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The title compound, C
24H
29NO
2, is one of the intermediates of the potent HIV protease inhibitor Indinavir. The oxazolidine ring adopts an envelope conformation. The orientation of the benzyl groups facilitates C—H
π interactions, forming molecular chains along the
a axis.
Supporting information
CCDC reference: 624970
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.101
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.81
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23A
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 2069
From the CIF: _diffrn_reflns_limit_ max hkl 11. 13. 20.
From the CIF: _diffrn_reflns_limit_ min hkl -11. -13. -19.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 11. 13. 22.
Calculated minimum hkl -11. -13. -22.
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 25.00
From the CIF: _reflns_number_total 2069
Count of symmetry unique reflns 2159
Completeness (_total/calc) 95.83%
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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
(2
S)-2-Benzyl-1-[(4
R)-4-benzyl-2,2-dimethyl-1,3-oxazolan-3-yl]pent-4-en-1-one
top
Crystal data top
C24H29NO2 | F(000) = 784 |
Mr = 363.48 | Dx = 1.126 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3930 reflections |
a = 10.0061 (12) Å | θ = 2.3–21.2° |
b = 11.5146 (14) Å | µ = 0.07 mm−1 |
c = 18.602 (2) Å | T = 273 K |
V = 2143.3 (4) Å3 | Block, colourless |
Z = 4 | 0.19 × 0.13 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1832 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −11→11 |
10985 measured reflections | k = −13→13 |
2069 independent reflections | l = −19→20 |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.202P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2069 reflections | Δρmax = 0.11 e Å−3 |
265 parameters | Δρmin = −0.18 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 1532 Friedels pairs |
Primary atom site location: structure-invariant direct methods | |
Special details top
Experimental. 1H NMR (CDCl3): δ 1.55 (s, 3H), 1.65 (s, 3H), 1.89 (d,
1H, J = 12.8 Hz), 2.20–2.60 (m, 3H), 2.75 (dd, 1H,
J = 4.5, 12.8 Hz), 2.85 (m, 1H), 3.20 (dd, 1H, J =
9.8, 12.8 Hz), 3.61–3.75 (m, 1H), 3.85 (m, 1H), 5.14
(dd, 2H, J = 8.6, 128 Hz), 5.80 (m, 1H), 7.01 (d,
