The crystal structure of the title compound, C
21H
17Cl
2NO
3, shows that there are no intra- or intermolecular π–π stacking interactions. The structure is stabilized by C—H
O and C—H
Cl hydrogen bonds, which form a nine-membered ring.
Supporting information
CCDC reference: 282514
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.048
- wR factor = 0.129
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
2-(5-Benzyloxy-2,4-dichlorophenyl)-4,5,6,7-tetrahydro -isoindole-1,3-dione
top
Crystal data top
C21H17Cl2NO3 | F(000) = 832 |
Mr = 402.26 | Dx = 1.381 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.1705 (17) Å | Cell parameters from 1743 reflections |
b = 11.0375 (15) Å | θ = 2.3–20.4° |
c = 15.078 (2) Å | µ = 0.36 mm−1 |
β = 107.232 (3)° | T = 292 K |
V = 1934.6 (5) Å3 | Plate, colorless |
Z = 4 | 0.30 × 0.20 × 0.08 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2169 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
φ and ω scans | h = −14→9 |
9530 measured reflections | k = −10→13 |
3386 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.1448P] where P = (Fo2 + 2Fc2)/3 |
3386 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.23 e Å−3 |
27 restraints | Δρmin = −0.18 e Å−3 |
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 | Occ. (<1) |
C1 | 0.6454 (3) | 0.3843 (3) | −0.1096 (2) | 0.0793 (10) | |
H1 | 0.5864 | 0.3360 | −0.1458 | 0.095* | |
C2 | 0.7282 (4) | 0.4262 (4) | −0.1466 (3) | 0.0963 (12) | |
H2 | 0.7250 | 0.4055 | −0.2071 | 0.116* | |
C3 | 0.8142 (4) | 0.4970 (3) | −0.0965 (4) | 0.0941 (13) | |
H3 | 0.8702 | 0.5250 | −0.1221 | 0.113* | |
C4 | 0.8185 (3) | 0.5270 (4) | −0.0086 (4) | 0.1052 (14) | |
H4 | 0.8779 | 0.5758 | 0.0264 | 0.126* | |
C5 | 0.7348 (3) | 0.4856 (3) | 0.0300 (3) | 0.0831 (10) | |
H5 | 0.7376 | 0.5078 | 0.0901 | 0.100* | |
C6 | 0.6477 (2) | 0.4117 (2) | −0.0209 (2) | 0.0552 (7) | |
C7 | 0.5602 (3) | 0.3606 (3) | 0.0202 (2) | 0.0609 (8) | |
H7A | 0.5550 | 0.4097 | 0.0721 | 0.073* | |
H7B | 0.4851 | 0.3584 | −0.0259 | 0.073* | |
C8 | 0.5297 (2) | 0.1709 (2) | 0.08693 (19) | 0.0525 (7) | |
C9 | 0.5662 (2) | 0.0514 (3) | 0.10922 (19) | 0.0532 (7) | |
C10 | 0.5046 (2) | −0.0265 (3) | 0.1473 (2) | 0.0589 (8) | |
H10 | 0.5303 | −0.1053 | 0.1622 | 0.071* | |
C11 | 0.4046 (2) | 0.0128 (3) | 0.1632 (2) | 0.0575 (8) | |
C12 | 0.3668 (2) | 0.1306 (3) | 0.14141 (19) | 0.0531 (7) | |
C13 | 0.4296 (2) | 0.2085 (2) | 0.10410 (19) | 0.0548 (7) | |
H13 | 0.4043 | 0.2877 | 0.0902 | 0.066* | |
C14 | 0.1526 (3) | 0.1600 (3) | 0.0951 (2) | 0.0635 (8) | |
C15 | 0.2569 (3) | 0.2062 (2) | 0.2451 (2) | 0.0552 (7) | |
C16 | 0.0727 (2) | 0.1994 (3) | 0.1479 (2) | 0.0584 (8) | |
C17 | −0.0540 (3) | 0.2081 (4) | 0.1114 (2) | 0.0842 (10) | |
H17A | −0.0844 | 0.1358 | 0.0760 | 0.101* | 0.571 (15) |
H17B | −0.0750 | 0.2774 | 0.0703 | 0.101* | 0.571 (15) |
H17C | −0.0868 | 0.1279 | 0.0961 | 0.101* | 0.429 (15) |
H17D | −0.0745 | 0.2564 | 0.0551 | 0.101* | 0.429 (15) |
C18 | −0.1047 (9) | 0.2214 (12) | 0.1908 (7) | 0.081 (3) | 0.571 (15) |
H18A | −0.1844 | 0.2465 | 0.1668 | 0.097* | 0.571 (15) |
H18B | −0.1029 | 0.1436 | 0.2211 | 0.097* | 0.571 (15) |
C19 | −0.0398 (6) | 0.3127 (11) | 0.2605 (8) | 0.089 (3) | 0.571 (15) |
H19A | −0.0780 | 0.3240 | 0.3079 | 0.107* | 0.571 (15) |
H19B | −0.0391 | 0.3900 | 0.2300 | 0.107* | 0.571 (15) |
C18' | −0.1003 (14) | 0.2764 (14) | 0.1809 (8) | 0.083 (4) | 0.429 (15) |
H18C | −0.0920 | 0.3627 | 0.1725 | 0.100* | 0.429 (15) |
H18D | −0.1819 | 0.2593 | 0.1673 | 0.100* | 0.429 (15) |
C19' | −0.0410 (8) | 0.2446 (16) | 0.2818 (8) | 0.086 (4) | 0.429 (15) |
H19C | −0.0745 | 0.2914 | 0.3217 | 0.103* | 0.429 (15) |
H19D | −0.0525 | 0.1593 | 0.2920 | 0.103* | 0.429 (15) |
C20 | 0.0840 (3) | 0.2705 (3) | 0.3058 (2) | 0.0814 (10) | |
H20A | 0.1296 | 0.3372 | 0.3396 | 0.098* | 0.571 (15) |
H20B | 0.0847 | 0.2059 | 0.3496 | 0.098* | 0.571 (15) |
H20C | 0.0934 | 0.3577 | 0.3114 | 0.098* | 0.429 (15) |
H20D | 0.1243 | 0.2348 | 0.3654 | 0.098* | 0.429 (15) |
C21 | 0.1338 (2) | 0.2271 (3) | 0.2349 (2) | 0.0558 (7) | |
Cl1 | 0.69019 (6) | 0.00164 (7) | 0.08764 (6) | 0.0668 (3) | |
Cl2 | 0.32666 (8) | −0.08528 (7) | 0.21096 (7) | 0.0873 (3) | |
N1 | 0.26349 (18) | 0.1708 (2) | 0.15839 (16) | 0.0551 (6) | |
O1 | 0.59801 (16) | 0.23995 (16) | 0.05071 (15) | 0.0648 (6) | |
O2 | 0.33881 (18) | 0.21413 (19) | 0.31394 (15) | 0.0766 (6) | |
O3 | 0.13170 (19) | 0.1262 (3) | 0.01700 (17) | 0.0947 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.065 (2) | 0.096 (3) | 0.079 (3) | −0.0126 (19) | 0.0247 (19) | 0.0008 (19) |
C2 | 0.090 (3) | 0.127 (3) | 0.082 (3) | −0.002 (3) | 0.042 (2) | 0.019 (2) |
C3 | 0.087 (3) | 0.080 (3) | 0.138 (4) | 0.001 (2) | 0.068 (3) | 0.030 (3) |
C4 | 0.082 (3) | 0.091 (3) | 0.154 (4) | −0.035 (2) | 0.053 (3) | −0.019 (3) |
C5 | 0.080 (2) | 0.082 (2) | 0.096 (3) | −0.014 (2) | 0.040 (2) | −0.021 (2) |
C6 | 0.0483 (17) | 0.0517 (17) | 0.069 (2) | 0.0042 (14) | 0.0224 (15) | 0.0065 (15) |
C7 | 0.0561 (18) | 0.0587 (18) | 0.075 (2) | 0.0070 (15) | 0.0303 (16) | 0.0075 (15) |
C8 | 0.0406 (15) | 0.0560 (17) | 0.0642 (18) | −0.0009 (13) | 0.0207 (14) | 0.0034 (14) |
