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Conformational analyses and structural comparison of the title spiropyrazolebarbiturate, C19H16N4O4·C3H6O·H2O, and the related structure 3-bromo-1,4-diphenyl-1,2,7,9-tetraazaspiro[5.4]dec-2-ene-6,8,10-trione acetone solvate [Bruno, Rotondo, Nicoló, Foti, Grassi & Risitano (2005). Acta Cryst. E61, o142-o144], are presented. Both compounds were synthesized by cycloaddition of C-H and C-Br nitrilimines, generated in situ, starting from the same substrate [Foti, Grassi & Risitano (2005). Synlett. Submitted]. However, different experimental conditions led to products with reverse regioselectivity.
Supporting information
CCDC reference: 262474
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.170
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.626
Test value = 0.600
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.33
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.63 e/A 3
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1989); cell refinement: XSCANS; data reduction: XPREPW (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Bruker, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and WinGX-PC (Version 1.6.4.05; Farrugia, 1999).
4-(4-Methoxyphenyl)-3-phenyl-2,4,8,10-tetraazaspiro[5.4]dec-1-ene-6,8,10-trione
acetone solvate monohydrate
top
Crystal data top
C19H16N4O4·C3H6O·H2O | F(000) = 928 |
Mr = 440.45 | Dx = 1.298 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 61 reflections |
a = 6.1539 (10) Å | θ = 5.7–20.5° |
b = 10.7908 (17) Å | µ = 0.10 mm−1 |
c = 34.057 (6) Å | T = 298 K |
β = 94.504 (14)° | Prismatic, colourless |
V = 2254.6 (6) Å3 | 0.58 × 0.48 × 0.34 mm |
Z = 4 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.022 |
ω scans | θmax = 25°, θmin = 2.2° |
Absorption correction: ψ scan (North et al., 1968) | h = −1→6 |
Tmin = 0.873, Tmax = 0.964 | k = −12→12 |
10362 measured reflections | l = −40→40 |
3815 independent reflections | 3 standard reflections every 197 reflections |
2715 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0825P)2 + 1.0558P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.055 | (Δ/σ)max = 0.004 |
wR(F2) = 0.17 | Δρmax = 0.63 e Å−3 |
S = 1.05 | Δρmin = −0.19 e Å−3 |
3815 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
