The molecules of the title compound, C
21H
20N
2O
3, are linked by O—H
O and C—H
N hydrogen bonds, and by π–π interactions. The cyclobutane ring is puckered, with a dihedral angle of 11.55 (3)° between the two planes. The phenyl ring shows positional disorder.
Supporting information
CCDC reference: 232180
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.134
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact C19B .. C20B = 3.03 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact C20B .. C20B = 2.90 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2824
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3049
Completeness (_total/calc) 92.62%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C16 - C17 = 1.38 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.50 Deg.
C21A -C16 -C21B 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.10 Deg.
C19A -C18 -C19B 1.555 1.555 1.555
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 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
5 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-[2-Hydroxyimino-2-(3-methyl-3-phenylcyclobutyl)ethyl]isoindole-1,3-dione
top
Crystal data top
C21H20N2O3 | F(000) = 736 |
Mr = 348.39 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9229 reflections |
a = 14.6497 (14) Å | θ = 1.5–29.6° |
b = 5.6976 (3) Å | µ = 0.09 mm−1 |
c = 21.965 (2) Å | T = 293 K |
β = 109.095 (7)° | Plate, colourless |
V = 1732.5 (3) Å3 | 0.80 × 0.34 × 0.08 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 1590 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube | Rint = 0.071 |
Plane graphite monochromator | θmax = 25.0°, θmin = 1.5° |
Detector resolution: 6.67 pixels mm-1 | h = −17→16 |
φ scans | k = −6→6 |
5446 measured reflections | l = −18→26 |
2824 independent reflections | |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
2824 reflections | Δρmax = 0.19 e Å−3 |
264 parameters | Δρmin = −0.18 e Å−3 |
246 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0115 (19) |
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 | 0.29214 (15) | 1.3772 (3) | 0.36620 (9) | 0.0686 (6) | |
O2 | 0.47806 (13) | 0.7194 (4) | 0.39785 (8) | 0.0621 (5) | |
O3 | 0.44960 (17) | 1.1764 (4) | 0.20556 (10) | 0.0938 (8) | |