2H, J = 6.8 Hz), 7.11–7.32 (m, 8H). |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.53561 (18) | 0.73286 (14) | 0.79416 (9) | 0.0686 (5) | |
O2 | 0.70312 (18) | 0.80858 (14) | 0.99131 (9) | 0.0685 (5) | |
N1 | 0.61033 (17) | 0.84793 (14) | 0.88289 (10) | 0.0482 (4) | |
C1 | 0.6490 (2) | 0.75085 (19) | 0.93062 (13) | 0.0586 (6) | |
C2 | 0.6435 (3) | 0.9197 (2) | 0.99535 (13) | 0.0654 (7) | |
H2A | 0.6965 | 0.9720 | 1.0247 | 0.079* | |
H2B | 0.5539 | 0.9151 | 1.0151 | 0.079* | |
C3 | 0.6408 (2) | 0.95905 (18) | 0.91781 (12) | 0.0497 (5) | |
H3 | 0.5684 | 1.0150 | 0.9099 | 0.060* | |
C4 | 0.7741 (2) | 1.0089 (2) | 0.89280 (15) | 0.0562 (6) | |
H4A | 0.8456 | 0.9581 | 0.9085 | 0.067* | |
H4B | 0.7754 | 1.0111 | 0.8407 | 0.067* | |
C5 | 0.7989 (2) | 1.12866 (19) | 0.92122 (13) | 0.0546 (6) | |
C6 | 0.7340 (2) | 1.22289 (19) | 0.89251 (15) | 0.0626 (6) | |
H6 | 0.6768 | 1.2121 | 0.8536 | 0.075* | |
C7 | 0.7513 (3) | 1.3327 (2) | 0.91975 (17) | 0.0767 (8) | |
H7 | 0.7047 | 1.3949 | 0.9000 | 0.092* | |
C8 | 0.8366 (4) | 1.3506 (2) | 0.97577 (18) | 0.0910 (10) | |
H8 | 0.8494 | 1.4249 | 0.9941 | 0.109* | |
C9 | 0.9025 (4) | 1.2591 (3) | 1.0044 (2) | 0.1195 (14) | |
H9 | 0.9601 | 1.2705 | 1.0430 | 0.143* | |
C10 | 0.8851 (4) | 1.1494 (2) | 0.9770 (2) | 0.0986 (11) | |
H10 | 0.9330 | 1.0879 | 0.9966 | 0.118* | |
C11 | 0.5534 (2) | 0.83061 (18) | 0.81805 (13) | 0.0520 (5) | |
C12 | 0.5063 (2) | 0.9344 (2) | 0.77493 (13) | 0.0573 (6) | |
H12 | 0.5379 | 1.0060 | 0.7979 | 0.069* | |
C13 | 0.5603 (3) | 0.9283 (3) | 0.69837 (14) | 0.0676 (7) | |
H13A | 0.5399 | 0.8525 | 0.6784 | 0.081* | |
H13B | 0.5151 | 0.9861 | 0.6692 | 0.081* | |
C14 | 0.7080 (3) | 0.9483 (2) | 0.69401 (14) | 0.0626 (6) | |
C15 | 0.7591 (3) | 1.0588 (3) | 0.69392 (15) | 0.0723 (7) | |
H15 | 0.7005 | 1.1215 | 0.6946 | 0.087* | |
C16 | 0.8934 (4) | 1.0795 (4) | 0.69289 (19) | 0.0982 (11) | |
H16 | 0.9259 | 1.1551 | 0.6925 | 0.118* | |
C17 | 0.9789 (4) | 0.9873 (5) | 0.6924 (2) | 0.1218 (15) | |
H17 | 1.0706 | 1.0004 | 0.6929 | 0.146* | |
C18 | 0.9319 (4) | 0.8770 (5) | 0.6912 (3) | 0.1350 (17) | |
H18 | 0.9910 | 0.8147 | 0.6896 | 0.162* | |
C19 | 0.7955 (4) | 0.8576 (3) | 0.6924 (2) | 0.1001 (10) | |
H19 | 0.7632 | 0.7819 | 0.6921 | 0.120* | |
C20 | 0.7597 (3) | 0.6792 (2) | 0.89876 (18) | 0.0832 (9) | |
H20A | 0.7915 | 0.6248 | 0.9340 | 0.125* | |
H20B | 0.8316 | 0.7292 | 0.8843 | 0.125* | |
H20C | 0.7266 | 0.6378 | 0.8577 | 0.125* | |
C21 | 0.5285 (3) | 0.6798 (2) | 0.95281 (17) | 0.0855 (9) | |
H21A | 0.4634 | 0.7296 | 0.9748 | 0.128* | |
H21B | 0.5555 | 0.6211 | 0.9865 | 0.128* | |
H21C | 0.4901 | 0.6435 | 0.9112 | 0.128* | |
C22 | 0.3524 (3) | 0.9341 (3) | 0.77338 (15) | 0.0768 (8) | |
H22A | 0.3232 | 1.0043 | 0.7492 | 0.092* | |
H22B | 0.3237 | 0.8690 | 0.7441 | 0.092* | |
C23 | 0.2799 (8) | 0.9268 (8) | 0.8450 (4) | 0.078 (3) | 0.578 (14) |
H23 | 0.2969 | 0.8633 | 0.8745 | 0.093* | 0.578 (14) |
C24 | 0.1974 (10) | 1.0030 (10) | 0.8666 (6) | 0.120 (4) | 0.578 (14) |
H24A | 0.1787 | 1.0673 | 0.8381 | 0.144* | 0.578 (14) |
H24B | 0.1556 | 0.9945 | 0.9110 | 0.144* | 0.578 (14) |
C23A | 0.2993 (10) | 0.9857 (12) | 0.8426 (5) | 0.085 (4) | 0.422 (14) |
H23A | 0.3208 | 1.0600 | 0.8583 | 0.102* | 0.422 (14) |
C24A | 0.223 (2) | 0.9184 (14) | 0.8768 (8) | 0.146 (7) | 0.422 (14) |
H24C | 0.2048 | 0.8447 | 0.8589 | 0.175* | 0.422 (14) |
H24D | 0.1857 | 0.9424 | 0.9201 | 0.175* | 0.422 (14) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0831 (12) | 0.0529 (9) | 0.0699 (11) | −0.0158 (9) | −0.0081 (9) | −0.0130 (8) |
O2 | 0.0807 (11) | 0.0639 (10) | 0.0609 (11) | 0.0000 (9) | −0.0163 (9) | 0.0069 (8) |
N1 | 0.0515 (10) | 0.0421 (9) | 0.0509 (11) | −0.0014 (8) | −0.0021 (8) | −0.0023 (8) |
C1 | 0.0644 (13) | 0.0494 (12) | 0.0620 (15) | −0.0009 (11) | −0.0053 (13) | 0.0046 (11) |
C2 | 0.0751 (15) | 0.0658 (15) | 0.0555 (16) | −0.0013 (14) | −0.0032 (13) | −0.0048 (12) |
C3 | 0.0526 (12) | 0.0473 (11) | 0.0491 (14) | 0.0037 (10) | −0.0041 (10) | −0.0069 (10) |
C4 | 0.0550 (14) | 0.0534 (12) | 0.0601 (16) | 0.0000 (10) | −0.0035 (11) | −0.0084 (11) |
C5 | 0.0548 (12) | 0.0519 (12) | 0.0570 (14) | −0.0051 (10) | −0.0080 (12) | −0.0022 (10) |
C6 | 0.0686 (15) | 0.0551 (12) | 0.0642 (16) | −0.0087 (11) | −0.0159 (13) | 0.0036 (12) |
C7 | 0.0873 (18) | 0.0526 (13) | 0.090 (2) | −0.0048 (13) | −0.0182 (17) | 0.0082 (13) |
C8 | 0.120 (3) | 0.0523 (15) | 0.100 (2) | −0.0141 (16) | −0.026 (2) | −0.0071 (16) |
C9 | 0.157 (3) | 0.0738 (18) | 0.127 (3) | −0.012 (2) | −0.088 (3) | −0.0119 (18) |
C10 | 0.114 (2) | 0.0596 (16) | 0.122 (3) | 0.0034 (16) | −0.066 (2) | −0.0003 (17) |
C11 | 0.0484 (11) | 0.0545 (13) | 0.0531 (14) | −0.0071 (10) | −0.0003 (10) | −0.0056 (11) |
C12 | 0.0567 (13) | 0.0606 (13) | 0.0548 (15) | −0.0030 (11) | −0.0104 (11) | −0.0028 (11) |
C13 | 0.0749 (17) | 0.0763 (16) | 0.0515 (16) | −0.0054 (14) | −0.0096 (12) | 0.0007 (13) |
C14 | 0.0668 (15) | 0.0740 (16) | 0.0470 (15) | 0.0021 (13) | 0.0009 (11) | 0.0023 (12) |
C15 | 0.0745 (18) | 0.0820 (17) | 0.0604 (18) | −0.0042 (15) | −0.0009 (13) | 0.0048 (14) |
C16 | 0.083 (2) | 0.130 (3) | 0.081 (2) | −0.030 (2) | 0.0013 (17) | 0.016 (2) |
C17 | 0.064 (2) | 0.180 (4) | 0.122 (3) | −0.008 (3) | 0.011 (2) | 0.038 (3) |
C18 | 0.092 (3) | 0.152 (4) | 0.161 (4) | 0.038 (3) | 0.036 (3) | 0.044 (4) |
C19 | 0.098 (2) | 0.089 (2) | 0.114 (3) | 0.0113 (19) | 0.027 (2) | 0.011 (2) |
C20 | 0.0876 (19) | 0.0590 (14) | 0.103 (2) | 0.0194 (14) | −0.0152 (18) | −0.0024 (15) |
C21 | 0.0934 (19) | 0.0775 (18) | 0.086 (2) | −0.0248 (16) | −0.0024 (17) | 0.0197 (16) |
C22 | 0.0588 (14) | 0.105 (2) | 0.0667 (17) | 0.0108 (16) | −0.0122 (13) | −0.0055 (16) |
C23 | 0.058 (4) | 0.101 (6) | 0.073 (5) | −0.012 (4) | 0.003 (3) | −0.010 (4) |
C24 | 0.104 (6) | 0.147 (8) | 0.107 (6) | 0.024 (6) | 0.026 (4) | −0.005 (6) |
C23A | 0.049 (5) | 0.099 (8) | 0.108 (7) | −0.004 (6) | −0.008 (4) | −0.014 (7) |
C24A | 0.145 (13) | 0.178 (15) | 0.114 (10) | −0.017 (13) | 0.056 (9) | 0.029 (10) |
Geometric parameters (Å, º) top
O1—C11 | 1.223 (3) | C13—H13A | 0.9700 |
O2—C2 | 1.414 (3) | C13—H13B | 0.9700 |
O2—C1 | 1.418 (3) | C14—C19 | 1.364 (4) |
N1—C11 | 1.349 (3) | C14—C15 | 1.370 (4) |
N1—C3 | 1.467 (3) | C15—C16 | 1.365 (4) |
N1—C1 | 1.479 (3) | C15—H15 | 0.9300 |
C1—C20 | 1.503 (4) | C16—C17 | 1.363 (6) |
C1—C21 | 1.515 (4) | C16—H16 | 0.9300 |
C2—C3 | 1.512 (3) | C17—C18 | 1.355 (6) |
C2—H2A | 0.9700 | C17—H17 | 0.9300 |
C2—H2B | 0.9700 | C18—C19 | 1.383 (6) |
C3—C4 | 1.525 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9800 | C19—H19 | 0.9300 |
C4—C5 | 1.498 (3) | C20—H20A | 0.9600 |
C4—H4A | 0.9700 | C20—H20B | 0.9600 |
C4—H4B | 0.9700 | C20—H20C | 0.9600 |
C5—C10 | 1.370 (4) | C21—H21A | 0.9600 |
C5—C6 | 1.373 (3) | C21—H21B | 0.9600 |
C6—C7 | 1.373 (3) | C21—H21C | 0.9600 |
C6—H6 | 0.9300 | C22—C23A | 1.513 (8) |
C7—C8 | 1.363 (4) | C22—C23 | 1.519 (7) |
C7—H7 | 0.9300 | C22—H22A | 0.9700 |
C8—C9 | 1.353 (5) | C22—H22B | 0.9700 |
C8—H8 | 0.9300 | C23—C24 | 1.270 (8) |
C9—C10 | 1.373 (4) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—H24A | 0.9300 |
C10—H10 | 0.9300 | C24—H24B | 0.9300 |
C11—C12 | 1.515 (3) | C23A—C24A | 1.259 (10) |
C12—C13 | 1.525 (4) | C23A—H23A | 0.9300 |
C12—C22 | 1.540 (3) | C24A—H24C | 0.9300 |
C12—H12 | 0.9800 | C24A—H24D | 0.9300 |
C13—C14 | 1.498 (4) | | |
| | | |
C2—O2—C1 | 107.79 (18) | C14—C13—H13A | 109.0 |
C11—N1—C3 | 127.79 (17) | C12—C13—H13A | 109.0 |
C11—N1—C1 | 122.39 (17) | C14—C13—H13B | 109.0 |
C3—N1—C1 | 109.81 (16) | C12—C13—H13B | 109.0 |
O2—C1—N1 | 102.92 (16) | H13A—C13—H13B | 107.8 |
O2—C1—C20 | 106.9 (2) | C19—C14—C15 | 118.1 (3) |
N1—C1—C20 | 111.8 (2) | C19—C14—C13 | 121.1 (3) |
O2—C1—C21 | 109.9 (2) | C15—C14—C13 | 120.7 (3) |
N1—C1—C21 | 111.3 (2) | C16—C15—C14 | 122.0 (3) |
C20—C1—C21 | 113.4 (2) | C16—C15—H15 | 119.0 |
O2—C2—C3 | 103.17 (19) | C14—C15—H15 | 119.0 |
O2—C2—H2A | 111.1 | C17—C16—C15 | 118.8 (4) |
C3—C2—H2A | 111.1 | C17—C16—H16 | 120.6 |
O2—C2—H2B | 111.1 | C15—C16—H16 | 120.6 |
C3—C2—H2B | 111.1 | C18—C17—C16 | 120.8 (4) |
H2A—C2—H2B | 109.1 | C18—C17—H17 | 119.6 |
N1—C3—C2 | 99.49 (17) | C16—C17—H17 | 119.6 |
N1—C3—C4 | 112.01 (18) | C17—C18—C19 | 119.5 (4) |
C2—C3—C4 | 112.9 (2) | C17—C18—H18 | 120.2 |
N1—C3—H3 | 110.7 | C19—C18—H18 | 120.2 |
C2—C3—H3 | 110.7 | C14—C19—C18 | 120.7 (4) |
C4—C3—H3 | 110.7 | C14—C19—H19 | 119.6 |
C5—C4—C3 | 112.6 (2) | C18—C19—H19 | 119.6 |
C5—C4—H4A | 109.1 | C1—C20—H20A | 109.5 |
C3—C4—H4A | 109.1 | C1—C20—H20B | 109.5 |
C5—C4—H4B | 109.1 | H20A—C20—H20B | 109.5 |
C3—C4—H4B | 109.1 | C1—C20—H20C | 109.5 |
H4A—C4—H4B | 107.8 | H20A—C20—H20C | 109.5 |
C10—C5—C6 | 117.0 (2) | H20B—C20—H20C | 109.5 |
C10—C5—C4 | 122.2 (2) | C1—C21—H21A | 109.5 |
C6—C5—C4 | 120.8 (2) | C1—C21—H21B | 109.5 |
C5—C6—C7 | 121.6 (2) | H21A—C21—H21B | 109.5 |
C5—C6—H6 | 119.2 | C1—C21—H21C | 109.5 |
C7—C6—H6 | 119.2 | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 120.0 (3) | H21B—C21—H21C | 109.5 |
C8—C7—H7 | 120.0 | C23A—C22—C12 | 109.5 (5) |
C6—C7—H7 | 120.0 | C23—C22—C12 | 117.5 (4) |
C9—C8—C7 | 119.2 (3) | C23A—C22—H22A | 87.8 |
C9—C8—H8 | 120.4 | C23—C22—H22A | 107.9 |
C7—C8—H8 | 120.4 | C12—C22—H22A | 107.9 |
C8—C9—C10 | 120.6 (3) | C23A—C22—H22B | 132.6 |
C8—C9—H9 | 119.7 | C23—C22—H22B | 107.9 |
C10—C9—H9 | 119.7 | C12—C22—H22B | 107.9 |
C5—C10—C9 | 121.4 (3) | H22A—C22—H22B | 107.2 |
C5—C10—H10 | 119.3 | C24—C23—C22 | 123.4 (11) |
C9—C10—H10 | 119.3 | C24—C23—H23 | 118.3 |
O1—C11—N1 | 121.5 (2) | C22—C23—H23 | 118.3 |
O1—C11—C12 | 119.3 (2) | C23—C24—H24A | 120.0 |
N1—C11—C12 | 119.22 (18) | C23—C24—H24B | 120.0 |
C11—C12—C13 | 110.4 (2) | H24A—C24—H24B | 120.0 |
C11—C12—C22 | 108.6 (2) | C24A—C23A—C22 | 113.7 (15) |
C13—C12—C22 | 109.7 (2) | C24A—C23A—H23A | 123.2 |
C11—C12—H12 | 109.4 | C22—C23A—H23A | 123.2 |
C13—C12—H12 | 109.4 | C23A—C24A—H24C | 120.0 |
C22—C12—H12 | 109.4 | C23A—C24A—H24D | 120.0 |
C14—C13—C12 | 113.1 (2) | H24C—C24A—H24D | 120.0 |
| | | |
C2—O2—C1—N1 | 26.5 (2) | C3—N1—C11—O1 | 178.5 (2) |
C2—O2—C1—C20 | 144.3 (2) | C1—N1—C11—O1 | −2.9 (3) |
C2—O2—C1—C21 | −92.2 (2) | C3—N1—C11—C12 | −3.5 (3) |
C11—N1—C1—O2 | −179.85 (18) | C1—N1—C11—C12 | 175.0 (2) |
C3—N1—C1—O2 | −1.1 (2) | O1—C11—C12—C13 | −52.3 (3) |
C11—N1—C1—C20 | 65.8 (3) | N1—C11—C12—C13 | 129.7 (2) |
C3—N1—C1—C20 | −115.4 (2) | O1—C11—C12—C22 | 68.0 (3) |
C11—N1—C1—C21 | −62.2 (3) | N1—C11—C12—C22 | −110.1 (2) |
C3—N1—C1—C21 | 116.6 (2) | C11—C12—C13—C14 | −70.1 (3) |
C1—O2—C2—C3 | −41.4 (2) | C22—C12—C13—C14 | 170.3 (2) |
C11—N1—C3—C2 | 156.6 (2) | C12—C13—C14—C19 | 95.8 (3) |
C1—N1—C3—C2 | −22.1 (2) | C12—C13—C14—C15 | −82.0 (3) |
C11—N1—C3—C4 | −83.9 (3) | C19—C14—C15—C16 | −0.6 (5) |
C1—N1—C3—C4 | 97.4 (2) | C13—C14—C15—C16 | 177.3 (3) |
O2—C2—C3—N1 | 37.4 (2) | C14—C15—C16—C17 | −0.4 (6) |
O2—C2—C3—C4 | −81.5 (2) | C15—C16—C17—C18 | 1.6 (7) |
N1—C3—C4—C5 | 173.19 (19) | C16—C17—C18—C19 | −1.7 (8) |
C2—C3—C4—C5 | −75.5 (2) | C15—C14—C19—C18 | 0.4 (6) |
C3—C4—C5—C10 | 103.4 (3) | C13—C14—C19—C18 | −177.4 (4) |
C3—C4—C5—C6 | −75.8 (3) | C17—C18—C19—C14 | 0.7 (8) |
C10—C5—C6—C7 | −2.0 (4) | C11—C12—C22—C23A | 81.1 (6) |
C4—C5—C6—C7 | 177.3 (3) | C13—C12—C22—C23A | −158.2 (6) |
C5—C6—C7—C8 | 1.3 (5) | C11—C12—C22—C23 | 53.0 (5) |
C6—C7—C8—C9 | −0.6 (5) | C13—C12—C22—C23 | 173.6 (5) |
C7—C8—C9—C10 | 0.8 (7) | C23A—C22—C23—C24 | 42.7 (13) |
C6—C5—C10—C9 | 2.1 (5) | C12—C22—C23—C24 | 121.6 (10) |
C4—C5—C10—C9 | −177.2 (4) | C23—C22—C23A—C24A | −9.9 (13) |
C8—C9—C10—C5 | −1.5 (7) | C12—C22—C23A—C24A | −122.4 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O1 | 0.97 | 2.56 | 2.881 (4) | 100 |
C20—H20C···O1 | 0.96 | 2.50 | 3.032 (4) | 115 |
C21—H21C···O1 | 0.96 | 2.45 | 3.015 (4) | 117 |
C4—H4B···Cg1 | 0.97 | 2.88 | 3.815 (2) | 163 |
C2—H2A···Cg1i | 0.97 | 3.23 | 3.896 (2) | 128 |
Symmetry code: (i) −x+3/2, −y+2, z+1/2. |
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