Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042213/cv2292sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042213/cv2292Isup2.hkl |
CCDC reference: 663695
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.060
- wR factor = 0.141
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12
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 29.97 From the CIF: _reflns_number_total 10705 Count of symmetry unique reflns 5639 Completeness (_total/calc) 189.84% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 5066 Fraction of Friedel pairs measured 0.898 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C29A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C29B = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 478
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For details of the synthesis, see: Martirosyan et al. (2000, 2004). For details of the pharmacological properties of compounds of this family, see: De Clercq (1996). For crystal structures of related compounds, see: Karapetyan et al. (2002); Tamazyan et al. (2002).
The title compound was synthesized by cycloalkylation of ethyl-2-[2,3-dichloropropyl(phenyl)carboxamido]-2-phenylacetate in phase-transfer catalysis condition as it is described by (Martirosyan et al., 2000, 2004). The crystals were grown from ethanol solution.
All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2–1.5Ueq(C). SADI and SIMI restrains were applied to positional and thermal parameters of disordered atoms in pyrrolidine rings.
The interest to X-ray structural investigation of the title compound is stipulated by its potentially HIV-1 RT inhibition properties. This compound belongs to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs) (De Clercq, 1996) with butterfly-like conformation (Karapetyan et al., 2002; Tamazyan et al., 2002).
All four (2S,4R), (2S,4S), (2R,4R) and (2R,4 s) isomers of the title compound are present in crystal structure. The molecules crystallized in the monoclinic space group P21 with two independent molecules (Fig. 1). Each of two symmetry independent molecules corresponds to mixture of pairs of two isomers (2R,4R), (2R,4S) and (2S,4R), (2S,4S) respectively. In pair (2R,4R) (2R,4S) isomers are in ratio ~7:3, while in pair (2S,4R) (2S,4S) the isomers are in ratio ~1:1.
For details of the synthesis, see: Martirosyan et al. (2000, 2004). For details of the pharmacological properties of compounds of this family, see: De Clercq (1996). For crystal structures of related compounds, see: Karapetyan et al. (2002); Tamazyan et al. (2002).
Data collection: CAD-4 Manual (Enraf–Nonius, 1988); cell refinement: CAD-4 Manual (Enraf–Nonius, 1988); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C20H20ClNO3 | F(000) = 752 |
Mr = 357.82 | Dx = 1.292 Mg m−3 |
Monoclinic, P21 | Melting point: 471 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4241 (19) Å | Cell parameters from 22 reflections |
b = 10.073 (2) Å | θ = 13–15° |
c = 19.849 (4) Å | µ = 0.23 mm−1 |
β = 102.52 (3)° | T = 293 K |
V = 1839.5 (7) Å3 | Irregular, colourless |
Z = 4 | 0.36 × 0.32 × 0.30 mm |
Enraf–Nonius CAD-4 diffractometer | 5925 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 30.0°, θmin = 1.1° |
θ/2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.875, Tmax = 0.927 | l = −27→27 |
11300 measured reflections | 3 standard reflections every 180 min |
10705 independent reflections | intensity decay: none |
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)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.2357P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
10705 reflections | Δρmax = 0.26 e Å−3 |
527 parameters | Δρmin = −0.18 e Å−3 |
