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In the structure of the title compound, C
20H
23FN
2O
2, there are two independent molecules showing different conformations. The molecules form centrosymmetric dimers
via O—H
N or O—H
O hydrogen bonds.
Supporting information
CCDC reference: 282572
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.169
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N4
Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C24 .. 5.19 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C32 - C33 .. 5.74 su
PLAT355_ALERT_3_C Long O-H Bond (0.82A) O3 - H46 ... 1.03 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C6 - C7 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C26 - C27 ... 1.44 Ang.
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
4-[4-Dimethylamino-1-(4-fluorophenyl)-1-hydroxybutyl]-3-
(hydroxymethyl)benzonitrile
top
Crystal data top
C20H23FN2O2 | Z = 4 |
Mr = 342.41 | F(000) = 728.00 |
Triclinic, P1 | Dx = 1.214 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 8.1512 (5) Å | Cell parameters from 6362 reflections |
b = 12.4991 (6) Å | θ = 2.2–27.4° |
c = 18.928 (1) Å | µ = 0.09 mm−1 |
α = 100.708 (1)° | T = 295 K |
β = 96.0057 (8)° | Block, colorless |
γ = 94.896 (3)° | 0.41 × 0.28 × 0.24 mm |
V = 1873.6 (2) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4412 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.947, Tmax = 0.980 | k = −16→16 |
16267 measured reflections | l = −24→24 |
8398 independent reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[0.0028Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.169 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.39 e Å−3 |
6842 reflections | Δρmin = −0.41 e Å−3 |
451 parameters | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.6611 (2) | 1.2782 (1) | 0.1972 (1) | 0.0893 (6) | |
F2 | 0.8388 (2) | 0.6644 (2) | 0.30276 (9) | 0.1131 (8) | |
O1 | 0.2838 (2) | 1.1075 (1) | 0.43657 (7) | 0.0479 (4) | |
O2 | 0.7674 (2) | 0.9845 (1) | 0.44271 (9) | 0.0564 (5) | |
O3 | 0.3860 (2) | 0.6202 (1) | 0.00455 (8) | 0.0568 (5) | |
O4 | 0.1525 (3) | 0.5675 (1) | 0.0820 (1) | 0.0782 (6) | |
N1 | 0.4866 (4) | 0.5378 (2) | 0.3791 (2) | 0.125 (1) | |
N2 | 0.0954 (3) | 1.2732 (2) | 0.4501 (1) | 0.0639 (7) | |
N3 | −0.1738 (4) | 1.0411 (2) | 0.1274 (2) | 0.095 (1) | |
N4 | 0.8642 (2) | 0.6249 (1) | −0.1262 (1) | 0.0638 (5) | |
C1 | 0.2640 (3) | 1.0544 (2) | 0.3622 (1) | 0.0432 (6) | |
C2 | 0.3164 (3) | 0.9386 (2) | 0.3629 (1) | 0.0437 (6) | |
