Download citation
Download citation
link to html
The title compound (systematic name: 9-benzyl-1,9-di­hydroxy-9H-indolo­[1,2-c][1,2,3]­oxa­diazo­le), C16H12N2O3, was synthesized as part of a series of sydnones to determine substituent effects on the sydnone ring. The are two independent mol­ecules in the asymmetric unit. There is interest in finding substituents for the sydnone ring that would allow for the release of NO via ring opening. Observed bond distances and angles for the sydnone ring are consistent with previously published structures, suggesting that the substituents used have little effect towards destabilization of the ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020082/lh6259sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020082/lh6259Isup2.hkl
Contains datablock I

CCDC reference: 251733

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.146
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.75 Deg.
Author Response: The data set is lacking 31 expected reflections below a resolution of 0.6, this is out of a data set of 6005(4887 observed). The data set includes reflections out to a 2theta value of 28.23 degrees.

Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O5A - C5A .. 6.96 su
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997-2000); cell refinement: SAINT-Plus (Bruker, 1997-1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1995).

4-hydroxy-4-benzylsydno[3,4-a](4H)indole top
Crystal data top
C16H12N2O3Z = 4
Mr = 280.28F(000) = 584
Triclinic, P1Dx = 1.382 Mg m3
Hall symbol: -P 1Melting point: 426 K
a = 9.502 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.906 (3) ÅCell parameters from 6477 reflections
c = 13.676 (3) Åθ = 2.3–28.1°
α = 105.712 (17)°µ = 0.10 mm1
β = 108.29 (2)°T = 298 K
γ = 101.13 (2)°Rectangular, colorless
V = 1347.1 (7) Å30.40 × 0.30 × 0.25 mm
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
6005 independent reflections
Radiation source: fine-focus sealed tube4886 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 1997-1999)
h = 1212
Tmin = 0.901, Tmax = 0.976k = 1515
11422 measured reflectionsl = 1718
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
6005 reflections(Δ/σ)max < 0.001
381 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.19 e Å3
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.

Mean-plane data from final SHELX refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 8.1127 (0.0046) x + 7.8485 (0.0066) y - 0.2533 (0.0094) z = 3.1676 (0.0041)

* 0.0038 (0.0010) C14A * 0.0010 (0.0011) C15A * -0.0046 (0.0012) C16A * 0.0033 (0.0013) C17A * 0.0016 (0.0012) C18A * -0.0051 (0.0011) C19A

Rms deviation of fitted atoms = 0.0035

- 2.6464 (0.0056) x + 10.8309 (0.0051) y + 2.0412 (0.0082) z = 10.1654 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 51.34 (0.06)

* -0.0122 (0.0007) N3A * -0.0104 (0.0007) C6A * 0.0256 (0.0008) C7A * -0.0296 (0.0007) C12A * 0.0266 (0.0007) C4A

Rms deviation of fitted atoms = 0.0224

- 2.4963 (0.0051) x + 11.1286 (0.0049) y + 1.1567 (0.0078) z = 9.9972 (0.0045)

Angle to previous plane (with approximate e.s.d.) = 3.74 (0.07)

* 0.0051 (0.0009) C6A * -0.0063 (0.0009) C7A * 0.0011 (0.0010) C8A * 0.0055 (0.0010) C9A * -0.0069 (0.0010) C10A * 0.0015 (0.0010) C11A

Rms deviation of fitted atoms = 0.0050

- 2.8753 (0.0060) x + 10.7764 (0.0051) y + 2.2230 (0.0082) z = 10.1658 (0.0040)

Angle to previous plane (with approximate e.s.d.) = 4.64 (0.07)

* 0.0024 (0.0007) O1A * 0.0000 (0.0007) N2A * -0.0026 (0.0008) N3A * 0.0038 (0.0007) C4A * -0.0037 (0.0007) C5A

Rms deviation of fitted atoms = 0.0029

- 3.4270 (0.0061) x + 7.5076 (0.0061) y - 10.0366 (0.0072) z = 5.8654 (0.0058)

Angle to previous plane (with approximate e.s.d.) = 72.28 (0.05)

* -0.0077 (0.0009) C14B * 0.0040 (0.0010) C15B * 0.0019 (0.0011) C16B * -0.0042 (0.0012) C17B * 0.0004 (0.0012) C18B * 0.0056 (0.0010) C19B