478 restraints | Absolute structure: Flack (1983), with how many Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (6) |
C20H20ClNO3 | V = 1839.5 (7) Å3 |
Mr = 357.82 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.4241 (19) Å | µ = 0.23 mm−1 |
b = 10.073 (2) Å | T = 293 K |
c = 19.849 (4) Å | 0.36 × 0.32 × 0.30 mm |
β = 102.52 (3)° |
Enraf–Nonius CAD-4 diffractometer | 5925 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.875, Tmax = 0.927 | 3 standard reflections every 180 min |
11300 measured reflections | intensity decay: none |
10705 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.141 | Δρmax = 0.26 e Å−3 |
S = 1.03 | Δρmin = −0.18 e Å−3 |
10705 reflections | Absolute structure: Flack (1983), with how many Friedel pairs? |
527 parameters | Absolute structure parameter: 0.06 (6) |
478 restraints |
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 | Occ. (<1) | |
ClA | 0.2307 (2) | −0.24427 (15) | 0.64892 (11) | 0.0765 (6) | 0.488 (3) |
C5A | 0.1090 (5) | −0.0052 (3) | 0.67783 (16) | 0.0522 (8) | 0.488 (3) |
H5AB | 0.2033 | 0.0129 | 0.7073 | 0.063* | 0.488 (3) |
H5AA | 0.0433 | −0.0366 | 0.7058 | 0.063* | 0.488 (3) |
C4A | 0.1206 (3) | −0.10374 (18) | 0.62151 (12) | 0.0519 (13) | 0.488 (3) |
H4A | 0.0230 | −0.1330 | 0.5984 | 0.062* | 0.488 (3) |
C3A | 0.1874 (5) | −0.0246 (5) | 0.5713 (2) | 0.0491 (8) | 0.488 (3) |
H3AA | 0.2913 | −0.0132 | 0.5878 | 0.059* | 0.488 (3) |
H3AB | 0.1681 | −0.0646 | 0.5258 | 0.059* | 0.488 (3) |
ClB | 0.2574 (2) | −0.23266 (13) | 0.65602 (12) | 0.0707 (5) | 0.512 (3) |
C5B | 0.0877 (2) | −0.0178 (5) | 0.6710 (2) | 0.0522 (8) | 0.512 (3) |
H5BA | 0.1107 | −0.0082 | 0.7208 | 0.063* | 0.512 (3) |
H5BB | 0.0089 | −0.0811 | 0.6580 | 0.063* | 0.512 (3) |
C4B | 0.2200 (3) | −0.06090 (19) | 0.64475 (10) | 0.0486 (12) | 0.512 (3) |
H4B | 0.3051 | −0.0091 | 0.6674 | 0.058* | 0.512 (3) |
C3B | 0.1750 (6) | −0.0220 (5) | 0.56936 (13) | 0.0493 (8) | 0.512 (3) |
H3BA | 0.2588 | −0.0140 | 0.5486 | 0.059* | 0.512 (3) |
H3BB | 0.1079 | −0.0862 | 0.5435 | 0.059* | 0.512 (3) |
N2 | 0.1058 (2) | 0.10411 (17) | 0.57210 (9) | 0.0444 (5) | |
C1 | 0.0469 (2) | 0.1191 (2) | 0.63468 (11) | 0.0465 (6) | |
C6 | 0.1208 (3) | 0.2370 (3) | 0.67887 (12) | 0.0558 (6) | |
O7 | 0.26410 (18) | 0.23518 (18) | 0.68232 (9) | 0.0657 (5) | |
C8 | 0.3490 (3) | 0.3431 (2) | 0.71983 (13) | 0.0839 (10) | |
H8B | 0.2967 | 0.3817 | 0.7521 | 0.101* | |
H8A | 0.4407 | 0.3090 | 0.7460 | 0.101* | |
C9 | 0.3759 (4) | 0.4439 (3) | 0.67220 (17) | 0.1180 (16) | |
H9A | 0.4264 | 0.4052 | 0.6399 | 0.177* | |
H9B | 0.4341 | 0.5135 | 0.6974 | 0.177* | |
H9C | 0.2850 | 0.4801 | 0.6477 | 0.177* | |
O10 | 0.0596 (2) | 0.3113 (2) | 0.70958 (10) | 0.0787 (6) | |
C11 | −0.1186 (3) | 0.1324 (2) | 0.61935 (13) | 0.0535 (6) | |
C12 | −0.1998 (3) | 0.1426 (3) | 0.55303 (15) | 0.0660 (8) | |
H12 | −0.1547 | 0.1417 | 0.5157 | 0.079* | |
C13 | −0.3520 (3) | 0.1544 (3) | 0.54218 (19) | 0.0855 (10) | |
H13 | −0.4077 | 0.1615 | 0.4975 | 0.103* | |
C14 | −0.4184 (3) | 0.1554 (3) | 0.5970 (2) | 0.0893 (11) | |
H14 | −0.5187 | 0.1651 | 0.5895 | 0.107* | |
C15 | −0.3374 (4) | 0.1419 (3) | 0.6633 (2) | 0.0871 (10) | |
H15 | −0.3828 | 0.1403 | 0.7005 | 0.105* | |
C16 | −0.1891 (3) | 0.1310 (3) | 0.67392 (15) | 0.0663 (8) | |
H16 | −0.1345 | 0.1224 | 0.7187 | 0.080* | |
C17 | 0.1162 (2) | 0.2116 (2) | 0.53205 (12) | 0.0496 (6) | |
C18 | 0.1774 (3) | 0.1935 (2) | 0.46970 (12) | 0.0495 (6) | |
C19 | 0.2730 (3) | 0.2881 (3) | 0.45560 (13) | 0.0612 (7) | |
H19 | 0.2988 | 0.3595 | 0.4854 | 0.073* | |
C20 | 0.3304 (3) | 0.2773 (3) | 0.39760 (15) | 0.0777 (9) | |
H20 | 0.3941 | 0.3419 | 0.3885 | 0.093* | |
C21 | 0.2949 (4) | 0.1739 (4) | 0.35388 (15) | 0.0849 (10) | |
H21 | 0.3367 | 0.1660 | 0.3157 | 0.102* | |
C22 | 0.1962 (4) | 0.0794 (3) | 0.36581 (15) | 0.0826 (10) | |
