The title compound, (6,7-dimethoxy-3,4-dihydro-2
H-chromen-4-yl)(5-methoxy-2,2-dimethyl-2
H-chromen-6-yl)methanone, C
24H
25O
6, is a modified rotenoid. In the crystal structure, the chromene ring is disordered, together with its attached methyl and methoxy groups. The molecules are packed as layers parallel to the
ac plane. These layers are interconnected through C—H
O interactions to form a three-dimensional network.
Supporting information
CCDC reference: 282689
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.084
- wR factor = 0.199
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C16
| Author Response: The neighboring atoms to C16 are disordered.
|
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.90 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.65 Ratio
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C22
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.11
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14B
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6A
| Author Response: The neighboring atoms to C16 are disordered.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
| Author Response: The neighboring atoms to C16 are disordered.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6B
| Author Response: The neighboring atoms to C16 are disordered.
|
PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.20 Deg.
C22 -O6A -H22F 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 43.60 Deg.
C24B -C16 -C24A 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.90 Deg.
C15A -C16 -C15B 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 16.20 Deg.
H22C -C22 -H22E 1.555 1.555 1.555
1 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
14 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
(6,7-dimethoxy-3,4-dihydro-2
H-chromen-4-yl)(5-methoxy-2,2-
dimethyl-2
H-chromen-6-yl)methanone
top
Crystal data top
C24H25O6 | Z = 2 |
Mr = 410.45 | F(000) = 436 |
Triclinic, P1 | Dx = 1.302 Mg m−3 |
Hall symbol: -P 1 | Melting point: 391-392K K |
a = 9.7861 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4999 (15) Å | Cell parameters from 10872 reflections |
c = 10.7337 (15) Å | θ = 2.0–25.0° |
α = 72.329 (3)° | µ = 0.09 mm−1 |
β = 88.734 (3)° | T = 293 K |
γ = 84.930 (3)° | Block, colorless |
V = 1046.8 (3) Å3 | 0.45 × 0.38 × 0.32 mm |
Data collection top
