The title compound, C
26H
26N
2O
3, crystallizes as a racemic mixture of
R,
R and
S,
S enantiomers. The two independent molecules show a similar conformation. They are connected
via C—H
O and C—H
π interactions to form ribbons along the
a axis.
Supporting information
CCDC reference: 277741
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.010 Å
- R factor = 0.055
- wR factor = 0.129
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C113
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C113 -C118 1.36 Ang.
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.76
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.97 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.02 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C117
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C118
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C126
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C225
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C119
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C213
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT411_ALERT_2_C Short Inter H...H Contact H17 .. H27 .. 2.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H121 .. CG2 .. 2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H221 .. CG1 .. 2.92 Ang.
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 25.97
From the CIF: _reflns_number_total 4339
Count of symmetry unique reflns 4336
Completeness (_total/calc) 100.07%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
14 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
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).
(3RS,4RS)-3-(2-Furyl)-2-phenetyl-4-(pyrrolidin-1-ylcarbonyl)-3,4-
dihydroisoquinolin-1(2
H)-one
top
Crystal data top
C26H26N2O3 | Dx = 1.268 Mg m−3 |
Mr = 414.49 | Melting point: 413 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 22 reflections |
a = 11.9675 (15) Å | θ = 16.1–17.3° |
b = 11.066 (2) Å | µ = 0.08 mm−1 |
c = 32.7891 (14) Å | T = 290 K |
V = 4342.3 (10) Å3 | Prism, yellow |
Z = 8 | 0.26 × 0.2 × 0.2 mm |
F(000) = 1760 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.076 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 1.2° |
Graphite monochromator | h = 0→14 |
non–profiled ω/2θ scans | k = 0→13 |
8655 measured reflections | l = −40→40 |
4339 independent reflections | 3 standard reflections every 120 min |
2189 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: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0463P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
4339 reflections | Δρmax = 0.16 e Å−3 |
559 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: see text |
Primary atom site location: structure-invariant direct methods | |
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 | |
C11 | 0.4414 (5) | 0.7522 (5) | 0.67879 (18) | 0.0412 (15) | |
C13 | 0.2644 (5) | 0.6743 (5) | 0.70754 (19) | 0.0411 (15) | |
H13 | 0.2398 | 0.6648 | 0.7359 | 0.049* | |
C14 | 0.2937 (5) | 0.5481 (5) | 0.69051 (16) | 0.0377 (15) | |
H14 | 0.2248 | 0.5027 | 0.6854 | 0.045* | |
C15 | 0.3587 (5) | 0.5611 (5) | 0.65120 (19) | 0.0396 (15) | |
C16 | 0.4303 (5) | 0.6564 (5) | 0.64675 (17) | 0.0396 (15) | |
C17 | 0.4967 (5) | 0.6665 (6) | 0.61218 (19) | 0.0519 (17) | |
H17 | 0.5449 | 0.7318 | 0.6093 | 0.062* | |
C18 | 0.4911 (7) | 0.5798 (7) | 0.5822 (2) | 0.063 (2) | |
H18 | 0.5373 | 0.5847 | 0.5594 | 0.076* | |
