437 (7) | 0.0569 (8) | 0.0480 (7) | 0.0022 (7) | 0.0030 (6) | −0.0006 (7) |
C26 | 0.0531 (10) | 0.0542 (10) | 0.0483 (9) | 0.0019 (8) | 0.0016 (7) | −0.0010 (8) |
C27 | 0.0870 (15) | 0.0640 (13) | 0.0657 (12) | −0.0053 (12) | 0.0249 (11) | 0.0031 (11) |
C28 | 0.0497 (9) | 0.0530 (10) | 0.0501 (9) | 0.0070 (8) | 0.0020 (7) | 0.0015 (8) |
C29 | 0.0491 (10) | 0.0729 (13) | 0.0653 (11) | 0.0069 (10) | 0.0020 (8) | −0.0027 (10) |
C29' | 0.0597 (11) | 0.0583 (11) | 0.0675 (12) | −0.0008 (9) | 0.0019 (9) | −0.0100 (10) |
C30 | 0.0679 (13) | 0.0844 (17) | 0.0850 (16) | 0.0154 (13) | 0.0252 (12) | −0.0024 (14) |
C30' | 0.0893 (17) | 0.0610 (13) | 0.0643 (12) | 0.0051 (12) | −0.0050 (11) | −0.0114 (11) |
C31 | 0.0968 (18) | 0.0700 (14) | 0.0616 (12) | 0.0209 (13) | 0.0157 (12) | −0.0028 (11) |
C32 | 0.0473 (9) | 0.0642 (11) | 0.0471 (8) | 0.0056 (8) | 0.0018 (7) | −0.0038 (8) |
C33 | 0.0425 (8) | 0.0670 (11) | 0.0532 (9) | −0.0011 (8) | 0.0077 (7) | −0.0064 (9) |
O34 | 0.0496 (7) | 0.1202 (14) | 0.0510 (7) | −0.0102 (9) | 0.0076 (6) | 0.0045 (9) |
C35 | 0.0448 (9) | 0.0653 (12) | 0.0576 (10) | 0.0076 (8) | 0.0086 (7) | −0.0026 (9) |
C36 | 0.0624 (13) | 0.098 (2) | 0.0962 (17) | −0.0139 (14) | −0.0192 (12) | 0.0274 (16) |
C36' | 0.0692 (14) | 0.0867 (18) | 0.0895 (17) | −0.0045 (13) | 0.0094 (12) | 0.0181 (15) |
C37 | 0.0785 (17) | 0.138 (3) | 0.125 (3) | −0.023 (2) | −0.0403 (18) | 0.038 (2) |
C37' | 0.0887 (17) | 0.107 (2) | 0.0891 (17) | 0.0135 (18) | 0.0053 (14) | 0.0357 (17) |
C38 | 0.0717 (16) | 0.129 (3) | 0.0914 (19) | 0.0191 (18) | −0.0141 (14) | 0.0214 (19) |
Geometric parameters (Å, º) top
N1—C2 | 1.345 (2) | C19—C20 | 1.382 (3) |
N1—C6 | 1.341 (2) | C19—C20' | 1.390 (3) |
C7—O8 | 1.223 (3) | C20—C21 | 1.397 (4) |
C7—N9 | 1.355 (2) | C20—H20A | 0.930 |
N9—C10 | 1.485 (2) | C20'—C21' | 1.385 (4) |
N9—C16 | 1.468 (2) | C20'—H20B | 0.930 |
C17—O18 | 1.414 (2) | C21—C22 | 1.369 (5) |
C23—O24 | 1.227 (3) | C21—H21A | 0.930 |
C23—N25 | 1.358 (3) | C21'—C22 | 1.358 (5) |
N25—C26 | 1.489 (3) | C21'—H21B | 0.930 |
N25—C32 | 1.472 (2) | C22—H22A | 0.930 |
C33—O34 | 1.414 (2) | C26—C27 | 1.520 (3) |
O18—H18 | 0.91 (3) | C26—C28 | 1.530 (3) |
O34—H34 | 0.89 (3) | C26—H26A | 0.980 |
C2—C3 | 1.385 (3) | C27—H27A | 0.960 |
C2—C23 | 1.507 (3) | C27—H27B | 0.960 |
C3—C4 | 1.378 (3) | C27—H27C | 0.960 |
C3—H3A | 0.930 | C28—C29 | 1.382 (3) |
C4—C5 | 1.383 (3) | C28—C29' | 1.388 (3) |
C4—H4A | 0.930 | C29—C30 | 1.392 (3) |
C5—C6 | 1.387 (3) | C29—H29A | 0.930 |