H3 | 0.4598 | 1.1933 | 0.1713 | 0.141* | |
N1 | 0.38789 (15) | 1.0564 (4) | 0.36671 (9) | 0.0501 (6) | |
N2 | 0.37331 (17) | 1.0161 (4) | 0.19729 (11) | 0.0630 (7) | |
C1 | 0.27605 (18) | 0.8280 (5) | 0.24993 (12) | 0.0510 (7) | |
H1 | 0.2986 | 0.7099 | 0.2840 | 0.061* | |
C2 | 0.21488 (18) | 0.7136 (5) | 0.18621 (13) | 0.0586 (7) | |
H2A | 0.2193 | 0.5437 | 0.1865 | 0.070* | |
H2B | 0.2270 | 0.7781 | 0.1487 | 0.070* | |
C3 | 0.12050 (19) | 0.8063 (4) | 0.19532 (12) | 0.0524 (7) | |
C4 | 0.18415 (19) | 0.9527 (5) | 0.25386 (13) | 0.0608 (8) | |
H4A | 0.1831 | 1.1199 | 0.2455 | 0.073* | |
H4B | 0.1708 | 0.9214 | 0.2935 | 0.073* | |
C5 | 0.33062 (19) | 1.2001 (5) | 0.39102 (12) | 0.0506 (7) | |
C6 | 0.32923 (17) | 1.0865 (4) | 0.45192 (11) | 0.0463 (6) | |
C7 | 0.2859 (2) | 1.1549 (5) | 0.49549 (13) | 0.0581 (7) | |
H7 | 0.2492 | 1.2914 | 0.4898 | 0.070* | |
C8 | 0.2991 (2) | 1.0109 (5) | 0.54867 (13) | 0.0619 (8) | |
H8 | 0.2707 | 1.0524 | 0.5793 | 0.074* | |
C9 | 0.35269 (19) | 0.8100 (5) | 0.55721 (12) | 0.0597 (8) | |
H9 | 0.3596 | 0.7174 | 0.5933 | 0.072* | |
C10 | 0.39679 (18) | 0.7416 (5) | 0.51341 (11) | 0.0524 (7) | |
H10 | 0.4330 | 0.6045 | 0.5191 | 0.063* | |
C11 | 0.38482 (17) | 0.8865 (4) | 0.46032 (11) | 0.0454 (6) | |
C12 | 0.42437 (18) | 0.8668 (5) | 0.40660 (12) | 0.0485 (7) | |
C13 | 0.4137 (2) | 1.1150 (5) | 0.30983 (11) | 0.0567 (7) | |
H13A | 0.4816 | 1.0803 | 0.3186 | 0.068* | |
H13B | 0.4050 | 1.2824 | 0.3021 | 0.068* | |
C14 | 0.35564 (19) | 0.9859 (5) | 0.24946 (12) | 0.0508 (7) | |
C15 | 0.0661 (2) | 0.6128 (5) | 0.21697 (17) | 0.0768 (9) | |
H15A | 0.1106 | 0.5238 | 0.2510 | 0.115* | |
H15B | 0.0355 | 0.5110 | 0.1813 | 0.115* | |
H15C | 0.0179 | 0.6816 | 0.2323 | 0.115* | |
C16 | 0.05588 (19) | 0.9572 (5) | 0.14145 (13) | 0.0574 (8) | |
C17 | −0.0427 (2) | 0.9725 (5) | 0.12865 (15) | 0.0676 (9) | |
H17 | −0.0716 | 0.8770 | 0.1515 | 0.081* | |
C18 | −0.0997 (3) | 1.1243 (7) | 0.08327 (19) | 0.0889 (12) | |
H18 | −0.1666 | 1.1098 | 0.0691 | 0.107* | |
C19A | −0.0559 (10) | 1.298 (3) | 0.0592 (8) | 0.093 (4) | 0.52 (3) |
H19A | −0.0925 | 1.4169 | 0.0336 | 0.112* | 0.52 (3) |
C20A | 0.0421 (9) | 1.293 (3) | 0.0734 (8) | 0.095 (4) | 0.52 (3) |
H20A | 0.0721 | 1.4001 | 0.0542 | 0.114* | 0.52 (3) |