C3 | 0.4792 (3) | 0.9240 (2) | 0.3901 (1) | 0.0442 (6) | |
C4 | 0.6148 (3) | 1.0175 (2) | 0.4180 (1) | 0.0531 (7) | |
C5 | 0.5179 (3) | 0.8185 (2) | 0.3924 (1) | 0.0512 (7) | |
C6 | 0.4024 (3) | 0.7282 (2) | 0.3689 (1) | 0.0581 (7) | |
C7 | 0.4482 (4) | 0.6215 (2) | 0.3740 (2) | 0.081 (1) | |
C8 | 0.2435 (3) | 0.7425 (2) | 0.3414 (1) | 0.0649 (8) | |
C9 | 0.2037 (3) | 0.8456 (2) | 0.3386 (1) | 0.0585 (7) | |
C10 | 0.3757 (2) | 1.1151 (2) | 0.3188 (1) | 0.0424 (6) | |
C11 | 0.4011 (3) | 1.0664 (2) | 0.2491 (1) | 0.0496 (6) | |
C12 | 0.4969 (3) | 1.1202 (2) | 0.2081 (1) | 0.0578 (8) | |
C13 | 0.5672 (3) | 1.2233 (2) | 0.2371 (1) | 0.0595 (8) | |
C14 | 0.5471 (3) | 1.2759 (2) | 0.3060 (1) | 0.0593 (8) | |
C15 | 0.4508 (3) | 1.2198 (2) | 0.3462 (1) | 0.0515 (7) | |
C16 | 0.0817 (3) | 1.0513 (2) | 0.3292 (1) | 0.0532 (7) | |
C17 | 0.0156 (3) | 1.1614 (2) | 0.3254 (1) | 0.0655 (8) | |
C18 | −0.0396 (3) | 1.2203 (2) | 0.3947 (2) | 0.0718 (9) | |
C19 | 0.1611 (5) | 1.3780 (3) | 0.4350 (2) | 0.100 (1) | |
C20 | 0.0431 (5) | 1.2887 (4) | 0.5224 (2) | 0.115 (2) | |
C21 | 0.4605 (3) | 0.7212 (2) | 0.0481 (1) | 0.0462 (6) | |
C22 | 0.3224 (3) | 0.7949 (2) | 0.0692 (1) | 0.0434 (6) | |
C23 | 0.2013 (3) | 0.7625 (2) | 0.1114 (1) | 0.0449 (6) | |
C24 | 0.1914 (3) | 0.6584 (2) | 0.1407 (1) | 0.0543 (7) | |
C25 | 0.0763 (3) | 0.8288 (2) | 0.1261 (1) | 0.0463 (6) | |
C26 | 0.0684 (3) | 0.9256 (2) | 0.1012 (1) | 0.0490 (6) | |
C27 | −0.0649 (3) | 0.9913 (2) | 0.1171 (1) | 0.0602 (8) | |
C28 | 0.1877 (3) | 0.9582 (2) | 0.0604 (1) | 0.0517 (7) | |
C29 | 0.3118 (3) | 0.8927 (2) | 0.0452 (1) | 0.0511 (7) | |
C30 | 0.5644 (3) | 0.7050 (2) | 0.1174 (1) | 0.0479 (6) | |
C31 | 0.6201 (3) | 0.7938 (2) | 0.1728 (1) | 0.0571 (7) | |
C32 | 0.7119 (3) | 0.7810 (3) | 0.2354 (1) | 0.0688 (9) | |
C33 | 0.7484 (3) | 0.6790 (3) | 0.2410 (1) | 0.0732 (9) | |
C34 | 0.6987 (3) | 0.5889 (3) | 0.1880 (2) | 0.0721 (9) | |
C35 | 0.6055 (3) | 0.6029 (2) | 0.1245 (1) | 0.0604 (7) | |
C36 | 0.5755 (3) | 0.7672 (2) | −0.0002 (1) | 0.0593 (7) | |
C37 | 0.7049 (3) | 0.6915 (2) | −0.0251 (1) | 0.0665 (8) | |
C38 | 0.7400 (4) | 0.6952 (2) | −0.0996 (1) | 0.0731 (9) | |
C39 | 1.0293 (4) | 0.6700 (3) | −0.0938 (3) | 0.120 (1) | |
C40 | 0.8525 (7) | 0.6089 (4) | −0.2044 (2) | 0.139 (2) | |
H1 | 0.5787 | 1.0664 | 0.4566 | 0.064* | |
H2 | 0.6322 | 1.0546 | 0.3795 | 0.065* | |
H3 | 0.6271 | 0.8079 | 0.4107 | 0.063* | |
H4 | 0.1638 | 0.6807 | 0.3243 | 0.075* | |
H5 | 0.0944 | 0.8554 | 0.3200 | 0.069* | |
H6 | 0.3492 | 0.9945 | 0.2297 | 0.060* | |
H7 | 0.5142 | 1.0863 | 0.1606 | 0.072* | |
H8 | 0.5968 | 1.3486 | 0.3246 | 0.073* | |
H9 | 0.4365 | 1.2535 | 0.3941 | 0.063* | |
H10 | 0.0703 | 1.0087 | 0.2816 | 0.063* | |
H11 | 0.0138 | 1.0163 | 0.3579 | 0.063* | |
H12 | 0.1037 | 1.2080 | 0.3145 | 0.079* | |
H13 | −0.0740 | 1.1505 | 0.2875 | 0.079* | |
H14 | −0.1017 | 1.1671 | 0.4140 | 0.088* | |
H15 | −0.1087 | 1.2741 | 0.3839 | 0.088* | |
H16 | 0.2472 | 1.3668 | 0.4051 | 0.121* | |
H17 | 0.2040 | 1.4259 | 0.4793 | 0.121* | |
H18 | 0.0749 | 1.4094 | 0.4109 | 0.121* | |
H19 | 0.1346 | 1.2863 | 0.5574 | 0.144* | |
H20 | 0.0014 | 1.3579 | 0.5330 | 0.144* | |
H21 | −0.0417 | 1.2324 | 0.5238 | 0.144* | |
H22 | 0.7564 | 0.9594 | 0.4854 | 0.070* | |
H23 | 0.2258 | 1.1694 | 0.4400 | 0.059* | |
H24 | 0.2962 | 0.6527 | 0.1660 | 0.067* | |
H25 | 0.1092 | 0.6592 | 0.1727 | 0.066* | |
H26 | −0.0074 | 0.8065 | 0.1533 | 0.056* | |
H27 | 0.1833 | 1.0248 | 0.0433 | 0.064* | |
H28 | 0.3932 | 0.9147 | 0.0168 | 0.063* | |
H29 | 0.5941 | 0.8643 | 0.1665 | 0.068* | |
H30 | 0.7498 | 0.8419 | 0.2734 | 0.080* | |
H31 | 0.7278 | 0.5189 | 0.1941 | 0.091* | |
H32 | 0.5695 | 0.5425 | 0.0860 | 0.074* | |
H33 | 0.6313 | 0.8355 | 0.0253 | 0.074* | |
H34 | 0.5099 | 0.7779 | −0.0423 | 0.074* | |
H35 | 0.6639 | 0.6188 | −0.0231 | 0.085* | |
H36 | 0.8051 | 0.7125 | 0.0069 | 0.084* | |
H37 | 0.6391 | 0.6734 | −0.1310 | 0.095* | |
H38 | 0.7779 | 0.7687 | −0.1010 | 0.095* | |
H39 | 1.0739 | 0.7147 | −0.1242 | 0.141* | |
H40 | 1.0259 | 0.7133 | −0.0471 | 0.140* | |
H41 | 1.0974 | 0.6129 | −0.0896 | 0.140* | |
H42 | 0.8129 | 0.6706 | −0.2205 | 0.178* | |
H43 | 0.7771 | 0.5456 | −0.2242 | 0.178* | |
H44 | 0.9583 | 0.5982 | −0.2197 | 0.178* | |
H45 | 0.1582 | 0.4989 | 0.1008 | 0.096* | |
H46 | 0.2899 | 0.5932 | 0.0307 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.086 (1) | 0.089 (1) | 0.114 (1) | 0.008 (1) | 0.048 (1) | 0.057 (1) |
F2 | 0.088 (1) | 0.183 (2) | 0.072 (1) | 0.015 (1) | −0.0120 (9) | 0.044 (1) |
O1 | 0.0550 (9) | 0.0497 (9) | 0.0411 (8) | 0.0098 (7) | 0.0078 (6) | 0.0118 (7) |
O2 | 0.0452 (8) | 0.066 (1) | 0.064 (1) | 0.0038 (8) | 0.0065 (7) | 0.0301 (8) |
O3 | 0.064 (1) | 0.0496 (9) | 0.0524 (9) | 0.0099 (8) | 0.0082 (7) | −0.0024 (7) |
O4 | 0.127 (2) | 0.043 (1) | 0.070 (1) | 0.003 (1) | 0.028 (1) | 0.0165 (8) |
N1 | 0.139 (3) | 0.049 (2) | 0.187 (4) | 0.017 (2) | 0.025 (2) | 0.022 (2) |
N2 | 0.069 (1) | 0.062 (1) | 0.065 (1) | 0.018 (1) | 0.014 (1) | 0.016 (1) |
N3 | 0.097 (2) | 0.090 (2) | 0.119 (2) | 0.046 (2) | 0.050 (2) | 0.039 (2) |
N4 | 0.068 (1) | 0.061 (1) | 0.064 (1) | 0.017 (1) | 0.013 (1) | 0.015 (1) |
C1 | 0.045 (1) | 0.047 (1) | 0.038 (1) | 0.000 (1) | 0.0053 (9) | 0.0105 (9) |
C2 | 0.049 (1) | 0.044 (1) | 0.038 (1) | −0.003 (1) | 0.0102 (9) | 0.0102 (9) |
C3 | 0.049 (1) | 0.042 (1) | 0.042 (1) | 0.001 (1) | 0.0126 (9) | 0.0108 (9) |
C4 | 0.046 (1) | 0.049 (1) | 0.066 (2) | −0.002 (1) | 0.002 (1) | 0.022 (1) |
C5 | 0.058 (1) | 0.044 (1) | 0.054 (1) | 0.007 (1) | 0.015 (1) | 0.011 (1) |
C6 | 0.075 (2) | 0.041 (1) | 0.060 (1) | 0.003 (1) | 0.020 (1) | 0.009 (1) |
C7 | 0.093 (2) | 0.044 (2) | 0.105 (2) | 0.001 (2) | 0.024 (2) | 0.011 (2) |
C8 | 0.073 (2) | 0.044 (1) | 0.071 (2) | −0.013 (1) | 0.009 (1) | 0.003 (1) |
C9 | 0.057 (1) | 0.052 (1) | 0.063 (2) | −0.009 (1) | 0.002 (1) | 0.011 (1) |
C10 | 0.041 (1) | 0.043 (1) | 0.046 (1) | 0.004 (1) | 0.0052 (9) | 0.0151 (9) |
C11 | 0.052 (1) | 0.050 (1) | 0.048 (1) | 0.004 (1) | 0.007 (1) | 0.014 (1) |
C12 | 0.062 (1) | 0.065 (2) | 0.054 (1) | 0.013 (1) | 0.018 (1) | 0.022 (1) |
C13 | 0.051 (1) | 0.066 (2) | 0.077 (2) | 0.016 (1) | 0.024 (1) | 0.041 (1) |
C14 | 0.053 (1) | 0.045 (1) | 0.086 (2) | 0.007 (1) | 0.013 (1) | 0.025 (1) |
C15 | 0.053 (1) | 0.046 (1) | 0.057 (1) | 0.004 (1) | 0.009 (1) | 0.014 (1) |
C16 | 0.047 (1) | 0.062 (1) | 0.050 (1) | −0.001 (1) | 0.002 (1) | 0.015 (1) |
C17 | 0.051 (1) | 0.078 (2) | 0.067 (2) | 0.009 (1) | −0.007 (1) | 0.021 (1) |
C18 | 0.052 (1) | 0.070 (2) | 0.097 (2) | 0.010 (1) | 0.016 (1) | 0.021 (2) |
C19 | 0.095 (2) | 0.056 (2) | 0.150 (3) | 0.010 (2) | 0.018 (2) | 0.015 (2) |
C20 | 0.145 (3) | 0.135 (3) | 0.080 (2) | 0.067 (3) | 0.041 (2) | 0.019 (2) |
C21 | 0.055 (1) | 0.042 (1) | 0.043 (1) | 0.010 (1) | 0.0124 (9) | 0.0060 (9) |
C22 | 0.049 (1) | 0.039 (1) | 0.042 (1) | 0.006 (1) | 0.0079 (9) | 0.0070 (9) |
C23 | 0.053 (1) | 0.038 (1) | 0.044 (1) | 0.004 (1) | 0.0094 (9) | 0.0071 (9) |
C24 | 0.068 (1) | 0.045 (1) | 0.054 (1) | 0.009 (1) | 0.019 (1) | 0.013 (1) |
C25 | 0.047 (1) | 0.044 (1) | 0.048 (1) | 0.005 (1) | 0.0128 (9) | 0.008 (1) |
C26 | 0.052 (1) | 0.044 (1) | 0.052 (1) | 0.010 (1) | 0.009 (1) | 0.006 (1) |
C27 | 0.065 (1) | 0.055 (1) | 0.068 (2) | 0.019 (1) | 0.021 (1) | 0.016 (1) |
C28 | 0.061 (1) | 0.037 (1) | 0.061 (1) | 0.010 (1) | 0.014 (1) | 0.015 (1) |
C29 | 0.056 (1) | 0.047 (1) | 0.056 (1) | 0.006 (1) | 0.020 (1) | 0.015 (1) |
C30 | 0.048 (1) | 0.054 (1) | 0.045 (1) | 0.013 (1) | 0.0167 (9) | 0.008 (1) |
C31 | 0.051 (1) | 0.065 (2) | 0.054 (1) | 0.002 (1) | 0.015 (1) | 0.005 (1) |
C32 | 0.053 (1) | 0.092 (2) | 0.055 (2) | −0.002 (1) | 0.012 (1) | 0.000 (1) |
C33 | 0.051 (1) | 0.126 (3) | 0.045 (1) | 0.010 (2) | 0.005 (1) | 0.024 (2) |
C34 | 0.069 (2) | 0.087 (2) | 0.072 (2) | 0.029 (2) | 0.016 (1) | 0.033 (2) |
C35 | 0.067 (1) | 0.065 (2) | 0.052 (1) | 0.020 (1) | 0.010 (1) | 0.013 (1) |
C36 | 0.063 (1) | 0.068 (2) | 0.055 (1) | 0.018 (1) | 0.023 (1) | 0.019 (1) |
C37 | 0.068 (2) | 0.088 (2) | 0.054 (1) | 0.029 (2) | 0.023 (1) | 0.023 (1) |
C38 | 0.100 (2) | 0.067 (2) | 0.070 (2) | 0.036 (2) | 0.039 (2) | 0.030 (1) |
C39 | 0.066 (2) | 0.095 (3) | 0.190 (4) | −0.010 (2) | 0.043 (2) | −0.004 (3) |
C40 | 0.249 (5) | 0.131 (4) | 0.064 (2) | 0.094 (4) | 0.051 (3) | 0.035 (2) |
Geometric parameters (Å, º) top
F1—C13 | 1.360 (3) | C34—C35 | 1.400 (4) |
F2—C33 | 1.366 (3) | C36—C37 | 1.530 (4) |
O1—C1 | 1.426 (2) | C37—C38 | 1.477 (4) |
O2—C4 | 1.405 (3) | O1—H23 | 0.9358 |
O3—C21 | 1.421 (2) | O2—H22 | 0.9286 |
O4—C24 | 1.421 (3) | O3—H46 | 1.0354 |
N1—C7 | 1.136 (4) | O4—H45 | 0.9896 |
N2—C18 | 1.457 (3) | C4—H1 | 0.9500 |
N2—C19 | 1.462 (4) | C4—H2 | 0.9500 |
N2—C20 | 1.460 (4) | C5—H3 | 0.9500 |
N3—C27 | 1.140 (4) | C8—H4 | 0.9500 |
N4—C38 | 1.465 (4) | C9—H5 | 0.9500 |
N4—C39 | 1.441 (4) | C11—H6 | 0.9500 |
N4—C40 | 1.448 (4) | C12—H7 | 0.9500 |
C1—C2 | 1.546 (3) | C14—H8 | 0.9500 |
C1—C10 | 1.532 (3) | C15—H9 | 0.9500 |
C1—C16 | 1.544 (3) | C16—H10 | 0.9500 |
C2—C3 | 1.412 (3) | C16—H11 | 0.9500 |
C2—C9 | 1.391 (3) | C17—H12 | 0.9500 |
C3—C4 | 1.515 (3) | C17—H13 | 0.9500 |
C3—C5 | 1.389 (3) | C18—H14 | 0.9500 |
C5—C6 | 1.379 (3) | C18—H15 | 0.9500 |
C6—C7 | 1.433 (4) | C19—H16 | 0.9500 |
C6—C8 | 1.383 (4) | C19—H17 | 0.9500 |
C8—C9 | 1.365 (4) | C19—H18 | 0.9500 |
C10—C11 | 1.390 (3) | C20—H19 | 0.9500 |
C10—C15 | 1.379 (3) | C20—H20 | 0.9500 |
C11—C12 | 1.376 (4) | C20—H21 | 0.9500 |
C12—C13 | 1.355 (3) | C24—H25 | 0.9500 |
C13—C14 | 1.380 (4) | C24—H24 | 0.9500 |
C14—C15 | 1.384 (4) | C25—H26 | 0.9500 |
C16—C17 | 1.531 (4) | C28—H27 | 0.9500 |
C17—C16 | 1.531 (4) | C29—H28 | 0.9500 |
C17—C18 | 1.513 (4) | C31—H29 | 0.9500 |
C18—C17 | 1.513 (4) | C32—H30 | 0.9500 |
C21—C22 | 1.553 (3) | C34—H31 | 0.9500 |
C21—C30 | 1.541 (3) | C35—H32 | 0.9500 |
C21—C36 | 1.525 (3) | C36—H34 | 0.9500 |
C22—C23 | 1.411 (3) | C36—H33 | 0.9500 |
C22—C29 | 1.387 (3) | C37—H36 | 0.9500 |
C23—C24 | 1.506 (3) | C37—H35 | 0.9500 |
C23—C25 | 1.386 (3) | C38—H38 | 0.9500 |
C25—C26 | 1.383 (3) | C38—H37 | 0.9500 |
C26—C27 | 1.440 (4) | C39—H39 | 0.9500 |
C26—C28 | 1.383 (3) | C39—H41 | 0.9500 |
C28—C29 | 1.375 (3) | C39—H40 | 0.9500 |
C30—C31 | 1.385 (3) | C40—H44 | 0.9500 |
C30—C35 | 1.373 (4) | C40—H42 | 0.9500 |
C31—C32 | 1.377 (4) | C40—H43 | 0.9500 |
C32—C33 | 1.354 (4) | H12—C17 | 0.9500 |
C33—C34 | 1.361 (4) | H13—C17 | 0.9500 |
| | | |
F1—C13—C12 | 119.4 (2) | N2—C19—H18 | 109.5843 |
F1—C13—C14 | 118.1 (2) | N2—C20—H19 | 109.9906 |
F2—C33—C32 | 119.0 (3) | N2—C20—H21 | 109.3036 |
F2—C33—C34 | 117.7 (3) | N2—C20—H20 | 109.1139 |
O1—C1—C2 | 104.8 (2) | N4—C38—H37 | 108.2004 |
O1—C1—C10 | 111.0 (2) | N4—C38—H38 | 108.3198 |
O1—C1—C16 | 109.7 (2) | N4—C39—H39 | 107.9926 |
O2—C4—C3 | 114.2 (2) | N4—C39—H41 | 110.2409 |
O3—C21—C22 | 109.0 (2) | N4—C39—H40 | 110.1620 |
O3—C21—C30 | 112.2 (2) | N4—C40—H44 | 110.0375 |
O3—C21—C36 | 103.8 (2) | N4—C40—H42 | 110.3062 |
O4—C24—C23 | 109.2 (2) | N4—C40—H43 | 108.0529 |
N1—C7—C6 | 178.7 (3) | C1—C16—H10 | 107.4187 |
N2—C18—C17 | 114.5 (2) | C1—C16—H11 | 107.6328 |
C20—N2—C18 | 111.6 (2) | C2—C9—H5 | 117.8347 |
C19—N2—C18 | 110.8 (2) | C3—C4—H1 | 108.6112 |
C20—N2—C19 | 110.3 (3) | C3—C4—H2 | 107.9809 |
N3—C27—C26 | 177.4 (3) | C3—C5—H3 | 119.2794 |
N4—C38—C37 | 115.0 (2) | H2—C4—H1 | 109.4567 |
C39—N4—C38 | 111.4 (2) | H3—C5—C6 | 118.6823 |
C40—N4—C38 | 110.0 (3) | C6—C8—H4 | 119.8251 |
C40—N4—C39 | 110.5 (3) | H4—C8—C9 | 120.7319 |
C1—C2—C3 | 120.9 (2) | C8—C9—H5 | 119.3747 |
C1—C2—C9 | 121.2 (2) | C10—C11—H6 | 118.3105 |
C10—C1—C2 | 110.3 (2) | C10—C15—H9 | 118.6042 |
C16—C1—C2 | 112.3 (2) | C11—C12—H7 | 121.3595 |
C1—C10—C11 | 120.5 (2) | H6—C11—C12 | 119.9006 |
C1—C10—C15 | 121.8 (2) | H7—C12—C13 | 120.2078 |
C16—C1—C10 | 108.7 (2) | C13—C14—H8 | 120.6400 |
C1—C16—C17 | 117.1 (2) | H8—C14—C15 | 121.5792 |
C2—C3—C4 | 123.7 (2) | C14—C15—H9 | 119.6482 |
C9—C2—C3 | 117.9 (2) | H10—C16—C17 | 108.3860 |
C2—C3—C5 | 118.6 (2) | H11—C16—C17 | 106.6692 |
C2—C9—C8 | 122.8 (2) | C16—C17—H12 | 107.0552 |
C5—C3—C4 | 117.7 (2) | C16—C17—H13 | 108.9191 |
C3—C5—C6 | 122.0 (2) | H11—C16—H10 | 109.4639 |
C5—C6—C7 | 119.6 (2) | H12—C17—C18 | 106.6503 |
C5—C6—C8 | 119.2 (2) | C17—C18—H14 | 107.0365 |
C8—C6—C7 | 121.1 (2) | H13—C17—C18 | 109.2686 |
C6—C8—C9 | 119.4 (2) | C17—C18—H15 | 109.1399 |
C10—C11—C12 | 121.8 (2) | H13—C17—H12 | 109.4576 |
C15—C10—C11 | 117.7 (2) | H15—C18—H14 | 109.4604 |
C10—C15—C14 | 121.7 (2) | H17—C19—H16 | 109.4683 |
C11—C12—C13 | 118.4 (2) | H18—C19—H16 | 109.4814 |
C12—C13—C14 | 122.6 (3) | H18—C19—H17 | 109.4691 |
C13—C14—C15 | 117.8 (2) | H21—C20—H19 | 109.4728 |
C16—C17—C18 | 115.3 (2) | H20—C20—H19 | 109.4729 |
C21—C22—C23 | 120.9 (2) | H21—C20—H20 | 109.4722 |
C21—C22—C29 | 120.8 (2) | C21—C36—H34 | 108.3222 |
C30—C21—C22 | 109.3 (2) | C21—C36—H33 | 109.1995 |
C36—C21—C22 | 113.4 (2) | C22—C29—H28 | 118.4870 |
C21—C30—C31 | 120.3 (2) | C23—C24—H24 | 108.7975 |
C21—C30—C35 | 120.5 (2) | C23—C24—H25 | 110.1543 |
C36—C21—C30 | 109.1 (2) | C23—C25—H26 | 119.2281 |
C21—C36—C37 | 113.6 (2) | H24—C24—H25 | 109.4581 |
C22—C23—C24 | 125.5 (2) | H26—C25—C26 | 119.0384 |
C29—C22—C23 | 118.3 (2) | C26—C28—H27 | 120.1478 |
C22—C23—C25 | 118.7 (2) | H27—C28—C29 | 120.8784 |
C22—C29—C28 | 122.6 (2) | C28—C29—H28 | 118.9570 |
C25—C23—C24 | 115.7 (2) | C30—C31—H29 | 118.3088 |
C23—C25—C26 | 121.7 (2) | C30—C35—H32 | 118.9933 |
C25—C26—C27 | 119.8 (2) | C31—C32—H30 | 121.2035 |
C25—C26—C28 | 119.7 (2) | H29—C31—C32 | 120.4346 |
C28—C26—C27 | 120.5 (2) | H30—C32—C33 | 120.8039 |
C26—C28—C29 | 119.0 (2) | C33—C34—H31 | 120.5060 |
C30—C31—C32 | 121.3 (3) | H31—C34—C35 | 121.3502 |
C35—C30—C31 | 119.1 (2) | C34—C35—H32 | 120.9061 |
C30—C35—C34 | 120.1 (2) | H34—C36—C37 | 107.4553 |
C31—C32—C33 | 118.0 (2) | H33—C36—C37 | 108.6989 |
C32—C33—C34 | 123.4 (3) | C36—C37—H36 | 109.0083 |
C33—C34—C35 | 118.1 (3) | C36—C37—H35 | 108.0662 |
C36—C37—C38 | 112.6 (2) | H33—C36—H34 | 109.4590 |
H23—O1—C1 | 107.5397 | H36—C37—C38 | 108.7753 |
O2—C4—H1 | 108.8113 | H35—C37—C38 | 108.9046 |
O2—C4—H2 | 107.7586 | C37—C38—H37 | 107.8317 |
H22—O2—C4 | 108.4510 | C37—C38—H38 | 107.9203 |
H46—O3—C21 | 106.6261 | H35—C37—H36 | 109.4604 |
O4—C24—H24 | 109.0070 | H37—C38—H38 | 109.4620 |
H45—O4—C24 | 109.1558 | H41—C39—H39 | 109.4716 |
O4—C24—H25 | 110.1765 | H40—C39—H39 | 109.4771 |
N2—C18—H14 | 107.9267 | H40—C39—H41 | 109.4728 |
N2—C18—H15 | 108.6452 | H42—C40—H44 | 109.4672 |
N2—C19—H16 | 109.6273 | H43—C40—H44 | 109.4749 |
N2—C19—H17 | 109.1965 | H43—C40—H42 | 109.4792 |
| | | |
C19—N2—C18—C17 | 79.9 (3) | C1—C16—C17—C18 | −81.6 (3) |
C20—N2—C18—C17 | −156.8 (2) | C16—C17—C18—N2 | 75.9 (3) |
C39—N4—C38—C37 | −74.5 (3) | O3—C21—C22—C23 | 62.5 (2) |
C40—N4—C38—C37 | 162.7 (2) | O3—C21—C22—C29 | −115.5 (2) |
O1—C1—C2—C3 | −61.7 (3) | C30—C21—C22—C23 | −60.5 (2) |
O1—C1—C2—C9 | 116.5 (2) | C30—C21—C22—C29 | 121.6 (2) |