297 parameters | Extinction coefficient: 0.0082 (16) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6797 (3) | 0.7143 (2) | 0.09216 (6) | 0.0686 (6) | |
O2 | 0.2571 (3) | 0.4425 (2) | 0.02063 (6) | 0.0700 (6) | |
O3 | 0.0064 (3) | 0.8323 (2) | 0.03206 (6) | 0.0697 (6) | |
C1 | 0.5025 (4) | 0.6899 (3) | 0.07625 (7) | 0.0525 (7) | |
N2 | 0.4623 (3) | 0.5767 (2) | 0.05858 (6) | 0.0563 (6) | |
H2 | 0.5613 | 0.5208 | 0.0623 | 0.068* | |
C3 | 0.2785 (4) | 0.5455 (3) | 0.03557 (8) | 0.0552 (7) | |
N4 | 0.1231 (3) | 0.6350 (2) | 0.02953 (6) | 0.0579 (6) | |
H4 | 0.006 | 0.6147 | 0.0155 | 0.069* | |
C5 | 0.1349 (4) | 0.7539 (3) | 0.04354 (8) | 0.0529 (7) | |
C6 | 0.3094 (4) | 0.7770 (2) | 0.07688 (7) | 0.0494 (6) | |
C7 | 0.3824 (5) | 0.9102 (3) | 0.07878 (8) | 0.0595 (7) | |
H7 | 0.4433 | 0.9493 | 0.0579 | 0.071* | |
N8 | 0.3547 (4) | 0.9653 (2) | 0.11101 (7) | 0.0562 (6) | |
N9 | 0.2653 (3) | 0.88387 (19) | 0.13655 (6) | 0.0496 (5) | |
C10 | 0.1973 (4) | 0.7664 (2) | 0.11719 (7) | 0.0451 (6) | |
H10 | 0.0386 | 0.7671 | 0.1116 | 0.054* | |
C11 | 0.1520 (4) | 0.9336 (2) | 0.16715 (8) | 0.0506 (6) | |
C12 | −0.0110 (5) | 0.8662 (3) | 0.18369 (9) | 0.0621 (8) | |
H12 | −0.0496 | 0.7882 | 0.1738 | 0.075* | |
C13 | −0.1150 (6) | 0.9143 (3) | 0.21460 (10) | 0.0747 (9) | |
H13 | −0.2241 | 0.8685 | 0.2253 | 0.09* | |
C14 | −0.0599 (6) | 1.0294 (3) | 0.23004 (10) | 0.0801 (10) | |
H14 | −0.1285 | 1.0607 | 0.2513 | 0.096* | |
C15 | 0.0981 (6) | 1.0966 (3) | 0.21334 (9) | 0.0775 (10) | |
H15 | 0.1334 | 1.1752 | 0.223 | 0.093* | |
C16 | 0.2059 (5) | 1.0503 (3) | 0.18249 (9) | 0.0643 (8) | |
H16 | 0.3145 | 1.0968 | 0.172 | 0.077* | |
C17 | 0.2602 (4) | 0.6541 (2) | 0.14201 (7) | 0.0448 (6) | |
C18 | 0.1324 (4) | 0.5477 (3) | 0.13891 (8) | 0.0562 (7) | |
H18 | 0.0046 | 0.5474 | 0.1224 | 0.067* | |
C19 | 0.1932 (5) | 0.4428 (3) | 0.15998 (9) | 0.0640 (8) | |
H19 | 0.1063 | 0.3723 | 0.1576 | 0.077* | |
C20 | 0.3833 (5) | 0.4418 (3) | 0.18469 (8) | 0.0580 (7) | |
C21 | 0.5100 (5) | 0.5472 (3) | 0.18857 (8) | 0.0593 (7) | |
H21 | 0.6367 | 0.5477 | 0.2053 | 0.071* | |
C22 | 0.4472 (4) | 0.6521 (2) | 0.16731 (8) | 0.0526 (7) | |
H22 | 0.5328 | 0.7231 | 0.1701 | 0.063* | |
O4 | 0.4295 (4) | 0.33269 (19) | 0.20402 (7) | 0.0783 (7) | |
C23 | 0.6243 (6) | 0.3266 (4) | 0.22933 (12) | 0.0954 (12) | |