Rms deviation of fitted atoms = 0.0046

1.4271 (0.0056) x + 3.7764 (0.0069) y + 8.9339 (0.0072) z = 4.1664 (0.0060)

Angle to previous plane (with approximate e.s.d.) = 57.79 (0.05)

* -0.0050 (0.0007) N3B * 0.0073 (0.0007) C6B * -0.0065 (0.0008) C7B * 0.0033 (0.0007) C12B * 0.0010 (0.0008) C4B

Rms deviation of fitted atoms = 0.0051

1.3977 (0.0059) x + 3.9600 (0.0072) y + 8.8117 (0.0073) z = 4.2825 (0.0051)

Angle to previous plane (with approximate e.s.d.) = 0.94 (0.11)

* -0.0053 (0.0009) C6B * 0.0018 (0.0009) C7B * 0.0031 (0.0010) C8B * -0.0045 (0.0012) C9B * 0.0011 (0.0012) C10B * 0.0038 (0.0011) C11B

Rms deviation of fitted atoms = 0.0036

1.7641 (0.0058) x + 3.6965 (0.0079) y + 8.7020 (0.0078) z = 4.3642 (0.0068)

Angle to previous plane (with approximate e.s.d.) = 2.37 (0.12)

* 0.0095 (0.0008) O1B * -0.0036 (0.0007) N2B * -0.0042 (0.0008) N3B * 0.0095 (0.0007) C4B * -0.0112 (0.0008) C5B

Rms deviation of fitted atoms = 0.0082

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
xyzUiso*/Ueq
O1A0.06381 (11)0.91184 (9)0.23631 (7)0.0514 (3)
O3A0.38874 (11)1.02465 (9)0.58549 (8)0.0510 (3)
H3A0.46991.01640.62250.077*
N3A0.04449 (12)0.87778 (9)0.37416 (8)0.0398 (2)
O5A0.32522 (12)0.97072 (11)0.28399 (8)0.0571 (3)
C14A0.25884 (15)0.68517 (12)0.41996 (11)0.0422 (3)
C4A0.19893 (14)0.91401 (11)0.40119 (10)0.0390 (3)
C5A0.21751 (15)0.93699 (12)0.31043 (10)0.0427 (3)
C7A0.14545 (15)0.87376 (11)0.54491 (10)0.0409 (3)
N2A0.04404 (14)0.87417 (12)0.27835 (9)0.0521 (3)
C13A0.36584 (15)0.80779 (13)0.50322 (11)0.0456 (3)
H13A0.45230.83280.48260.055*
H13B0.40770.79990.57460.055*
C12A0.28376 (14)0.90847 (11)0.51301 (10)0.0397 (3)
C6A0.00500 (15)0.85209 (11)0.46019 (10)0.0410 (3)
C8A0.14229 (18)0.86358 (13)0.64249 (12)0.0521 (3)
H8A0.23390.87820.70160.063*
C11A0.13872 (17)0.81907 (13)0.46460 (13)0.0514 (3)
H11A0.23020.80500.40560.062*
C15A0.17663 (18)0.60081 (14)0.44962 (13)0.0545 (4)
H15A0.19080.61810.52320.065*
C19A0.23467 (19)0.65548 (14)0.30891 (12)0.0540 (4)
H19A0.29000.71060.28730.065*
C9A0.0013 (2)0.83097 (14)0.65003 (13)0.0583 (4)
H9A0.00520.82430.71540.070*
C10A0.1384 (2)0.80816 (13)0.56291 (14)0.0584 (4)
H10A0.23260.78500.57040.070*
C18A0.1313 (2)0.54699 (16)0.23084 (14)0.0675 (4)
H18A0.11630.52950.15710.081*
C16A0.0734 (2)0.49084 (15)0.37131 (18)0.0713 (5)