H22 | 0.1698 | 0.0095 | 0.3350 | 0.099* | |
C23 | 0.1378 (3) | 0.0891 (3) | 0.42295 (13) | 0.0635 (8) | |
H23 | 0.0713 | 0.0259 | 0.4308 | 0.076* | |
O24 | 0.07592 (19) | 0.32159 (17) | 0.54748 (9) | 0.0632 (5) | |
ClC | 0.12063 (14) | 0.02879 (11) | 0.87321 (7) | 0.0641 (4) | 0.650 (2) |
C30A | 0.1593 (3) | 0.2336 (4) | 0.96650 (12) | 0.0508 (7) | 0.650 (2) |
H30A | 0.1815 | 0.1625 | 1.0001 | 0.061* | 0.650 (2) |
H30B | 0.0588 | 0.2599 | 0.9626 | 0.061* | 0.650 (2) |
C29A | 0.18275 (19) | 0.18999 (18) | 0.90027 (13) | 0.0519 (10) | 0.650 (2) |
H29A | 0.1332 | 0.2529 | 0.8653 | 0.062* | 0.650 (2) |
C28A | 0.3450 (2) | 0.2071 (4) | 0.9068 (2) | 0.0449 (6) | 0.650 (2) |
H28A | 0.3986 | 0.1312 | 0.9292 | 0.054* | 0.650 (2) |
H28B | 0.3686 | 0.2204 | 0.8621 | 0.054* | 0.650 (2) |
ClD | 0.1432 (3) | 0.0064 (2) | 0.89083 (17) | 0.0753 (8) | 0.350 (2) |
C30B | 0.1468 (4) | 0.2354 (5) | 0.9680 (3) | 0.0505 (9) | 0.350 (2) |
H30C | 0.1132 | 0.2022 | 1.0077 | 0.061* | 0.350 (2) |
H30D | 0.0639 | 0.2632 | 0.9328 | 0.061* | 0.350 (2) |
C29B | 0.2338 (3) | 0.1378 (3) | 0.94182 (19) | 0.0500 (18) | 0.350 (2) |
H29B | 0.2945 | 0.0958 | 0.9826 | 0.060* | 0.350 (2) |
C28B | 0.3383 (5) | 0.2067 (8) | 0.9050 (4) | 0.0450 (9) | 0.350 (2) |
H28C | 0.4235 | 0.1528 | 0.9047 | 0.054* | 0.350 (2) |
H28D | 0.2918 | 0.2303 | 0.8580 | 0.054* | 0.350 (2) |
N27 | 0.37485 (18) | 0.32630 (18) | 0.94957 (9) | 0.0409 (4) | |
C26 | 0.2614 (2) | 0.3526 (2) | 0.98875 (11) | 0.0411 (5) | |
C31 | 0.1797 (2) | 0.4832 (2) | 0.96391 (13) | 0.0490 (6) | |
O32 | 0.16150 (18) | 0.49700 (18) | 0.89589 (9) | 0.0601 (5) | |
C33 | 0.0942 (3) | 0.6224 (3) | 0.86960 (12) | 0.0808 (9) | |
H33A | −0.0074 | 0.6227 | 0.8724 | 0.097* | |
H33B | 0.1426 | 0.6955 | 0.8971 | 0.097* | |
C34 | 0.1062 (5) | 0.6376 (4) | 0.79866 (14) | 0.1121 (13) | |
H34A | 0.2069 | 0.6434 | 0.7967 | 0.168* | |
H34B | 0.0568 | 0.7171 | 0.7799 | 0.168* | |
H34C | 0.0628 | 0.5624 | 0.7723 | 0.168* | |
O35 | 0.1314 (2) | 0.55831 (19) | 0.99991 (10) | 0.0706 (5) | |
C36 | 0.3196 (2) | 0.3580 (2) | 1.06703 (11) | 0.0443 (5) | |
C37 | 0.4658 (3) | 0.3550 (2) | 1.09670 (12) | 0.0518 (6) | |
H37 | 0.5329 | 0.3481 | 1.0687 | 0.062* | |
C38 | 0.5144 (3) | 0.3623 (3) | 1.16785 (13) | 0.0673 (8) | |
H38 | 0.6134 | 0.3614 | 1.1874 | 0.081* | |
C39 | 0.4150 (4) | 0.3707 (3) | 1.20928 (14) | 0.0748 (9) | |
H39 | 0.4471 | 0.3758 | 1.2569 | 0.090* | |
C40 | 0.2698 (4) | 0.3717 (3) | 1.18081 (14) | 0.0741 (8) | |
H40 | 0.2030 | 0.3768 | 1.2090 | 0.089* | |
C41 | 0.2218 (3) | 0.3650 (3) | 1.10988 (13) | 0.0578 (7) | |
H41 | 0.1225 | 0.3651 | 1.0907 | 0.069* | |
C42 | 0.4682 (2) | 0.4255 (2) | 0.94158 (11) | 0.0423 (5) | |
C43 | 0.5815 (2) | 0.3977 (2) | 0.90132 (11) | 0.0416 (5) | |
C44 | 0.6580 (2) | 0.2789 (2) | 0.90635 (12) | 0.0510 (6) | |
H44 | 0.6377 | 0.2115 | 0.9349 | 0.061* | |
C45 | 0.7639 (3) | 0.2612 (3) | 0.86901 (14) | 0.0619 (7) | |
H45 | 0.8160 | 0.1822 | 0.8731 | 0.074* | |
C46 | 0.7935 (3) | 0.3590 (3) | 0.82573 (14) | 0.0662 (8) | |
H46 | 0.8629 | 0.3449 | 0.7995 | 0.079* | |
C47 | 0.7198 (3) | 0.4781 (3) | 0.82140 (14) | 0.0611 (7) | |
H47 | 0.7406 | 0.5454 | 0.7930 | 0.073* | |
C48 | 0.6145 (3) | 0.4970 (2) | 0.85964 (12) | 0.0526 (6) | |
H48 | 0.5657 | 0.5776 | 0.8571 | 0.063* | |
O49 | 0.45967 (17) | 0.53440 (16) | 0.96811 (8) | 0.0525 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
ClA | 0.1017 (12) | 0.0510 (8) | 0.0724 (10) | 0.0228 (9) | 0.0096 (9) | 0.0096 (8) |
C5A | 0.0620 (16) | 0.0495 (15) | 0.0422 (15) | 0.0035 (14) | 0.0049 (14) | 0.0008 (13) |
C4A | 0.065 (3) | 0.039 (2) | 0.047 (3) | 0.004 (2) | 0.001 (2) | −0.002 (2) |
C3A | 0.0587 (15) | 0.0433 (14) | 0.0461 (14) | 0.0072 (13) | 0.0130 (13) | 0.0014 (13) |