H23A | 0.6356 | 0.2464 | 0.2416 | 0.143* | |
H23B | 0.6211 | 0.3893 | 0.2493 | 0.143* | |
H23C | 0.7477 | 0.3399 | 0.2143 | 0.143* | |
O6 | 0.4508 (4) | 0.1929 (3) | 0.00438 (9) | 0.1016 (9) | |
H6A | 0.3145 | 0.1534 | −0.0033 | 0.152* | |
H6B | 0.411 | 0.2736 | 0.0133 | 0.152* | |
O5 | 0.7859 (4) | 0.3853 (3) | 0.06342 (8) | 0.1055 (9) | |
C24 | 0.7947 (6) | 0.2704 (5) | 0.08364 (12) | 0.0941 (12) | |
C25 | 0.6377 (11) | 0.2547 (6) | 0.11286 (19) | 0.167 (3) | |
H25A | 0.5003 | 0.2292 | 0.1001 | 0.25* | |
H25B | 0.6196 | 0.3318 | 0.1263 | 0.25* | |
H25C | 0.6892 | 0.1927 | 0.1315 | 0.25* | |
C26 | 0.9403 (11) | 0.1750 (6) | 0.07292 (17) | 0.173 (3) | |
H26A | 0.9128 | 0.1564 | 0.0454 | 0.259* | |
H26B | 0.9177 | 0.1019 | 0.0881 | 0.259* | |
H26C | 1.0881 | 0.2026 | 0.078 | 0.259* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0349 (10) | 0.0963 (15) | 0.0727 (13) | −0.0060 (10) | −0.0066 (9) | −0.0200 (11) |
O2 | 0.0532 (12) | 0.0738 (14) | 0.0807 (14) | 0.0064 (10) | −0.0080 (10) | −0.0338 (12) |
O3 | 0.0610 (12) | 0.0781 (14) | 0.0670 (12) | 0.0164 (11) | −0.0131 (10) | −0.0059 (11) |
C1 | 0.0362 (14) | 0.0731 (18) | 0.0477 (14) | −0.0027 (12) | −0.0002 (11) | −0.0123 (13) |
N2 | 0.0355 (12) | 0.0699 (15) | 0.0621 (13) | 0.0079 (10) | −0.0045 (10) | −0.0193 (12) |
C3 | 0.0396 (15) | 0.0704 (18) | 0.0548 (15) | 0.0018 (13) | −0.0008 (12) | −0.0162 (14) |
N4 | 0.0385 (12) | 0.0717 (15) | 0.0610 (13) | 0.0050 (11) | −0.0121 (10) | −0.0224 (12) |
C5 | 0.0427 (15) | 0.0665 (17) | 0.0491 (14) | 0.0026 (13) | 0.0008 (12) | −0.0093 (13) |
C6 | 0.0382 (14) | 0.0609 (16) | 0.0485 (14) | −0.0021 (12) | 0.0003 (11) | −0.0103 (12) |
C7 | 0.0579 (17) | 0.0667 (18) | 0.0548 (16) | −0.0119 (14) | 0.0093 (13) | −0.0045 (14) |
N8 | 0.0557 (14) | 0.0551 (13) | 0.0587 (14) | −0.0117 (11) | 0.0101 (11) | −0.0052 (11) |
N9 | 0.0508 (13) | 0.0454 (12) | 0.0531 (12) | −0.0082 (10) | 0.0085 (10) | −0.0077 (10) |
C10 | 0.0337 (13) | 0.0517 (14) | 0.0496 (14) | −0.0036 (11) | 0.0007 (10) | −0.0102 (11) |
C11 | 0.0510 (15) | 0.0489 (15) | 0.0521 (14) | 0.0013 (12) | 0.0044 (12) | −0.0042 (12) |
C12 | 0.0593 (18) | 0.0575 (17) | 0.0714 (18) | −0.0068 (14) | 0.0163 (14) | −0.0115 (14) |
C13 | 0.073 (2) | 0.074 (2) | 0.082 (2) | 0.0015 (17) | 0.0337 (17) | −0.0009 (17) |