H16A0.01940.43460.39270.086*
C17A0.0497 (2)0.46379 (16)0.26182 (17)0.0726 (5)
H17A0.02080.39010.20930.087*
N3B0.78504 (12)0.72564 (10)0.03365 (8)0.0442 (3)
O3B0.72381 (11)0.99693 (9)0.06274 (8)0.0538 (3)
H3B0.80271.03420.05880.081*
O1B0.98113 (12)0.72160 (11)0.00281 (9)0.0643 (3)
C12B0.67248 (14)0.87303 (11)0.00974 (10)0.0407 (3)
C7B0.58262 (14)0.79513 (11)0.03645 (10)0.0401 (3)
C14B0.52104 (15)0.73598 (12)0.21101 (10)0.0418 (3)
C13B0.57398 (16)0.86318 (12)0.12691 (11)0.0452 (3)
H13C0.48330.88860.12570.054*
H13D0.63470.91920.14920.054*
C6B0.65269 (15)0.70994 (12)0.06281 (10)0.0425 (3)
O5B0.99882 (13)0.87069 (11)0.07826 (10)0.0713 (4)
C4B0.80143 (14)0.81551 (12)0.00627 (10)0.0425 (3)
C19B0.61095 (17)0.70102 (15)0.26917 (11)0.0531 (3)
H19B0.70140.75800.25870.064*
N2B0.88544 (15)0.66495 (13)0.03915 (11)0.0609 (3)
C5B0.93047 (16)0.81594 (14)0.03500 (12)0.0522 (4)
C8B0.44961 (16)0.80003 (14)0.05550 (12)0.0508 (3)
H8B0.39950.85630.03880.061*
C15B0.38509 (16)0.64930 (14)0.23059 (11)0.0516 (3)
H15B0.32160.67090.19370.062*
C11B0.59983 (19)0.62972 (14)0.10828 (12)0.0567 (4)
H11B0.65120.57440.12580.068*
C18B0.5683 (2)0.58295 (17)0.34242 (13)0.0652 (4)
H18B0.63050.56080.38020.078*
C16B0.3427 (2)0.53138 (15)0.30412 (13)0.0636 (4)
H16B0.25150.47400.31620.076*
C9B0.3922 (2)0.71922 (17)0.10006 (14)0.0620 (4)
H9B0.30180.72100.11250.074*
C10B0.4663 (2)0.63578 (16)0.12644 (14)0.0647 (4)
H10B0.42540.58310.15680.078*
C17B0.4351 (2)0.49881 (16)0.35943 (14)0.0678 (5)
H17B0.40680.41920.40860.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0469 (5)0.0629 (6)0.0357 (5)0.0116 (5)0.0085 (4)0.0168 (4)
O3A0.0425 (5)0.0487 (5)0.0467 (5)0.0078 (4)0.0069 (4)0.0107 (4)
N3A0.0378 (5)0.0372 (5)0.0371 (5)0.0095 (4)0.0095 (4)0.0094 (4)
O5A0.0495 (6)0.0779 (7)0.0472 (5)0.0130 (5)0.0195 (5)0.0307 (5)
C14A0.0463 (7)0.0464 (7)0.0487 (7)0.0242 (6)0.0254 (6)0.0238 (6)
C4A0.0378 (6)0.0381 (6)0.0386 (6)0.0112 (5)0.0125 (5)0.0129 (5)
C5A0.0443 (7)0.0427 (7)0.0349 (6)0.0112 (5)0.0095 (5)0.0127 (5)
C7A0.0460 (7)0.0364 (6)0.0406 (6)0.0131 (5)0.0179 (6)0.0124 (5)
N2A0.0430 (6)0.0613 (7)0.0393 (6)0.0101 (5)0.0069 (5)0.0136 (5)
C13A0.0419 (7)0.0551 (8)0.0453 (7)0.0193 (6)0.0165 (6)0.0237 (6)
C12A0.0383 (6)0.0430 (7)0.0357 (6)0.0109 (5)0.0122 (5)0.0144 (5)