ClB | 0.0894 (11) | 0.0492 (8) | 0.0690 (10) | 0.0161 (8) | 0.0074 (9) | 0.0114 (8) |
C5B | 0.0619 (16) | 0.0492 (15) | 0.0427 (15) | 0.0040 (14) | 0.0049 (14) | 0.0013 (13) |
C4B | 0.058 (3) | 0.040 (2) | 0.045 (3) | 0.005 (2) | 0.005 (2) | 0.0037 (19) |
C3B | 0.0592 (15) | 0.0434 (14) | 0.0460 (14) | 0.0071 (13) | 0.0129 (13) | 0.0013 (12) |
N2 | 0.0533 (11) | 0.0383 (9) | 0.0418 (10) | 0.0074 (8) | 0.0106 (8) | −0.0008 (8) |
C1 | 0.0525 (13) | 0.0431 (12) | 0.0456 (12) | 0.0020 (10) | 0.0146 (10) | 0.0024 (10) |
C6 | 0.0608 (14) | 0.0561 (15) | 0.0508 (13) | −0.0007 (12) | 0.0124 (11) | −0.0097 (11) |
O7 | 0.0565 (10) | 0.0642 (11) | 0.0733 (11) | −0.0020 (9) | 0.0077 (9) | −0.0194 (9) |
C8 | 0.0738 (18) | 0.083 (2) | 0.090 (2) | −0.0084 (17) | 0.0052 (16) | −0.0283 (18) |
C9 | 0.123 (3) | 0.0574 (19) | 0.150 (4) | −0.015 (2) | −0.022 (3) | 0.005 (2) |
O10 | 0.0799 (12) | 0.0732 (12) | 0.0892 (12) | −0.0046 (10) | 0.0318 (10) | −0.0367 (10) |
C11 | 0.0533 (13) | 0.0443 (12) | 0.0625 (15) | 0.0039 (11) | 0.0118 (12) | −0.0029 (11) |
C12 | 0.0531 (15) | 0.0670 (16) | 0.0745 (18) | 0.0062 (13) | 0.0059 (13) | 0.0021 (14) |
C13 | 0.0629 (18) | 0.086 (2) | 0.100 (2) | 0.0059 (16) | −0.0004 (17) | 0.0073 (19) |
C14 | 0.0501 (16) | 0.082 (2) | 0.137 (3) | 0.0083 (15) | 0.0226 (18) | −0.004 (2) |
C15 | 0.0699 (18) | 0.081 (2) | 0.120 (3) | 0.0031 (16) | 0.0416 (18) | −0.0055 (19) |
C16 | 0.0635 (16) | 0.0672 (17) | 0.0742 (17) | 0.0044 (13) | 0.0281 (13) | −0.0060 (14) |
C17 | 0.0469 (12) | 0.0443 (12) | 0.0545 (14) | 0.0005 (10) | 0.0043 (11) | 0.0028 (10) |
C18 | 0.0543 (13) | 0.0485 (12) | 0.0437 (12) | 0.0044 (11) | 0.0064 (11) | 0.0098 (10) |
C19 | 0.0700 (16) | 0.0573 (16) | 0.0555 (14) | −0.0004 (12) | 0.0120 (13) | 0.0088 (11) |
C20 | 0.0855 (19) | 0.080 (2) | 0.0714 (18) | −0.0111 (17) | 0.0253 (15) | 0.0161 (16) |
C21 | 0.113 (2) | 0.095 (2) | 0.0530 (16) | −0.007 (2) | 0.0319 (17) | 0.0052 (16) |
C22 | 0.122 (3) | 0.079 (2) | 0.0484 (16) | −0.0094 (19) | 0.0223 (16) | −0.0092 (14) |
C23 | 0.0758 (17) | 0.0649 (16) | 0.0465 (14) | −0.0104 (14) | 0.0062 (13) | 0.0035 (12) |
O24 | 0.0763 (11) | 0.0434 (9) | 0.0706 (11) | 0.0116 (9) | 0.0176 (9) | 0.0036 (8) |
ClC | 0.0604 (6) | 0.0631 (6) | 0.0698 (7) | −0.0207 (5) | 0.0168 (5) | −0.0220 (5) |
C30A | 0.0422 (13) | 0.0531 (14) | 0.0588 (14) | −0.0083 (12) | 0.0144 (12) | −0.0077 (12) |
C29A | 0.0456 (19) | 0.055 (2) | 0.054 (2) | −0.0075 (17) | 0.0071 (17) | −0.0024 (17) |
C28A | 0.0437 (12) | 0.0430 (12) | 0.0497 (13) | −0.0070 (11) | 0.0137 (11) | −0.0062 (11) |
ClD | 0.0652 (13) | 0.0575 (12) | 0.1014 (18) | −0.0216 (11) | 0.0140 (12) | −0.0222 (12) |
C30B | 0.0420 (16) | 0.0527 (17) | 0.0582 (16) | −0.0079 (15) | 0.0142 (15) | −0.0080 (15) |
C29B | 0.041 (3) | 0.043 (3) | 0.058 (4) | −0.012 (3) | −0.006 (3) | −0.004 (3) |
C28B | 0.0440 (15) | 0.0429 (15) | 0.0496 (16) | −0.0071 (14) | 0.0136 (14) | −0.0064 (14) |
N27 | 0.0388 (9) | 0.0394 (9) | 0.0458 (9) | −0.0011 (8) | 0.0117 (8) | −0.0005 (8) |
C26 | 0.0382 (10) | 0.0408 (11) | 0.0456 (11) | 0.0008 (9) | 0.0122 (9) | 0.0001 (9) |
C31 | 0.0420 (12) | 0.0501 (13) | 0.0558 (14) | −0.0004 (10) | 0.0128 (11) | 0.0011 (11) |
O32 | 0.0611 (10) | 0.0619 (10) | 0.0561 (10) | 0.0168 (9) | 0.0098 (8) | 0.0119 (8) |
C33 | 0.082 (2) | 0.0752 (19) | 0.082 (2) | 0.0255 (16) | 0.0124 (16) | 0.0243 (16) |
C34 | 0.159 (3) | 0.096 (3) | 0.086 (2) | 0.032 (3) | 0.036 (2) | 0.033 (2) |
O35 | 0.0787 (11) | 0.0618 (11) | 0.0754 (12) | 0.0242 (9) | 0.0258 (10) | −0.0020 (9) |
C36 | 0.0508 (12) | 0.0368 (11) | 0.0468 (12) | −0.0022 (10) | 0.0140 (10) | −0.0007 (9) |
C37 | 0.0508 (13) | 0.0571 (14) | 0.0484 (12) | −0.0038 (11) | 0.0123 (11) | 0.0038 (11) |
C38 | 0.0686 (17) | 0.0745 (18) | 0.0527 (15) | −0.0119 (14) | −0.0006 (13) | 0.0069 (14) |
C39 | 0.101 (2) | 0.0788 (19) | 0.0420 (14) | −0.0110 (17) | 0.0107 (15) | 0.0008 (13) |
C40 | 0.100 (2) | 0.0754 (19) | 0.0571 (15) | 0.0012 (17) | 0.0401 (15) | −0.0006 (13) |
C41 | 0.0609 (14) | 0.0604 (15) | 0.0563 (14) | 0.0036 (12) | 0.0222 (12) | 0.0001 (12) |
C42 | 0.0404 (12) | 0.0431 (11) | 0.0420 (12) | 0.0000 (9) | 0.0060 (10) | 0.0037 (10) |
C43 | 0.0375 (11) | 0.0430 (11) | 0.0423 (12) | −0.0057 (9) | 0.0043 (9) | −0.0037 (9) |
C44 | 0.0458 (12) | 0.0488 (13) | 0.0605 (14) | −0.0018 (11) | 0.0160 (11) | 0.0045 (11) |
C45 | 0.0434 (12) | 0.0550 (13) | 0.0896 (18) | 0.0077 (12) | 0.0197 (13) | −0.0027 (15) |
C46 | 0.0548 (14) | 0.0804 (19) | 0.0701 (16) | −0.0030 (14) | 0.0284 (12) | −0.0092 (15) |
C47 | 0.0635 (15) | 0.0665 (16) | 0.0583 (15) | −0.0052 (13) | 0.0241 (12) | 0.0096 (12) |
C48 | 0.0537 (13) | 0.0471 (13) | 0.0581 (14) | 0.0008 (11) | 0.0145 (12) | 0.0046 (11) |
O49 | 0.0587 (9) | 0.0416 (8) | 0.0604 (10) | −0.0070 (7) | 0.0202 (8) | −0.0066 (8) |
ClA—C4A | 1.7701 (18) | ClC—C29A | 1.7697 (17) |
C5A—C4A | 1.516 (2) | C30A—C29A | 1.448 (2) |
C5A—C1 | 1.559 (4) | C30A—C26 | 1.541 (4) |
C5A—H5AB | 0.9700 | C30A—H30A | 0.9700 |
C5A—H5AA | 0.9700 | C30A—H30B | 0.9700 |
C4A—C3A | 1.516 (2) | C29A—C28A | 1.516 (2) |
C4A—H4A | 0.9800 | C29A—H29A | 0.9800 |
C3A—N2 | 1.510 (5) | C28A—N27 | 1.462 (5) |
C3A—H3AA | 0.9700 | C28A—H28A | 0.9700 |
C3A—H3AB | 0.9700 | C28A—H28B | 0.9700 |
ClB—C4B | 1.7702 (18) | ClD—C29B | 1.769 (2) |
C5B—C4B | 1.516 (2) | C30B—C29B | 1.447 (3) |
C5B—C1 | 1.565 (5) | C30B—C26 | 1.593 (5) |
C5B—H5BA | 0.9700 | C30B—H30C | 0.9700 |
C5B—H5BB | 0.9700 | C30B—H30D | 0.9700 |
C4B—C3B | 1.516 (2) | C29B—C28B | 1.516 (2) |
C4B—H4B | 0.9800 | C29B—H29B | 0.9800 |
C3B—N2 | 1.434 (6) | C28B—N27 | 1.490 (9) |
C3B—H3BA | 0.9700 | C28B—H28C | 0.9700 |
C3B—H3BB | 0.9700 | C28B—H28D | 0.9700 |
N2—C17 | 1.359 (3) | N27—C42 | 1.363 (3) |
N2—C1 | 1.474 (3) | N27—C26 | 1.476 (3) |
C1—C11 | 1.528 (3) | C26—C36 | 1.532 (3) |
C1—C6 | 1.549 (3) | C26—C31 | 1.549 (3) |
C6—O10 | 1.191 (3) | C31—O35 | 1.196 (3) |
C6—O7 | 1.338 (3) | C31—O32 | 1.331 (3) |
O7—C8 | 1.455 (3) | O32—C33 | 1.458 (3) |
C8—C9 | 1.447 (2) | C33—C34 | 1.445 (2) |
C8—H8B | 0.9700 | C33—H33A | 0.9700 |
C8—H8A | 0.9700 | C33—H33B | 0.9700 |
C9—H9A | 0.9600 | C34—H34A | 0.9600 |
C9—H9B | 0.9600 | C34—H34B | 0.9600 |
C9—H9C | 0.9600 | C34—H34C | 0.9600 |
C11—C12 | 1.376 (4) | C36—C37 | 1.376 (3) |
C11—C16 | 1.388 (4) | C36—C41 | 1.385 (3) |
C12—C13 | 1.408 (4) | C37—C38 | 1.389 (4) |
C12—H12 | 0.9300 | C37—H37 | 0.9300 |
C13—C14 | 1.368 (5) | C38—C39 | 1.377 (4) |
C13—H13 | 0.9300 | C38—H38 | 0.9300 |
C14—C15 | 1.377 (5) | C39—C40 | 1.362 (4) |
C14—H14 | 0.9300 | C39—H39 | 0.9300 |
C15—C16 | 1.372 (4) | C40—C41 | 1.384 (4) |
C15—H15 | 0.9300 | C40—H40 | 0.9300 |
C16—H16 | 0.9300 | C41—H41 | 0.9300 |
C17—O24 | 1.231 (3) | C42—O49 | 1.227 (3) |
C17—C18 | 1.486 (4) | C42—C43 | 1.493 (3) |
C18—C19 | 1.381 (4) | C43—C48 | 1.376 (3) |
C18—C23 | 1.399 (3) | C43—C44 | 1.389 (3) |
C19—C20 | 1.378 (4) | C44—C45 | 1.378 (3) |
C19—H19 | 0.9300 | C44—H44 | 0.9300 |
C20—C21 | 1.351 (4) | C45—C46 | 1.375 (4) |
C20—H20 | 0.9300 | C45—H45 | 0.9300 |
C21—C22 | 1.387 (5) | C46—C47 | 1.380 (4) |
C21—H21 | 0.9300 | C46—H46 | 0.9300 |
C22—C23 | 1.367 (4) | C47—C48 | 1.386 (4) |
C22—H22 | 0.9300 | C47—H47 | 0.9300 |
C23—H23 | 0.9300 | C48—H48 | 0.9300 |
C4A—C5A—C1 | 101.5 (2) | C29A—C30A—C26 | 106.7 (2) |
C4A—C5A—H5AB | 111.5 | C29A—C30A—H30A | 110.4 |
C1—C5A—H5AB | 111.5 | C26—C30A—H30A | 110.4 |
C4A—C5A—H5AA | 111.5 | C29A—C30A—H30B | 110.4 |
C1—C5A—H5AA | 111.5 | C26—C30A—H30B | 110.4 |
H5AB—C5A—H5AA | 109.3 | H30A—C30A—H30B | 108.6 |
C3A—C4A—C5A | 104.3 (3) | C30A—C29A—C28A | 103.8 (3) |
C3A—C4A—ClA | 108.8 (2) | C30A—C29A—ClC | 116.6 (2) |
C5A—C4A—ClA | 115.3 (2) | C28A—C29A—ClC | 113.0 (2) |
C3A—C4A—H4A | 109.4 | C30A—C29A—H29A | 107.7 |
C5A—C4A—H4A | 109.4 | C28A—C29A—H29A | 107.7 |
ClA—C4A—H4A | 109.4 | ClC—C29A—H29A | 107.7 |
N2—C3A—C4A | 99.2 (3) | N27—C28A—C29A | 101.9 (2) |
N2—C3A—H3AA | 111.9 | N27—C28A—H28A | 111.4 |
C4A—C3A—H3AA | 111.9 | C29A—C28A—H28A | 111.4 |
N2—C3A—H3AB | 111.9 | N27—C28A—H28B | 111.4 |
C4A—C3A—H3AB | 111.9 | C29A—C28A—H28B | 111.4 |
H3AA—C3A—H3AB | 109.6 | H28A—C28A—H28B | 109.3 |
C4B—C5B—C1 | 103.4 (3) | C29B—C30B—C26 | 101.0 (2) |
C4B—C5B—H5BA | 111.1 | C29B—C30B—H30C | 111.6 |
C1—C5B—H5BA | 111.1 | C26—C30B—H30C | 111.6 |
C4B—C5B—H5BB | 111.1 | C29B—C30B—H30D | 111.6 |
C1—C5B—H5BB | 111.1 | C26—C30B—H30D | 111.6 |
H5BA—C5B—H5BB | 109.0 | H30C—C30B—H30D | 109.4 |
C3B—C4B—C5B | 101.0 (3) | C30B—C29B—C28B | 109.9 (4) |
C3B—C4B—ClB | 112.5 (3) | C30B—C29B—ClD | 118.2 (3) |
C5B—C4B—ClB | 113.1 (3) | C28B—C29B—ClD | 110.5 (4) |
C3B—C4B—H4B | 110.0 | C30B—C29B—H29B | 105.8 |
C5B—C4B—H4B | 110.0 | C28B—C29B—H29B | 105.8 |
ClB—C4B—H4B | 110.0 | ClD—C29B—H29B | 105.8 |
N2—C3B—C4B | 102.9 (3) | N27—C28B—C29B | 100.0 (4) |
N2—C3B—H3BA | 111.2 | N27—C28B—H28C | 111.8 |
C4B—C3B—H3BA | 111.2 | C29B—C28B—H28C | 111.8 |
N2—C3B—H3BB | 111.2 | N27—C28B—H28D | 111.8 |
C4B—C3B—H3BB | 111.2 | C29B—C28B—H28D | 111.8 |
H3BA—C3B—H3BB | 109.1 | H28C—C28B—H28D | 109.5 |
C17—N2—C3B | 126.3 (2) | C42—N27—C28A | 125.6 (2) |
C17—N2—C1 | 119.94 (18) | C42—N27—C26 | 119.27 (18) |
C3B—N2—C1 | 112.4 (2) | C28A—N27—C26 | 112.56 (17) |
C17—N2—C3A | 125.2 (2) | C42—N27—C28B | 126.5 (2) |
C1—N2—C3A | 112.52 (19) | C26—N27—C28B | 111.0 (2) |
N2—C1—C11 | 113.30 (18) | N27—C26—C36 | 113.57 (17) |
N2—C1—C6 | 110.52 (19) | N27—C26—C30A | 100.82 (18) |
C11—C1—C6 | 111.10 (19) | C36—C26—C30A | 112.45 (19) |
N2—C1—C5A | 102.4 (2) | N27—C26—C31 | 110.59 (18) |
C11—C1—C5A | 115.2 (2) | C36—C26—C31 | 109.67 (18) |
C6—C1—C5A | 103.64 (19) | C30A—C26—C31 | 109.43 (19) |
N2—C1—C5B | 101.4 (2) | N27—C26—C30B | 105.0 (2) |
C11—C1—C5B | 107.86 (19) | C36—C26—C30B | 111.2 (3) |
C6—C1—C5B | 112.3 (2) | C31—C26—C30B | 106.5 (2) |
O10—C6—O7 | 125.3 (2) | O35—C31—O32 | 123.9 (2) |
O10—C6—C1 | 124.3 (2) | O35—C31—C26 | 125.0 (2) |
O7—C6—C1 | 110.1 (2) | O32—C31—C26 | 110.95 (19) |
C6—O7—C8 | 116.9 (2) | C31—O32—C33 | 113.84 (19) |
C9—C8—O7 | 110.2 (2) | C34—C33—O32 | 108.7 (2) |
C9—C8—H8B | 109.6 | C34—C33—H33A | 110.0 |
O7—C8—H8B | 109.6 | O32—C33—H33A | 110.0 |
C9—C8—H8A | 109.6 | C34—C33—H33B | 110.0 |
O7—C8—H8A | 109.6 | O32—C33—H33B | 110.0 |
H8B—C8—H8A | 108.1 | H33A—C33—H33B | 108.3 |
C8—C9—H9A | 109.5 | C33—C34—H34A | 109.5 |
C8—C9—H9B | 109.5 | C33—C34—H34B | 109.5 |
H9A—C9—H9B | 109.5 | H34A—C34—H34B | 109.5 |
C8—C9—H9C | 109.5 | C33—C34—H34C | 109.5 |
H9A—C9—H9C | 109.5 | H34A—C34—H34C | 109.5 |
H9B—C9—H9C | 109.5 | H34B—C34—H34C | 109.5 |
C12—C11—C16 | 119.1 (2) | C37—C36—C41 | 118.4 (2) |
C12—C11—C1 | 122.0 (2) | C37—C36—C26 | 122.5 (2) |
C16—C11—C1 | 119.0 (2) | C41—C36—C26 | 119.0 (2) |
C11—C12—C13 | 119.3 (3) | C36—C37—C38 | 120.8 (2) |
C11—C12—H12 | 120.3 | C36—C37—H37 | 119.6 |
C13—C12—H12 | 120.3 | C38—C37—H37 | 119.6 |
C14—C13—C12 | 120.3 (3) | C39—C38—C37 | 119.6 (3) |
C14—C13—H13 | 119.8 | C39—C38—H38 | 120.2 |
C12—C13—H13 | 119.8 | C37—C38—H38 | 120.2 |
C13—C14—C15 | 120.4 (3) | C40—C39—C38 | 120.3 (3) |
C13—C14—H14 | 119.8 | C40—C39—H39 | 119.8 |
C15—C14—H14 | 119.8 | C38—C39—H39 | 119.8 |
C16—C15—C14 | 119.3 (3) | C39—C40—C41 | 120.0 (3) |
C16—C15—H15 | 120.3 | C39—C40—H40 | 120.0 |
C14—C15—H15 | 120.3 | C41—C40—H40 | 120.0 |
C15—C16—C11 | 121.6 (3) | C40—C41—C36 | 120.8 (3) |