C14 | 0.103 (3) | 0.067 (2) | 0.075 (2) | 0.013 (2) | 0.035 (2) | −0.0078 (17) |
C15 | 0.111 (3) | 0.0526 (17) | 0.072 (2) | 0.0004 (18) | 0.025 (2) | −0.0134 (15) |
C16 | 0.083 (2) | 0.0500 (15) | 0.0619 (17) | −0.0090 (15) | 0.0162 (15) | −0.0082 (14) |
C17 | 0.0381 (13) | 0.0463 (14) | 0.0495 (13) | −0.0036 (11) | 0.0011 (11) | −0.0103 (11) |
C18 | 0.0469 (15) | 0.0560 (16) | 0.0641 (16) | −0.0088 (13) | −0.0052 (13) | −0.0064 (13) |
C19 | 0.0613 (18) | 0.0509 (16) | 0.079 (2) | −0.0143 (14) | 0.0010 (15) | −0.0051 (15) |
C20 | 0.0611 (18) | 0.0516 (16) | 0.0618 (17) | 0.0045 (14) | 0.0081 (14) | −0.0003 (13) |
C21 | 0.0516 (16) | 0.0634 (18) | 0.0610 (16) | −0.0013 (14) | −0.0075 (13) | −0.0016 (14) |
C22 | 0.0474 (15) | 0.0495 (15) | 0.0595 (16) | −0.0091 (12) | −0.0059 (12) | −0.0044 (12) |
O4 | 0.0859 (16) | 0.0577 (12) | 0.0904 (16) | 0.0035 (11) | 0.0008 (13) | 0.0128 (11) |
C23 | 0.087 (3) | 0.088 (3) | 0.110 (3) | 0.021 (2) | −0.001 (2) | 0.031 (2) |
O6 | 0.0757 (17) | 0.128 (2) | 0.0986 (19) | 0.0208 (16) | −0.0058 (14) | −0.0228 (17) |
O5 | 0.0818 (17) | 0.137 (2) | 0.0973 (19) | 0.0265 (17) | 0.0048 (14) | −0.0056 (18) |
C24 | 0.071 (2) | 0.135 (4) | 0.076 (2) | −0.018 (2) | 0.0027 (19) | −0.036 (3) |
C25 | 0.184 (6) | 0.149 (5) | 0.181 (6) | −0.051 (4) | 0.102 (5) | −0.037 (4) |
C26 | 0.181 (6) | 0.204 (7) | 0.132 (4) | 0.111 (5) | 0.003 (4) | 0.004 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.208 (3) | C15—H15 | 0.93 |
O2—C3 | 1.225 (3) | C16—H16 | 0.93 |
O3—C5 | 1.202 (3) | C17—C22 | 1.383 (3) |
C1—N2 | 1.376 (3) | C17—C18 | 1.391 (4) |
C1—C6 | 1.517 (4) | C18—C19 | 1.376 (4) |
N2—C3 | 1.367 (3) | C18—H18 | 0.93 |
N2—H2 | 0.86 | C19—C20 | 1.386 (4) |
C3—N4 | 1.364 (3) | C19—H19 | 0.93 |
N4—C5 | 1.369 (3) | C20—O4 | 1.368 (3) |
N4—H4 | 0.86 | C20—C21 | 1.379 (4) |
C5—C6 | 1.521 (3) | C21—C22 | 1.382 (4) |
C6—C7 | 1.506 (4) | C21—H21 | 0.93 |
C6—C10 | 1.589 (3) | C22—H22 | 0.93 |
C7—N8 | 1.272 (3) | O4—C23 | 1.422 (4) |
C7—H7 | 0.93 | C23—H23A | 0.96 |
N8—N9 | 1.381 (3) | C23—H23B | 0.96 |
N9—C11 | 1.405 (3) | C23—H23C | 0.96 |
N9—C10 | 1.475 (3) | O6—H6A | 0.9595 |
C10—C17 | 1.510 (4) | O6—H6B | 0.9595 |
C10—H10 | 0.98 | O5—C24 | 1.417 (5) |
C11—C12 | 1.393 (4) | C24—C26 | 1.432 (6) |
C11—C16 | 1.393 (4) | C24—C25 | 1.450 (6) |
C12—C13 | 1.376 (4) | C25—H25A | 0.96 |
C12—H12 | 0.93 | C25—H25B | 0.96 |
C13—C14 | 1.381 (5) | C25—H25C | 0.96 |
C13—H13 | 0.93 | C26—H26A | 0.96 |
C14—C15 | 1.372 (5) | C26—H26B | 0.96 |
C14—H14 | 0.93 | C26—H26C | 0.96 |
C15—C16 | 1.380 (4) | | |
| | | |
O1—C1—N2 | 121.0 (3) | C14—C15—H15 | 119.2 |
O1—C1—C6 | 122.6 (2) | C16—C15—H15 | 119.2 |
N2—C1—C6 | 116.3 (2) | C15—C16—C11 | 119.9 (3) |
C3—N2—C1 | 125.6 (2) | C15—C16—H16 | 120.1 |
C3—N2—H2 | 117.2 | C11—C16—H16 | 120.1 |
C1—N2—H2 | 117.2 | C22—C17—C18 | 118.2 (2) |
O2—C3—N4 | 121.9 (2) | C22—C17—C10 | 121.7 (2) |
O2—C3—N2 | 121.3 (3) | C18—C17—C10 | 120.1 (2) |
N4—C3—N2 | 116.8 (2) | C19—C18—C17 | 120.7 (2) |
C3—N4—C5 | 126.5 (2) | C19—C18—H18 | 119.6 |
C3—N4—H4 | 116.8 | C17—C18—H18 | 119.6 |
C5—N4—H4 | 116.8 | C18—C19—C20 | 120.3 (3) |
O3—C5—N4 | 122.1 (2) | C18—C19—H19 | 119.8 |
O3—C5—C6 | 122.4 (2) | C20—C19—H19 | 119.8 |
N4—C5—C6 | 115.4 (2) | O4—C20—C21 | 124.7 (3) |
C7—C6—C1 | 111.2 (2) | O4—C20—C19 | 115.6 (3) |
C7—C6—C5 | 112.3 (2) | C21—C20—C19 | 119.7 (3) |
C1—C6—C5 | 113.3 (2) | C20—C21—C22 | 119.5 (2) |
C7—C6—C10 | 100.4 (2) | C20—C21—H21 | 120.3 |
C1—C6—C10 | 111.2 (2) | C22—C21—H21 | 120.3 |
C5—C6—C10 | 107.7 (2) | C21—C22—C17 | 121.6 (2) |
N8—C7—C6 | 115.1 (3) | C21—C22—H22 | 119.2 |
N8—C7—H7 | 122.5 | C17—C22—H22 | 119.2 |
C6—C7—H7 | 122.5 | C20—O4—C23 | 117.7 (3) |
C7—N8—N9 | 109.4 (2) | O4—C23—H23A | 109.5 |
N8—N9—C11 | 118.0 (2) | O4—C23—H23B | 109.5 |
N8—N9—C10 | 112.29 (19) | H23A—C23—H23B | 109.5 |
C11—N9—C10 | 121.3 (2) | O4—C23—H23C | 109.5 |
N9—C10—C17 | 112.84 (19) | H23A—C23—H23C | 109.5 |
N9—C10—C6 | 101.33 (19) | H23B—C23—H23C | 109.5 |
C17—C10—C6 | 115.6 (2) | H6A—O6—H6B | 104.5 |
N9—C10—H10 | 108.9 | O5—C24—C26 | 120.4 (4) |
C17—C10—H10 | 108.9 | O5—C24—C25 | 115.7 (4) |
C6—C10—H10 | 108.9 | C26—C24—C25 | 123.7 (6) |
C12—C11—C16 | 118.6 (3) | C24—C25—H25A | 109.5 |
C12—C11—N9 | 121.0 (2) | C24—C25—H25B | 109.5 |
C16—C11—N9 | 120.4 (2) | H25A—C25—H25B | 109.5 |
C13—C12—C11 | 120.3 (3) | C24—C25—H25C | 109.5 |
C13—C12—H12 | 119.8 | H25A—C25—H25C | 109.5 |
C11—C12—H12 | 119.8 | H25B—C25—H25C | 109.5 |
C12—C13—C14 | 121.0 (3) | C24—C26—H26A | 109.5 |
C12—C13—H13 | 119.5 | C24—C26—H26B | 109.5 |
C14—C13—H13 | 119.5 | H26A—C26—H26B | 109.5 |
C15—C14—C13 | 118.6 (3) | C24—C26—H26C | 109.5 |
C15—C14—H14 | 120.7 | H26A—C26—H26C | 109.5 |
C13—C14—H14 | 120.7 | H26B—C26—H26C | 109.5 |
C14—C15—C16 | 121.5 (3) | | |
| | | |
O1—C1—N2—C3 | −171.0 (3) | C5—C6—C10—N9 | −127.9 (2) |
C6—C1—N2—C3 | 13.0 (4) | C7—C6—C10—C17 | −132.7 (2) |
C1—N2—C3—O2 | 179.3 (3) | C1—C6—C10—C17 | −15.0 (3) |
C1—N2—C3—N4 | 0.5 (4) | C5—C6—C10—C17 | 109.7 (2) |
O2—C3—N4—C5 | −177.3 (3) | N8—N9—C11—C12 | 154.0 (2) |
N2—C3—N4—C5 | 1.5 (4) | C10—N9—C11—C12 | 8.3 (4) |
C3—N4—C5—O3 | 168.4 (3) | N8—N9—C11—C16 | −28.2 (4) |
C3—N4—C5—C6 | −16.4 (4) | C10—N9—C11—C16 | −173.9 (2) |
O1—C1—C6—C7 | 30.4 (4) | C16—C11—C12—C13 | −0.2 (4) |
N2—C1—C6—C7 | −153.7 (2) | N9—C11—C12—C13 | 177.6 (3) |
O1—C1—C6—C5 | 158.0 (3) | C11—C12—C13—C14 | −0.4 (5) |
N2—C1—C6—C5 | −26.1 (3) | C12—C13—C14—C15 | 1.4 (6) |
O1—C1—C6—C10 | −80.6 (3) | C13—C14—C15—C16 | −1.8 (6) |
N2—C1—C6—C10 | 95.4 (3) | C14—C15—C16—C11 | 1.2 (5) |
O3—C5—C6—C7 | −30.3 (4) | C12—C11—C16—C15 | −0.2 (5) |
N4—C5—C6—C7 | 154.5 (2) | N9—C11—C16—C15 | −178.0 (3) |
O3—C5—C6—C1 | −157.3 (3) | N9—C10—C17—C22 | −32.3 (3) |
N4—C5—C6—C1 | 27.5 (3) | C6—C10—C17—C22 | 83.7 (3) |
O3—C5—C6—C10 | 79.3 (3) | N9—C10—C17—C18 | 149.7 (2) |
N4—C5—C6—C10 | −95.9 (3) | C6—C10—C17—C18 | −94.3 (3) |
C1—C6—C7—N8 | −111.4 (3) | C22—C17—C18—C19 | −1.1 (4) |
C5—C6—C7—N8 | 120.5 (3) | C10—C17—C18—C19 | 177.0 (2) |
C10—C6—C7—N8 | 6.4 (3) | C17—C18—C19—C20 | 0.0 (4) |
C6—C7—N8—N9 | 1.1 (3) | C18—C19—C20—O4 | −179.5 (3) |
C7—N8—N9—C11 | −157.7 (2) | C18—C19—C20—C21 | 1.0 (4) |
C7—N8—N9—C10 | −9.1 (3) | O4—C20—C21—C22 | 179.7 (3) |
N8—N9—C10—C17 | 136.5 (2) | C19—C20—C21—C22 | −0.9 (4) |
C11—N9—C10—C17 | −76.0 (3) | C20—C21—C22—C17 | −0.3 (4) |
N8—N9—C10—C6 | 12.3 (3) | C18—C17—C22—C21 | 1.2 (4) |
C11—N9—C10—C6 | 159.7 (2) | C10—C17—C22—C21 | −176.8 (2) |
C7—C6—C10—N9 | −10.3 (2) | C21—C20—O4—C23 | −1.3 (5) |
C1—C6—C10—N9 | 107.4 (2) | C19—C20—O4—C23 | 179.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O2i | 0.86 | 2.05 | 2.909 (3) | 175 |
O6—H6A···O3i | 0.96 | 2.14 | 2.997 (3) | 148 |
C10—H10···O1ii | 0.98 | 2.33 | 3.280 (3) | 164 |
O6—H6B···O2 | 0.96 | 2.08 | 3.014 (4) | 165 |
N2—H2···O5 | 0.86 | 2.01 | 2.865 (4) | 172 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z. |
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