At 93 K, the five-membered pyrrolidine ring of the title compound [systematic name: 6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)(pyrrolidin-1-yl)methanone], C
22H
31NO
2, has an envelope geometry with one of the β C atoms at the flap position, displaced by 0.610 (3) Å from the plane defined by the other four atoms. There is a weak intermolecular C—H
O hydrogen bond involving the carbonyl O atom
Supporting information
CCDC reference: 601182
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.091
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
| Author Response:
This is an all-light atom structure. Therefore under the
Instructions of the referee the data were merged.
|
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.626 1.000
Tmin(prime) and Tmax expected: 0.944 0.981
RR(prime) = 0.651
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.65
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
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 28.10
From the CIF: _reflns_number_total 2585
Count of symmetry unique reflns 2635
Completeness (_total/calc) 98.10%
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
2 ALERT level B = Potentially serious problem
2 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
0 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
3-Methoxy-4 b,8-dimethyl-8-(4-pyrrolidin-1-ylcarbonyl)- 4 b,5,6,7,8,8a,9,10-octahydrophenanthrene
top
Crystal data top
C22H31NO2 | F(000) = 744 |
Mr = 341.48 | Dx = 1.192 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5585 reflections |
a = 9.2758 (18) Å | θ = 2.6–28.0° |
b = 14.886 (3) Å | µ = 0.08 mm−1 |
c = 13.785 (3) Å | T = 93 K |
V = 1903.5 (7) Å3 | Chunk, colorless |
Z = 4 | 0.75 × 0.45 × 0.25 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2585 independent reflections |
Radiation source: fine-focus sealed tube | 2279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ and ω scans | θmax = 28.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.626, Tmax = 1.000 | k = −19→19 |
14559 measured reflections | l = −18→18 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0484P)2 + 0.2838P] where P = (Fo2 + 2Fc2)/3 |
2585 reflections | (Δ/σ)max = 0.003 |
226 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.15 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 | |
O1 | 0.59356 (14) | 0.90772 (9) | 0.08878 (9) | 0.0289 (3) | |
O2 | 0.44186 (15) | 0.76340 (9) | 0.64408 (9) | 0.0301 (3) | |
N | 0.39072 (17) | 0.86844 (10) | 0.01274 (10) | 0.0236 (3) | |
C1 | 0.24187 (19) | 0.88297 (13) | 0.31516 (12) | 0.0239 (4) | |
H1A | 0.2145 | 0.8250 | 0.3452 | 0.029* | |
H1B | 0.2044 | 0.9318 | 0.3569 | 0.029* | |
C2 | 0.1719 (2) | 0.88990 (13) | 0.21468 (12) | 0.0252 (4) | |
H2A | 0.1986 | 0.8366 | 0.1756 | 0.030* | |
H2B | 0.0657 | 0.8904 | 0.2219 | 0.030* | |
C3 | 0.21957 (18) | 0.97454 (12) | 0.16211 (12) | 0.0225 (4) | |
H3A | 0.1834 | 1.0274 | 0.1983 | 0.027* | |
H3B | 0.1744 | 0.9754 | 0.0971 | 0.027* | |
C4 | 0.38468 (18) | 0.98374 (11) | 0.14995 (12) | 0.0207 (3) | |
C5 | 0.44866 (19) | 0.97751 (12) | 0.25524 (12) | 0.0202 (3) | |
H5A | 0.3964 | 1.0256 | 0.2917 | 0.024* | |
C6 | 0.6086 (2) | 1.00169 (13) | 0.26885 (12) | 0.0245 (4) | |
H6A | 0.6700 | 0.9496 | 0.2518 | 0.029* | |
H6B | 0.6348 | 1.0525 | 0.2260 | 0.029* | |
C7 | 0.6323 (2) | 1.02760 (13) | 0.37482 (13) | 0.0267 (4) | |
H7A | 0.7367 | 1.0360 | 0.3867 | 0.032* | |
H7B | 0.5834 | 1.0854 | 0.3881 | 0.032* | |
C8 | 0.57468 (19) | 0.95660 (12) | 0.44322 (12) | 0.0230 (4) | |
C9 | 0.47141 (19) | 0.89334 (12) | 0.41449 (12) | 0.0210 (3) | |
C10 | 0.40862 (19) | 0.88955 (11) | 0.31058 (11) | 0.0196 (3) | |
C11 | 0.4266 (2) | 0.82727 (12) | 0.48101 (12) | 0.0226 (4) | |
H11A | 0.3576 | 0.7837 | 0.4616 | 0.027* | |
C12 | 0.48205 (19) | 0.82488 (13) | 0.57483 (12) | 0.0242 (4) | |
C13 | 0.5846 (2) | 0.88813 (13) | 0.60337 (12) | 0.0266 (4) | |
H13A | 0.6234 | 0.8866 | 0.6671 | 0.032* | |
C14 | 0.62918 (19) | 0.95285 (13) | 0.53849 (13) | 0.0262 (4) | |
H14A | 0.6984 | 0.9960 | 0.5585 | 0.031* | |
C15 | 0.46182 (19) | 0.91706 (12) | 0.08132 (12) | 0.0214 (3) | |
C16 | 0.4146 (2) | 1.07791 (12) | 0.10641 (13) | 0.0273 (4) | |
H16A | 0.3742 | 1.0812 | 0.0408 | 0.041* | |
H16B | 0.5189 | 1.0882 | 0.1036 | 0.041* | |
H16C | 0.3697 | 1.1239 | 0.1473 | 0.041* | |
C17 | 0.4684 (2) | 0.80344 (12) | 0.26266 (12) | 0.0241 (4) | |
H17A | 0.4394 | 0.7509 | 0.3008 | 0.036* | |
H17B | 0.5739 | 0.8067 | 0.2600 | 0.036* | |
H17C | 0.4299 | 0.7981 | 0.1967 | 0.036* | |
C18 | 0.3480 (2) | 0.69287 (14) | 0.61449 (14) | 0.0315 (4) | |
H18A | 0.3276 | 0.6537 | 0.6700 | 0.047* | |
H18B | 0.3942 | 0.6578 | 0.5630 | 0.047* | |
H18C | 0.2577 | 0.7185 | 0.5901 | 0.047* | |
C19 | 0.24717 (19) | 0.88113 (12) | −0.03151 (12) | 0.0228 (4) | |
H19A | 0.2288 | 0.9453 | −0.0457 | 0.027* | |
H19B | 0.1700 | 0.8582 | 0.0115 | 0.027* | |
C20 | 0.2566 (2) | 0.82600 (13) | −0.12504 (13) | 0.0299 (4) | |
H20A | 0.1612 | 0.8012 | −0.1429 | 0.036* | |
H20B | 0.2932 | 0.8630 | −0.1794 | 0.036* | |
C21 | 0.3619 (2) | 0.75130 (13) | −0.10018 (14) | 0.0317 (4) | |
H21A | 0.4037 | 0.7241 | −0.1594 | 0.038* | |
H21C | 0.3152 | 0.7038 | −0.0610 | 0.038* | |
C22 | 0.4756 (2) | 0.80137 (14) | −0.04180 (14) | 0.0321 (4) | |
H22C | 0.5272 | 0.7602 | 0.0027 | 0.039* | |
H22A | 0.5465 | 0.8309 | −0.0850 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0204 (6) | 0.0389 (7) | 0.0274 (6) | −0.0001 (6) | 0.0013 (5) | −0.0038 (6) |
O2 | 0.0316 (7) | 0.0369 (7) | 0.0217 (6) | −0.0050 (6) | −0.0012 (5) | 0.0039 (6) |
N | 0.0239 (8) | 0.0247 (7) | 0.0220 (6) | 0.0042 (7) | −0.0021 (6) | −0.0033 (6) |
C1 | 0.0214 (9) | 0.0281 (9) | 0.0222 (7) | −0.0051 (8) | −0.0020 (7) | −0.0007 (7) |
C2 | 0.0183 (8) | 0.0339 (10) | 0.0234 (8) | −0.0034 (8) | −0.0020 (6) | −0.0029 (8) |
C3 | 0.0198 (8) | 0.0253 (9) | 0.0225 (7) | 0.0018 (7) | −0.0024 (7) | −0.0042 (7) |
C4 | 0.0197 (8) | 0.0207 (8) | 0.0215 (7) | −0.0004 (7) | −0.0023 (7) | 0.0012 (7) |
C5 | 0.0188 (8) | 0.0206 (8) | 0.0212 (7) | −0.0002 (7) | −0.0009 (6) | −0.0010 (6) |
C6 | 0.0216 (9) | 0.0273 (9) | 0.0247 (8) | −0.0034 (8) | −0.0006 (7) | 0.0016 (7) |
C7 | 0.0235 (9) | 0.0285 (9) | 0.0282 (8) | −0.0053 (8) | −0.0050 (7) | −0.0010 (7) |
C8 | 0.0191 (8) | 0.0259 (9) | 0.0240 (8) | 0.0005 (7) | 0.0002 (6) | −0.0030 (7) |
C9 | 0.0176 (7) | 0.0249 (8) | 0.0205 (7) | 0.0038 (7) | −0.0008 (6) | −0.0029 (7) |
C10 | 0.0197 (8) | 0.0204 (8) | 0.0188 (7) | −0.0004 (7) | −0.0012 (6) | −0.0004 (6) |
C11 | 0.0198 (8) | 0.0259 (8) | 0.0222 (8) | −0.0002 (7) | 0.0013 (6) | −0.0023 (7) |
C12 | 0.0212 (8) | 0.0298 (9) | 0.0217 (7) | 0.0036 (8) | 0.0034 (7) | 0.0010 (7) |
C13 | 0.0206 (8) | 0.0375 (10) | 0.0217 (7) | 0.0023 (8) | −0.0032 (7) | −0.0036 (8) |
C14 | 0.0193 (8) | 0.0326 (10) | 0.0266 (8) | −0.0010 (8) | −0.0040 (7) | −0.0048 (8) |
C15 | 0.0224 (9) | 0.0232 (8) | 0.0187 (7) | −0.0010 (7) | 0.0010 (7) | 0.0027 (7) |
C16 | 0.0314 (10) | 0.0229 (8) | 0.0277 (8) | −0.0020 (8) | −0.0054 (8) | 0.0042 (7) |
C17 | 0.0281 (9) | 0.0229 (9) | 0.0212 (7) | 0.0009 (7) | −0.0007 (7) | −0.0011 (7) |
C18 | 0.0320 (11) | 0.0355 (10) | 0.0272 (8) | −0.0047 (9) | 0.0025 (8) | 0.0047 (9) |
C19 | 0.0224 (8) | 0.0235 (8) | 0.0225 (7) | 0.0003 (7) | −0.0037 (7) | 0.0000 (7) |
C20 | 0.0325 (10) | 0.0327 (10) | 0.0246 (8) | 0.0006 (9) | −0.0039 (8) | −0.0051 (8) |
C21 | 0.0375 (11) | 0.0289 (10) | 0.0287 (9) | 0.0048 (9) | −0.0024 (8) | −0.0084 (8) |
C22 | 0.0319 (10) | 0.0348 (11) | 0.0295 (9) | 0.0092 (9) | −0.0017 (8) | −0.0088 (8) |
Geometric parameters (Å, º) top
O1—C15 | 1.234 (2) | C9—C11 | 1.407 (2) |
O2—C12 | 1.374 (2) | C9—C10 | 1.547 (2) |
O2—C18 | 1.423 (2) | C10—C17 | 1.545 (2) |
N—C15 | 1.361 (2) | C11—C12 | 1.392 (2) |
N—C19 | 1.477 (2) | C11—H11A | 0.9500 |
N—C22 | 1.477 (2) | C12—C13 | 1.395 (3) |
C1—C2 | 1.533 (2) | C13—C14 | 1.378 (3) |
C1—C10 | 1.551 (2) | C13—H13A | 0.9500 |
C1—H1A | 0.9900 | C14—H14A | 0.9500 |
C1—H1B | 0.9900 | C16—H16A | 0.9800 |
C2—C3 | 1.519 (3) | C16—H16B | 0.9800 |
C2—H2A | 0.9900 | C16—H16C | 0.9800 |
C2—H2B | 0.9900 | C17—H17A | 0.9800 |
C3—C4 | 1.547 (2) | C17—H17B | 0.9800 |
C3—H3A | 0.9900 | C17—H17C | 0.9800 |
C3—H3B | 0.9900 | C18—H18A | 0.9800 |
C4—C15 | 1.547 (2) | C18—H18B | 0.9800 |
C4—C16 | 1.550 (2) | C18—H18C | 0.9800 |
C4—C5 | 1.571 (2) | C19—C20 | 1.531 (2) |
C5—C6 | 1.538 (2) | C19—H19A | 0.9900 |
C5—C10 | 1.560 (2) | C19—H19B | 0.9900 |
C5—H5A | 1.0000 | C20—C21 | 1.519 (3) |
C6—C7 | 1.527 (2) | C20—H20A | 0.9900 |
C6—H6A | 0.9900 | C20—H20B | 0.9900 |
C6—H6B | 0.9900 | C21—C22 | 1.522 (3) |
C7—C8 | 1.514 (2) | C21—H21A | 0.9900 |
C7—H7A | 0.9900 | C21—H21C | 0.9900 |
C7—H7B | 0.9900 | C22—H22C | 0.9900 |
C8—C9 | 1.400 (2) | C22—H22A | 0.9900 |
C8—C14 | 1.408 (2) | | |
| | | |
C12—O2—C18 | 117.26 (14) | C12—C11—C9 | 120.94 (17) |
C15—N—C19 | 130.98 (15) | C12—C11—H11A | 119.5 |
C15—N—C22 | 117.05 (15) | C9—C11—H11A | 119.5 |
C19—N—C22 | 110.91 (14) | O2—C12—C11 | 124.21 (17) |
C2—C1—C10 | 112.41 (14) | O2—C12—C13 | 116.01 (15) |
C2—C1—H1A | 109.1 | C11—C12—C13 | 119.77 (17) |
C10—C1—H1A | 109.1 | C14—C13—C12 | 119.56 (16) |
C2—C1—H1B | 109.1 | C14—C13—H13A | 120.2 |
C10—C1—H1B | 109.1 | C12—C13—H13A | 120.2 |
H1A—C1—H1B | 107.9 | C13—C14—C8 | 121.68 (17) |
C3—C2—C1 | 111.31 (15) | C13—C14—H14A | 119.2 |
C3—C2—H2A | 109.4 | C8—C14—H14A | 119.2 |
C1—C2—H2A | 109.4 | O1—C15—N | 118.53 (16) |
C3—C2—H2B | 109.4 | O1—C15—C4 | 118.65 (16) |
C1—C2—H2B | 109.4 | N—C15—C4 | 122.82 (15) |
H2A—C2—H2B | 108.0 | C4—C16—H16A | 109.5 |
C2—C3—C4 | 114.43 (14) | C4—C16—H16B | 109.5 |
C2—C3—H3A | 108.7 | H16A—C16—H16B | 109.5 |
C4—C3—H3A | 108.7 | C4—C16—H16C | 109.5 |
C2—C3—H3B | 108.7 | H16A—C16—H16C | 109.5 |
C4—C3—H3B | 108.7 | H16B—C16—H16C | 109.5 |
H3A—C3—H3B | 107.6 | C10—C17—H17A | 109.5 |
C15—C4—C3 | 117.88 (14) | C10—C17—H17B | 109.5 |
C15—C4—C16 | 105.11 (14) | H17A—C17—H17B | 109.5 |
C3—C4—C16 | 107.43 (15) | C10—C17—H17C | 109.5 |
C15—C4—C5 | 110.64 (14) | H17A—C17—H17C | 109.5 |
C3—C4—C5 | 105.59 (14) | H17B—C17—H17C | 109.5 |
C16—C4—C5 | 110.08 (14) | O2—C18—H18A | 109.5 |
C6—C5—C10 | 111.48 (14) | O2—C18—H18B | 109.5 |
C6—C5—C4 | 117.61 (14) | H18A—C18—H18B | 109.5 |
C10—C5—C4 | 114.29 (14) | O2—C18—H18C | 109.5 |
C6—C5—H5A | 103.8 | H18A—C18—H18C | 109.5 |
C10—C5—H5A | 103.8 | H18B—C18—H18C | 109.5 |
C4—C5—H5A | 103.8 | N—C19—C20 | 103.16 (14) |
C7—C6—C5 | 108.34 (14) | N—C19—H19A | 111.1 |
C7—C6—H6A | 110.0 | C20—C19—H19A | 111.1 |
C5—C6—H6A | 110.0 | N—C19—H19B | 111.1 |
C7—C6—H6B | 110.0 | C20—C19—H19B | 111.1 |
C5—C6—H6B | 110.0 | H19A—C19—H19B | 109.1 |
H6A—C6—H6B | 108.4 | C21—C20—C19 | 103.84 (14) |
C8—C7—C6 | 111.64 (15) | C21—C20—H20A | 111.0 |
C8—C7—H7A | 109.3 | C19—C20—H20A | 111.0 |
C6—C7—H7A | 109.3 | C21—C20—H20B | 111.0 |
C8—C7—H7B | 109.3 | C19—C20—H20B | 111.0 |
C6—C7—H7B | 109.3 | H20A—C20—H20B | 109.0 |
H7A—C7—H7B | 108.0 | C20—C21—C22 | 101.91 (15) |
C9—C8—C14 | 118.86 (16) | C20—C21—H21A | 111.4 |
C9—C8—C7 | 122.32 (15) | C22—C21—H21A | 111.4 |
C14—C8—C7 | 118.80 (16) | C20—C21—H21C | 111.4 |
C8—C9—C11 | 119.17 (15) | C22—C21—H21C | 111.4 |
C8—C9—C10 | 122.95 (15) | H21A—C21—H21C | 109.3 |
C11—C9—C10 | 117.81 (15) | N—C22—C21 | 103.34 (16) |
C17—C10—C9 | 106.92 (14) | N—C22—H22C | 111.1 |
C17—C10—C1 | 108.85 (15) | C21—C22—H22C | 111.1 |
C9—C10—C1 | 109.87 (14) | N—C22—H22A | 111.1 |
C17—C10—C5 | 113.69 (13) | C21—C22—H22A | 111.1 |
C9—C10—C5 | 109.41 (14) | H22C—C22—H22A | 109.1 |
C1—C10—C5 | 108.07 (14) | | |
| | | |
C10—C1—C2—C3 | −54.5 (2) | C4—C5—C10—C9 | −177.31 (13) |
C1—C2—C3—C4 | 56.7 (2) | C6—C5—C10—C1 | 165.91 (14) |
C2—C3—C4—C15 | 68.2 (2) | C4—C5—C10—C1 | −57.70 (18) |
C2—C3—C4—C16 | −173.44 (14) | C8—C9—C11—C12 | 0.9 (3) |
C2—C3—C4—C5 | −55.98 (18) | C10—C9—C11—C12 | 177.99 (16) |
C15—C4—C5—C6 | 62.35 (19) | C18—O2—C12—C11 | 6.3 (3) |
C3—C4—C5—C6 | −169.05 (15) | C18—O2—C12—C13 | −174.11 (16) |
C16—C4—C5—C6 | −53.4 (2) | C9—C11—C12—O2 | 178.92 (16) |
C15—C4—C5—C10 | −71.23 (18) | C9—C11—C12—C13 | −0.7 (3) |
C3—C4—C5—C10 | 57.36 (18) | O2—C12—C13—C14 | −179.15 (16) |
C16—C4—C5—C10 | 173.03 (14) | C11—C12—C13—C14 | 0.5 (3) |
C10—C5—C6—C7 | −67.59 (18) | C12—C13—C14—C8 | −0.5 (3) |
C4—C5—C6—C7 | 157.61 (15) | C9—C8—C14—C13 | 0.7 (3) |
C5—C6—C7—C8 | 52.0 (2) | C7—C8—C14—C13 | −177.95 (17) |
C6—C7—C8—C9 | −20.4 (2) | C19—N—C15—O1 | −161.33 (16) |
C6—C7—C8—C14 | 158.18 (17) | C22—N—C15—O1 | 5.6 (2) |
C14—C8—C9—C11 | −0.9 (3) | C19—N—C15—C4 | 18.4 (3) |
C7—C8—C9—C11 | 177.74 (17) | C22—N—C15—C4 | −174.64 (16) |
C14—C8—C9—C10 | −177.83 (16) | C3—C4—C15—O1 | −161.87 (16) |
C7—C8—C9—C10 | 0.8 (3) | C16—C4—C15—O1 | 78.54 (19) |
C8—C9—C10—C17 | 110.02 (18) | C5—C4—C15—O1 | −40.3 (2) |
C11—C9—C10—C17 | −66.97 (19) | C3—C4—C15—N | 18.4 (2) |
C8—C9—C10—C1 | −132.01 (17) | C16—C4—C15—N | −101.20 (18) |
C11—C9—C10—C1 | 51.0 (2) | C5—C4—C15—N | 140.00 (16) |
C8—C9—C10—C5 | −13.5 (2) | C15—N—C19—C20 | 160.51 (17) |
C11—C9—C10—C5 | 169.49 (15) | C22—N—C19—C20 | −7.04 (19) |
C2—C1—C10—C17 | −69.84 (19) | N—C19—C20—C21 | 29.74 (19) |
C2—C1—C10—C9 | 173.40 (14) | C19—C20—C21—C22 | −40.9 (2) |
C2—C1—C10—C5 | 54.08 (19) | C15—N—C22—C21 | 172.25 (15) |
C6—C5—C10—C17 | −73.14 (18) | C19—N—C22—C21 | −18.3 (2) |
C4—C5—C10—C17 | 63.25 (19) | C20—C21—C22—N | 36.00 (19) |
C6—C5—C10—C9 | 46.30 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O1i | 0.95 | 2.44 | 3.377 (2) | 169 |
Symmetry code: (i) −x+3/2, −y+2, z+1/2. |