C21A | 0.0980 (15) | 1.125 (3) | 0.1176 (8) | 0.077 (4) | 0.52 (3) |
H21A | 0.1650 | 1.1321 | 0.1302 | 0.093* | 0.52 (3) |
C19B | −0.0618 (14) | 1.210 (3) | 0.0355 (9) | 0.103 (4) | 0.48 (3) |
H19B | −0.1023 | 1.2780 | −0.0021 | 0.124* | 0.48 (3) |
C20B | 0.0305 (12) | 1.192 (4) | 0.0455 (9) | 0.103 (4) | 0.48 (3) |
H20B | 0.0561 | 1.2651 | 0.0169 | 0.123* | 0.48 (3) |
C21B | 0.0910 (15) | 1.072 (4) | 0.0959 (8) | 0.079 (4) | 0.48 (3) |
H21B | 0.1564 | 1.0640 | 0.1008 | 0.095* | 0.48 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0918 (14) | 0.0610 (12) | 0.0553 (11) | 0.0149 (11) | 0.0273 (11) | 0.0140 (10) |
O2 | 0.0676 (11) | 0.0782 (14) | 0.0460 (10) | 0.0170 (11) | 0.0262 (9) | 0.0037 (9) |
O3 | 0.1143 (17) | 0.121 (2) | 0.0577 (13) | −0.0440 (15) | 0.0441 (13) | −0.0083 (13) |
N1 | 0.0611 (12) | 0.0595 (14) | 0.0329 (10) | 0.0038 (11) | 0.0197 (10) | 0.0057 (10) |
N2 | 0.0740 (15) | 0.0792 (16) | 0.0436 (12) | −0.0200 (13) | 0.0299 (12) | −0.0053 (11) |
C1 | 0.0596 (15) | 0.0558 (16) | 0.0391 (13) | 0.0044 (12) | 0.0182 (12) | 0.0078 (11) |
C2 | 0.0693 (17) | 0.0571 (16) | 0.0546 (16) | −0.0038 (14) | 0.0277 (14) | −0.0082 (13) |
C3 | 0.0621 (15) | 0.0532 (16) | 0.0454 (14) | −0.0011 (13) | 0.0222 (13) | −0.0028 (12) |
C4 | 0.0595 (16) | 0.079 (2) | 0.0440 (14) | 0.0038 (14) | 0.0168 (13) | −0.0114 (14) |
C5 | 0.0583 (15) | 0.0564 (16) | 0.0368 (13) | 0.0030 (13) | 0.0149 (12) | 0.0004 (12) |
C6 | 0.0506 (14) | 0.0550 (16) | 0.0343 (13) | −0.0009 (12) | 0.0153 (11) | 0.0014 (11) |
C7 | 0.0669 (17) | 0.0646 (18) | 0.0481 (15) | 0.0039 (14) | 0.0259 (14) | −0.0031 (13) |
C8 | 0.0712 (18) | 0.083 (2) | 0.0403 (14) | −0.0031 (17) | 0.0306 (14) | 0.0017 (15) |
C9 | 0.0649 (16) | 0.079 (2) | 0.0365 (14) | −0.0042 (16) | 0.0180 (13) | 0.0092 (13) |
C10 | 0.0559 (14) | 0.0656 (17) | 0.0365 (13) | 0.0027 (13) | 0.0162 (12) | 0.0092 (12) |
C11 | 0.0486 (13) | 0.0559 (15) | 0.0325 (12) | −0.0012 (12) | 0.0145 (11) | 0.0001 (11) |
C12 | 0.0494 (14) | 0.0580 (16) | 0.0375 (13) | −0.0010 (13) | 0.0137 (12) | −0.0034 (12) |
C13 | 0.0697 (17) | 0.0701 (18) | 0.0366 (13) | −0.0087 (14) | 0.0258 (13) | 0.0042 (13) |
C14 | 0.0616 (16) | 0.0614 (17) | 0.0346 (13) | 0.0020 (13) | 0.0229 (12) | 0.0032 (12) |
C15 | 0.089 (2) | 0.068 (2) | 0.085 (2) | −0.0030 (17) | 0.0443 (19) | 0.0117 (17) |
C16 | 0.0548 (17) | 0.0625 (18) | 0.0515 (16) | −0.0086 (14) | 0.0128 (14) | −0.0046 (13) |
C17 | 0.0642 (19) | 0.077 (2) | 0.0610 (18) | −0.0088 (15) | 0.0198 (15) | −0.0073 (16) |
C18 | 0.065 (2) | 0.113 (3) | 0.076 (2) | 0.002 (2) | 0.005 (2) | −0.001 (2) |
C19A | 0.084 (5) | 0.113 (9) | 0.067 (7) | −0.001 (6) | 0.004 (6) | 0.031 (6) |
C20A | 0.083 (5) | 0.112 (8) | 0.080 (8) | −0.014 (5) | 0.013 (6) | 0.035 (6) |
C21A | 0.070 (5) | 0.106 (8) | 0.046 (7) | −0.015 (5) | 0.006 (6) | 0.020 (6) |
C19B | 0.094 (6) | 0.122 (10) | 0.067 (7) | 0.016 (7) | −0.009 (6) | 0.003 (7) |
C20B | 0.107 (6) | 0.135 (10) | 0.064 (7) | 0.021 (7) | 0.024 (7) | 0.039 (7) |
C21B | 0.068 (6) | 0.115 (11) | 0.054 (8) | −0.001 (6) | 0.021 (7) | 0.035 (7) |
Geometric parameters (Å, º) top
O1—C5 | 1.197 (3) | C9—H9 | 0.9300 |
O2—C12 | 1.208 (3) | C10—C11 | 1.392 (4) |
O3—N2 | 1.408 (3) | C10—H10 | 0.9300 |
O3—H3 | 0.8200 | C11—C12 | 1.479 (4) |
N1—C12 | 1.384 (3) | C13—C14 | 1.512 (4) |
N1—C5 | 1.397 (4) | C13—H13A | 0.9700 |
N1—C13 | 1.458 (3) | C13—H13B | 0.9700 |
N2—C14 | 1.266 (4) | C15—H15A | 0.9600 |
C1—C14 | 1.475 (4) | C15—H15B | 0.9600 |
C1—C2 | 1.538 (3) | C15—H15C | 0.9600 |
C1—C4 | 1.549 (4) | C16—C21A | 1.33 (2) |
C1—H1 | 0.9800 | C16—C17 | 1.381 (4) |
C2—C3 | 1.553 (4) | C16—C21B | 1.42 (2) |
C2—H2A | 0.9700 | C17—C18 | 1.376 (4) |
C2—H2B | 0.9700 | C17—H17 | 0.9300 |
C3—C16 | 1.517 (4) | C18—C19A | 1.376 (15) |
C3—C15 | 1.525 (4) | C18—C19B | 1.424 (19) |
C3—C4 | 1.560 (3) | C18—H18 | 0.9300 |
C4—H4A | 0.9700 | C19A—C20A | 1.366 (19) |
C4—H4B | 0.9700 | C19A—H19A | 0.9300 |
C5—C6 | 1.492 (4) | C20A—C21A | 1.42 (2) |
C6—C7 | 1.367 (4) | C20A—H20A | 0.9300 |
C6—C11 | 1.377 (4) | C21A—H21A | 0.9300 |
C7—C8 | 1.388 (4) | C19B—C20B | 1.30 (2) |
C7—H7 | 0.9300 | C19B—H19B | 0.9300 |
C8—C9 | 1.366 (4) | C20B—C21B | 1.36 (2) |
C8—H8 | 0.9300 | C20B—H20B | 0.9300 |
C9—C10 | 1.379 (4) | C21B—H21B | 0.9300 |
| | | |
N2—O3—H3 | 109.5 | O2—C12—C11 | 128.7 (3) |
C12—N1—C5 | 111.8 (2) | N1—C12—C11 | 105.9 (2) |
C12—N1—C13 | 124.5 (2) | N1—C13—C14 | 114.3 (2) |
C5—N1—C13 | 123.3 (2) | N1—C13—H13A | 108.7 |
C14—N2—O3 | 111.1 (2) | C14—C13—H13A | 108.7 |
C14—C1—C2 | 118.6 (3) | N1—C13—H13B | 108.7 |
C14—C1—C4 | 115.1 (2) | C14—C13—H13B | 108.7 |
C2—C1—C4 | 89.24 (18) | H13A—C13—H13B | 107.6 |
C14—C1—H1 | 110.8 | N2—C14—C1 | 119.0 (2) |
C2—C1—H1 | 110.8 | N2—C14—C13 | 120.3 (2) |
C4—C1—H1 | 110.8 | C1—C14—C13 | 120.6 (3) |
C1—C2—C3 | 91.0 (2) | C3—C15—H15A | 109.5 |
C1—C2—H2A | 113.5 | C3—C15—H15B | 109.5 |
C3—C2—H2A | 113.5 | H15A—C15—H15B | 109.5 |
C1—C2—H2B | 113.5 | C3—C15—H15C | 109.5 |
C3—C2—H2B | 113.5 | H15A—C15—H15C | 109.5 |
H2A—C2—H2B | 110.8 | H15B—C15—H15C | 109.5 |
C16—C3—C15 | 113.4 (2) | C21A—C16—C17 | 117.5 (9) |
C16—C3—C2 | 116.5 (2) | C21A—C16—C21B | 22.5 (9) |
C15—C3—C2 | 111.9 (2) | C17—C16—C21B | 115.0 (8) |
C16—C3—C4 | 113.1 (2) | C21A—C16—C3 | 117.5 (8) |
C15—C3—C4 | 111.2 (3) | C17—C16—C3 | 122.6 (3) |
C2—C3—C4 | 88.32 (19) | C21B—C16—C3 | 122.1 (8) |
C1—C4—C3 | 90.3 (2) | C18—C17—C16 | 122.2 (3) |
C1—C4—H4A | 113.6 | C18—C17—H17 | 118.9 |
C3—C4—H4A | 113.6 | C16—C17—H17 | 118.9 |
C1—C4—H4B | 113.6 | C17—C18—C19A | 118.8 (6) |
C3—C4—H4B | 113.6 | C17—C18—C19B | 117.3 (7) |
H4A—C4—H4B | 110.9 | C19A—C18—C19B | 29.1 (6) |
O1—C5—N1 | 124.9 (3) | C17—C18—H18 | 120.6 |
O1—C5—C6 | 129.2 (3) | C19A—C18—H18 | 120.6 |
N1—C5—C6 | 105.9 (2) | C19B—C18—H18 | 114.0 |
C7—C6—C11 | 122.1 (2) | C20A—C19A—C18 | 119.0 (10) |
C7—C6—C5 | 130.5 (2) | C20A—C19A—H19A | 120.5 |
C11—C6—C5 | 107.3 (2) | C18—C19A—H19A | 120.5 |
C6—C7—C8 | 116.8 (3) | C19A—C20A—C21A | 119.9 (13) |
C6—C7—H7 | 121.6 | C19A—C20A—H20A | 120.1 |
C8—C7—H7 | 121.6 | C21A—C20A—H20A | 120.1 |
C9—C8—C7 | 121.8 (3) | C16—C21A—C20A | 121.1 (15) |
C9—C8—H8 | 119.1 | C16—C21A—H21A | 119.5 |
C7—C8—H8 | 119.1 | C20A—C21A—H21A | 119.5 |
C8—C9—C10 | 121.4 (3) | C20B—C19B—C18 | 118.8 (11) |
C8—C9—H9 | 119.3 | C20B—C19B—H19B | 120.6 |
C10—C9—H9 | 119.3 | C18—C19B—H19B | 120.6 |
C9—C10—C11 | 117.2 (3) | C19B—C20B—C21B | 123.0 (16) |
C9—C10—H10 | 121.4 | C19B—C20B—H20B | 118.5 |
C11—C10—H10 | 121.4 | C21B—C20B—H20B | 118.5 |
C6—C11—C10 | 120.6 (3) | C20B—C21B—C16 | 121.0 (17) |
C6—C11—C12 | 108.9 (2) | C20B—C21B—H21B | 119.5 |
C10—C11—C12 | 130.4 (2) | C16—C21B—H21B | 119.5 |
O2—C12—N1 | 125.4 (3) | | |
| | | |
C14—C1—C2—C3 | −126.7 (2) | C5—N1—C13—C14 | −102.0 (3) |