C19 | 0.4168 (8) | 0.4858 (7) | 0.5860 (3) | 0.067 (3) | |
H19 | 0.4109 | 0.4291 | 0.5652 | 0.081* | |
C21 | 0.8062 (5) | 0.7539 (5) | 0.51181 (19) | 0.0410 (15) | |
C23 | 0.9802 (5) | 0.8404 (5) | 0.48521 (19) | 0.0413 (15) | |
H23 | 1.0072 | 0.8550 | 0.4574 | 0.050* | |
C24 | 0.9477 (5) | 0.9625 (5) | 0.50395 (19) | 0.0416 (16) | |
H24 | 1.0160 | 1.0081 | 0.5099 | 0.050* | |
C25 | 0.8842 (5) | 0.9448 (5) | 0.54278 (17) | 0.0349 (14) | |
C26 | 0.8135 (5) | 0.8440 (5) | 0.54549 (18) | 0.0393 (15) | |
C27 | 0.7482 (5) | 0.8294 (5) | 0.5800 (2) | 0.0525 (17) | |
H27 | 0.7017 | 0.7623 | 0.5820 | 0.063* | |
C28 | 0.7507 (6) | 0.9116 (6) | 0.6113 (2) | 0.0605 (19) | |
H28 | 0.7055 | 0.9009 | 0.6341 | 0.073* | |
C29 | 0.8202 (8) | 1.0095 (6) | 0.6087 (3) | 0.060 (2) | |
H29 | 0.8216 | 1.0656 | 0.6298 | 0.072* | |
C110 | 0.3517 (7) | 0.4746 (6) | 0.6199 (2) | 0.058 (2) | |
H110 | 0.3026 | 0.4098 | 0.6223 | 0.069* | |
C111 | 0.3694 (6) | 0.8459 (5) | 0.73988 (18) | 0.0491 (18) | |
H11A | 0.2952 | 0.8692 | 0.7488 | 0.059* | |
H11B | 0.4070 | 0.9175 | 0.7297 | 0.059* | |
C112 | 0.4346 (6) | 0.7947 (5) | 0.7761 (2) | 0.0538 (18) | |
H11C | 0.3982 | 0.7219 | 0.7858 | 0.065* | |
H11D | 0.5095 | 0.7734 | 0.7674 | 0.065* | |
C113 | 0.4413 (5) | 0.8859 (5) | 0.81054 (19) | 0.0461 (16) | |
C114 | 0.3612 (7) | 0.8948 (7) | 0.8394 (2) | 0.077 (2) | |
H114 | 0.3015 | 0.8412 | 0.8382 | 0.092* | |
C115 | 0.3624 (10) | 0.9782 (8) | 0.8705 (3) | 0.087 (3) | |
H115 | 0.3043 | 0.9809 | 0.8894 | 0.105* | |
C116 | 0.4472 (9) | 1.0545 (9) | 0.8733 (3) | 0.092 (3) | |
H116 | 0.4505 | 1.1097 | 0.8946 | 0.111* | |
C117 | 0.5299 (9) | 1.0518 (10) | 0.8445 (3) | 0.113 (4) | |
H117 | 0.5884 | 1.1070 | 0.8457 | 0.136* | |
C118 | 0.5259 (7) | 0.9660 (9) | 0.8135 (3) | 0.102 (4) | |
H118 | 0.5831 | 0.9638 | 0.7944 | 0.122* | |
C119 | 0.1685 (5) | 0.7281 (5) | 0.68311 (19) | 0.0413 (15) | |
C120 | 0.0997 (6) | 0.6908 (6) | 0.6544 (2) | 0.070 (2) | |
H120 | 0.0986 | 0.6141 | 0.6427 | 0.084* | |
C121 | 0.0277 (6) | 0.7880 (6) | 0.6443 (2) | 0.069 (2) | |
H121 | −0.0288 | 0.7873 | 0.6248 | 0.083* | |
C122 | 0.0555 (6) | 0.8782 (6) | 0.6674 (2) | 0.0599 (19) | |
H122 | 0.0213 | 0.9537 | 0.6671 | 0.072* | |
C123 | 0.3666 (6) | 0.4791 (5) | 0.7213 (2) | 0.0443 (18) | |
C124 | 0.2349 (7) | 0.3022 (5) | 0.7159 (2) | 0.064 (2) | |
H12A | 0.2339 | 0.3035 | 0.6864 | 0.077* | |
H12B | 0.1652 | 0.3355 | 0.7261 | 0.077* | |
C125 | 0.2538 (7) | 0.1753 (5) | 0.7320 (3) | 0.084 (3) | |
H12C | 0.1833 | 0.1351 | 0.7373 | 0.101* | |
H12D | 0.2963 | 0.1275 | 0.7126 | 0.101* | |
C126 | 0.3163 (9) | 0.1929 (6) | 0.7694 (3) | 0.096 (3) | |
H12E | 0.3590 | 0.1209 | 0.7759 | 0.115* | |
H12F | 0.2659 | 0.2098 | 0.7918 | 0.115* | |
C127 | 0.3947 (7) | 0.3002 (6) | 0.7623 (2) | 0.073 (2) | |
H12G | 0.4063 | 0.3462 | 0.7871 | 0.088* | |
H12H | 0.4664 | 0.2742 | 0.7516 | 0.088* | |
C210 | 0.8887 (7) | 1.0260 (5) | 0.5749 (2) | 0.0493 (19) | |
H210 | 0.9375 | 1.0914 | 0.5739 | 0.059* | |
C211 | 0.8766 (6) | 0.6757 (5) | 0.44841 (18) | 0.0485 (17) | |
H21A | 0.8417 | 0.6013 | 0.4574 | 0.058* | |
H21B | 0.9516 | 0.6562 | 0.4393 | 0.058* | |
C212 | 0.8108 (6) | 0.7259 (6) | 0.4126 (2) | 0.064 (2) | |
H21C | 0.7359 | 0.7469 | 0.4214 | 0.077* | |
H21D | 0.8467 | 0.7986 | 0.4025 | 0.077* | |
C213 | 0.8049 (6) | 0.6339 (6) | 0.37929 (19) | 0.0510 (17) | |
C214 | 0.8875 (6) | 0.6227 (6) | 0.3504 (2) | 0.065 (2) | |