C5—H5A | 0.930 | C29'—C30' | 1.387 (3) |
C6—C7 | 1.509 (3) | C29'—H29B | 0.930 |
C10—C12 | 1.520 (3) | C30—C31 | 1.368 (4) |
C10—C11 | 1.523 (3) | C30—H30A | 0.930 |
C10—H10A | 0.980 | C30'—C31 | 1.372 (3) |
C11—H11A | 0.960 | C30'—H30B | 0.930 |
C11—H11B | 0.960 | C31—H31A | 0.930 |
C11—H11C | 0.960 | C32—C33 | 1.527 (3) |
C12—C13 | 1.373 (3) | C32—H32A | 0.970 |
C12—C13' | 1.383 (3) | C32—H32B | 0.970 |
C13—C14 | 1.398 (4) | C33—C35 | 1.514 (3) |
C13—H13A | 0.930 | C33—H33A | 0.980 |
C13'—C14' | 1.399 (4) | C35—C36 | 1.367 (3) |
C13'—H13B | 0.930 | C35—C36' | 1.373 (4) |
C14—C15 | 1.346 (5) | C36—C37 | 1.383 (4) |
C14—H14A | 0.930 | C36—H36A | 0.930 |
C14'—C15 | 1.361 (5) | C36'—C37' | 1.390 (4) |
C14'—H14B | 0.930 | C36'—H36B | 0.930 |
C15—H15A | 0.930 | C37—C38 | 1.363 (5) |
C16—C17 | 1.540 (2) | C37—H37A | 0.930 |
C16—H16A | 0.970 | C37'—C38 | 1.352 (5) |
C16—H16B | 0.970 | C37'—H37B | 0.930 |
C17—C19 | 1.510 (3) | C38—H38A | 0.930 |
C17—H17A | 0.980 | | |
| | | |
C6—N1—C2 | 118.54 (15) | C20—C19—C17 | 121.57 (18) |
O8—C7—N9 | 123.13 (19) | C20'—C19—C17 | 119.49 (19) |
O8—C7—C6 | 116.94 (17) | C19—C20—C21 | 120.0 (3) |
N9—C7—C6 | 119.79 (17) | C19—C20—H20A | 120.0 |
C7—N9—C10 | 116.40 (15) | C21—C20—H20A | 120.0 |
C7—N9—C16 | 122.86 (16) | C21'—C20'—C19 | 120.1 (3) |
C16—N9—C10 | 117.93 (14) | C21'—C20'—H20B | 119.9 |
O18—C17—C16 | 111.95 (13) | C19—C20'—H20B | 119.9 |
O18—C17—C19 | 111.27 (14) | C22—C21—C20 | 120.0 (3) |
C19—C17—C16 | 109.00 (15) | C22—C21—H21A | 120.0 |
O24—C23—N25 | 122.73 (18) | C20—C21—H21A | 120.0 |
O24—C23—C2 | 117.86 (19) | C22—C21'—C20' | 120.6 (3) |
N25—C23—C2 | 119.20 (17) | C22—C21'—H21B | 119.7 |
C23—N25—C26 | 122.52 (15) | C20'—C21'—H21B | 119.7 |
C23—N25—C32 | 115.58 (17) | C21'—C22—C21 | 120.3 (3) |
C32—N25—C26 | 118.94 (15) | C21'—C22—H22A | 119.8 |
O34—C33—C32 | 111.26 (18) | C21—C22—H22A | 119.8 |
O34—C33—C35 | 109.04 (15) | N25—C26—C27 | 112.30 (17) |
C35—C33—C32 | 108.30 (15) | N25—C26—C28 | 110.28 (15) |
N1—C2—C3 | 122.25 (18) | C27—C26—C28 | 113.61 (17) |
N1—C2—C23 | 116.04 (14) | N25—C26—H26A | 106.7 |
C3—C2—C23 | 121.48 (18) | C27—C26—H26A | 106.7 |
C4—C3—C2 | 118.8 (2) | C28—C26—H26A | 106.7 |
C4—C3—H3A | 120.6 | C26—C27—H27A | 109.5 |
C2—C3—H3A | 120.6 | C26—C27—H27B | 109.5 |
C3—C4—C5 | 119.40 (19) | H27A—C27—H27B | 109.5 |
C3—C4—H4A | 120.3 | C26—C27—H27C | 109.5 |
C5—C4—H4A | 120.3 | H27A—C27—H27C | 109.5 |
C4—C5—C6 | 118.63 (19) | H27B—C27—H27C | 109.5 |
C4—C5—H5A | 120.7 | C29—C28—C29' | 117.67 (18) |
C6—C5—H5A | 120.7 | C29—C28—C26 | 119.07 (17) |