Siemens SMART CCD area detector diffractometer | 3700 independent reflections |
Radiation source: fine-focus sealed tube | 3292 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.959, Tmax = 0.971 | l = −12→12 |
10872 measured reflections | |
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)] = 0.084 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.23 | w = 1/[σ2(Fo2) + (0.0678P)2 + 0.6285P] where P = (Fo2 + 2Fc2)/3 |
3700 reflections | (Δ/σ)max < 0.001 |
324 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.20 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) |
O1 | 0.1319 (3) | 0.0329 (2) | 0.5954 (2) | 0.0693 (6) | |
O2 | 0.6478 (2) | 0.1997 (3) | −0.0687 (2) | 0.0796 (8) | |
O3 | 0.0231 (2) | 0.3001 (2) | 0.8767 (2) | 0.0713 (7) | |
O4 | 0.0968 (2) | 0.5122 (2) | 0.7062 (2) | 0.0684 (6) | |
O5 | 0.4385 (3) | 0.2719 (4) | 0.4599 (2) | 0.1011 (10) | |
O6A | 0.2344 (3) | 0.3408 (3) | 0.1079 (2) | 0.0583 (11) | 0.776 (7) |
O6B | 0.3081 (11) | 0.4451 (11) | 0.1183 (9) | 0.071 (4) | 0.224 (7) |
C1 | 0.1640 (3) | 0.1401 (3) | 0.3635 (3) | 0.0628 (8) | |
H1A | 0.0656 | 0.1523 | 0.3488 | 0.075* | |
H1B | 0.2080 | 0.1257 | 0.2864 | 0.075* | |
C2 | 0.1982 (4) | 0.0214 (3) | 0.4795 (3) | 0.0719 (9) | |
H2A | 0.1716 | −0.0583 | 0.4619 | 0.086* | |
H2B | 0.2967 | 0.0105 | 0.4935 | 0.086* | |
C3 | 0.1276 (3) | 0.1569 (3) | 0.6133 (3) | 0.0529 (7) | |
C4 | 0.0779 (3) | 0.1636 (3) | 0.7329 (3) | 0.0580 (8) | |
H4A | 0.0508 | 0.0868 | 0.7945 | 0.070* | |
C5 | 0.0683 (3) | 0.2833 (3) | 0.7612 (3) | 0.0535 (7) | |
C6 | 0.1087 (3) | 0.3987 (3) | 0.6685 (3) | 0.0522 (7) | |
C7 | 0.1560 (3) | 0.3897 (3) | 0.5511 (3) | 0.0523 (7) | |
H7A | 0.1824 | 0.4668 | 0.4893 | 0.063* | |
C8 | 0.1665 (3) | 0.2701 (3) | 0.5197 (3) | 0.0502 (7) | |
C9 | 0.2132 (3) | 0.2652 (3) | 0.3868 (3) | 0.0527 (7) | |
H9A | 0.1694 | 0.3441 | 0.3214 | 0.063* | |
C10 | 0.3674 (3) | 0.2683 (3) | 0.3708 (3) | 0.0581 (8) | |
C11 | 0.4343 (3) | 0.2591 (3) | 0.2478 (3) | 0.0503 (7) | |
C12 | 0.3732 (3) | 0.2981 (4) | 0.1243 (3) | 0.0657 (9) | |
C13 | 0.4442 (3) | 0.2809 (4) | 0.0165 (3) | 0.0695 (9) | |
C16 | 0.5869 (4) | 0.2295 (4) | −0.1962 (3) | 0.0655 (9) | |
C17 | 0.5760 (3) | 0.2223 (3) | 0.0320 (3) | 0.0542 (7) | |
C18 | 0.6373 (3) | 0.1834 (4) | 0.1522 (3) | 0.0803 (11) | |
H18A | 0.7267 | 0.1434 | 0.1628 | 0.096* | |
C19 | 0.5669 (3) | 0.2032 (4) | 0.2564 (3) | 0.0699 (10) | |
H19A | 0.6109 | 0.1776 | 0.3373 | 0.084* | |
C20 | 0.0026 (5) | 0.1840 (4) | 0.9811 (3) | 0.0879 (12) | |
H20A | −0.0194 | 0.2087 | 1.0588 | 0.132* | |
H20B | 0.0849 | 0.1243 | 0.9957 | 0.132* | |
H20C | −0.0715 | 0.1399 | 0.9600 | 0.132* | |
C21 | 0.1667 (4) | 0.6201 (4) | 0.6305 (4) | 0.0775 (10) | |
H21A | 0.1595 | 0.6904 | 0.6709 | 0.116* | |
H21B | 0.1269 | 0.6531 | 0.5445 | 0.116* | |
H21C | 0.2616 | 0.5906 | 0.6243 | 0.116* | |
C22 | 0.2033 (5) | 0.4733 (5) | 0.0436 (5) | 0.1095 (16) | |
H22A | 0.1055 | 0.4929 | 0.0381 | 0.164* | 0.701 (11) |
H22B | 0.2422 | 0.5270 | 0.0895 | 0.164* | 0.701 (11) |
H22C | 0.2408 | 0.4932 | −0.0430 | 0.164* | 0.701 (11) |
H22D | 0.1618 | 0.5616 | 0.0363 | 0.164* | 0.299 (11) |
H22E | 0.2318 | 0.4690 | −0.0413 | 0.164* | 0.299 (11) |
H22F | 0.1380 | 0.4087 | 0.0786 | 0.164* | 0.299 (11) |
C14A | 0.3764 (5) | 0.2920 (9) | −0.1094 (5) | 0.083 (2) | 0.701 (11) |
H14A | 0.2827 | 0.3164 | −0.1198 | 0.099* | 0.701 (11) |
C15A | 0.4466 (6) | 0.2681 (10) | −0.2044 (6) | 0.084 (2) | 0.701 (11) |
H15A | 0.4011 | 0.2770 | −0.2822 | 0.101* | 0.701 (11) |
C23A | 0.6284 (15) | 0.1034 (12) | −0.2322 (13) | 0.195 (8) | 0.701 (11) |
H23A | 0.7265 | 0.0924 | −0.2383 | 0.293* | 0.701 (11) |
H23B | 0.5881 | 0.1101 | −0.3149 | 0.293* | 0.701 (11) |
H23C | 0.5970 | 0.0275 | −0.1663 | 0.293* | 0.701 (11) |
C24A | 0.6660 (12) | 0.3422 (14) | −0.2788 (11) | 0.168 (6) | 0.701 (11) |
H24A | 0.7600 | 0.3095 | −0.2843 | 0.253* | 0.701 (11) |
H24B | 0.6617 | 0.4133 | −0.2396 | 0.253* | 0.701 (11) |
H24C | 0.6267 | 0.3753 | −0.3650 | 0.253* | 0.701 (11) |
C14B | 0.439 (2) | 0.400 (2) | −0.1155 (13) | 0.109 (8) | 0.299 (11) |
H14B | 0.4020 | 0.4863 | −0.1226 | 0.131* | 0.299 (11) |
C15B | 0.4906 (17) | 0.364 (2) | −0.2128 (13) | 0.094 (6) | 0.299 (11) |
H15B | 0.4705 | 0.4198 | −0.2970 | 0.112* | 0.299 (11) |
C23B | 0.490 (3) | 0.122 (3) | −0.1934 (17) | 0.131 (10) | 0.299 (11) |
H23D | 0.5396 | 0.0497 | −0.2164 | 0.196* | 0.299 (11) |
H23E | 0.4166 | 0.1606 | −0.2548 | 0.196* | 0.299 (11) |
H23F | 0.4530 | 0.0893 | −0.1071 | 0.196* | 0.299 (11) |
C24B | 0.6831 (13) | 0.2456 (18) | −0.2955 (12) | 0.067 (5) | 0.299 (11) |
H24D | 0.7560 | 0.1752 | −0.2699 | 0.100* | 0.299 (11) |
H24E | 0.7198 | 0.3309 | −0.3118 | 0.100* | 0.299 (11) |