C9 | 0.0451 (16) | 0.0593 (18) | 0.0580 (18) | 0.0061 (14) | 0.0196 (14) | −0.0001 (14) |
C10 | 0.0555 (18) | 0.0521 (17) | 0.071 (2) | 0.0053 (14) | 0.0221 (16) | 0.0071 (15) |
C11 | 0.0538 (17) | 0.0578 (19) | 0.0674 (19) | −0.0045 (14) | 0.0281 (15) | 0.0033 (14) |
C12 | 0.0431 (16) | 0.0644 (19) | 0.0560 (18) | −0.0020 (14) | 0.0209 (14) | −0.0023 (14) |
C13 | 0.0489 (17) | 0.0488 (16) | 0.071 (2) | 0.0059 (13) | 0.0247 (15) | 0.0058 (14) |
C14 | 0.0523 (19) | 0.080 (2) | 0.061 (2) | −0.0015 (16) | 0.0216 (17) | 0.0069 (17) |
C15 | 0.0464 (18) | 0.0555 (18) | 0.065 (2) | −0.0033 (14) | 0.0180 (16) | −0.0090 (14) |
C16 | 0.0418 (16) | 0.077 (2) | 0.060 (2) | −0.0054 (14) | 0.0206 (15) | 0.0027 (15) |
C17 | 0.0459 (19) | 0.122 (3) | 0.086 (3) | −0.0023 (19) | 0.0207 (18) | −0.001 (2) |
C18 | 0.046 (4) | 0.100 (7) | 0.101 (6) | 0.001 (5) | 0.031 (4) | −0.005 (5) |
C19 | 0.068 (5) | 0.105 (6) | 0.110 (7) | −0.006 (4) | 0.051 (4) | −0.026 (5) |
C18' | 0.054 (6) | 0.093 (8) | 0.105 (7) | 0.002 (6) | 0.028 (5) | 0.007 (6) |
C19' | 0.068 (6) | 0.103 (8) | 0.101 (7) | 0.005 (5) | 0.045 (5) | 0.002 (6) |
C20 | 0.061 (2) | 0.107 (3) | 0.084 (2) | 0.0015 (19) | 0.0332 (19) | −0.019 (2) |
C21 | 0.0431 (16) | 0.0647 (19) | 0.064 (2) | −0.0026 (14) | 0.0224 (15) | −0.0022 (15) |
Cl1 | 0.0518 (4) | 0.0691 (5) | 0.0872 (6) | 0.0114 (4) | 0.0325 (4) | 0.0049 (4) |
Cl2 | 0.0882 (6) | 0.0746 (6) | 0.1199 (8) | −0.0041 (5) | 0.0629 (6) | 0.0185 (5) |
N1 | 0.0384 (13) | 0.0726 (16) | 0.0593 (15) | 0.0015 (11) | 0.0223 (12) | 0.0018 (12) |
O1 | 0.0502 (12) | 0.0558 (12) | 0.0990 (16) | 0.0080 (10) | 0.0385 (12) | 0.0190 (10) |
O2 | 0.0501 (13) | 0.1015 (17) | 0.0731 (15) | 0.0023 (12) | 0.0106 (12) | −0.0252 (12) |
O3 | 0.0695 (16) | 0.160 (2) | 0.0567 (15) | 0.0056 (15) | 0.0223 (13) | −0.0114 (15) |
Geometric parameters (Å, º) top
C1—C6 | 1.364 (4) | C14—C16 | 1.493 (4) |
C1—C2 | 1.369 (5) | C15—O2 | 1.211 (3) |
C1—H1 | 0.9300 | C15—N1 | 1.389 (3) |
C2—C3 | 1.344 (5) | C15—C21 | 1.478 (4) |
C2—H2 | 0.9300 | C16—C21 | 1.337 (4) |
C3—C4 | 1.352 (6) | C16—C17 | 1.479 (4) |
C3—H3 | 0.9300 | C17—C18 | 1.508 (9) |
C4—C5 | 1.392 (5) | C17—C18' | 1.529 (12) |
C4—H4 | 0.9300 | C17—H17A | 0.9700 |
C5—C6 | 1.376 (4) | C17—H17B | 0.9700 |
C5—H5 | 0.9300 | C17—H17C | 0.9700 |
C6—C7 | 1.493 (4) | C17—H17D | 0.9700 |
C7—O1 | 1.440 (3) | C18—C19 | 1.501 (10) |
C7—H7A | 0.9700 | C18—H18A | 0.9700 |
C7—H7B | 0.9700 | C18—H18B | 0.9700 |
C8—O1 | 1.357 (3) | C19—C20 | 1.531 (9) |
C8—C13 | 1.382 (4) | C19—H19A | 0.9700 |