N1—C6—C5 | 122.33 (18) | C29'—C28—C26 | 123.26 (17) |
N1—C6—C7 | 117.67 (16) | C28—C29—C30 | 120.9 (2) |
C5—C6—C7 | 119.67 (18) | C28—C29—H29A | 119.6 |
N9—C10—C12 | 110.50 (14) | C30—C29—H29A | 119.6 |
N9—C10—C11 | 110.99 (18) | C30'—C29'—C28 | 121.3 (2) |
C12—C10—C11 | 114.73 (18) | C30'—C29'—H29B | 119.4 |
N9—C10—H10A | 106.7 | C28—C29'—H29B | 119.4 |
C12—C10—H10A | 106.7 | C31—C30—C29 | 120.6 (2) |
C11—C10—H10A | 106.7 | C31—C30—H30A | 119.7 |
C10—C11—H11A | 109.5 | C29—C30—H30A | 119.7 |
C10—C11—H11B | 109.5 | C31—C30'—C29' | 120.2 (2) |
H11A—C11—H11B | 109.5 | C31—C30'—H30B | 119.9 |
C10—C11—H11C | 109.5 | C29'—C30'—H30B | 119.9 |
H11A—C11—H11C | 109.5 | C30—C31—C30' | 119.5 (2) |
H11B—C11—H11C | 109.5 | C30—C31—H31A | 120.3 |
C13—C12—C13' | 117.7 (2) | C30'—C31—H31A | 120.3 |
C13—C12—C10 | 123.3 (2) | N25—C32—C33 | 113.49 (15) |
C13'—C12—C10 | 118.9 (2) | N25—C32—H32A | 108.9 |
C12—C13—C14 | 120.9 (3) | C33—C32—H32A | 108.9 |
C12—C13—H13A | 119.6 | N25—C32—H32B | 108.9 |
C14—C13—H13A | 119.6 | C33—C32—H32B | 108.9 |
C12—C13'—C14' | 120.7 (3) | H32A—C32—H32B | 107.7 |
C12—C13'—H13B | 119.7 | O34—C33—H33A | 109.4 |
C14'—C13'—H13B | 119.7 | C35—C33—H33A | 109.4 |
C15—C14—C13 | 120.5 (3) | C32—C33—H33A | 109.4 |
C15—C14—H14A | 119.7 | C33—O34—H34 | 108 (2) |
C13—C14—H14A | 119.7 | C36—C35—C36' | 118.1 (2) |
C15—C14'—C13' | 120.1 (3) | C36—C35—C33 | 121.1 (2) |
C15—C14'—H14B | 119.9 | C36'—C35—C33 | 120.8 (2) |
C13'—C14'—H14B | 119.9 | C35—C36—C37 | 120.8 (3) |
C14—C15—C14' | 119.9 (3) | C35—C36—H36A | 119.6 |
C14—C15—H15A | 120.0 | C37—C36—H36A | 119.6 |
C14'—C15—H15A | 120.0 | C35—C36'—C37' | 121.0 (3) |
N9—C16—C17 | 116.23 (16) | C35—C36'—H36B | 119.5 |
N9—C16—H16A | 108.2 | C37'—C36'—H36B | 119.5 |
C17—C16—H16A | 108.2 | C38—C37—C36 | 120.4 (3) |
N9—C16—H16B | 108.2 | C38—C37—H37A | 119.8 |
C17—C16—H16B | 108.2 | C36—C37—H37A | 119.8 |
H16A—C16—H16B | 107.4 | C38—C37'—C36' | 119.9 (3) |
O18—C17—H17A | 108.2 | C38—C37'—H37B | 120.0 |
C19—C17—H17A | 108.2 | C36'—C37'—H37B | 120.0 |
C16—C17—H17A | 108.2 | C37'—C38—C37 | 119.7 (3) |
C17—O18—H18 | 109.3 (18) | C37'—C38—H38A | 120.1 |
C20—C19—C20' | 118.9 (2) | C37—C38—H38A | 120.1 |
| | | |
N1—C6—C7—O8 | 132.7 (2) | C16—C17—C19—C20 | 82.9 (2) |
N1—C6—C7—N9 | −43.1 (3) | O18—C17—C19—C20' | 139.89 (18) |
C6—C7—N9—C10 | 173.40 (17) | C16—C17—C19—C20' | −96.17 (19) |
C6—C7—N9—C16 | −26.0 (3) | C20'—C19—C20—C21 | −0.9 (3) |
C7—N9—C10—C11 | 95.0 (2) | C17—C19—C20—C21 | −179.9 (2) |