H24F | 0.6401 | 0.2417 | −0.3737 | 0.100* | 0.299 (11) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0917 (17) | 0.0555 (13) | 0.0612 (14) | −0.0143 (11) | 0.0081 (12) | −0.0166 (11) |
O2 | 0.0547 (13) | 0.130 (2) | 0.0537 (13) | 0.0144 (13) | 0.0025 (10) | −0.0337 (14) |
O3 | 0.0793 (16) | 0.0827 (16) | 0.0497 (12) | −0.0048 (12) | 0.0190 (11) | −0.0190 (11) |
O4 | 0.0850 (16) | 0.0611 (14) | 0.0608 (14) | −0.0027 (11) | 0.0087 (11) | −0.0225 (11) |
O5 | 0.0655 (16) | 0.195 (3) | 0.0597 (15) | −0.0201 (17) | 0.0006 (12) | −0.0607 (18) |
O6A | 0.0459 (16) | 0.079 (2) | 0.0452 (15) | 0.0121 (13) | −0.0039 (11) | −0.0164 (13) |
O6B | 0.078 (8) | 0.093 (9) | 0.045 (6) | 0.001 (6) | −0.006 (5) | −0.029 (5) |
C1 | 0.0603 (19) | 0.081 (2) | 0.0545 (18) | −0.0083 (16) | 0.0026 (14) | −0.0304 (17) |
C2 | 0.087 (3) | 0.062 (2) | 0.071 (2) | −0.0062 (18) | 0.0070 (19) | −0.0275 (17) |
C3 | 0.0526 (17) | 0.0555 (18) | 0.0474 (16) | −0.0047 (13) | −0.0013 (13) | −0.0106 (13) |
C4 | 0.0559 (18) | 0.0634 (19) | 0.0483 (17) | −0.0095 (14) | 0.0055 (13) | −0.0067 (14) |
C5 | 0.0447 (16) | 0.068 (2) | 0.0455 (16) | −0.0031 (13) | 0.0026 (12) | −0.0149 (14) |
C6 | 0.0503 (16) | 0.0564 (18) | 0.0490 (16) | 0.0014 (13) | −0.0029 (13) | −0.0163 (14) |
C7 | 0.0572 (17) | 0.0514 (17) | 0.0430 (15) | −0.0035 (13) | 0.0006 (13) | −0.0067 (13) |
C8 | 0.0470 (16) | 0.0592 (18) | 0.0418 (15) | 0.0018 (13) | −0.0034 (12) | −0.0127 (13) |
C9 | 0.0555 (17) | 0.0598 (18) | 0.0387 (15) | 0.0020 (13) | −0.0029 (12) | −0.0108 (13) |
C10 | 0.0637 (19) | 0.070 (2) | 0.0389 (15) | −0.0039 (15) | −0.0042 (14) | −0.0144 (14) |
C11 | 0.0505 (16) | 0.0552 (17) | 0.0433 (15) | −0.0065 (13) | −0.0008 (12) | −0.0117 (13) |
C12 | 0.063 (2) | 0.081 (2) | 0.0445 (17) | 0.0166 (16) | −0.0013 (14) | −0.0128 (15) |
C13 | 0.062 (2) | 0.096 (3) | 0.0424 (17) | 0.0149 (18) | −0.0014 (14) | −0.0150 (16) |
C16 | 0.071 (2) | 0.080 (2) | 0.0500 (18) | −0.0108 (17) | 0.0035 (15) | −0.0251 (16) |
C17 | 0.0448 (16) | 0.0680 (19) | 0.0485 (16) | −0.0033 (13) | 0.0012 (12) | −0.0164 (14) |
C18 | 0.0503 (18) | 0.128 (3) | 0.0519 (19) | 0.0205 (19) | −0.0055 (15) | −0.019 (2) |
C19 | 0.0509 (18) | 0.108 (3) | 0.0436 (17) | 0.0007 (17) | −0.0100 (14) | −0.0138 (17) |
C20 | 0.103 (3) | 0.103 (3) | 0.052 (2) | −0.017 (2) | 0.027 (2) | −0.015 (2) |
C21 | 0.086 (3) | 0.064 (2) | 0.088 (3) | −0.0080 (19) | −0.003 (2) | −0.031 (2) |
C22 | 0.097 (3) | 0.110 (4) | 0.108 (4) | 0.037 (3) | −0.016 (3) | −0.024 (3) |