C6A0.0444 (7)0.0341 (6)0.0430 (7)0.0110 (5)0.0185 (6)0.0102 (5)
C8A0.0613 (9)0.0545 (8)0.0456 (7)0.0192 (7)0.0240 (7)0.0203 (6)
C11A0.0445 (7)0.0434 (7)0.0607 (9)0.0089 (6)0.0223 (7)0.0110 (6)
C15A0.0708 (10)0.0533 (8)0.0639 (9)0.0291 (7)0.0429 (8)0.0309 (7)
C19A0.0722 (10)0.0498 (8)0.0521 (8)0.0228 (7)0.0332 (7)0.0228 (7)
C9A0.0784 (11)0.0498 (8)0.0583 (9)0.0177 (7)0.0421 (9)0.0197 (7)
C10A0.0623 (9)0.0436 (7)0.0736 (10)0.0091 (7)0.0421 (8)0.0138 (7)
C18A0.0848 (12)0.0614 (10)0.0535 (9)0.0277 (9)0.0272 (9)0.0120 (8)
C16A0.0777 (12)0.0507 (9)0.1077 (14)0.0206 (8)0.0620 (11)0.0301 (9)
C17A0.0628 (10)0.0533 (9)0.0873 (13)0.0132 (8)0.0308 (10)0.0047 (9)
N3B0.0394 (6)0.0493 (6)0.0365 (5)0.0142 (5)0.0099 (5)0.0094 (5)
O3B0.0517 (6)0.0442 (5)0.0586 (6)0.0054 (4)0.0289 (5)0.0053 (5)
O1B0.0462 (6)0.0707 (7)0.0671 (7)0.0224 (5)0.0228 (5)0.0069 (6)
C12B0.0386 (6)0.0414 (7)0.0416 (7)0.0088 (5)0.0190 (5)0.0125 (5)
C7B0.0409 (6)0.0431 (7)0.0325 (6)0.0084 (5)0.0136 (5)0.0117 (5)
C14B0.0420 (7)0.0503 (7)0.0358 (6)0.0154 (6)0.0126 (5)0.0214 (6)
C13B0.0504 (7)0.0474 (7)0.0466 (7)0.0162 (6)0.0234 (6)0.0235 (6)
C6B0.0423 (7)0.0467 (7)0.0332 (6)0.0099 (5)0.0126 (5)0.0110 (5)
O5B0.0558 (6)0.0720 (7)0.0754 (8)0.0002 (5)0.0413 (6)0.0054 (6)
C4B0.0377 (6)0.0461 (7)0.0354 (6)0.0073 (5)0.0119 (5)0.0082 (5)
C19B0.0479 (8)0.0660 (9)0.0415 (7)0.0131 (7)0.0170 (6)0.0164 (7)
N2B0.0555 (7)0.0660 (8)0.0615 (8)0.0294 (6)0.0210 (6)0.0175 (6)
C5B0.0397 (7)0.0520 (8)0.0477 (8)0.0043 (6)0.0174 (6)0.0018 (6)
C8B0.0495 (8)0.0615 (9)0.0521 (8)0.0192 (7)0.0278 (6)0.0249 (7)
C15B0.0457 (7)0.0630 (9)0.0453 (7)0.0133 (6)0.0152 (6)0.0232 (7)
C11B0.0684 (10)0.0548 (8)0.0510 (8)0.0187 (7)0.0228 (7)0.0256 (7)
C18B0.0635 (10)0.0788 (11)0.0479 (8)0.0311 (9)0.0186 (7)0.0115 (8)
C16B0.0580 (9)0.0592 (9)0.0552 (9)0.0026 (7)0.0071 (7)0.0211 (7)
C9B0.0608 (9)0.0759 (11)0.0640 (9)0.0182 (8)0.0398 (8)0.0304 (8)
C10B0.0752 (11)0.0681 (10)0.0630 (10)0.0123 (8)0.0385 (9)0.0343 (8)
C17B0.0739 (11)0.0567 (9)0.0535 (9)0.0210 (8)0.0081 (8)0.0095 (7)
Geometric parameters (Å, º) top
O1A—N2A1.3835 (16)N3B—N2B1.2994 (16)
O1A—C5A1.4098 (16)N3B—C4B1.3313 (18)
O3A—C12A1.4124 (16)N3B—C6B1.4282 (17)
O3A—H3A0.8200O3B—C12B1.4224 (16)
N3A—N2A1.3000 (16)O3B—H3B0.8200
N3A—C4A1.3435 (17)O1B—N2B1.3826 (18)
N3A—C6A1.4305 (17)O1B—C5B1.425 (2)