C7—N9—C16—C17 | 117.74 (19) | C20—C19—C20'—C21' | 0.5 (3) |
N1—C2—C23—O24 | 125.6 (2) | C17—C19—C20'—C21' | 179.6 (2) |
N1—C2—C23—N25 | −49.3 (2) | C19—C20—C21—C22 | 0.4 (4) |
C2—C23—N25—C26 | −28.8 (2) | C19—C20'—C21'—C22 | 0.4 (4) |
C2—C23—N25—C32 | 170.88 (15) | C20'—C21'—C22—C21 | −0.9 (5) |
C23—N25—C26—C27 | 132.52 (19) | C20—C21—C22—C21' | 0.5 (5) |
C23—N25—C32—C33 | −75.4 (2) | C3—C2—C23—O24 | −49.0 (3) |
C6—N1—C2—C3 | 0.2 (3) | C3—C2—C23—N25 | 136.1 (2) |
C6—N1—C2—C23 | −174.35 (18) | O24—C23—N25—C32 | −3.8 (3) |
N1—C2—C3—C4 | 0.0 (4) | O24—C23—N25—C26 | 156.5 (2) |
C23—C2—C3—C4 | 174.3 (2) | C32—N25—C26—C27 | −67.8 (2) |
C2—C3—C4—C5 | 0.1 (4) | C23—N25—C26—C28 | −99.67 (19) |
C3—C4—C5—C6 | −0.4 (4) | C32—N25—C26—C28 | 60.0 (2) |
C2—N1—C6—C5 | −0.6 (3) | N25—C26—C28—C29 | 89.7 (2) |
C2—N1—C6—C7 | −173.97 (18) | C27—C26—C28—C29 | −143.2 (2) |
C4—C5—C6—N1 | 0.7 (4) | N25—C26—C28—C29' | −89.9 (2) |
C4—C5—C6—C7 | 173.9 (2) | C27—C26—C28—C29' | 37.2 (3) |
C5—C6—C7—O8 | −40.9 (3) | C29'—C28—C29—C30 | 1.3 (3) |
C5—C6—C7—N9 | 143.3 (2) | C26—C28—C29—C30 | −178.3 (2) |
O8—C7—N9—C16 | 158.5 (2) | C29—C28—C29'—C30' | −2.1 (3) |
O8—C7—N9—C10 | −2.2 (3) | C26—C28—C29'—C30' | 177.5 (2) |
C7—N9—C10—C12 | −136.56 (18) | C28—C29—C30—C31 | 0.4 (4) |
C16—N9—C10—C12 | 61.8 (2) | C28—C29'—C30'—C31 | 1.3 (4) |
C16—N9—C10—C11 | −66.6 (2) | C29—C30—C31—C30' | −1.2 (4) |
N9—C10—C12—C13 | −111.7 (2) | C29'—C30'—C31—C30 | 0.4 (4) |
C11—C10—C12—C13 | 14.7 (3) | C26—N25—C32—C33 | 123.58 (19) |
N9—C10—C12—C13' | 65.2 (2) | N25—C32—C33—O34 | −65.1 (2) |
C11—C10—C12—C13' | −168.4 (2) | N25—C32—C33—C35 | 175.03 (17) |
C13'—C12—C13—C14 | −2.3 (4) | O34—C33—C35—C36 | −27.0 (3) |
C10—C12—C13—C14 | 174.6 (2) | C32—C33—C35—C36 | 94.2 (3) |
C13—C12—C13'—C14' | 2.6 (4) | O34—C33—C35—C36' | 154.8 (2) |
C10—C12—C13'—C14' | −174.5 (2) | C32—C33—C35—C36' | −84.0 (3) |
C12—C13—C14—C15 | −0.5 (5) | C36'—C35—C36—C37 | 1.7 (5) |
C12—C13'—C14'—C15 | −0.1 (5) | C33—C35—C36—C37 | −176.6 (3) |
C13—C14—C15—C14' | 3.1 (5) | C36—C35—C36'—C37' | −2.3 (4) |
C13'—C14'—C15—C14 | −2.8 (5) | C33—C35—C36'—C37' | 175.9 (3) |
C10—N9—C16—C17 | −81.94 (19) | C35—C36—C37—C38 | −0.3 (6) |
N9—C16—C17—O18 | −58.5 (2) | C35—C36'—C37'—C38 | 1.7 (5) |
N9—C16—C17—C19 | 177.96 (15) | C36'—C37'—C38—C37 | −0.2 (6) |
O18—C17—C19—C20 | −41.1 (2) | C36—C37—C38—C37' | −0.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O18—H18···N1 | 0.91 (3) | 1.82 (3) | 2.7343 (19) | 174 (3) |
O34—H34···O18 | 0.89 (3) | 1.84 (4) | 2.7300 (19) | 177 (3) |