C8—C9 | 1.401 (4) | C19—H19B | 0.9700 |
C9—C10 | 1.373 (4) | C18'—C19' | 1.519 (13) |
C9—Cl1 | 1.725 (3) | C18'—H18C | 0.9700 |
C10—C11 | 1.379 (4) | C18'—H18D | 0.9700 |
C10—H10 | 0.9300 | C19'—C20 | 1.483 (10) |
C11—C12 | 1.386 (4) | C19'—H19C | 0.9700 |
C11—Cl2 | 1.731 (3) | C19'—H19D | 0.9700 |
C12—C13 | 1.377 (4) | C20—C21 | 1.458 (4) |
C12—N1 | 1.426 (3) | C20—H20A | 0.9700 |
C13—H13 | 0.9300 | C20—H20B | 0.9700 |
C14—O3 | 1.188 (4) | C20—H20C | 0.9700 |
C14—N1 | 1.408 (4) | C20—H20D | 0.9700 |
| | | |
C6—C1—C2 | 121.4 (3) | C16—C17—H17A | 109.7 |
C6—C1—H1 | 119.3 | C18—C17—H17A | 109.7 |
C2—C1—H1 | 119.3 | C16—C17—H17B | 109.7 |
C3—C2—C1 | 120.8 (4) | C18—C17—H17B | 109.7 |
C3—C2—H2 | 119.6 | H17A—C17—H17B | 108.2 |
C1—C2—H2 | 119.6 | C16—C17—H17C | 109.9 |
C2—C3—C4 | 119.4 (4) | C18'—C17—H17C | 113.8 |
C2—C3—H3 | 120.3 | C16—C17—H17D | 109.4 |
C4—C3—H3 | 120.3 | C18'—C17—H17D | 106.1 |
C3—C4—C5 | 120.5 (4) | H17C—C17—H17D | 108.1 |
C3—C4—H4 | 119.7 | C19—C18—C17 | 111.6 (8) |
C5—C4—H4 | 119.7 | C19—C18—H18A | 109.3 |
C6—C5—C4 | 120.0 (4) | C17—C18—H18A | 109.3 |
C6—C5—H5 | 120.0 | C19—C18—H18B | 109.3 |
C4—C5—H5 | 120.0 | C17—C18—H18B | 109.3 |
C1—C6—C5 | 117.9 (3) | H18A—C18—H18B | 108.0 |
C1—C6—C7 | 120.9 (3) | C18—C19—C20 | 110.6 (9) |
C5—C6—C7 | 121.2 (3) | C18—C19—H19A | 109.5 |
O1—C7—C6 | 106.4 (2) | C20—C19—H19A | 109.5 |
O1—C7—H7A | 110.5 | C18—C19—H19B | 109.5 |
C6—C7—H7A | 110.5 | C20—C19—H19B | 109.5 |
O1—C7—H7B | 110.5 | H19A—C19—H19B | 108.1 |
C6—C7—H7B | 110.5 | C19'—C18'—C17 | 114.2 (10) |
H7A—C7—H7B | 108.6 | C19'—C18'—H18C | 108.7 |
O1—C8—C13 | 125.9 (2) | C17—C18'—H18C | 108.7 |
O1—C8—C9 | 115.9 (2) | C19'—C18'—H18D | 108.7 |
C13—C8—C9 | 118.2 (3) | C17—C18'—H18D | 108.7 |
C10—C9—C8 | 121.1 (3) | H18C—C18'—H18D | 107.6 |
C10—C9—Cl1 | 119.7 (2) | C20—C19'—C18' | 110.5 (11) |
C8—C9—Cl1 | 119.2 (2) | C20—C19'—H19C | 109.6 |
C9—C10—C11 | 119.7 (3) | C18'—C19'—H19C | 109.6 |
C9—C10—H10 | 120.1 | C20—C19'—H19D | 109.6 |
C11—C10—H10 | 120.1 | C18'—C19'—H19D | 109.6 |
C10—C11—C12 | 120.1 (3) | H19C—C19'—H19D | 108.1 |
C10—C11—Cl2 | 119.8 (2) | C21—C20—C19' | 112.1 (6) |
C12—C11—Cl2 | 120.1 (2) | C21—C20—C19 | 109.9 (5) |
C13—C12—C11 | 119.8 (3) | C21—C20—H20A | 109.7 |
C13—C12—N1 | 120.3 (3) | C19—C20—H20A | 109.7 |
C11—C12—N1 | 119.8 (2) | C21—C20—H20B | 109.7 |
C12—C13—C8 | 121.0 (3) | C19—C20—H20B | 109.7 |
C12—C13—H13 | 119.5 | H20A—C20—H20B | 108.2 |
C8—C13—H13 | 119.5 | C21—C20—H20C | 109.0 |
O3—C14—N1 | 125.4 (3) | C19'—C20—H20C | 107.4 |
O3—C14—C16 | 129.6 (3) | C21—C20—H20D | 109.8 |