C14A | 0.045 (3) | 0.160 (7) | 0.051 (3) | 0.014 (3) | −0.011 (2) | −0.050 (4) |
C15A | 0.059 (3) | 0.148 (8) | 0.055 (3) | −0.002 (4) | −0.004 (2) | −0.049 (4) |
C23A | 0.214 (14) | 0.167 (10) | 0.257 (14) | 0.089 (10) | −0.124 (12) | −0.161 (11) |
C24A | 0.135 (9) | 0.207 (13) | 0.117 (8) | −0.089 (9) | −0.024 (6) | 0.043 (8) |
C14B | 0.101 (13) | 0.161 (19) | 0.049 (8) | 0.051 (13) | −0.007 (7) | −0.025 (9) |
C15B | 0.078 (10) | 0.146 (17) | 0.048 (7) | 0.009 (10) | −0.006 (6) | −0.021 (9) |
C23B | 0.16 (2) | 0.17 (2) | 0.090 (12) | −0.094 (19) | 0.024 (12) | −0.050 (12) |
C24B | 0.053 (6) | 0.111 (13) | 0.048 (6) | 0.001 (7) | 0.007 (5) | −0.044 (8) |
Geometric parameters (Å, º) top
O1—C3 | 1.370 (4) | C16—C15A | 1.394 (7) |
O1—C2 | 1.422 (4) | C16—C23A | 1.508 (8) |
O2—C17 | 1.345 (3) | C16—C24A | 1.510 (9) |
O2—C16 | 1.439 (4) | C16—C23B | 1.527 (16) |
O3—C5 | 1.363 (3) | C16—C15B | 1.592 (19) |
O3—C20 | 1.409 (4) | C17—C18 | 1.364 (4) |
O4—C6 | 1.365 (4) | C18—C19 | 1.360 (5) |
O4—C21 | 1.402 (4) | C18—H18A | 0.9300 |
O5—C10 | 1.207 (4) | C19—H19A | 0.9300 |
O6A—C22 | 1.362 (5) | C20—H20A | 0.9600 |
O6A—C12 | 1.390 (4) | C20—H20B | 0.9600 |
O6A—H22F | 1.1203 | C20—H20C | 0.9600 |
O6B—C22 | 1.273 (11) | C21—H21A | 0.9600 |
O6B—C12 | 1.600 (11) | C21—H21B | 0.9600 |
O6B—H22B | 1.0004 | C21—H21C | 0.9600 |
C1—C2 | 1.489 (5) | C22—H22A | 0.9600 |
C1—C9 | 1.529 (4) | C22—H22B | 0.9601 |
C1—H1A | 0.9700 | C22—H22C | 0.9600 |
C1—H1B | 0.9700 | C22—H22D | 0.9601 |
C2—H2A | 0.9700 | C22—H22E | 0.9599 |
C2—H2B | 0.9700 | C22—H22F | 0.9600 |
C3—C8 | 1.380 (4) | C14A—C15A | 1.292 (7) |
C3—C4 | 1.383 (4) | C14A—H14A | 0.9300 |
C4—C5 | 1.374 (4) | C15A—H15A | 0.9300 |
C4—H4A | 0.9300 | C23A—H23A | 0.9600 |
C5—C6 | 1.396 (4) | C23A—H23B | 0.9600 |
C6—C7 | 1.360 (4) | C23A—H23C | 0.9600 |
C7—C8 | 1.391 (4) | C24A—H24A | 0.9600 |
C7—H7A | 0.9300 | C24A—H24B | 0.9600 |
C8—C9 | 1.503 (4) | C24A—H24C | 0.9600 |
C9—C10 | 1.517 (4) | C14B—C15B | 1.29 (2) |
C9—H9A | 0.9800 | C14B—H14B | 0.9300 |
C10—C11 | 1.487 (4) | C15B—H15B | 0.9300 |
C11—C19 | 1.369 (4) | C23B—H23D | 0.9600 |
C11—C12 | 1.394 (4) | C23B—H23E | 0.9600 |
C12—C13 | 1.386 (4) | C23B—H23F | 0.9600 |
C13—C17 | 1.370 (4) | C24B—H24D | 0.9600 |
C13—C14A | 1.487 (6) | C24B—H24E | 0.9600 |
C13—C14B | 1.576 (18) | C24B—H24F | 0.9600 |
C16—C24B | 1.388 (12) | | |
| | | |
C3—O1—C2 | 115.6 (2) | C23A—C16—C15B | 151.5 (8) |
C17—O2—C16 | 121.4 (2) | C24A—C16—C15B | 73.9 (9) |
C5—O3—C20 | 117.7 (3) | C23B—C16—C15B | 105.4 (13) |
C6—O4—C21 | 116.6 (2) | O2—C17—C18 | 118.2 (3) |
C22—O6A—C12 | 116.1 (3) | O2—C17—C13 | 121.7 (3) |
C22—O6A—H22F | 44.2 | C18—C17—C13 | 120.1 (3) |
C12—O6A—H22F | 160.3 | C19—C18—C17 | 119.7 (3) |
C22—O6B—C12 | 108.2 (7) | C19—C18—H18A | 120.2 |
C22—O6B—H22B | 48.1 | C17—C18—H18A | 120.2 |
C12—O6B—H22B | 156.3 | C18—C19—C11 | 123.0 (3) |
C2—C1—C9 | 109.5 (3) | C18—C19—H19A | 118.5 |
C2—C1—H1A | 109.8 | C11—C19—H19A | 118.5 |
C9—C1—H1A | 109.8 | O3—C20—H20A | 109.5 |
C2—C1—H1B | 109.8 | O3—C20—H20B | 109.5 |
C9—C1—H1B | 109.8 | H20A—C20—H20B | 109.5 |
H1A—C1—H1B | 108.2 | O3—C20—H20C | 109.5 |
O1—C2—C1 | 112.9 (3) | H20A—C20—H20C | 109.5 |
O1—C2—H2A | 109.0 | H20B—C20—H20C | 109.5 |
C1—C2—H2A | 109.0 | O4—C21—H21A | 109.5 |
O1—C2—H2B | 109.0 | O4—C21—H21B | 109.5 |
C1—C2—H2B | 109.0 | H21A—C21—H21B | 109.5 |
H2A—C2—H2B | 107.8 | O4—C21—H21C | 109.5 |
O1—C3—C8 | 123.8 (3) | H21A—C21—H21C | 109.5 |
O1—C3—C4 | 115.4 (3) | H21B—C21—H21C | 109.5 |
C8—C3—C4 | 120.8 (3) | O6B—C22—O6A | 63.8 (6) |
C5—C4—C3 | 120.4 (3) | O6B—C22—H22A | 145.5 |
C5—C4—H4A | 119.8 | O6A—C22—H22A | 109.8 |
C3—C4—H4A | 119.8 | O6B—C22—H22B | 50.9 |
O3—C5—C4 | 124.9 (3) | O6A—C22—H22B | 109.7 |
O3—C5—C6 | 115.3 (3) | H22A—C22—H22B | 109.5 |
C4—C5—C6 | 119.8 (3) | O6B—C22—H22C | 104.3 |
C7—C6—O4 | 125.8 (3) | O6A—C22—H22C | 109.0 |
C7—C6—C5 | 118.7 (3) | H22A—C22—H22C | 109.5 |
O4—C6—C5 | 115.5 (3) | H22B—C22—H22C | 109.5 |
C6—C7—C8 | 122.7 (3) | O6B—C22—H22D | 110.8 |
C6—C7—H7A | 118.7 | O6A—C22—H22D | 153.6 |
C8—C7—H7A | 118.7 | H22A—C22—H22D | 58.7 |
C3—C8—C7 | 117.7 (3) | H22B—C22—H22D | 60.0 |
C3—C8—C9 | 121.1 (3) | H22C—C22—H22D | 97.4 |
C7—C8—C9 | 121.2 (3) | O6B—C22—H22E | 108.5 |
C8—C9—C10 | 112.4 (2) | O6A—C22—H22E | 96.3 |
C8—C9—C1 | 108.7 (2) | H22A—C22—H22E | 105.9 |
C10—C9—C1 | 111.4 (3) | H22B—C22—H22E | 124.6 |
C8—C9—H9A | 108.1 | H22C—C22—H22E | 16.2 |
C10—C9—H9A | 108.1 | H22D—C22—H22E | 109.5 |
C1—C9—H9A | 108.1 | O6B—C22—H22F | 109.1 |
O5—C10—C11 | 118.8 (3) | O6A—C22—H22F | 54.4 |
O5—C10—C9 | 120.6 (3) | H22A—C22—H22F | 55.4 |
C11—C10—C9 | 120.5 (2) | H22B—C22—H22F | 125.6 |
C19—C11—C12 | 116.5 (3) | H22C—C22—H22F | 125.0 |
C19—C11—C10 | 117.4 (3) | H22D—C22—H22F | 109.5 |