O5A—C5A1.2214 (16)C12B—C4B1.5092 (19)
C14A—C15A1.3784 (19)C12B—C7B1.5290 (17)
C14A—C19A1.3940 (19)C12B—C13B1.5402 (19)
C14A—C13A1.504 (2)C7B—C8B1.3767 (19)
C4A—C5A1.3962 (18)C7B—C6B1.3821 (19)
C4A—C12A1.5147 (18)C14B—C19B1.3858 (19)
C7A—C8A1.3813 (18)C14B—C15B1.387 (2)
C7A—C6A1.3873 (19)C14B—C13B1.5062 (19)
C7A—C12A1.5284 (17)C13B—H13C0.9700
C13A—C12A1.5500 (18)C13B—H13D0.9700
C13A—H13A0.9700C6B—C11B1.372 (2)
C13A—H13B0.9700O5B—C5B1.2179 (18)
C6A—C11A1.3712 (19)C4B—C5B1.3995 (18)
C8A—C9A1.389 (2)C19B—C18B1.381 (2)
C8A—H8A0.9300C19B—H19B0.9300
C11A—C10A1.385 (2)C8B—C9B1.385 (2)
C11A—H11A0.9300C8B—H8B0.9300
C15A—C16A1.382 (2)C15B—C16B1.381 (2)
C15A—H15A0.9300C15B—H15B0.9300
C19A—C18A1.370 (2)C11B—C10B1.379 (2)
C19A—H19A0.9300C11B—H11B0.9300
C9A—C10A1.380 (2)C18B—C17B1.363 (3)
C9A—H9A0.9300C18B—H18B0.9300
C10A—H10A0.9300C16B—C17B1.372 (3)
C18A—C17A1.378 (3)C16B—H16B0.9300
C18A—H18A0.9300C9B—C10B1.385 (3)
C16A—C17A1.377 (3)C9B—H9B0.9300
C16A—H16A0.9300C10B—H10B0.9300
C17A—H17A0.9300C17B—H17B0.9300
N2A···N3Bi3.040 (2)H9A···O5Biv2.711
H3A···O5Aii1.914H3B···O5Bv1.899
O5A···H13Diii2.612O5B···H9Avi2.711
N2A—O1A—C5A111.76 (9)N2B—N3B—C4B117.92 (12)
C12A—O3A—H3A109.5N2B—N3B—C6B129.62 (12)
N2A—N3A—C4A117.14 (11)C4B—N3B—C6B112.45 (11)
N2A—N3A—C6A130.36 (11)C12B—O3B—H3B109.5
C4A—N3A—C6A112.47 (11)N2B—O1B—C5B111.80 (10)
C15A—C14A—C19A117.82 (14)O3B—C12B—C4B114.01 (11)
C15A—C14A—C13A121.47 (12)O3B—C12B—C7B107.73 (10)
C19A—C14A—C13A120.66 (12)C4B—C12B—C7B99.37 (11)
N3A—C4A—C5A105.29 (11)O3B—C12B—C13B109.53 (11)
N3A—C4A—C12A110.17 (11)C4B—C12B—C13B112.89 (10)
C5A—C4A—C12A144.44 (12)C7B—C12B—C13B112.93 (11)
O5A—C5A—C4A137.25 (12)C8B—C7B—C6B118.48 (12)
O5A—C5A—O1A119.01 (11)C8B—C7B—C12B129.84 (12)
C4A—C5A—O1A103.75 (11)C6B—C7B—C12B111.67 (11)
C8A—C7A—C6A118.16 (13)C19B—C14B—C15B117.84 (13)
C8A—C7A—C12A129.99 (12)C19B—C14B—C13B120.26 (12)
C6A—C7A—C12A111.84 (11)C15B—C14B—C13B121.87 (12)
N3A—N2A—O1A102.05 (10)C14B—C13B—C12B113.42 (11)
C14A—C13A—C12A112.91 (11)C14B—C13B—H13C108.9
C14A—C13A—H13A109.0C12B—C13B—H13C108.9
C12A—C13A—H13A109.0C14B—C13B—H13D108.9
C14A—C13A—H13B109.0C12B—C13B—H13D108.9
C12A—C13A—H13B109.0H13C—C13B—H13D107.7
H13A—C13A—H13B107.8C11B—C6B—C7B124.48 (13)
O3A—C12A—C4A110.28 (10)C11B—C6B—N3B129.66 (13)
O3A—C12A—C7A111.74 (10)C7B—C6B—N3B105.86 (11)
C4A—C12A—C7A99.50 (10)N3B—C4B—C5B105.60 (13)
O3A—C12A—C13A111.97 (10)N3B—C4B—C12B110.63 (11)
C4A—C12A—C13A111.31 (10)C5B—C4B—C12B143.64 (13)
C7A—C12A—C13A111.42 (10)C18B—C19B—C14B121.05 (14)
C11A—C6A—C7A125.12 (13)C18B—C19B—H19B119.5
C11A—C6A—N3A129.06 (13)C14B—C19B—H19B119.5
C7A—C6A—N3A105.75 (11)N3B—N2B—O1B101.68 (12)
C7A—C8A—C9A118.24 (15)O5B—C5B—C4B137.41 (16)
C7A—C8A—H8A120.9O5B—C5B—O1B119.61 (13)
C9A—C8A—H8A120.9C4B—C5B—O1B102.95 (12)
C6A—C11A—C10A115.44 (15)C7B—C8B—C9B118.45 (14)
C6A—C11A—H11A122.3C7B—C8B—H8B120.8
C10A—C11A—H11A122.3C9B—C8B—H8B120.8
C14A—C15A—C16A120.77 (15)C16B—C15B—C14B120.89 (15)
C14A—C15A—H15A119.6C16B—C15B—H15B119.6
C16A—C15A—H15A119.6C14B—C15B—H15B119.6
C18A—C19A—C14A121.61 (15)C6B—C11B—C10B116.18 (15)
C18A—C19A—H19A119.2C6B—C11B—H11B121.9
C14A—C19A—H19A119.2C10B—C11B—H11B121.9
C10A—C9A—C8A121.63 (14)C17B—C18B—C19B120.11 (16)
C10A—C9A—H9A119.2C17B—C18B—H18B119.9
C8A—C9A—H9A119.2C19B—C18B—H18B119.9
C9A—C10A—C11A121.40 (14)C17B—C16B—C15B120.01 (16)
C9A—C10A—H10A119.3C17B—C16B—H16B120.0
C11A—C10A—H10A119.3C15B—C16B—H16B120.0
C19A—C18A—C17A119.84 (16)C10B—C9B—C8B121.51 (14)
C19A—C18A—H18A120.1C10B—C9B—H9B119.2
C17A—C18A—H18A120.1C8B—C9B—H9B119.2
C17A—C16A—C15A120.56 (15)C11B—C10B—C9B120.89 (14)
C17A—C16A—H16A119.7C11B—C10B—H10B119.6
C15A—C16A—H16A119.7C9B—C10B—H10B119.6
C16A—C17A—C18A119.40 (17)C18B—C17B—C16B120.08 (16)
C16A—C17A—H17A120.3C18B—C17B—H17B120.0
C18A—C17A—H17A120.3C16B—C17B—H17B120.0
N2A—N3A—C4A—C5A0.67 (15)O3B—C12B—C7B—C8B60.84 (17)
C6A—N3A—C4A—C5A179.07 (10)C4B—C12B—C7B—C8B179.90 (13)
N2A—N3A—C4A—C12A177.95 (11)C13B—C12B—C7B—C8B60.24 (18)
C6A—N3A—C4A—C12A3.64 (14)O3B—C12B—C7B—C6B118.16 (12)
N3A—C4A—C5A—O5A179.62 (16)C4B—C12B—C7B—C6B0.91 (13)
C12A—C4A—C5A—O5A4.0 (3)C13B—C12B—C7B—C6B120.76 (12)
N3A—C4A—C5A—O1A0.70 (13)C19B—C14B—C13B—C12B91.04 (15)
C12A—C4A—C5A—O1A176.32 (16)C15B—C14B—C13B—C12B86.92 (15)
N2A—O1A—C5A—O5A179.66 (12)O3B—C12B—C13B—C14B177.02 (10)
N2A—O1A—C5A—C4A0.58 (14)C4B—C12B—C13B—C14B48.82 (15)
C4A—N3A—N2A—O1A0.29 (14)C7B—C12B—C13B—C14B62.92 (15)
C6A—N3A—N2A—O1A178.36 (11)C8B—C7B—C6B—C11B0.8 (2)
C5A—O1A—N2A—N3A0.21 (13)C12B—C7B—C6B—C11B178.36 (12)
C15A—C14A—C13A—C12A91.37 (15)C8B—C7B—C6B—N3B179.58 (11)
C19A—C14A—C13A—C12A85.83 (15)C12B—C7B—C6B—N3B1.30 (14)
N3A—C4A—C12A—O3A122.54 (11)N2B—N3B—C6B—C11B2.8 (2)