N1—C14—C16 | 105.0 (3) | C19'—C20—H20D | 110.4 |
O2—C15—N1 | 124.4 (3) | H20C—C20—H20D | 108.0 |
O2—C15—C21 | 129.0 (3) | C16—C21—C20 | 124.3 (3) |
N1—C15—C21 | 106.6 (3) | C16—C21—C15 | 108.6 (3) |
C21—C16—C17 | 124.4 (3) | C20—C21—C15 | 127.1 (3) |
C21—C16—C14 | 109.2 (3) | C15—N1—C14 | 110.5 (2) |
C17—C16—C14 | 126.3 (3) | C15—N1—C12 | 123.8 (2) |
C16—C17—C18 | 109.7 (5) | C14—N1—C12 | 124.8 (2) |
C16—C17—C18' | 109.4 (7) | C8—O1—C7 | 118.2 (2) |
| | | |
C6—C1—C2—C3 | −0.6 (6) | C16—C17—C18—C19 | 45.3 (14) |
C1—C2—C3—C4 | −0.1 (6) | C17—C18—C19—C20 | −63.7 (17) |
C2—C3—C4—C5 | −0.1 (6) | C16—C17—C18'—C19' | −40.1 (17) |
C3—C4—C5—C6 | 1.1 (6) | C17—C18'—C19'—C20 | 59 (2) |
C2—C1—C6—C5 | 1.5 (5) | C18'—C19'—C20—C21 | −45.1 (16) |
C2—C1—C6—C7 | −177.0 (3) | C18—C19—C20—C21 | 46.3 (13) |
C4—C5—C6—C1 | −1.7 (5) | C17—C16—C21—C20 | −0.4 (5) |
C4—C5—C6—C7 | 176.8 (3) | C14—C16—C21—C20 | 179.3 (3) |
C1—C6—C7—O1 | 81.3 (3) | C17—C16—C21—C15 | 179.6 (3) |
C5—C6—C7—O1 | −97.2 (3) | C14—C16—C21—C15 | −0.8 (3) |
O1—C8—C9—C10 | 179.3 (3) | C19'—C20—C21—C16 | 18.0 (8) |
C13—C8—C9—C10 | −0.1 (4) | C19—C20—C21—C16 | −15.7 (7) |
O1—C8—C9—Cl1 | −1.1 (3) | C19'—C20—C21—C15 | −162.0 (7) |
C13—C8—C9—Cl1 | 179.5 (2) | C19—C20—C21—C15 | 164.3 (6) |
C8—C9—C10—C11 | 0.6 (4) | O2—C15—C21—C16 | −175.6 (3) |
Cl1—C9—C10—C11 | −179.0 (2) | N1—C15—C21—C16 | 2.8 (3) |
C9—C10—C11—C12 | −0.4 (4) | O2—C15—C21—C20 | 4.4 (5) |
C9—C10—C11—Cl2 | 179.9 (2) | N1—C15—C21—C20 | −177.2 (3) |
C10—C11—C12—C13 | −0.2 (4) | O2—C15—N1—C14 | 174.7 (3) |
Cl2—C11—C12—C13 | 179.5 (2) | C21—C15—N1—C14 | −3.9 (3) |
C10—C11—C12—N1 | −179.8 (3) | O2—C15—N1—C12 | 4.9 (4) |
Cl2—C11—C12—N1 | −0.1 (4) | C21—C15—N1—C12 | −173.6 (2) |
C11—C12—C13—C8 | 0.7 (4) | O3—C14—N1—C15 | −176.6 (3) |
N1—C12—C13—C8 | −179.8 (3) | C16—C14—N1—C15 | 3.4 (3) |
O1—C8—C13—C12 | −179.8 (3) | O3—C14—N1—C12 | −7.0 (5) |
C9—C8—C13—C12 | −0.5 (4) | C16—C14—N1—C12 | 173.0 (2) |
O3—C14—C16—C21 | 178.5 (3) | C13—C12—N1—C15 | −99.8 (3) |
N1—C14—C16—C21 | −1.5 (3) | C11—C12—N1—C15 | 79.8 (4) |
O3—C14—C16—C17 | −1.9 (6) | C13—C12—N1—C14 | 91.9 (3) |
N1—C14—C16—C17 | 178.1 (3) | C11—C12—N1—C14 | −88.5 (4) |
C21—C16—C17—C18 | −14.2 (7) | C13—C8—O1—C7 | −5.2 (4) |
C14—C16—C17—C18 | 166.3 (6) | C9—C8—O1—C7 | 175.5 (2) |
C21—C16—C17—C18' | 11.3 (8) | C6—C7—O1—C8 | −176.8 (2) |
C14—C16—C17—C18' | −168.3 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20A···Cl1i | 0.97 | 2.81 | 3.745 (4) | 163 |
C10—H10···O2ii | 0.93 | 2.51 | 3.393 (4) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |