The title compound, C21H22N2O3, (2S,12βS)-methyl 2-[(1E)-1-formyl-1-propenyl]-1,2,6,7,12,12b-hexahydroindolo[2,3-α]quinolizine-3-carboxylic acid, exhibits a rare vallesiachotamane skeleton. Intermolecular hydrogen bonding results in the formation of a chain.
Supporting information
CCDC reference: 298704
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.007 Å
- R factor = 0.046
- wR factor = 0.180
- Data-to-parameter ratio = 7.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.90
| Author Response: The intensities measurements were extended to
theta(max)= 68.00 degrees but 200 reflections could not
be measured due to scintillator-collimator collision predicted.
The total reflections measured was 1844, but 19 were
rejected after data reduction and refinement.
|
Alert level C
REFLT03_ALERT_1_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 67.90
From the CIF: _diffrn_reflns_theta_full 67.90
From the CIF: _reflns_number_total 1825
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 1955
Completeness (_total/calc) 93.35%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.39
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 67.90
From the CIF: _reflns_number_total 1825
Count of symmetry unique reflns 1955
Completeness (_total/calc) 93.35%
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
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: In the present paper several Institutions are involved, and
three different groups with graduation students of Chemisty,
Crystallography and Biology. All the cited persons have contributed
to the present paper, as described below:
|
Extract obtention C.M.A.T.
Isolation, L.K.
Spectrocopic analysis C.M.A.O., C.C.S.
Biological activity F.M.S.
Data collection I.V.
Solution, refinement, drawings J.R.S.
Preparation of first CIF I.V.
Improvements of the draft of submission I.V., J.R.S., C.M.A.T.
Submission and dealing with referees and proofs I.V.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(2
S,12
βS)-methyl
2-[(1E)-1-formyl-1-propenyl]-1,2,6,7,12,12
b-hexahydroindolo[2,3-
α]quinolizine- 3-carboxylic acid
top
Crystal data top
C21H22N2O3 | Dx = 1.262 Mg m−3 |
Mr = 350.41 | Melting point = 250–251 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 7.194 (1) Å | θ = 15.1–30.9° |
b = 9.859 (1) Å | µ = 0.69 mm−1 |
c = 25.995 (6) Å | T = 297 K |
V = 1843.7 (5) Å3 | Block, brown |
Z = 4 | 0.18 × 0.15 × 0.08 mm |
F(000) = 744 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube | θmax = 67.9°, θmin = 3.4° |
Graphite monochromator | h = 0→8 |
non–profiled ω/2θ scans | k = 0→11 |
1844 measured reflections | l = −1→31 |
1825 independent reflections | 2 standard reflections every 120 min |
1411 reflections with I > 2σ(I) | intensity decay: < 1% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.1038P)2 + 0.2785P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.180 | (Δ/σ)max = 0.001 |
S = 1.23 | Δρmax = 0.34 e Å−3 |
1825 reflections | Δρmin = −0.32 e Å−3 |
247 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0035 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | |
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 | |
O1 | 0.0690 (6) | 0.1755 (4) | 0.07480 (16) | 0.0610 (11) | |
O2 | 0.1367 (7) | 0.4961 (6) | 0.20929 (15) | 0.0875 (17) | |
O3 | −0.1581 (7) | 0.4249 (6) | 0.21388 (15) | 0.0765 (14) | |
N1 | −0.1308 (5) | 0.5153 (4) | −0.06429 (15) | 0.0407 (10) | |
H1 | −0.235 (8) | 0.454 (5) | −0.060 (2) | 0.049* | |
C2 | 0.0080 (6) | 0.5230 (5) | −0.02828 (18) | 0.0378 (11) | |
C3 | 0.0060 (6) | 0.4463 (5) | 0.02088 (19) | 0.0385 (11) | |
H3 | 0.047 (7) | 0.339 (6) | 0.0168 (18) | 0.046* | |
N4 | 0.1463 (5) | 0.5083 (5) | 0.05499 (16) | 0.0468 (11) | |
C5 | 0.3252 (6) | 0.5401 (6) | 0.0305 (2) | 0.0546 (15) | |
H5A | 0.3760 | 0.4583 | 0.0153 | 0.065* | |
H5B | 0.4118 | 0.5715 | 0.0565 | 0.065* | |
C6 | 0.3048 (7) | 0.6477 (6) | −0.0106 (2) | 0.0558 (15) | |
H6A | 0.2885 | 0.7360 | 0.0053 | 0.067* | |
H6B | 0.4160 | 0.6506 | −0.0317 | 0.067* | |
C7 | 0.1389 (6) | 0.6148 (5) | −0.04349 (18) | 0.0402 (11) | |
C8 | 0.0824 (7) | 0.6653 (5) | −0.09289 (18) | 0.0439 (12) | |
C9 | 0.1593 (9) | 0.7551 (6) | −0.1287 (2) | 0.0554 (15) | |
H9 | 0.2719 | 0.7982 | −0.1222 | 0.066* | |
C10 | 0.0650 (10) | 0.7779 (6) | −0.1735 (2) | 0.0667 (18) | |
H10 | 0.1146 | 0.8380 | −0.1974 | 0.080* | |
C11 | −0.1040 (9) | 0.7138 (7) | −0.1846 (2) | 0.0659 (17) | |
H11 | −0.1653 | 0.7327 | −0.2153 | 0.079* | |
C12 | −0.1787 (8) | 0.6243 (6) | −0.1508 (2) | 0.0550 (14) | |
H12 | −0.2890 | 0.5795 | −0.1584 | 0.066* | |
C13 | −0.0872 (7) | 0.6009 (5) | −0.10443 (19) | 0.0450 (12) | |
C14 | −0.1836 (6) | 0.4477 (5) | 0.04733 (17) | 0.0387 (11) | |
H14A | −0.2675 | 0.3909 | 0.0276 | 0.046* | |
H14B | −0.2318 | 0.5395 | 0.0461 | 0.046* | |
C15 | −0.1882 (6) | 0.3996 (5) | 0.10365 (18) | 0.0404 (11) | |
H15 | −0.2961 | 0.4441 | 0.1193 | 0.049* | |
C16 | −0.0193 (7) | 0.4539 (5) | 0.13216 (19) | 0.0446 (12) | |
C17 | 0.1298 (7) | 0.5030 (6) | 0.10590 (19) | 0.0450 (12) | |
H17 | 0.229 (8) | 0.548 (5) | 0.123 (2) | 0.054* | |
C18 | −0.5303 (8) | 0.2660 (8) | 0.1573 (3) | 0.0698 (18) | |
H18A | −0.4988 | 0.3583 | 0.1651 | 0.105* | |
H18B | −0.5684 | 0.2204 | 0.1882 | 0.105* | |