C4—C1—C2—C3 | −8.3 (2) | O3—N2—C14—C1 | 178.5 (2) |
C1—C2—C3—C16 | 123.3 (2) | O3—N2—C14—C13 | 0.1 (4) |
C1—C2—C3—C15 | −104.0 (3) | C2—C1—C14—N2 | −2.4 (4) |
C1—C2—C3—C4 | 8.2 (2) | C4—C1—C14—N2 | −106.2 (3) |
C14—C1—C4—C3 | 129.7 (2) | C2—C1—C14—C13 | 176.0 (2) |
C2—C1—C4—C3 | 8.2 (2) | C4—C1—C14—C13 | 72.2 (3) |
C16—C3—C4—C1 | −126.4 (3) | N1—C13—C14—N2 | −177.8 (3) |
C15—C3—C4—C1 | 104.7 (3) | N1—C13—C14—C1 | 3.9 (4) |
C2—C3—C4—C1 | −8.2 (2) | C15—C3—C16—C21A | −177.3 (10) |
C12—N1—C5—O1 | 178.6 (2) | C2—C3—C16—C21A | −45.3 (10) |
C13—N1—C5—O1 | 4.7 (4) | C4—C3—C16—C21A | 54.9 (10) |
C12—N1—C5—C6 | −1.2 (3) | C15—C3—C16—C17 | 20.8 (4) |
C13—N1—C5—C6 | −175.2 (2) | C2—C3—C16—C17 | 152.8 (3) |
O1—C5—C6—C7 | −1.3 (4) | C4—C3—C16—C17 | −107.0 (3) |
N1—C5—C6—C7 | 178.6 (3) | C15—C3—C16—C21B | −151.8 (11) |
O1—C5—C6—C11 | −179.7 (3) | C2—C3—C16—C21B | −19.8 (11) |
N1—C5—C6—C11 | 0.2 (3) | C4—C3—C16—C21B | 80.4 (11) |
C11—C6—C7—C8 | −1.0 (4) | C21A—C16—C17—C18 | 12.6 (10) |
C5—C6—C7—C8 | −179.2 (2) | C21B—C16—C17—C18 | −12.4 (11) |
C6—C7—C8—C9 | −0.1 (4) | C3—C16—C17—C18 | 174.5 (3) |
C7—C8—C9—C10 | 0.5 (4) | C16—C17—C18—C19A | −13.2 (12) |
C8—C9—C10—C11 | 0.3 (4) | C16—C17—C18—C19B | 19.8 (11) |
C7—C6—C11—C10 | 1.8 (4) | C17—C18—C19A—C20A | 9.8 (16) |
C5—C6—C11—C10 | −179.7 (2) | C19B—C18—C19A—C20A | −85 (3) |
C7—C6—C11—C12 | −177.8 (2) | C18—C19A—C20A—C21A | −6.3 (18) |
C5—C6—C11—C12 | 0.8 (3) | C17—C16—C21A—C20A | −8.8 (14) |
C9—C10—C11—C6 | −1.4 (3) | C21B—C16—C21A—C20A | 81 (4) |
C9—C10—C11—C12 | 178.0 (2) | C3—C16—C21A—C20A | −171.6 (9) |
C5—N1—C12—O2 | −177.8 (2) | C19A—C20A—C21A—C16 | 6.0 (18) |
C13—N1—C12—O2 | −4.0 (4) | C17—C18—C19B—C20B | −17.0 (15) |
C5—N1—C12—C11 | 1.7 (3) | C19A—C18—C19B—C20B | 84 (2) |
C13—N1—C12—C11 | 175.6 (2) | C18—C19B—C20B—C21B | 8 (2) |
C6—C11—C12—O2 | 178.0 (2) | C19B—C20B—C21B—C16 | 0 (2) |
C10—C11—C12—O2 | −1.5 (4) | C21A—C16—C21B—C20B | −100 (5) |
C6—C11—C12—N1 | −1.6 (3) | C17—C16—C21B—C20B | 2.2 (17) |
C10—C11—C12—N1 | 179.0 (2) | C3—C16—C21B—C20B | 175.3 (10) |
C12—N1—C13—C14 | 84.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 2.01 | 2.814 (3) | 165 |
C9—H9···N2ii | 0.93 | 2.59 | 3.522 (4) | 176 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z+1/2. |