C12—C11—C10 | 126.1 (3) | H22E—C22—H22F | 109.5 |
C13—C12—O6A | 117.4 (3) | C15A—C14A—C13 | 120.6 (4) |
C13—C12—C11 | 121.2 (3) | C15A—C14A—H14A | 119.7 |
O6A—C12—C11 | 120.9 (3) | C13—C14A—H14A | 119.7 |
C13—C12—O6B | 118.7 (4) | C14A—C15A—C16 | 123.3 (5) |
O6A—C12—O6B | 55.1 (4) | C14A—C15A—H15A | 118.3 |
C11—C12—O6B | 99.9 (4) | C16—C15A—H15A | 118.3 |
C17—C13—C12 | 119.4 (3) | C16—C23A—H23A | 109.5 |
C17—C13—C14A | 115.7 (3) | C16—C23A—H23B | 109.5 |
C12—C13—C14A | 123.2 (3) | C16—C23A—H23C | 109.5 |
C17—C13—C14B | 107.2 (7) | C16—C24A—H24A | 109.5 |
C12—C13—C14B | 119.5 (6) | C16—C24A—H24B | 109.5 |
C14A—C13—C14B | 50.7 (8) | C16—C24A—H24C | 109.5 |
C24B—C16—C15A | 129.2 (7) | C15B—C14B—C13 | 113.0 (16) |
C24B—C16—O2 | 113.1 (6) | C15B—C14B—H14B | 123.5 |
C15A—C16—O2 | 115.7 (3) | C13—C14B—H14B | 123.5 |
C24B—C16—C23A | 65.8 (8) | C14B—C15B—C16 | 123.5 (13) |
C15A—C16—C23A | 114.9 (6) | C14B—C15B—H15B | 118.2 |
O2—C16—C23A | 102.2 (5) | C16—C15B—H15B | 118.2 |
C24B—C16—C24A | 43.6 (7) | C16—C23B—H23D | 109.5 |
C15A—C16—C24A | 110.5 (6) | C16—C23B—H23E | 109.5 |
O2—C16—C24A | 103.1 (5) | H23D—C23B—H23E | 109.5 |
C23A—C16—C24A | 109.4 (9) | C16—C23B—H23F | 109.5 |
C24B—C16—C23B | 113.2 (10) | H23D—C23B—H23F | 109.5 |
C15A—C16—C23B | 62.6 (11) | H23E—C23B—H23F | 109.5 |
O2—C16—C23B | 108.6 (8) | C16—C24B—H24D | 109.5 |
C23A—C16—C23B | 55.9 (10) | C16—C24B—H24E | 109.5 |
C24A—C16—C23B | 147.1 (9) | H24D—C24B—H24E | 109.5 |
C24B—C16—C15B | 111.3 (9) | C16—C24B—H24F | 109.5 |
C15A—C16—C15B | 42.9 (7) | H24D—C24B—H24F | 109.5 |
O2—C16—C15B | 104.5 (6) | H24E—C24B—H24F | 109.5 |
| | | |
C3—O1—C2—C1 | −41.1 (4) | O6A—C12—C13—C17 | −171.4 (3) |
C9—C1—C2—O1 | 62.1 (4) | C11—C12—C13—C17 | 1.3 (6) |
C2—O1—C3—C8 | 8.7 (4) | O6B—C12—C13—C17 | 125.4 (6) |
C2—O1—C3—C4 | −172.7 (3) | O6A—C12—C13—C14A | −6.7 (7) |
O1—C3—C4—C5 | −179.6 (3) | C11—C12—C13—C14A | 166.0 (5) |
C8—C3—C4—C5 | −0.9 (5) | O6B—C12—C13—C14A | −69.9 (8) |
C20—O3—C5—C4 | 9.2 (5) | O6A—C12—C13—C14B | 53.4 (12) |
C20—O3—C5—C6 | −169.7 (3) | C11—C12—C13—C14B | −133.9 (11) |
C3—C4—C5—O3 | −178.8 (3) | O6B—C12—C13—C14B | −9.8 (13) |
C3—C4—C5—C6 | 0.1 (4) | C17—O2—C16—C24B | 158.6 (8) |
C21—O4—C6—C7 | −15.0 (4) | C17—O2—C16—C15A | −7.1 (6) |
C21—O4—C6—C5 | 164.7 (3) | C17—O2—C16—C23A | −132.7 (8) |
O3—C5—C6—C7 | 179.5 (3) | C17—O2—C16—C24A | 113.8 (8) |
C4—C5—C6—C7 | 0.5 (4) | C17—O2—C16—C23B | −74.9 (12) |
O3—C5—C6—O4 | −0.3 (4) | C17—O2—C16—C15B | 37.3 (9) |
C4—C5—C6—O4 | −179.2 (3) | C16—O2—C17—C18 | 175.7 (3) |
O4—C6—C7—C8 | 179.4 (3) | C16—O2—C17—C13 | −3.4 (5) |
C5—C6—C7—C8 | −0.3 (4) | C12—C13—C17—O2 | 177.9 (3) |
O1—C3—C8—C7 | 179.7 (3) | C14A—C13—C17—O2 | 12.1 (6) |
C4—C3—C8—C7 | 1.1 (4) | C14B—C13—C17—O2 | −42.1 (11) |
O1—C3—C8—C9 | 2.0 (4) | C12—C13—C17—C18 | −1.1 (6) |
C4—C3—C8—C9 | −176.6 (3) | C14A—C13—C17—C18 | −167.0 (5) |
C6—C7—C8—C3 | −0.5 (4) | C14B—C13—C17—C18 | 138.9 (10) |
C6—C7—C8—C9 | 177.2 (3) | O2—C17—C18—C19 | −179.1 (4) |
C3—C8—C9—C10 | −104.9 (3) | C13—C17—C18—C19 | −0.1 (6) |
C7—C8—C9—C10 | 77.5 (3) | C17—C18—C19—C11 | 1.2 (6) |
C3—C8—C9—C1 | 18.8 (4) | C12—C11—C19—C18 | −1.1 (5) |
C7—C8—C9—C1 | −158.8 (3) | C10—C11—C19—C18 | 176.9 (4) |
C2—C1—C9—C8 | −48.3 (3) | C12—O6B—C22—O6A | 29.1 (5) |
C2—C1—C9—C10 | 76.1 (3) | C12—O6A—C22—O6B | −36.3 (6) |
C8—C9—C10—O5 | 1.2 (4) | C17—C13—C14A—C15A | −11.0 (10) |
C1—C9—C10—O5 | −121.0 (4) | C12—C13—C14A—C15A | −176.3 (7) |
C8—C9—C10—C11 | 177.7 (3) | C14B—C13—C14A—C15A | 80.7 (10) |
C1—C9—C10—C11 | 55.4 (4) | C13—C14A—C15A—C16 | 0.8 (13) |
O5—C10—C11—C19 | 25.3 (5) | C24B—C16—C15A—C14A | −154.7 (11) |
C9—C10—C11—C19 | −151.2 (3) | O2—C16—C15A—C14A | 8.1 (11) |
O5—C10—C11—C12 | −157.0 (4) | C23A—C16—C15A—C14A | 127.0 (11) |
C9—C10—C11—C12 | 26.5 (5) | C24A—C16—C15A—C14A | −108.6 (11) |
C22—O6A—C12—C13 | −76.3 (5) | C23B—C16—C15A—C14A | 106.7 (12) |
C22—O6A—C12—C11 | 111.0 (4) | C15B—C16—C15A—C14A | −75.5 (11) |
C22—O6A—C12—O6B | 31.0 (5) | C17—C13—C14B—C15B | 50.3 (19) |
C19—C11—C12—C13 | −0.2 (5) | C12—C13—C14B—C15B | −169.7 (13) |
C10—C11—C12—C13 | −177.9 (3) | C14A—C13—C14B—C15B | −59.2 (15) |
C19—C11—C12—O6A | 172.2 (3) | C13—C14B—C15B—C16 | −16 (3) |
C10—C11—C12—O6A | −5.5 (5) | C24B—C16—C15B—C14B | −147.8 (19) |
C19—C11—C12—O6B | −132.7 (5) | C15A—C16—C15B—C14B | 87 (2) |
C10—C11—C12—O6B | 49.6 (6) | O2—C16—C15B—C14B | −25 (2) |
C22—O6B—C12—C13 | 73.6 (8) | C23A—C16—C15B—C14B | 134 (2) |
C22—O6B—C12—O6A | −31.4 (5) | C24A—C16—C15B—C14B | −125 (2) |
C22—O6B—C12—C11 | −152.3 (6) | C23B—C16—C15B—C14B | 89 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O6A | 0.97 | 2.51 | 3.018 (4) | 113 |
C9—H9A···O6A | 0.98 | 2.37 | 2.863 (4) | 110 |
C14A—H14A···O3i | 0.93 | 2.56 | 3.456 (5) | 161 |
Symmetry code: (i) x, y, z−1. |