C15—C16—H16 | 119.2 | C40—C41—H41 | 119.6 |
C11—C16—H16 | 119.2 | C36—C41—H41 | 119.6 |
O24—C17—N2 | 120.4 (2) | O49—C42—N27 | 120.1 (2) |
O24—C17—C18 | 120.9 (2) | O49—C42—C43 | 121.2 (2) |
N2—C17—C18 | 118.7 (2) | N27—C42—C43 | 118.68 (19) |
C19—C18—C23 | 118.5 (2) | C48—C43—C44 | 119.2 (2) |
C19—C18—C17 | 118.2 (2) | C48—C43—C42 | 117.8 (2) |
C23—C18—C17 | 123.3 (2) | C44—C43—C42 | 122.9 (2) |
C20—C19—C18 | 120.4 (3) | C45—C44—C43 | 119.9 (2) |
C20—C19—H19 | 119.8 | C45—C44—H44 | 120.1 |
C18—C19—H19 | 119.8 | C43—C44—H44 | 120.1 |
C21—C20—C19 | 120.7 (3) | C46—C45—C44 | 120.8 (3) |
C21—C20—H20 | 119.7 | C46—C45—H45 | 119.6 |
C19—C20—H20 | 119.7 | C44—C45—H45 | 119.6 |
C20—C21—C22 | 120.1 (3) | C45—C46—C47 | 119.6 (3) |
C20—C21—H21 | 119.9 | C45—C46—H46 | 120.2 |
C22—C21—H21 | 119.9 | C47—C46—H46 | 120.2 |
C23—C22—C21 | 119.8 (3) | C46—C47—C48 | 119.7 (2) |
C23—C22—H22 | 120.1 | C46—C47—H47 | 120.2 |
C21—C22—H22 | 120.1 | C48—C47—H47 | 120.2 |
C22—C23—C18 | 120.5 (3) | C43—C48—C47 | 120.8 (2) |
C22—C23—H23 | 119.8 | C43—C48—H48 | 119.6 |
C18—C23—H23 | 119.8 | C47—C48—H48 | 119.6 |
C1—C5A—C4A—C3A | 44.9 (3) | C26—C30A—C29A—C28A | 37.6 (3) |
C1—C5A—C4A—ClA | 164.2 (2) | C26—C30A—C29A—ClC | 162.62 (17) |
C5A—C4A—C3A—N2 | −40.5 (3) | C30A—C29A—C28A—N27 | −35.1 (3) |
ClA—C4A—C3A—N2 | −164.10 (19) | ClC—C29A—C28A—N27 | −162.4 (2) |
C1—C5B—C4B—C3B | −41.5 (3) | C26—C30B—C29B—C28B | −35.2 (5) |
C1—C5B—C4B—ClB | −161.96 (19) | C26—C30B—C29B—ClD | −163.2 (3) |
C5B—C4B—C3B—N2 | 40.8 (4) | C30B—C29B—C28B—N27 | 36.4 (5) |
ClB—C4B—C3B—N2 | 161.7 (3) | ClD—C29B—C28B—N27 | 168.6 (3) |
C4B—C3B—N2—C17 | 141.0 (3) | C29A—C28A—N27—C42 | −140.9 (2) |
C4B—C3B—N2—C1 | −25.4 (4) | C29A—C28A—N27—C26 | 20.6 (3) |
C4B—C3B—N2—C3A | 68 (3) | C29A—C28A—N27—C28B | −26 (7) |
C4A—C3A—N2—C17 | −175.8 (2) | C29B—C28B—N27—C42 | 179.0 (2) |
C4A—C3A—N2—C3B | −66 (3) | C29B—C28B—N27—C28A | 112 (7) |
C4A—C3A—N2—C1 | 21.7 (3) | C29B—C28B—N27—C26 | −21.7 (4) |
C17—N2—C1—C11 | 76.7 (2) | C42—N27—C26—C36 | −75.4 (2) |
C3B—N2—C1—C11 | −116.0 (3) | C28A—N27—C26—C36 | 121.8 (2) |
C3A—N2—C1—C11 | −119.8 (3) | C28B—N27—C26—C36 | 123.6 (3) |
C17—N2—C1—C6 | −48.8 (3) | C42—N27—C26—C30A | 164.10 (19) |
C3B—N2—C1—C6 | 118.6 (3) | C28A—N27—C26—C30A | 1.3 (3) |
C3A—N2—C1—C6 | 114.8 (3) | C28B—N27—C26—C30A | 3.1 (3) |
C17—N2—C1—C5A | −158.7 (2) | C42—N27—C26—C31 | 48.4 (2) |
C3B—N2—C1—C5A | 8.7 (3) | C28A—N27—C26—C31 | −114.4 (2) |
C3A—N2—C1—C5A | 4.9 (3) | C28B—N27—C26—C31 | −112.6 (3) |
C17—N2—C1—C5B | −168.0 (2) | C42—N27—C26—C30B | 162.9 (3) |
C3B—N2—C1—C5B | −0.7 (3) | C28A—N27—C26—C30B | 0.1 (3) |
C3A—N2—C1—C5B | −4.5 (3) | C28B—N27—C26—C30B | 1.9 (4) |
C4A—C5A—C1—N2 | −29.6 (3) | C29A—C30A—C26—N27 | −24.3 (3) |
C4A—C5A—C1—C11 | 93.8 (3) | C29A—C30A—C26—C36 | −145.6 (2) |
C4A—C5A—C1—C6 | −144.7 (3) | C29A—C30A—C26—C31 | 92.3 (3) |
C4A—C5A—C1—C5B | 55.1 (11) | C29A—C30A—C26—C30B | 140 (4) |
C4B—C5B—C1—N2 | 26.5 (3) | C29B—C30B—C26—N27 | 19.8 (4) |
C4B—C5B—C1—C11 | 145.8 (2) | C29B—C30B—C26—C36 | −103.5 (4) |
C4B—C5B—C1—C6 | −91.5 (3) | C29B—C30B—C26—C30A | 4 (4) |
C4B—C5B—C1—C5A | −70.7 (11) | C29B—C30B—C26—C31 | 137.1 (3) |
N2—C1—C6—O10 | 142.2 (2) | N27—C26—C31—O35 | −146.5 (2) |
C11—C1—C6—O10 | 15.5 (3) | C36—C26—C31—O35 | −20.5 (3) |
C5A—C1—C6—O10 | −108.7 (3) | C30A—C26—C31—O35 | 103.3 (3) |
C5B—C1—C6—O10 | −105.4 (3) | C30B—C26—C31—O35 | 99.9 (3) |
N2—C1—C6—O7 | −43.4 (3) | N27—C26—C31—O32 | 37.6 (2) |
C11—C1—C6—O7 | −170.0 (2) | C36—C26—C31—O32 | 163.61 (18) |
C5A—C1—C6—O7 | 65.7 (3) | C30A—C26—C31—O32 | −72.6 (2) |
C5B—C1—C6—O7 | 69.1 (3) | C30B—C26—C31—O32 | −75.9 (3) |
O10—C6—O7—C8 | −8.1 (4) | O35—C31—O32—C33 | 8.1 (3) |
C1—C6—O7—C8 | 177.55 (19) | C26—C31—O32—C33 | −176.0 (2) |
C6—O7—C8—C9 | −98.2 (3) | C31—O32—C33—C34 | 168.8 (3) |