H18C | −0.6302 | 0.2644 | 0.1328 | 0.105* | |
C19 | −0.3656 (7) | 0.1960 (6) | 0.1352 (2) | 0.0505 (13) | |
H19 | −0.3660 | 0.1020 | 0.1381 | 0.061* | |
C20 | −0.2169 (7) | 0.2490 (5) | 0.11177 (18) | 0.0403 (11) | |
C21 | −0.0774 (7) | 0.1514 (6) | 0.0970 (2) | 0.0493 (13) | |
H21 | −0.1010 | 0.0612 | 0.1052 | 0.059* | |
C22 | −0.0239 (8) | 0.4563 (6) | 0.1873 (2) | 0.0540 (14) | |
C23 | 0.1407 (13) | 0.5064 (11) | 0.2635 (2) | 0.115 (4) | |
H23A | 0.0669 | 0.5825 | 0.2741 | 0.172* | |
H23B | 0.2666 | 0.5189 | 0.2748 | 0.172* | |
H23C | 0.0913 | 0.4249 | 0.2783 | 0.172* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.053 (2) | 0.055 (2) | 0.075 (2) | 0.022 (2) | 0.009 (2) | 0.003 (2) |
O2 | 0.080 (3) | 0.135 (5) | 0.047 (2) | −0.036 (4) | −0.010 (2) | −0.001 (3) |
O3 | 0.073 (3) | 0.106 (4) | 0.050 (2) | −0.013 (3) | 0.009 (2) | 0.004 (2) |
N1 | 0.0333 (19) | 0.047 (2) | 0.041 (2) | −0.004 (2) | −0.0015 (17) | 0.003 (2) |
C2 | 0.033 (2) | 0.036 (2) | 0.045 (2) | 0.001 (2) | −0.003 (2) | −0.001 (2) |
C3 | 0.029 (2) | 0.044 (3) | 0.042 (2) | −0.001 (2) | −0.005 (2) | −0.005 (2) |
N4 | 0.0278 (18) | 0.063 (3) | 0.049 (2) | −0.002 (2) | −0.0071 (17) | −0.004 (2) |
C5 | 0.026 (2) | 0.085 (4) | 0.053 (3) | −0.004 (3) | −0.004 (2) | −0.008 (3) |
C6 | 0.037 (3) | 0.072 (4) | 0.057 (3) | −0.017 (3) | −0.002 (2) | −0.008 (3) |
C7 | 0.036 (2) | 0.043 (3) | 0.042 (2) | −0.009 (2) | 0.002 (2) | −0.010 (2) |
C8 | 0.043 (3) | 0.040 (3) | 0.049 (3) | −0.004 (2) | 0.000 (2) | −0.007 (2) |
C9 | 0.064 (4) | 0.047 (3) | 0.055 (3) | −0.013 (3) | 0.008 (3) | −0.001 (3) |
C10 | 0.089 (5) | 0.056 (4) | 0.055 (3) | −0.006 (4) | 0.009 (4) | 0.001 (3) |
C11 | 0.082 (4) | 0.066 (4) | 0.049 (3) | −0.001 (4) | −0.009 (3) | 0.006 (3) |
C12 | 0.056 (3) | 0.059 (3) | 0.050 (3) | −0.005 (3) | −0.009 (3) | −0.008 (3) |
C13 | 0.040 (2) | 0.046 (3) | 0.049 (3) | 0.002 (2) | −0.001 (2) | −0.002 (3) |
C14 | 0.028 (2) | 0.044 (3) | 0.045 (2) | 0.000 (2) | −0.0036 (19) | −0.003 (2) |
C15 | 0.029 (2) | 0.047 (3) | 0.045 (2) | 0.005 (2) | 0.002 (2) | −0.002 (2) |
C16 | 0.043 (3) | 0.045 (3) | 0.045 (3) | −0.001 (3) | −0.007 (2) | 0.003 (3) |
C17 | 0.038 (2) | 0.055 (3) | 0.042 (2) | −0.001 (3) | −0.008 (2) | −0.004 (3) |
C18 | 0.044 (3) | 0.087 (5) | 0.078 (4) | −0.004 (3) | 0.012 (3) | 0.009 (4) |
C19 | 0.043 (3) | 0.059 (3) | 0.049 (3) | −0.004 (3) | −0.008 (2) | 0.006 (3) |
C20 | 0.038 (2) | 0.041 (3) | 0.042 (2) | 0.002 (2) | −0.008 (2) | −0.005 (2) |
C21 | 0.047 (3) | 0.047 (3) | 0.054 (3) | 0.005 (3) | −0.008 (3) | 0.002 (3) |
C22 | 0.057 (3) | 0.051 (3) | 0.055 (3) | −0.005 (3) | −0.004 (3) | 0.007 (3) |
C23 | 0.137 (8) | 0.160 (9) | 0.047 (3) | −0.047 (8) | −0.024 (4) | 0.006 (5) |
Geometric parameters (Å, º) top
O1—C21 | 1.225 (6) | C10—H10 | 0.9300 |
O2—C22 | 1.347 (7) | C11—C12 | 1.356 (8) |
O2—C23 | 1.412 (7) | C11—H11 | 0.9300 |
O3—C22 | 1.228 (7) | C12—C13 | 1.392 (7) |
N1—C2 | 1.370 (6) | C12—H12 | 0.9300 |
N1—C13 | 1.379 (6) | C14—C15 | 1.539 (7) |
N1—H1 | 0.97 (5) | C14—H14A | 0.9700 |
C2—C7 | 1.365 (6) | C14—H14B | 0.9700 |
C2—C3 | 1.485 (7) | C15—C16 | 1.520 (7) |
N4—C3 | 1.476 (6) | C15—C20 | 1.514 (7) |
C3—H3 | 1.11 (5) | C15—H15 | 0.9800 |
N4—C5 | 1.469 (6) | C16—C17 | 1.360 (7) |
N4—C17 | 1.330 (6) | C16—C22 | 1.433 (8) |
C3—C14 | 1.527 (6) | C17—H17 | 0.95 (6) |
C5—C6 | 1.514 (8) | C18—C19 | 1.487 (8) |
C5—H5A | 0.9700 | C18—H18A | 0.9600 |
C5—H5B | 0.9700 | C18—H18B | 0.9600 |
C6—C7 | 1.503 (6) | C18—H18C | 0.9600 |
C6—H6A | 0.9700 | C19—C20 | 1.337 (7) |
C6—H6B | 0.9700 | C19—H19 | 0.9300 |
C7—C8 | 1.436 (7) | C20—C21 | 1.442 (7) |
C8—C9 | 1.399 (7) | C21—H21 | 0.9300 |
C8—C13 | 1.407 (7) | C23—H23A | 0.9600 |
C9—C10 | 1.366 (8) | C23—H23B | 0.9600 |
C9—H9 | 0.9300 | C23—H23C | 0.9600 |
C10—C11 | 1.400 (8) | | |
| | | |
C22—O2—C23 | 117.5 (6) | N1—C13—C12 | 130.5 (5) |
C2—N1—C13 | 108.5 (4) | N1—C13—C8 | 108.2 (4) |
C2—N1—H1 | 122 (3) | C12—C13—C8 | 121.3 (5) |
C13—N1—H1 | 130 (3) | C3—C14—C15 | 116.4 (4) |
C7—C2—N1 | 110.0 (4) | C3—C14—H14A | 108.2 |
C7—C2—C3 | 126.4 (4) | C15—C14—H14A | 108.2 |
N1—C2—C3 | 123.5 (4) | C3—C14—H14B | 108.2 |
N4—C3—C2 | 107.4 (4) | C15—C14—H14B | 108.2 |
C2—C3—C14 | 113.0 (4) | H14A—C14—H14B | 107.3 |
N4—C3—H3 | 106 (3) | C14—C15—C16 | 109.8 (4) |
C2—C3—H3 | 114 (3) | C14—C15—C20 | 115.9 (4) |
C14—C3—H3 | 107 (3) | C16—C15—C20 | 112.7 (4) |
C3—N4—C5 | 115.3 (4) | C14—C15—H15 | 105.9 |
C3—N4—C17 | 121.4 (4) | C16—C15—H15 | 105.9 |
C5—N4—C17 | 121.1 (4) | C20—C15—H15 | 105.9 |
N4—C3—C14 | 109.7 (4) | C15—C16—C17 | 120.7 (4) |
N4—C5—C6 | 111.7 (4) | C15—C16—C22 | 118.3 (5) |
N4—C5—H5A | 109.3 | C17—C16—C22 | 120.9 (5) |
C6—C5—H5A | 109.3 | N4—C17—C16 | 125.7 (5) |
N4—C5—H5B | 109.3 | N4—C17—H17 | 112 (3) |
C6—C5—H5B | 109.3 | C16—C17—H17 | 122 (3) |
H5A—C5—H5B | 107.9 | C19—C18—H18A | 109.5 |
C7—C6—C5 | 109.1 (4) | C19—C18—H18B | 109.5 |
C7—C6—H6A | 109.9 | H18A—C18—H18B | 109.5 |
C5—C6—H6A | 109.9 | C19—C18—H18C | 109.5 |
C7—C6—H6B | 109.9 | H18A—C18—H18C | 109.5 |
C5—C6—H6B | 109.9 | H18B—C18—H18C | 109.5 |
H6A—C6—H6B | 108.3 | C20—C19—C18 | 129.2 (6) |
C2—C7—C8 | 107.1 (4) | C20—C19—H19 | 115.4 |
C2—C7—C6 | 121.7 (4) | C18—C19—H19 | 115.4 |
C8—C7—C6 | 131.2 (5) | C19—C20—C21 | 114.7 (5) |
C9—C8—C13 | 119.1 (5) | C19—C20—C15 | 123.8 (5) |
C9—C8—C7 | 134.6 (5) | C21—C20—C15 | 121.5 (5) |
C13—C8—C7 | 106.3 (4) | O1—C21—C20 | 126.5 (5) |
C10—C9—C8 | 118.3 (6) | O1—C21—H21 | 116.7 |
C10—C9—H9 | 120.8 | C20—C21—H21 | 116.7 |
C8—C9—H9 | 120.8 | O3—C22—O2 | 120.5 (5) |
C9—C10—C11 | 122.2 (6) | O3—C22—C16 | 125.3 (5) |
C9—C10—H10 | 118.9 | O2—C22—C16 | 114.2 (5) |
C11—C10—H10 | 118.9 | O2—C23—H23A | 109.5 |
C12—C11—C10 | 120.3 (6) | O2—C23—H23B | 109.5 |
C12—C11—H11 | 119.9 | H23A—C23—H23B | 109.5 |
C10—C11—H11 | 119.9 | O2—C23—H23C | 109.5 |
C11—C12—C13 | 118.8 (6) | H23A—C23—H23C | 109.5 |
C11—C12—H12 | 120.6 | H23B—C23—H23C | 109.5 |
C13—C12—H12 | 120.6 | | |
| | | |
C13—N1—C2—C7 | 1.6 (6) | C11—C12—C13—C8 | −1.7 (8) |
C13—N1—C2—C3 | 178.7 (4) | C9—C8—C13—N1 | 178.2 (5) |
C7—C2—C3—N4 | 12.2 (7) | C7—C8—C13—N1 | −0.3 (5) |
N1—C2—C3—N4 | −164.4 (4) | C9—C8—C13—C12 | 0.4 (7) |
C7—C2—C3—C14 | 133.3 (5) | C7—C8—C13—C12 | −178.2 (5) |
N1—C2—C3—C14 | −43.3 (6) | N4—C3—C14—C15 | −46.7 (6) |
C2—C3—N4—C17 | 152.3 (5) | C2—C3—C14—C15 | −166.5 (4) |
C14—C3—N4—C17 | 29.1 (7) | C3—C14—C15—C20 | −88.7 (5) |
C2—C3—N4—C5 | −44.3 (6) | C3—C14—C15—C16 | 40.5 (6) |
C14—C3—N4—C5 | −167.5 (5) | C20—C15—C16—C17 | 114.5 (6) |
C17—N4—C5—C6 | −131.9 (5) | C14—C15—C16—C17 | −16.4 (7) |
C3—N4—C5—C6 | 64.7 (6) | C20—C15—C16—C22 | −67.5 (6) |
N4—C5—C6—C7 | −45.4 (6) | C14—C15—C16—C22 | 161.6 (5) |
N1—C2—C7—C8 | −1.8 (6) | C5—N4—C17—C16 | −168.9 (6) |
C3—C2—C7—C8 | −178.8 (5) | C3—N4—C17—C16 | −6.4 (9) |
N1—C2—C7—C6 | 178.0 (4) | C22—C16—C17—N4 | −178.4 (6) |
C3—C2—C7—C6 | 1.0 (8) | C15—C16—C17—N4 | −0.5 (9) |
C5—C6—C7—C2 | 15.3 (7) | C18—C19—C20—C21 | 177.2 (5) |
C5—C6—C7—C8 | −164.9 (5) | C18—C19—C20—C15 | 0.6 (8) |
C2—C7—C8—C9 | −176.9 (6) | C16—C15—C20—C19 | 116.3 (5) |
C6—C7—C8—C9 | 3.3 (10) | C14—C15—C20—C19 | −115.9 (5) |
C2—C7—C8—C13 | 1.3 (5) | C16—C15—C20—C21 | −60.0 (6) |
C6—C7—C8—C13 | −178.5 (5) | C14—C15—C20—C21 | 67.7 (6) |
C13—C8—C9—C10 | 0.7 (8) | C19—C20—C21—O1 | 179.2 (5) |
C7—C8—C9—C10 | 178.8 (6) | C15—C20—C21—O1 | −4.1 (8) |
C8—C9—C10—C11 | −0.5 (9) | C23—O2—C22—O3 | −3.0 (10) |
C9—C10—C11—C12 | −0.8 (9) | C23—O2—C22—C16 | 177.4 (7) |
C10—C11—C12—C13 | 1.9 (9) | C17—C16—C22—O3 | 173.6 (6) |
C2—N1—C13—C12 | 176.8 (5) | C15—C16—C22—O3 | −4.4 (9) |
C2—N1—C13—C8 | −0.8 (5) | C17—C16—C22—O2 | −6.9 (9) |
C11—C12—C13—N1 | −179.0 (6) | C15—C16—C22—O2 | 175.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.97 (5) | 1.94 (6) | 2.877 (5) | 163 (5) |
C3—H3···O1 | 1.11 (5) | 2.21 (5) | 3.049 (6) | 131 (3) |
Symmetry code: (i) x−1/2, −y+1/2, −z. |