H214 | 0.9461 | 0.6778 | 0.3504 | 0.078* | |
C215 | 0.8863 (9) | 0.5334 (9) | 0.3216 (3) | 0.089 (3) | |
H215 | 0.9433 | 0.5262 | 0.3024 | 0.106* | |
C216 | 0.7974 (9) | 0.4545 (9) | 0.3221 (3) | 0.090 (3) | |
H216 | 0.7950 | 0.3933 | 0.3027 | 0.108* | |
C217 | 0.7134 (8) | 0.4618 (9) | 0.3496 (3) | 0.095 (3) | |
H217 | 0.6549 | 0.4065 | 0.3494 | 0.114* | |
C218 | 0.7173 (7) | 0.5536 (8) | 0.3778 (2) | 0.076 (2) | |
H218 | 0.6591 | 0.5617 | 0.3964 | 0.091* | |
C219 | 1.0725 (5) | 0.7821 (5) | 0.50893 (19) | 0.0409 (14) | |
C220 | 1.1428 (6) | 0.8173 (6) | 0.5393 (2) | 0.063 (2) | |
H220 | 1.1457 | 0.8928 | 0.5517 | 0.075* | |
C221 | 1.2106 (6) | 0.7158 (6) | 0.5482 (2) | 0.066 (2) | |
H221 | 1.2668 | 0.7123 | 0.5677 | 0.079* | |
C222 | 1.1798 (6) | 0.6270 (6) | 0.5237 (2) | 0.062 (2) | |
H222 | 1.2111 | 0.5500 | 0.5235 | 0.074* | |
C223 | 0.8760 (6) | 1.0358 (5) | 0.47367 (18) | 0.0407 (16) | |
C224 | 0.8413 (5) | 1.2244 (5) | 0.4377 (2) | 0.0484 (16) | |
H22A | 0.7708 | 1.2482 | 0.4499 | 0.058* | |
H22B | 0.8266 | 1.1814 | 0.4125 | 0.058* | |
C225 | 0.9147 (7) | 1.3328 (6) | 0.4303 (3) | 0.084 (3) | |
H22C | 0.9624 | 1.3197 | 0.4068 | 0.101* | |
H22D | 0.8698 | 1.4044 | 0.4256 | 0.101* | |
C226 | 0.9825 (7) | 1.3459 (6) | 0.4679 (2) | 0.070 (2) | |
H22E | 0.9429 | 1.3934 | 0.4881 | 0.084* | |
H22F | 1.0532 | 1.3849 | 0.4619 | 0.084* | |
C227 | 1.0012 (6) | 1.2171 (5) | 0.4832 (2) | 0.0510 (18) | |
H22G | 1.0718 | 1.1852 | 0.4734 | 0.061* | |
H22H | 1.0003 | 1.2141 | 0.5127 | 0.061* | |
N11 | 0.3319 (4) | 0.3692 (4) | 0.73213 (15) | 0.0476 (13) | |
N12 | 0.3603 (4) | 0.7566 (4) | 0.70693 (14) | 0.0420 (12) | |
N21 | 0.9066 (4) | 1.1498 (4) | 0.46591 (14) | 0.0391 (11) | |
N22 | 0.8842 (4) | 0.7580 (4) | 0.48290 (14) | 0.0387 (12) | |
O11 | 0.5199 (4) | 0.8240 (4) | 0.67821 (15) | 0.0588 (13) | |
O12 | 0.1431 (4) | 0.8458 (4) | 0.69241 (14) | 0.0610 (13) | |
O13 | 0.4511 (5) | 0.5252 (4) | 0.73539 (18) | 0.0660 (16) | |
O21 | 0.7307 (4) | 0.6782 (4) | 0.51179 (14) | 0.0596 (13) | |
O22 | 1.0955 (4) | 0.6646 (3) | 0.49873 (14) | 0.0591 (12) | |
O23 | 0.7911 (5) | 0.9915 (4) | 0.45902 (18) | 0.0637 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.043 (4) | 0.031 (3) | 0.049 (4) | 0.000 (3) | −0.007 (3) | 0.009 (3) |
C13 | 0.047 (4) | 0.034 (3) | 0.042 (4) | −0.007 (3) | 0.000 (3) | 0.003 (3) |
C14 | 0.043 (4) | 0.032 (3) | 0.039 (4) | −0.008 (3) | −0.012 (3) | 0.008 (3) |
C15 | 0.044 (4) | 0.029 (3) | 0.046 (4) | 0.010 (3) | −0.015 (3) | −0.006 (3) |
C16 | 0.039 (4) | 0.043 (3) | 0.037 (4) | 0.002 (3) | −0.003 (3) | 0.001 (3) |
C17 | 0.060 (4) | 0.046 (4) | 0.050 (4) | 0.007 (3) | 0.003 (4) | 0.008 (3) |
C18 | 0.077 (6) | 0.068 (5) | 0.046 (4) | 0.028 (4) | 0.005 (4) | 0.003 (4) |
C19 | 0.095 (8) | 0.054 (5) | 0.053 (6) | 0.017 (5) | −0.005 (5) | −0.016 (4) |
C21 | 0.042 (4) | 0.029 (3) | 0.053 (4) | 0.003 (3) | −0.014 (3) | −0.001 (3) |
C23 | 0.043 (4) | 0.041 (3) | 0.040 (4) | −0.002 (3) | 0.000 (3) | 0.000 (3) |
C24 | 0.042 (4) | 0.028 (3) | 0.054 (4) | −0.004 (3) | −0.005 (3) | −0.002 (3) |
C25 | 0.041 (4) | 0.033 (3) | 0.030 (3) | 0.009 (3) | −0.004 (3) | 0.003 (3) |
C26 | 0.037 (3) | 0.029 (3) | 0.051 (4) | 0.004 (3) | −0.003 (3) | 0.002 (3) |
C27 | 0.046 (4) | 0.053 (4) | 0.058 (5) | −0.002 (3) | 0.003 (4) | 0.007 (4) |
C28 | 0.065 (5) | 0.073 (5) | 0.044 (4) | 0.013 (4) | 0.006 (4) | 0.001 (4) |
C29 | 0.076 (7) | 0.065 (5) | 0.040 (5) | 0.022 (4) | −0.011 (5) | −0.015 (4) |
C110 | 0.082 (6) | 0.036 (4) | 0.055 (5) | 0.006 (4) | −0.013 (5) | −0.003 (4) |
C111 | 0.066 (5) | 0.033 (3) | 0.048 (4) | 0.007 (3) | −0.020 (4) | −0.015 (3) |
C112 | 0.062 (5) | 0.045 (4) | 0.054 (4) | 0.016 (3) | −0.007 (4) | −0.005 (3) |
C113 | 0.048 (4) | 0.048 (4) | 0.043 (4) | 0.005 (3) | −0.008 (3) | −0.008 (3) |
C114 | 0.084 (6) | 0.065 (5) | 0.082 (6) | −0.017 (4) | 0.025 (5) | −0.018 (4) |
C115 | 0.127 (9) | 0.076 (6) | 0.059 (6) | −0.013 (6) | 0.041 (6) | −0.032 (5) |
C116 | 0.096 (8) | 0.101 (7) | 0.080 (7) | 0.021 (6) | −0.014 (6) | −0.057 (6) |
C117 | 0.071 (7) | 0.141 (9) | 0.127 (10) | −0.018 (7) | −0.004 (7) | −0.085 (8) |
C118 | 0.055 (5) | 0.134 (8) | 0.115 (8) | −0.015 (6) | 0.010 (6) | −0.080 (7) |
C119 | 0.042 (4) | 0.029 (3) | 0.053 (4) | 0.000 (3) | 0.006 (3) | −0.004 (3) |
C120 | 0.060 (5) | 0.046 (4) | 0.104 (6) | 0.007 (4) | −0.028 (5) | −0.018 (4) |
C121 | 0.068 (5) | 0.054 (4) | 0.084 (6) | 0.016 (4) | −0.032 (4) | −0.001 (4) |
C122 | 0.054 (4) | 0.052 (4) | 0.074 (5) | 0.015 (4) | −0.009 (4) | 0.005 (4) |
C123 | 0.046 (4) | 0.035 (3) | 0.052 (4) | 0.001 (3) | −0.007 (4) | 0.004 (3) |
C124 | 0.066 (5) | 0.038 (3) | 0.089 (6) | −0.007 (3) | 0.002 (4) | 0.021 (4) |
C125 | 0.086 (6) | 0.038 (4) | 0.128 (8) | −0.020 (4) | −0.014 (6) | 0.033 (4) |
C126 | 0.160 (9) | 0.051 (4) | 0.077 (6) | −0.020 (5) | −0.024 (6) | 0.030 (4) |
C127 | 0.096 (6) | 0.058 (4) | 0.065 (5) | 0.010 (4) | −0.009 (5) | 0.009 (4) |
C210 | 0.060 (5) | 0.040 (4) | 0.048 (5) | −0.001 (4) | −0.008 (4) | −0.007 (4) |
C211 | 0.064 (4) | 0.035 (3) | 0.047 (4) | 0.015 (3) | −0.006 (3) | −0.008 (3) |
C212 | 0.082 (6) | 0.060 (4) | 0.049 (4) | 0.005 (4) | −0.007 (4) | −0.015 (4) |
C213 | 0.062 (5) | 0.052 (4) | 0.039 (4) | 0.007 (4) | −0.005 (3) | −0.005 (3) |
C214 | 0.079 (5) | 0.060 (4) | 0.057 (5) | −0.010 (4) | 0.011 (4) | −0.004 (4) |
C215 | 0.102 (9) | 0.090 (6) | 0.074 (7) | 0.009 (6) | 0.026 (6) | −0.006 (6) |
C216 | 0.129 (9) | 0.093 (6) | 0.049 (5) | −0.020 (7) | −0.017 (6) | −0.023 (5) |
C217 | 0.066 (6) | 0.112 (7) | 0.106 (8) | −0.026 (6) | −0.003 (6) | −0.053 (7) |
C218 | 0.054 (5) | 0.101 (6) | 0.072 (6) | 0.002 (5) | 0.004 (4) | −0.025 (5) |
C219 | 0.035 (3) | 0.038 (3) | 0.050 (4) | −0.005 (3) | 0.005 (3) | 0.003 (3) |
C220 | 0.065 (5) | 0.047 (4) | 0.075 (5) | 0.015 (4) | −0.022 (4) | −0.011 (4) |
C221 | 0.049 (4) | 0.063 (5) | 0.087 (6) | 0.007 (4) | −0.016 (4) | 0.006 (4) |
C222 | 0.040 (4) | 0.050 (4) | 0.095 (6) | 0.008 (3) | −0.005 (4) | 0.022 (4) |
C223 | 0.052 (4) | 0.033 (3) | 0.037 (4) | −0.008 (3) | −0.002 (3) | 0.000 (3) |
C224 | 0.056 (4) | 0.038 (3) | 0.051 (4) | 0.013 (3) | −0.012 (3) | 0.009 (3) |
C225 | 0.127 (8) | 0.036 (4) | 0.089 (6) | −0.007 (4) | −0.032 (6) | 0.010 (4) |
C226 | 0.090 (5) | 0.051 (4) | 0.069 (5) | −0.018 (4) | −0.019 (5) | 0.007 (4) |
C227 | 0.058 (4) | 0.038 (3) | 0.057 (4) | −0.013 (3) | −0.016 (4) | 0.003 (3) |
N11 | 0.060 (4) | 0.033 (3) | 0.050 (3) | −0.002 (3) | −0.009 (3) | 0.013 (3) |
N12 | 0.049 (3) | 0.033 (3) | 0.044 (3) | −0.001 (2) | −0.004 (3) | −0.009 (2) |
N21 | 0.043 (3) | 0.034 (3) | 0.040 (3) | 0.000 (2) | −0.004 (3) | 0.000 (2) |
N22 | 0.041 (3) | 0.031 (3) | 0.044 (3) | 0.003 (2) | −0.011 (3) | −0.007 (2) |
O11 | 0.051 (3) | 0.046 (3) | 0.079 (3) | −0.017 (2) | −0.003 (2) | −0.004 (2) |
O12 | 0.065 (3) | 0.044 (2) | 0.075 (3) | 0.006 (2) | −0.012 (3) | −0.005 (2) |
O13 | 0.069 (4) | 0.046 (3) | 0.083 (4) | −0.010 (3) | −0.031 (4) | 0.015 (3) |
O21 | 0.053 (3) | 0.046 (2) | 0.080 (3) | −0.019 (2) | −0.014 (3) | 0.003 (2) |
O22 | 0.052 (3) | 0.040 (2) | 0.084 (3) | 0.008 (2) | −0.010 (3) | 0.001 (2) |
O23 | 0.065 (4) | 0.042 (2) | 0.084 (4) | −0.011 (2) | −0.038 (3) | 0.010 (2) |
Geometric parameters (Å, º) top
C11—O11 | 1.231 (7) | C121—C122 | 1.296 (9) |
C11—N12 | 1.340 (7) | C121—H121 | 0.9300 |
C11—C16 | 1.498 (8) | C122—O12 | 1.379 (8) |
C13—N12 | 1.466 (7) | C122—H122 | 0.9300 |
C13—C119 | 1.521 (8) | C123—O13 | 1.223 (8) |
C13—C14 | 1.544 (7) | C123—N11 | 1.333 (7) |
C13—H13 | 0.9800 | C124—N11 | 1.476 (8) |
C14—C15 | 1.513 (8) | C124—C125 | 1.517 (8) |
C14—C123 | 1.538 (9) | C124—H12A | 0.9700 |
C14—H14 | 0.9800 | C124—H12B | 0.9700 |
C15—C16 | 1.367 (8) | C125—C126 | 1.450 (10) |
C15—C110 | 1.406 (9) | C125—H12C | 0.9700 |
C16—C17 | 1.389 (8) | C125—H12D | 0.9700 |
C17—C18 | 1.376 (9) | C126—C127 | 1.531 (10) |
C17—H17 | 0.9300 | C126—H12E | 0.9700 |
C18—C19 | 1.373 (11) | C126—H12F | 0.9700 |
C18—H18 | 0.9300 | C127—N11 | 1.458 (8) |
C19—C110 | 1.363 (12) | C127—H12G | 0.9700 |
C19—H19 | 0.9300 | C127—H12H | 0.9700 |
C21—O21 | 1.232 (7) | C210—H210 | 0.9300 |
C21—N22 | 1.332 (7) | C211—N22 | 1.455 (7) |
C21—C26 | 1.490 (8) | C211—C212 | 1.519 (8) |
C23—N22 | 1.469 (7) | C211—H21A | 0.9700 |
C23—C219 | 1.497 (8) | C211—H21B | 0.9700 |
C23—C24 | 1.534 (8) | C212—C213 | 1.495 (8) |
C23—H23 | 0.9800 | C212—H21C | 0.9700 |
C24—C25 | 1.496 (8) | C212—H21D | 0.9700 |
C24—C223 | 1.543 (8) | C213—C218 | 1.374 (10) |
C24—H24 | 0.9800 | C213—C214 | 1.375 (9) |
C25—C210 | 1.386 (9) | C214—C215 | 1.367 (10) |
C25—C26 | 1.404 (7) | C214—H214 | 0.9300 |
C26—C27 | 1.384 (8) | C215—C216 | 1.377 (13) |
C27—C28 | 1.372 (9) | C215—H215 | 0.9300 |
C27—H27 | 0.9300 | C216—C217 | 1.351 (11) |
C28—C29 | 1.368 (10) | C216—H216 | 0.9300 |
C28—H28 | 0.9300 | C217—C218 | 1.376 (10) |
C29—C210 | 1.392 (11) | C217—H217 | 0.9300 |
C29—H29 | 0.9300 | C218—H218 | 0.9300 |
C110—H110 | 0.9300 | C219—C220 | 1.361 (8) |
C111—N12 | 1.468 (6) | C219—O22 | 1.370 (6) |
C111—C112 | 1.530 (8) | C220—C221 | 1.416 (9) |
C111—H11A | 0.9700 | C220—H220 | 0.9300 |
C111—H11B | 0.9700 | C221—C222 | 1.321 (9) |
C112—C113 | 1.516 (8) | C221—H221 | 0.9300 |
C112—H11C | 0.9700 | C222—O22 | 1.365 (8) |
C112—H11D | 0.9700 | C222—H222 | 0.9300 |
C113—C118 | 1.349 (10) | C223—O23 | 1.226 (8) |
C113—C114 | 1.351 (9) | C223—N21 | 1.337 (7) |
C114—C115 | 1.375 (10) | C224—N21 | 1.465 (7) |
C114—H114 | 0.9300 | C224—C225 | 1.506 (9) |
C115—C116 | 1.324 (13) | C224—H22A | 0.9700 |
C115—H115 | 0.9300 | C224—H22B | 0.9700 |
C116—C117 | 1.367 (12) | C225—C226 | 1.482 (10) |
C116—H116 | 0.9300 | C225—H22C | 0.9700 |
C117—C118 | 1.392 (11) | C225—H22D | 0.9700 |
C117—H117 | 0.9300 | C226—C227 | 1.527 (8) |
C118—H118 | 0.9300 | C226—H22E | 0.9700 |
C119—C120 | 1.318 (8) | C226—H22F | 0.9700 |
C119—O12 | 1.373 (6) | C227—N21 | 1.468 (8) |
C120—C121 | 1.419 (9) | C227—H22G | 0.9700 |
C120—H120 | 0.9300 | C227—H22H | 0.9700 |
| | | |
O11—C11—N12 | 122.7 (6) | N11—C124—H12A | 111.2 |
O11—C11—C16 | 120.9 (6) | C125—C124—H12A | 111.2 |
N12—C11—C16 | 116.4 (5) | N11—C124—H12B | 111.2 |
N12—C13—C119 | 109.9 (4) | C125—C124—H12B | 111.2 |
N12—C13—C14 | 112.3 (5) | H12A—C124—H12B | 109.1 |
C119—C13—C14 | 109.6 (5) | C126—C125—C124 | 104.2 (6) |
N12—C13—H13 | 108.3 | C126—C125—H12C | 110.9 |
C119—C13—H13 | 108.3 | C124—C125—H12C | 110.9 |
C14—C13—H13 | 108.3 | C126—C125—H12D | 110.9 |
C15—C14—C123 | 108.4 (5) | C124—C125—H12D | 110.9 |
C15—C14—C13 | 109.8 (4) | H12C—C125—H12D | 108.9 |
C123—C14—C13 | 109.9 (5) | C125—C126—C127 | 107.0 (6) |
C15—C14—H14 | 109.6 | C125—C126—H12E | 110.3 |
C123—C14—H14 | 109.6 | C127—C126—H12E | 110.3 |
C13—C14—H14 | 109.6 | C125—C126—H12F | 110.3 |
C16—C15—C110 | 119.0 (7) | C127—C126—H12F | 110.3 |
C16—C15—C14 | 119.1 (5) | H12E—C126—H12F | 108.6 |
C110—C15—C14 | 121.8 (6) | N11—C127—C126 | 101.1 (6) |
C15—C16—C17 | 120.5 (6) | N11—C127—H12G | 111.5 |
C15—C16—C11 | 121.8 (5) | C126—C127—H12G | 111.5 |
C17—C16—C11 | 117.7 (5) | N11—C127—H12H | 111.5 |
C18—C17—C16 | 120.0 (6) | C126—C127—H12H | 111.5 |
C18—C17—H17 | 120.0 | H12G—C127—H12H | 109.4 |
C16—C17—H17 | 120.0 | C25—C210—C29 | 119.8 (7) |
C19—C18—C17 | 119.6 (7) | C25—C210—H210 | 120.1 |
C19—C18—H18 | 120.2 | C29—C210—H210 | 120.1 |
C17—C18—H18 | 120.2 | N22—C211—C212 | 113.9 (5) |
C110—C19—C18 | 120.9 (8) | N22—C211—H21A | 108.8 |
C110—C19—H19 | 119.6 | C212—C211—H21A | 108.8 |
C18—C19—H19 | 119.6 | N22—C211—H21B | 108.8 |
O21—C21—N22 | 122.5 (6) | C212—C211—H21B | 108.8 |
O21—C21—C26 | 119.9 (6) | H21A—C211—H21B | 107.7 |
N22—C21—C26 | 117.6 (5) | C213—C212—C211 | 109.9 (5) |
N22—C23—C219 | 109.6 (5) | C213—C212—H21C | 109.7 |
N22—C23—C24 | 111.7 (5) | C211—C212—H21C | 109.7 |
C219—C23—C24 | 111.0 (5) | C213—C212—H21D | 109.7 |
N22—C23—H23 | 108.1 | C211—C212—H21D | 109.7 |
C219—C23—H23 | 108.1 | H21C—C212—H21D | 108.2 |
C24—C23—H23 | 108.1 | C218—C213—C214 | 117.7 (6) |
C25—C24—C23 | 110.8 (5) | C218—C213—C212 | 120.1 (7) |
C25—C24—C223 | 109.5 (5) | C214—C213—C212 | 122.1 (7) |
C23—C24—C223 | 110.3 (5) | C215—C214—C213 | 122.3 (8) |
C25—C24—H24 | 108.8 | C215—C214—H214 | 118.9 |
C23—C24—H24 | 108.8 | C213—C214—H214 | 118.9 |
C223—C24—H24 | 108.8 | C214—C215—C216 | 117.2 (9) |
C210—C25—C26 | 119.4 (6) | C214—C215—H215 | 121.4 |
C210—C25—C24 | 122.9 (6) | C216—C215—H215 | 121.4 |
C26—C25—C24 | 117.7 (5) | C217—C216—C215 | 123.1 (8) |
C27—C26—C25 | 119.0 (6) | C217—C216—H216 | 118.5 |
C27—C26—C21 | 119.6 (5) | C215—C216—H216 | 118.5 |
C25—C26—C21 | 121.3 (5) | C216—C217—C218 | 117.8 (8) |
C28—C27—C26 | 121.4 (6) | C216—C217—H217 | 121.1 |
C28—C27—H27 | 119.3 | C218—C217—H217 | 121.1 |
C26—C27—H27 | 119.3 | C213—C218—C217 | 121.9 (8) |
C29—C28—C27 | 119.5 (7) | C213—C218—H218 | 119.1 |
C29—C28—H28 | 120.2 | C217—C218—H218 | 119.1 |
C27—C28—H28 | 120.2 | C220—C219—O22 | 109.1 (5) |
C28—C29—C210 | 120.7 (7) | C220—C219—C23 | 135.4 (5) |
C28—C29—H29 | 119.6 | O22—C219—C23 | 115.5 (5) |
C210—C29—H29 | 119.6 | C219—C220—C221 | 106.1 (6) |
C19—C110—C15 | 119.9 (8) | C219—C220—H220 | 127.0 |
C19—C110—H110 | 120.0 | C221—C220—H220 | 127.0 |
C15—C110—H110 | 120.0 | C222—C221—C220 | 107.8 (6) |
N12—C111—C112 | 111.1 (4) | C222—C221—H221 | 126.1 |
N12—C111—H11A | 109.4 | C220—C221—H221 | 126.1 |
C112—C111—H11A | 109.4 | C221—C222—O22 | 110.1 (6) |
N12—C111—H11B | 109.4 | C221—C222—H222 | 125.0 |
C112—C111—H11B | 109.4 | O22—C222—H222 | 125.0 |
H11A—C111—H11B | 108.0 | O23—C223—N21 | 122.0 (6) |
C113—C112—C111 | 111.0 (5) | O23—C223—C24 | 120.2 (6) |
C113—C112—H11C | 109.4 | N21—C223—C24 | 117.8 (6) |
C111—C112—H11C | 109.4 | N21—C224—C225 | 103.9 (5) |
C113—C112—H11D | 109.4 | N21—C224—H22A | 111.0 |
C111—C112—H11D | 109.4 | C225—C224—H22A | 111.0 |
H11C—C112—H11D | 108.0 | N21—C224—H22B | 111.0 |
C118—C113—C114 | 115.6 (7) | C225—C224—H22B | 111.0 |
C118—C113—C112 | 122.1 (7) | H22A—C224—H22B | 109.0 |
C114—C113—C112 | 122.3 (6) | C226—C225—C224 | 105.2 (6) |
C113—C114—C115 | 124.2 (8) | C226—C225—H22C | 110.7 |
C113—C114—H114 | 117.9 | C224—C225—H22C | 110.7 |
C115—C114—H114 | 117.9 | C226—C225—H22D | 110.7 |
C116—C115—C114 | 119.1 (9) | C224—C225—H22D | 110.7 |
C116—C115—H115 | 120.5 | H22C—C225—H22D | 108.8 |
C114—C115—H115 | 120.5 | C225—C226—C227 | 105.2 (6) |
C115—C116—C117 | 119.6 (8) | C225—C226—H22E | 110.7 |
C115—C116—H116 | 120.2 | C227—C226—H22E | 110.7 |
C117—C116—H116 | 120.2 | C225—C226—H22F | 110.7 |
C116—C117—C118 | 119.6 (9) | C227—C226—H22F | 110.7 |
C116—C117—H117 | 120.2 | H22E—C226—H22F | 108.8 |
C118—C117—H117 | 120.2 | N21—C227—C226 | 103.5 (5) |
C113—C118—C117 | 121.8 (9) | N21—C227—H22G | 111.1 |
C113—C118—H118 | 119.1 | C226—C227—H22G | 111.1 |
C117—C118—H118 | 119.1 | N21—C227—H22H | 111.1 |
C120—C119—O12 | 108.5 (6) | C226—C227—H22H | 111.1 |
C120—C119—C13 | 136.5 (5) | H22G—C227—H22H | 109.0 |
O12—C119—C13 | 115.0 (5) | C123—N11—C127 | 119.8 (6) |
C119—C120—C121 | 108.0 (6) | C123—N11—C124 | 127.4 (6) |
C119—C120—H120 | 126.0 | C127—N11—C124 | 112.7 (5) |
C121—C120—H120 | 126.0 | C11—N12—C13 | 123.7 (5) |
C122—C121—C120 | 106.9 (6) | C11—N12—C111 | 118.5 (5) |
C122—C121—H121 | 126.5 | C13—N12—C111 | 117.8 (5) |
C120—C121—H121 | 126.5 | C223—N21—C224 | 120.4 (5) |
C121—C122—O12 | 110.1 (6) | C223—N21—C227 | 128.0 (5) |
C121—C122—H122 | 124.9 | C224—N21—C227 | 111.6 (4) |
O12—C122—H122 | 124.9 | C21—N22—C211 | 119.2 (5) |
O13—C123—N11 | 122.5 (7) | C21—N22—C23 | 122.2 (5) |
O13—C123—C14 | 120.7 (6) | C211—N22—C23 | 118.5 (5) |
N11—C123—C14 | 116.8 (6) | C119—O12—C122 | 106.4 (5) |
N11—C124—C125 | 102.9 (6) | C222—O22—C219 | 106.9 (5) |
| | | |
O11—C11—N12—C13 | 178.2 (5) | O21—C21—N22—C23 | −173.8 (5) |
O11—C11—N12—C111 | −4.0 (8) | O21—C21—N22—C211 | 4.2 (8) |
C16—C11—N12—C13 | −0.1 (8) | C26—C21—N22—C23 | 5.2 (8) |
C16—C11—N12—C111 | 177.7 (5) | C26—C21—N22—C211 | −176.8 (5) |
O11—C11—C16—C15 | 166.1 (6) | O21—C21—C26—C25 | −167.7 (5) |
O11—C11—C16—C17 | −13.1 (8) | O21—C21—C26—C27 | 11.3 (8) |
N12—C11—C16—C15 | −15.6 (8) | N22—C21—C26—C25 | 13.3 (8) |
N12—C11—C16—C17 | 165.2 (5) | N22—C21—C26—C27 | −167.7 (5) |
C14—C13—N12—C11 | 31.5 (8) | C24—C23—N22—C21 | −36.8 (7) |
C14—C13—N12—C111 | −146.3 (5) | C24—C23—N22—C211 | 145.2 (5) |
C119—C13—N12—C11 | −90.7 (6) | C219—C23—N22—C21 | 86.7 (6) |
C119—C13—N12—C111 | 91.5 (6) | C219—C23—N22—C211 | −91.4 (6) |
N12—C13—C14—C15 | −46.2 (6) | N22—C23—C24—C25 | 49.4 (7) |
N12—C13—C14—C123 | 72.9 (6) | N22—C23—C24—C223 | −72.0 (6) |
C119—C13—C14—C15 | 76.2 (6) | C219—C23—C24—C25 | −73.3 (6) |
C119—C13—C14—C123 | −164.7 (5) | C219—C23—C24—C223 | 165.4 (5) |
C13—C14—C15—C16 | 33.9 (7) | C23—C24—C25—C26 | −34.0 (7) |
C13—C14—C15—C110 | −149.2 (6) | C23—C24—C25—C210 | 148.9 (6) |
C123—C14—C15—C16 | −86.1 (6) | C223—C24—C25—C26 | 87.9 (6) |
C123—C14—C15—C110 | 90.7 (7) | C223—C24—C25—C210 | −89.2 (7) |
C14—C15—C16—C11 | −3.5 (8) | C24—C25—C26—C21 | 3.1 (8) |
C14—C15—C16—C17 | 175.7 (5) | C24—C25—C26—C27 | −175.9 (5) |
C110—C15—C16—C11 | 179.6 (5) | C210—C25—C26—C21 | −179.7 (5) |
C110—C15—C16—C17 | −1.2 (9) | C210—C25—C26—C27 | 1.3 (9) |
C11—C16—C17—C18 | 178.9 (5) | C21—C26—C27—C28 | −178.6 (6) |
C15—C16—C17—C18 | −0.3 (9) | C25—C26—C27—C28 | 0.5 (9) |
C16—C17—C18—C19 | 2.3 (10) | C26—C27—C28—C29 | −0.9 (10) |
C17—C18—C19—C110 | −2.7 (12) | C27—C28—C29—C210 | −0.4 (11) |
C19—C110—C15—C14 | −176.0 (7) | C29—C210—C25—C24 | 174.5 (6) |
C19—C110—C15—C16 | 0.9 (11) | C29—C210—C25—C26 | −2.6 (10) |
C15—C110—C19—C18 | 1.1 (13) | C25—C210—C29—C28 | 2.2 (11) |
C112—C111—N12—C11 | −88.6 (7) | C212—C211—N22—C21 | 90.1 (7) |
C112—C111—N12—C13 | 89.4 (7) | C212—C211—N22—C23 | −91.8 (7) |
N12—C111—C112—C113 | −178.5 (6) | N22—C211—C212—C213 | −178.4 (6) |
C111—C112—C113—C114 | 87.4 (8) | C211—C212—C213—C214 | −86.2 (8) |
C111—C112—C113—C118 | −90.4 (9) | C211—C212—C213—C218 | 91.2 (8) |
C112—C113—C114—C115 | −178.2 (8) | C212—C213—C214—C215 | 175.3 (7) |
C118—C113—C114—C115 | −0.3 (13) | C218—C213—C214—C215 | −2.1 (12) |
C112—C113—C118—C117 | 178.1 (8) | C212—C213—C218—C217 | −174.8 (8) |
C114—C113—C118—C117 | 0.2 (14) | C214—C213—C218—C217 | 2.6 (13) |
C113—C114—C115—C116 | −0.9 (16) | C213—C214—C215—C216 | 0.9 (14) |
C114—C115—C116—C117 | 2.1 (18) | C214—C215—C216—C217 | −0.3 (17) |
C115—C116—C117—C118 | −2.3 (18) | C215—C216—C217—C218 | 0.8 (17) |
C116—C117—C118—C113 | 1.1 (17) | C216—C217—C218—C213 | −2.0 (16) |
C13—C119—O12—C122 | 179.8 (5) | C23—C219—O22—C222 | −179.2 (5) |
C120—C119—O12—C122 | −0.5 (7) | C220—C219—O22—C222 | 1.0 (7) |
O12—C119—C13—N12 | −49.2 (7) | O22—C219—C23—N22 | 46.1 (7) |
O12—C119—C13—C14 | −173.0 (5) | O22—C219—C23—C24 | 169.9 (5) |
C120—C119—C13—N12 | 131.3 (8) | C220—C219—C23—N22 | −134.1 (7) |
C120—C119—C13—C14 | 7.5 (10) | C220—C219—C23—C24 | −10.3 (10) |
O12—C119—C120—C121 | 0.6 (8) | O22—C219—C220—C221 | −0.7 (7) |
C13—C119—C120—C121 | −179.9 (7) | C23—C219—C220—C221 | 179.6 (6) |
C119—C120—C121—C122 | −0.5 (9) | C219—C220—C221—C222 | 0.1 (8) |
C120—C121—C122—O12 | 0.2 (9) | C220—C221—C222—O22 | 0.5 (9) |
C121—C122—O12—C119 | 0.2 (8) | C221—C222—O22—C219 | −0.9 (8) |
O13—C123—N11—C124 | −176.9 (7) | O23—C223—N21—C224 | −2.9 (10) |
O13—C123—N11—C127 | 1.0 (11) | O23—C223—N21—C227 | 175.7 (7) |
C14—C123—N11—C124 | 4.3 (10) | C24—C223—N21—C224 | −179.4 (5) |
C14—C123—N11—C127 | −177.9 (6) | C24—C223—N21—C227 | −0.8 (9) |
O13—C123—C14—C13 | −51.9 (9) | O23—C223—C24—C23 | 54.3 (8) |
O13—C123—C14—C15 | 68.1 (8) | O23—C223—C24—C25 | −67.8 (8) |
N11—C123—C14—C13 | 127.0 (6) | N21—C223—C24—C23 | −129.1 (6) |
N11—C123—C14—C15 | −113.0 (6) | N21—C223—C24—C25 | 108.8 (6) |
C125—C124—N11—C123 | 167.2 (7) | C225—C224—N21—C223 | −168.1 (6) |
C125—C124—N11—C127 | −10.8 (8) | C225—C224—N21—C227 | 13.1 (7) |
N11—C124—C125—C126 | 28.3 (9) | N21—C224—C225—C226 | −28.4 (8) |
C124—C125—C126—C127 | −36.0 (10) | C224—C225—C226—C227 | 33.2 (8) |
C125—C126—C127—N11 | 28.4 (9) | C225—C226—C227—N21 | −24.6 (8) |
C126—C127—N11—C123 | 171.9 (6) | C226—C227—N21—C223 | −171.8 (6) |
C126—C127—N11—C124 | −10.0 (8) | C226—C227—N21—C224 | 6.9 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C122—H122···O11i | 0.93 | 2.49 | 3.342 (8) | 153 |
C222—H222···O21ii | 0.93 | 2.57 | 3.454 (8) | 160 |
C121—H121···Cg2iii | 0.93 | 2.89 | 3.681 (6) | 147 |
C221—H221···Cg1iv | 0.93 | 2.92 | 3.756 (5) | 149 |
Symmetry codes: (i) x−1/2, −y+2, z; (ii) x+1/2, −y+1, z; (iii) x−1, y, z; (iv) x+1, y, z. |