N2—C1—C11—C12 | −6.2 (3) | N27—C26—C36—C37 | 7.7 (3) |
C6—C1—C11—C12 | 118.9 (3) | C30A—C26—C36—C37 | 121.3 (2) |
C5A—C1—C11—C12 | −123.6 (3) | C31—C26—C36—C37 | −116.6 (2) |
C5B—C1—C11—C12 | −117.6 (3) | C30B—C26—C36—C37 | 125.8 (2) |
N2—C1—C11—C16 | 172.3 (2) | N27—C26—C36—C41 | −171.8 (2) |
C6—C1—C11—C16 | −62.6 (3) | C30A—C26—C36—C41 | −58.1 (3) |
C5A—C1—C11—C16 | 54.8 (3) | C31—C26—C36—C41 | 63.9 (3) |
C5B—C1—C11—C16 | 60.8 (3) | C30B—C26—C36—C41 | −53.6 (3) |
C16—C11—C12—C13 | 1.4 (4) | C41—C36—C37—C38 | −1.6 (4) |
C1—C11—C12—C13 | 179.9 (2) | C26—C36—C37—C38 | 178.9 (2) |
C11—C12—C13—C14 | −0.2 (5) | C36—C37—C38—C39 | 0.9 (4) |
C12—C13—C14—C15 | −1.4 (5) | C37—C38—C39—C40 | 0.2 (4) |
C13—C14—C15—C16 | 1.6 (5) | C38—C39—C40—C41 | −0.4 (5) |
C14—C15—C16—C11 | −0.3 (5) | C39—C40—C41—C36 | −0.3 (4) |
C12—C11—C16—C15 | −1.2 (4) | C37—C36—C41—C40 | 1.4 (4) |
C1—C11—C16—C15 | −179.7 (3) | C26—C36—C41—C40 | −179.2 (2) |
C3B—N2—C17—O24 | −165.9 (3) | C28A—N27—C42—O49 | 162.0 (2) |
C1—N2—C17—O24 | −0.4 (3) | C26—N27—C42—O49 | 1.6 (3) |
C3A—N2—C17—O24 | −161.7 (3) | C28B—N27—C42—O49 | 159.4 (4) |
C3B—N2—C17—C18 | 13.9 (4) | C28A—N27—C42—C43 | −19.1 (3) |
C1—N2—C17—C18 | 179.39 (19) | C26—N27—C42—C43 | −179.48 (18) |
C3A—N2—C17—C18 | 18.1 (4) | C28B—N27—C42—C43 | −21.7 (4) |
O24—C17—C18—C19 | 41.8 (3) | O49—C42—C43—C48 | −38.8 (3) |
N2—C17—C18—C19 | −138.0 (2) | N27—C42—C43—C48 | 142.4 (2) |
O24—C17—C18—C23 | −135.0 (3) | O49—C42—C43—C44 | 138.7 (2) |
N2—C17—C18—C23 | 45.2 (3) | N27—C42—C43—C44 | −40.2 (3) |
C23—C18—C19—C20 | −1.6 (4) | C48—C43—C44—C45 | −0.9 (3) |
C17—C18—C19—C20 | −178.6 (2) | C42—C43—C44—C45 | −178.3 (2) |
C18—C19—C20—C21 | −0.4 (4) | C43—C44—C45—C46 | −1.1 (4) |
C19—C20—C21—C22 | 2.1 (5) | C44—C45—C46—C47 | 2.2 (4) |
C20—C21—C22—C23 | −1.8 (5) | C45—C46—C47—C48 | −1.3 (4) |
C21—C22—C23—C18 | −0.3 (5) | C44—C43—C48—C47 | 1.8 (3) |
C19—C18—C23—C22 | 1.9 (4) | C42—C43—C48—C47 | 179.4 (2) |
C17—C18—C23—C22 | 178.8 (3) | C46—C47—C48—C43 | −0.7 (4) |
Experimental details
Crystal data | |
Chemical formula | C20H20ClNO3 |
Mr | 357.82 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 9.4241 (19), 10.073 (2), 19.849 (4) |
β (°) | 102.52 (3) |
V (Å3) | 1839.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.36 × 0.32 × 0.30 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.875, 0.927 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11300, 10705, 5925 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.141, 1.03 |
No. of reflections | 10705 |
No. of parameters | 527 |
No. of restraints | 478 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.18 |
Absolute structure | Flack (1983), with how many Friedel pairs? |
Absolute structure parameter | 0.06 (6) |
Computer programs: CAD-4 Manual (Enraf–Nonius, 1988), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000) and ORTEPII (Johnson, 1976), SHELXTL (Bruker, 2000).
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The interest to X-ray structural investigation of the title compound is stipulated by its potentially HIV-1 RT inhibition properties. This compound belongs to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs) (De Clercq, 1996) with butterfly-like conformation (Karapetyan et al., 2002; Tamazyan et al., 2002).
All four (2S,4R), (2S,4S), (2R,4R) and (2R,4 s) isomers of the title compound are present in crystal structure. The molecules crystallized in the monoclinic space group P21 with two independent molecules (Fig. 1). Each of two symmetry independent molecules corresponds to mixture of pairs of two isomers (2R,4R), (2R,4S) and (2S,4R), (2S,4S) respectively. In pair (2R,4R) (2R,4S) isomers are in ratio ~7:3, while in pair (2S,4R) (2S,4S) the isomers are in ratio ~1:1.