C10—C1—C2—C3 | 57.9 (2) | C36—C21—C22—C23 | 177.5 (2) |
C10—C1—C2—C9 | −123.9 (2) | C36—C21—C22—C29 | −0.4 (2) |
C16—C1—C2—C3 | 179.2 (2) | O3—C21—C30—C31 | −167.7 (2) |
C16—C1—C2—C9 | −2.5 (3) | O3—C21—C30—C35 | 13.5 (3) |
O1—C1—C10—C11 | 167.2 (2) | C22—C21—C30—C31 | −46.7 (3) |
O1—C1—C10—C15 | −14.4 (3) | C22—C21—C30—C35 | 134.6 (2) |
C2—C1—C10—C11 | 51.4 (2) | C36—C21—C30—C31 | 77.9 (3) |
C2—C1—C10—C15 | −130.2 (2) | C36—C21—C30—C35 | −100.9 (2) |
C16—C1—C10—C11 | −72.1 (2) | O3—C21—C36—C37 | −58.2 (2) |
C16—C1—C10—C15 | 106.3 (2) | C22—C21—C36—C37 | −176.4 (2) |
O1—C1—C16—C17 | 64.0 (3) | C30—C21—C36—C37 | 61.5 (2) |
C2—C1—C16—C17 | −179.8 (2) | C21—C22—C23—C24 | 0.7 (3) |
C10—C1—C16—C17 | −57.5 (3) | C21—C22—C23—C25 | −177.2 (2) |
C1—C2—C3—C4 | −2.0 (3) | C29—C22—C23—C24 | 178.6 (2) |
C1—C2—C3—C5 | 177.3 (2) | C29—C22—C23—C25 | 0.8 (3) |
C9—C2—C3—C4 | 179.7 (2) | C21—C22—C29—C28 | 177.5 (2) |
C9—C2—C3—C5 | −1.0 (3) | C23—C22—C29—C28 | −0.5 (3) |
C1—C2—C9—C8 | −176.9 (2) | C22—C23—C24—O4 | −66.8 (3) |
C3—C2—C9—C8 | 1.4 (4) | C25—C23—C24—O4 | 111.1 (2) |
C2—C3—C4—O2 | 179.9 (2) | C22—C23—C25—C26 | −0.6 (3) |
C5—C3—C4—O2 | 0.6 (3) | C24—C23—C25—C26 | −178.6 (2) |
C2—C3—C5—C6 | 0.1 (3) | C23—C25—C26—C27 | 179.3 (2) |
C4—C3—C5—C6 | 179.4 (2) | C23—C25—C26—C28 | −0.0 (3) |
C3—C5—C6—C7 | −178.6 (3) | C25—C26—C28—C29 | 0.4 (3) |
C3—C5—C6—C8 | 0.6 (4) | C27—C26—C28—C29 | −178.9 (2) |
C5—C6—C8—C9 | −0.4 (4) | C26—C28—C29—C22 | −0.1 (3) |
C7—C6—C8—C9 | 178.9 (2) | C21—C30—C31—C32 | 179.5 (2) |
C6—C8—C9—C2 | −0.7 (4) | C35—C30—C31—C32 | −1.8 (4) |
C1—C10—C11—C12 | 178.1 (2) | C21—C30—C35—C34 | −179.5 (2) |
C15—C10—C11—C12 | −0.3 (3) | C31—C30—C35—C34 | 1.8 (4) |
C1—C10—C15—C14 | −177.7 (2) | C30—C31—C32—C33 | 0.9 (4) |
C11—C10—C15—C14 | 0.7 (3) | C31—C32—C33—F2 | −179.8 (2) |
C10—C11—C12—C13 | −0.2 (4) | C31—C32—C33—C34 | −0.1 (4) |
C11—C12—C13—F1 | −179.4 (2) | F2—C33—C34—C35 | 179.8 (3) |
C11—C12—C13—C14 | 0.4 (4) | C32—C33—C34—C35 | 0.2 (4) |
F1—C13—C14—C15 | 179.8 (2) | C33—C34—C35—C30 | −1.0 (4) |
C12—C13—C14—C15 | −0.0 (3) | C21—C36—C37—C38 | 144.1 (2) |
C13—C14—C15—C10 | −0.5 (4) | C36—C37—C38—N4 | 179.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H23···N2 | 0.94 | 1.74 | 2.671 (3) | 172 |
O2—H22···O1i | 0.93 | 1.87 | 2.795 (2) | 172 |
O3—H46···O4 | 1.04 | 1.61 | 2.634 (3) | 171 |
O4—H45···N4ii | 0.99 | 1.70 | 2.686 (3) | 171 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z. |
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