C5A—C4A—C12A—O3A62.0 (2)C4B—N3B—C6B—C11B178.41 (13)
N3A—C4A—C12A—C7A5.01 (12)N2B—N3B—C6B—C7B177.57 (13)
C5A—C4A—C12A—C7A179.50 (18)C4B—N3B—C6B—C7B1.22 (14)
N3A—C4A—C12A—C13A112.56 (12)N2B—N3B—C4B—C5B1.39 (16)
C5A—C4A—C12A—C13A62.9 (2)C6B—N3B—C4B—C5B177.56 (10)
C8A—C7A—C12A—O3A57.53 (18)N2B—N3B—C4B—C12B178.29 (11)
C6A—C7A—C12A—O3A121.37 (12)C6B—N3B—C4B—C12B0.65 (14)
C8A—C7A—C12A—C4A173.96 (13)O3B—C12B—C4B—N3B114.15 (12)
C6A—C7A—C12A—C4A4.94 (13)C7B—C12B—C4B—N3B0.14 (13)
C8A—C7A—C12A—C13A68.56 (17)C13B—C12B—C4B—N3B120.02 (12)
C6A—C7A—C12A—C13A112.54 (12)O3B—C12B—C4B—C5B70.9 (2)
C14A—C13A—C12A—O3A175.62 (10)C7B—C12B—C4B—C5B174.83 (17)
C14A—C13A—C12A—C4A51.66 (14)C13B—C12B—C4B—C5B54.9 (2)
C14A—C13A—C12A—C7A58.41 (14)C15B—C14B—C19B—C18B1.4 (2)
C8A—C7A—C6A—C11A1.1 (2)C13B—C14B—C19B—C18B176.63 (13)
C12A—C7A—C6A—C11A179.84 (12)C4B—N3B—N2B—O1B0.13 (15)
C8A—C7A—C6A—N3A175.87 (11)C6B—N3B—N2B—O1B178.60 (11)
C12A—C7A—C6A—N3A3.17 (14)C5B—O1B—N2B—N3B1.20 (14)
N2A—N3A—C6A—C11A1.6 (2)N3B—C4B—C5B—O5B176.36 (17)
C4A—N3A—C6A—C11A176.53 (12)C12B—C4B—C5B—O5B1.2 (3)
N2A—N3A—C6A—C7A178.44 (12)N3B—C4B—C5B—O1B1.90 (13)
C4A—N3A—C6A—C7A0.30 (14)C12B—C4B—C5B—O1B177.01 (16)
C6A—C7A—C8A—C9A0.7 (2)N2B—O1B—C5B—O5B176.66 (12)
C12A—C7A—C8A—C9A179.50 (12)N2B—O1B—C5B—C4B1.98 (14)
C7A—C6A—C11A—C10A0.4 (2)C6B—C7B—C8B—C9B0.1 (2)
N3A—C6A—C11A—C10A175.90 (12)C12B—C7B—C8B—C9B179.02 (13)
C19A—C14A—C15A—C16A0.3 (2)C19B—C14B—C15B—C16B1.3 (2)
C13A—C14A—C15A—C16A177.00 (13)C13B—C14B—C15B—C16B176.75 (13)
C15A—C14A—C19A—C18A0.9 (2)C7B—C6B—C11B—C10B0.9 (2)
C13A—C14A—C19A—C18A176.42 (14)N3B—C6B—C11B—C10B179.50 (14)
C7A—C8A—C9A—C10A0.5 (2)C14B—C19B—C18B—C17B0.7 (2)
C8A—C9A—C10A—C11A1.3 (2)C14B—C15B—C16B—C17B0.4 (2)
C6A—C11A—C10A—C9A0.8 (2)C7B—C8B—C9B—C10B0.7 (2)
C14A—C19A—C18A—C17A0.7 (3)C6B—C11B—C10B—C9B0.3 (2)
C14A—C15A—C16A—C17A0.5 (3)C8B—C9B—C10B—C11B0.5 (3)
C15A—C16A—C17A—C18A0.7 (3)C19B—C18B—C17B—C16B0.3 (3)
C19A—C18A—C17A—C16A0.1 (3)C15B—C16B—C17B—C18B0.4 (3)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+2, z+1; (iii) x+1, y+2, z; (iv) x1, y, z+1; (v) x+2, y+2, z; (vi) x+1, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3A···O5Aii0.821.912.7240 (18)169
O3B—H3B···O5Bv0.821.902.7091 (19)169
Symmetry codes: (ii) x+1, y+2, z+1; (v) x+2, y+2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds