Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
28H
40N
4O
4·CHCl
3, crystallizes with two half-molecules of the macrocycle and one molecule of chloroform solvent in the asymmetric unit. Each macrocycle lies on a centre of inversion. The molecular structure is stabilized by N—H
O and C—H
O intramolecular interactions, and the crystal packing is stabilized by C—H
O and C—H
π intermolecular interactions.
Supporting information
CCDC reference: 620730
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.161
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C29
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O2
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O4
PLAT432_ALERT_2_C Short Inter X...Y Contact Cl3 .. C3 .. 3.22 Ang.
PLAT731_ALERT_1_C Bond Calc 0.898(19), Rep 0.899(9) ...... 2.11 su-Ra
N2 -H2B 1.555 1.555
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
1,8-Bis(3-formyl-2-oxido-5-methylbenzyl}-1,8-diaza-4,11-diazoniacyclotetradecane
chloroform solvate
top
Crystal data top
C28H40N4O4·CHCl3 | Z = 2 |
Mr = 616.01 | F(000) = 652 |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1366 (5) Å | Cell parameters from 3495 reflections |
b = 11.2816 (5) Å | θ = 2.0–25.0° |
c = 14.2124 (7) Å | µ = 0.34 mm−1 |
α = 69.564 (1)° | T = 293 K |
β = 84.559 (1)° | Block, yellow |
γ = 67.110 (1)° | 0.29 × 0.26 × 0.25 mm |
V = 1539.74 (12) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5878 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 28.0°, θmin = 2.0° |
ω scans | h = −14→14 |
17829 measured reflections | k = −14→14 |
7069 independent 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0823P)2 + 0.5118P] where P = (Fo2 + 2Fc2)/3 |
7069 reflections | (Δ/σ)max = 0.001 |
379 parameters | Δρmax = 0.69 e Å−3 |
4 restraints | Δρmin = −0.43 e Å−3 |
Special details top
Experimental. 4,11-diammonium-1,8-N,N'-bis{(3-formyl-2-oxido-5-methyl)benzyl}-1,4,8,11- tetra-azacyclotetradecane |
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 | |
C1 | 0.0050 (3) | 0.8854 (3) | 0.7527 (2) | 0.0834 (8) | |
H1A | 0.0310 | 0.9424 | 0.7761 | 0.125* | |
H1B | −0.0459 | 0.8452 | 0.8021 | 0.125* | |
H1C | −0.0463 | 0.9397 | 0.6908 | 0.125* | |
C2 | 0.1251 (2) | 0.7732 (2) | 0.73525 (15) | 0.0538 (5) | |
C3 | 0.2454 (2) | 0.73944 (19) | 0.77505 (14) | 0.0497 (4) | |
H3 | 0.2542 | 0.7878 | 0.8135 | 0.060* | |
C4 | 0.35595 (18) | 0.63460 (18) | 0.76012 (12) | 0.0426 (4) | |
C5 | 0.34739 (17) | 0.55977 (17) | 0.70034 (12) | 0.0407 (4) | |
C6 | 0.22160 (17) | 0.59600 (18) | 0.65827 (12) | 0.0410 (4) | |
C7 | 0.11554 (18) | 0.6989 (2) | 0.67672 (13) | 0.0482 (4) | |
H7 | 0.0341 | 0.7201 | 0.6493 | 0.058* | |
C8 | 0.4813 (2) | 0.6005 (2) | 0.80579 (15) | 0.0532 (5) | |
H8 | 0.5528 | 0.5340 | 0.7901 | 0.064* | |
C9 | 0.20974 (18) | 0.5187 (2) | 0.59475 (13) | 0.0456 (4) | |
H9A | 0.2484 | 0.4212 | 0.6315 | 0.055* | |
H9B | 0.1182 | 0.5426 | 0.5803 | 0.055* | |
C10 | 0.19447 (18) | 0.68522 (19) | 0.42880 (13) | 0.0469 (4) | |
H10A | 0.1500 | 0.7459 | 0.4664 | 0.056* | |
H10B | 0.1284 | 0.6743 | 0.3965 | 0.056* | |
C11 | 0.27054 (19) | 0.75145 (19) | 0.34845 (13) | 0.0498 (4) | |
H11A | 0.3165 | 0.6897 | 0.3119 | 0.060* | |
H11B | 0.2094 | 0.8342 | 0.3012 | 0.060* | |
C12 | 0.3122 (2) | 0.4430 (2) | 0.45447 (14) | 0.0487 (4) | |
H12A | 0.3421 | 0.4752 | 0.3875 | 0.058* | |
H12B | 0.2356 | 0.4249 | 0.4481 | 0.058* | |
C13 | 0.4186 (2) | 0.31061 (19) | 0.51634 (15) | 0.0510 (4) | |
H13A | 0.3806 | 0.2613 | 0.5729 | 0.061* | |
H13B | 0.4574 | 0.2535 | 0.4753 | 0.061* | |
C14 | 0.6322 (2) | 0.21277 (18) | 0.61211 (16) | 0.0529 (5) | |
H14A | 0.6754 | 0.1594 | 0.5692 | 0.063* | |
H14B | 0.5989 | 0.1570 | 0.6680 | 0.063* | |
C15 | 0.1705 (2) | 1.0779 (3) | 0.54136 (18) | 0.0699 (6) | |
H15A | 0.2104 | 1.0925 | 0.4776 | 0.105* | |
H15B | 0.0916 | 1.1557 | 0.5374 | 0.105* | |
H15C | 0.1506 | 0.9976 | 0.5583 | 0.105* | |
C16 | 0.26353 (19) | 1.0588 (2) | 0.62128 (14) | 0.0483 (4) | |
C17 | 0.39104 (19) | 0.97072 (19) | 0.63108 (14) | 0.0468 (4) | |
H17 | 0.4204 | 0.9202 | 0.5881 | 0.056* | |
C18 | 0.47940 (18) | 0.95343 (17) | 0.70331 (12) | 0.0413 (4) | |
C19 | 0.43978 (17) | 1.03102 (16) | 0.76933 (11) | 0.0384 (3) | |
C20 | 0.30609 (17) | 1.12130 (17) | 0.75957 (12) | 0.0407 (4) | |
C21 | 0.22303 (18) | 1.13237 (19) | 0.68785 (13) | 0.0453 (4) | |
H21 | 0.1362 | 1.1914 | 0.6836 | 0.054* | |
C22 | 0.6127 (2) | 0.8550 (2) | 0.71203 (15) | 0.0525 (4) | |
H22 | 0.6691 | 0.8502 | 0.7587 | 0.063* | |
C23 | 0.26149 (19) | 1.21183 (18) | 0.82268 (13) | 0.0463 (4) | |
H23A | 0.3079 | 1.2732 | 0.8048 | 0.056* | |
H23B | 0.1692 | 1.2673 | 0.8079 | 0.056* | |
C24 | 0.1927 (2) | 1.0639 (2) | 0.96753 (15) | 0.0567 (5) | |
H24A | 0.1744 | 1.0364 | 0.9148 | 0.068* | |
H24B | 0.1111 | 1.1275 | 0.9818 | 0.068* | |
C25 | 0.2446 (2) | 0.9387 (2) | 1.06130 (16) | 0.0593 (5) | |
H25A | 0.2662 | 0.9664 | 1.1127 | 0.071* | |
H25B | 0.1755 | 0.9051 | 1.0858 | 0.071* | |
C26 | 0.2798 (2) | 1.2214 (2) | 0.98808 (14) | 0.0529 (5) | |
H26A | 0.2798 | 1.1724 | 1.0593 | 0.063* | |
H26B | 0.1998 | 1.3024 | 0.9697 | 0.063* | |
C27 | 0.3952 (2) | 1.26439 (19) | 0.96819 (15) | 0.0542 (5) | |
H27A | 0.3816 | 1.3363 | 0.9032 | 0.065* | |
H27B | 0.4030 | 1.3004 | 1.0191 | 0.065* | |
C28 | 0.6367 (2) | 1.1780 (2) | 0.95207 (17) | 0.0601 (5) | |
H28A | 0.6539 | 1.1993 | 1.0086 | 0.072* | |
H28B | 0.6214 | 1.2585 | 0.8925 | 0.072* | |
C29 | 0.1760 (2) | 0.5116 (2) | 0.13106 (16) | 0.0566 (5) | |
H29 | 0.2613 | 0.4381 | 0.1560 | 0.068* | |
N1 | 0.27589 (14) | 0.55101 (14) | 0.49936 (10) | 0.0401 (3) | |
N2 | 0.52114 (15) | 0.33812 (14) | 0.55384 (12) | 0.0431 (3) | |
H2A | 0.486 (2) | 0.385 (2) | 0.5965 (16) | 0.073 (7)* | |
H2B | 0.554 (2) | 0.3862 (19) | 0.5012 (12) | 0.052 (6)* | |
N3 | 0.28326 (15) | 1.13394 (15) | 0.93124 (10) | 0.0438 (3) | |
N4 | 0.51743 (16) | 1.14565 (15) | 0.96955 (11) | 0.0448 (3) | |
H4A | 0.513 (2) | 1.114 (2) | 0.9202 (14) | 0.062 (6)* | |
H4B | 0.522 (2) | 1.0807 (18) | 1.0299 (10) | 0.057 (6)* | |
O1 | 0.50187 (18) | 0.65046 (18) | 0.86273 (12) | 0.0709 (4) | |
O2 | 0.44953 (13) | 0.46180 (15) | 0.68592 (12) | 0.0585 (4) | |
O3 | 0.65720 (17) | 0.77854 (18) | 0.66422 (14) | 0.0749 (5) | |
O4 | 0.52180 (12) | 1.02169 (13) | 0.83351 (9) | 0.0454 (3) | |
Cl1 | 0.13923 (8) | 0.62388 (9) | 0.19877 (6) | 0.0893 (2) | |
Cl2 | 0.06037 (7) | 0.43912 (8) | 0.14658 (6) | 0.0892 (2) | |
Cl3 | 0.18474 (9) | 0.59785 (8) | 0.00379 (5) | 0.0924 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0694 (15) | 0.0706 (15) | 0.0936 (19) | 0.0019 (12) | 0.0147 (14) | −0.0436 (15) |
C2 | 0.0547 (11) | 0.0479 (10) | 0.0485 (10) | −0.0074 (8) | 0.0127 (8) | −0.0207 (8) |
C3 | 0.0643 (12) | 0.0436 (9) | 0.0426 (9) | −0.0167 (8) | 0.0104 (8) | −0.0226 (8) |
C4 | 0.0516 (10) | 0.0415 (9) | 0.0353 (8) | −0.0159 (7) | 0.0043 (7) | −0.0164 (7) |
C5 | 0.0450 (9) | 0.0410 (8) | 0.0357 (8) | −0.0127 (7) | 0.0047 (7) | −0.0175 (7) |
C6 | 0.0449 (9) | 0.0459 (9) | 0.0325 (8) | −0.0176 (7) | 0.0072 (6) | −0.0148 (7) |
C7 | 0.0425 (9) | 0.0540 (10) | 0.0395 (9) | −0.0117 (8) | 0.0058 (7) | −0.0143 (8) |
C8 | 0.0609 (11) | 0.0544 (11) | 0.0506 (10) | −0.0207 (9) | −0.0017 (9) | −0.0255 (9) |
C9 | 0.0490 (9) | 0.0553 (10) | 0.0388 (8) | −0.0246 (8) | 0.0045 (7) | −0.0187 (8) |
C10 | 0.0416 (9) | 0.0517 (10) | 0.0377 (8) | −0.0057 (7) | −0.0021 (7) | −0.0166 (8) |
C11 | 0.0527 (10) | 0.0426 (9) | 0.0357 (8) | −0.0021 (8) | −0.0008 (7) | −0.0093 (7) |
C12 | 0.0603 (11) | 0.0524 (10) | 0.0408 (9) | −0.0224 (9) | 0.0010 (8) | −0.0230 (8) |
C13 | 0.0667 (12) | 0.0431 (9) | 0.0512 (10) | −0.0214 (9) | 0.0035 (9) | −0.0250 (8) |
C14 | 0.0580 (11) | 0.0328 (8) | 0.0567 (11) | −0.0080 (8) | 0.0050 (9) | −0.0133 (8) |
C15 | 0.0636 (13) | 0.0947 (17) | 0.0595 (13) | −0.0228 (12) | −0.0082 (10) | −0.0412 (13) |
C16 | 0.0550 (10) | 0.0546 (10) | 0.0398 (9) | −0.0210 (9) | −0.0022 (8) | −0.0200 (8) |
C17 | 0.0588 (11) | 0.0464 (9) | 0.0407 (9) | −0.0183 (8) | 0.0018 (8) | −0.0230 (8) |
C18 | 0.0505 (9) | 0.0390 (8) | 0.0345 (8) | −0.0149 (7) | 0.0016 (7) | −0.0151 (7) |
C19 | 0.0486 (9) | 0.0358 (8) | 0.0292 (7) | −0.0146 (7) | −0.0001 (6) | −0.0104 (6) |
C20 | 0.0499 (9) | 0.0389 (8) | 0.0309 (7) | −0.0130 (7) | −0.0005 (7) | −0.0132 (6) |
C21 | 0.0467 (9) | 0.0482 (9) | 0.0373 (8) | −0.0129 (8) | −0.0013 (7) | −0.0153 (7) |
C22 | 0.0554 (11) | 0.0535 (10) | 0.0474 (10) | −0.0120 (9) | 0.0000 (8) | −0.0252 (9) |
C23 | 0.0531 (10) | 0.0423 (9) | 0.0346 (8) | −0.0049 (7) | −0.0041 (7) | −0.0163 (7) |
C24 | 0.0501 (10) | 0.0751 (14) | 0.0453 (10) | −0.0222 (10) | 0.0031 (8) | −0.0230 (10) |
C25 | 0.0644 (12) | 0.0739 (14) | 0.0459 (10) | −0.0355 (11) | 0.0085 (9) | −0.0188 (10) |
C26 | 0.0589 (11) | 0.0527 (10) | 0.0396 (9) | −0.0041 (9) | −0.0027 (8) | −0.0253 (8) |
C27 | 0.0734 (13) | 0.0414 (9) | 0.0460 (10) | −0.0116 (9) | −0.0088 (9) | −0.0217 (8) |
C28 | 0.0770 (14) | 0.0577 (12) | 0.0564 (12) | −0.0378 (11) | 0.0035 (10) | −0.0184 (10) |
C29 | 0.0506 (11) | 0.0587 (12) | 0.0585 (12) | −0.0194 (9) | −0.0030 (9) | −0.0177 (10) |
N1 | 0.0452 (7) | 0.0424 (7) | 0.0324 (7) | −0.0134 (6) | 0.0015 (6) | −0.0162 (6) |
N2 | 0.0501 (8) | 0.0330 (7) | 0.0451 (8) | −0.0128 (6) | 0.0076 (6) | −0.0168 (6) |
N3 | 0.0492 (8) | 0.0475 (8) | 0.0326 (7) | −0.0116 (7) | 0.0009 (6) | −0.0187 (6) |
N4 | 0.0597 (9) | 0.0395 (8) | 0.0364 (7) | −0.0181 (7) | −0.0030 (6) | −0.0138 (6) |
O1 | 0.0853 (11) | 0.0798 (11) | 0.0633 (9) | −0.0329 (9) | −0.0093 (8) | −0.0378 (8) |
O2 | 0.0458 (7) | 0.0652 (9) | 0.0699 (9) | −0.0035 (6) | −0.0032 (6) | −0.0478 (8) |
O3 | 0.0693 (10) | 0.0773 (11) | 0.0772 (11) | −0.0033 (8) | 0.0002 (8) | −0.0523 (9) |
O4 | 0.0490 (7) | 0.0504 (7) | 0.0366 (6) | −0.0116 (5) | −0.0036 (5) | −0.0214 (5) |
Cl1 | 0.0933 (5) | 0.1053 (5) | 0.0847 (5) | −0.0307 (4) | −0.0087 (4) | −0.0548 (4) |
Cl2 | 0.0839 (5) | 0.0919 (5) | 0.1061 (6) | −0.0537 (4) | 0.0083 (4) | −0.0285 (4) |
Cl3 | 0.1177 (6) | 0.0947 (5) | 0.0660 (4) | −0.0497 (5) | 0.0198 (4) | −0.0221 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.514 (3) | C16—C17 | 1.366 (3) |
C1—H1A | 0.96 | C16—C21 | 1.401 (3) |
C1—H1B | 0.96 | C17—C18 | 1.401 (3) |
C1—H1C | 0.96 | C17—H17 | 0.93 |
C2—C3 | 1.362 (3) | C18—C19 | 1.427 (2) |
C2—C7 | 1.407 (3) | C18—C22 | 1.452 (3) |
C3—C4 | 1.398 (3) | C19—O4 | 1.301 (2) |
C3—H3 | 0.93 | C19—C20 | 1.426 (2) |
C4—C5 | 1.422 (2) | C20—C21 | 1.382 (2) |
C4—C8 | 1.448 (3) | C20—C23 | 1.502 (2) |
C5—O2 | 1.301 (2) | C21—H21 | 0.93 |
C5—C6 | 1.425 (2) | C22—O3 | 1.210 (2) |
C6—C7 | 1.378 (2) | C22—H22 | 0.93 |
C6—C9 | 1.501 (2) | C23—N3 | 1.473 (2) |
C7—H7 | 0.93 | C23—H23A | 0.97 |
C8—O1 | 1.217 (2) | C23—H23B | 0.97 |
C8—H8 | 0.93 | C24—N3 | 1.465 (3) |
C9—N1 | 1.479 (2) | C24—C25 | 1.517 (3) |
C9—H9A | 0.97 | C24—H24A | 0.97 |
C9—H9B | 0.97 | C24—H24B | 0.97 |
C10—N1 | 1.471 (2) | C25—C28ii | 1.513 (3) |
C10—C11 | 1.514 (3) | C25—H25A | 0.97 |
C10—H10A | 0.97 | C25—H25B | 0.97 |
C10—H10B | 0.97 | C26—N3 | 1.466 (2) |
C11—C14i | 1.504 (3) | C26—C27 | 1.512 (3) |
C11—H11A | 0.97 | C26—H26A | 0.97 |
C11—H11B | 0.97 | C26—H26B | 0.97 |
C12—N1 | 1.472 (2) | C27—N4 | 1.489 (2) |
C12—C13 | 1.521 (3) | C27—H27A | 0.97 |
C12—H12A | 0.97 | C27—H27B | 0.97 |
C12—H12B | 0.97 | C28—N4 | 1.487 (3) |
C13—N2 | 1.480 (3) | C28—C25ii | 1.513 (3) |
C13—H13A | 0.97 | C28—H28A | 0.97 |
C13—H13B | 0.97 | C28—H28B | 0.97 |
C14—N2 | 1.494 (2) | C29—Cl2 | 1.736 (2) |
C14—C11i | 1.504 (3) | C29—Cl3 | 1.743 (2) |
C14—H14A | 0.97 | C29—Cl1 | 1.753 (2) |
C14—H14B | 0.97 | C29—H29 | 0.98 |
C15—C16 | 1.512 (3) | N2—H2A | 0.902 (10) |
C15—H15A | 0.96 | N2—H2B | 0.899 (9) |
C15—H15B | 0.96 | N4—H4A | 0.905 (10) |
C15—H15C | 0.96 | N4—H4B | 0.903 (9) |
| | | |
C2—C1—H1A | 109.5 | C17—C18—C19 | 120.72 (16) |
C2—C1—H1B | 109.5 | C17—C18—C22 | 119.98 (16) |
H1A—C1—H1B | 109.5 | C19—C18—C22 | 119.30 (16) |
C2—C1—H1C | 109.5 | O4—C19—C20 | 121.95 (14) |
H1A—C1—H1C | 109.5 | O4—C19—C18 | 121.75 (16) |
H1B—C1—H1C | 109.5 | C20—C19—C18 | 116.29 (15) |
C3—C2—C7 | 117.38 (17) | C21—C20—C19 | 120.30 (15) |
C3—C2—C1 | 122.2 (2) | C21—C20—C23 | 121.16 (16) |
C7—C2—C1 | 120.4 (2) | C19—C20—C23 | 118.33 (15) |
C2—C3—C4 | 122.22 (18) | C20—C21—C16 | 123.10 (17) |
C2—C3—H3 | 118.9 | C20—C21—H21 | 118.5 |
C4—C3—H3 | 118.9 | C16—C21—H21 | 118.5 |
C3—C4—C5 | 120.77 (17) | O3—C22—C18 | 126.02 (19) |
C3—C4—C8 | 120.21 (17) | O3—C22—H22 | 117.0 |
C5—C4—C8 | 119.02 (16) | C18—C22—H22 | 117.0 |
O2—C5—C4 | 121.41 (16) | N3—C23—C20 | 112.74 (14) |
O2—C5—C6 | 121.75 (15) | N3—C23—H23A | 109.0 |
C4—C5—C6 | 116.84 (15) | C20—C23—H23A | 109.0 |
C7—C6—C5 | 119.94 (16) | N3—C23—H23B | 109.0 |
C7—C6—C9 | 122.09 (17) | C20—C23—H23B | 109.0 |
C5—C6—C9 | 117.97 (15) | H23A—C23—H23B | 107.8 |
C6—C7—C2 | 122.84 (18) | N3—C24—C25 | 113.20 (17) |
C6—C7—H7 | 118.6 | N3—C24—H24A | 108.9 |
C2—C7—H7 | 118.6 | C25—C24—H24A | 108.9 |
O1—C8—C4 | 126.2 (2) | N3—C24—H24B | 108.9 |
O1—C8—H8 | 116.9 | C25—C24—H24B | 108.9 |
C4—C8—H8 | 116.9 | H24A—C24—H24B | 107.8 |
N1—C9—C6 | 110.91 (14) | C28ii—C25—C24 | 115.44 (18) |
N1—C9—H9A | 109.5 | C28ii—C25—H25A | 108.4 |
C6—C9—H9A | 109.5 | C24—C25—H25A | 108.4 |
N1—C9—H9B | 109.5 | C28ii—C25—H25B | 108.4 |
C6—C9—H9B | 109.5 | C24—C25—H25B | 108.4 |
H9A—C9—H9B | 108.0 | H25A—C25—H25B | 107.5 |
N1—C10—C11 | 113.72 (15) | N3—C26—C27 | 111.88 (15) |
N1—C10—H10A | 108.8 | N3—C26—H26A | 109.2 |
C11—C10—H10A | 108.8 | C27—C26—H26A | 109.2 |
N1—C10—H10B | 108.8 | N3—C26—H26B | 109.2 |
C11—C10—H10B | 108.8 | C27—C26—H26B | 109.2 |
H10A—C10—H10B | 107.7 | H26A—C26—H26B | 107.9 |
C14i—C11—C10 | 114.36 (16) | N4—C27—C26 | 110.35 (15) |
C14i—C11—H11A | 108.7 | N4—C27—H27A | 109.6 |
C10—C11—H11A | 108.7 | C26—C27—H27A | 109.6 |
C14i—C11—H11B | 108.7 | N4—C27—H27B | 109.6 |
C10—C11—H11B | 108.7 | C26—C27—H27B | 109.6 |
H11A—C11—H11B | 107.6 | H27A—C27—H27B | 108.1 |
N1—C12—C13 | 112.65 (14) | N4—C28—C25ii | 112.64 (17) |
N1—C12—H12A | 109.1 | N4—C28—H28A | 109.1 |
C13—C12—H12A | 109.1 | C25ii—C28—H28A | 109.1 |
N1—C12—H12B | 109.1 | N4—C28—H28B | 109.1 |
C13—C12—H12B | 109.1 | C25ii—C28—H28B | 109.1 |
H12A—C12—H12B | 107.8 | H28A—C28—H28B | 107.8 |
N2—C13—C12 | 111.13 (15) | Cl2—C29—Cl3 | 109.77 (12) |
N2—C13—H13A | 109.4 | Cl2—C29—Cl1 | 111.25 (12) |
C12—C13—H13A | 109.4 | Cl3—C29—Cl1 | 110.06 (12) |
N2—C13—H13B | 109.4 | Cl2—C29—H29 | 108.6 |
C12—C13—H13B | 109.4 | Cl3—C29—H29 | 108.6 |
H13A—C13—H13B | 108.0 | Cl1—C29—H29 | 108.6 |
N2—C14—C11i | 111.47 (15) | C10—N1—C12 | 111.6 (1) |
N2—C14—H14A | 109.3 | C10—N1—C9 | 110.2 (1) |
C11i—C14—H14A | 109.3 | C12—N1—C9 | 112.3 (1) |
N2—C14—H14B | 109.3 | C13—N2—C14 | 114.5 (1) |
C11i—C14—H14B | 109.3 | C13—N2—H2A | 108.7 (17) |
H14A—C14—H14B | 108.0 | C14—N2—H2A | 105.8 (17) |
C16—C15—H15A | 109.5 | C13—N2—H2B | 108.9 (14) |
C16—C15—H15B | 109.5 | C14—N2—H2B | 107.6 (14) |
H15A—C15—H15B | 109.5 | H2A—N2—H2B | 111 (2) |
C16—C15—H15C | 109.5 | C24—N3—C26 | 112.6 (2) |
H15A—C15—H15C | 109.5 | C24—N3—C23 | 111.7 (2) |
H15B—C15—H15C | 109.5 | C26—N3—C23 | 111.0 (1) |
C17—C16—C21 | 116.93 (16) | C28—N4—C27 | 114.14 (16) |
C17—C16—C15 | 121.71 (18) | C28—N4—H4A | 105.5 (15) |
C21—C16—C15 | 121.36 (18) | C27—N4—H4A | 110.4 (16) |
C16—C17—C18 | 122.62 (16) | C28—N4—H4B | 112.2 (15) |
C16—C17—H17 | 118.7 | C27—N4—H4B | 105.4 (14) |
C18—C17—H17 | 118.7 | H4A—N4—H4B | 109 (2) |
| | | |
C7—C2—C3—C4 | −0.6 (3) | O4—C19—C20—C21 | 177.46 (16) |
C1—C2—C3—C4 | 179.1 (2) | C18—C19—C20—C21 | −1.3 (2) |
C2—C3—C4—C5 | 1.2 (3) | O4—C19—C20—C23 | 2.6 (2) |
C2—C3—C4—C8 | −178.66 (18) | C18—C19—C20—C23 | −176.13 (15) |
C3—C4—C5—O2 | −179.92 (17) | C19—C20—C21—C16 | −0.6 (3) |
C8—C4—C5—O2 | −0.1 (3) | C23—C20—C21—C16 | 174.16 (18) |
C3—C4—C5—C6 | −0.7 (2) | C17—C16—C21—C20 | 1.4 (3) |
C8—C4—C5—C6 | 179.14 (17) | C15—C16—C21—C20 | −177.7 (2) |
O2—C5—C6—C7 | 178.92 (17) | C17—C18—C22—O3 | −3.2 (3) |
C4—C5—C6—C7 | −0.3 (2) | C19—C18—C22—O3 | 176.4 (2) |
O2—C5—C6—C9 | −0.9 (3) | C21—C20—C23—N3 | 126.3 (2) |
C4—C5—C6—C9 | 179.95 (15) | C19—C20—C23—N3 | −58.9 (2) |
C5—C6—C7—C2 | 0.9 (3) | N3—C24—C25—C28ii | −65.6 (2) |
C9—C6—C7—C2 | −179.37 (17) | N3—C26—C27—N4 | −44.0 (2) |
C3—C2—C7—C6 | −0.4 (3) | C11—C10—N1—C12 | −76.9 (2) |
C1—C2—C7—C6 | 179.9 (2) | C11—C10—N1—C9 | 157.64 (15) |
C3—C4—C8—O1 | 4.0 (3) | C13—C12—N1—C10 | 167.81 (16) |
C5—C4—C8—O1 | −175.8 (2) | C13—C12—N1—C9 | −67.9 (2) |
C7—C6—C9—N1 | 111.7 (2) | C6—C9—N1—C10 | −77.51 (18) |
C5—C6—C9—N1 | −68.5 (2) | C6—C9—N1—C12 | 157.37 (15) |
N1—C10—C11—C14i | −64.3 (2) | C12—C13—N2—C14 | −177.72 (16) |
N1—C12—C13—N2 | −41.9 (2) | C11i—C14—N2—C13 | −177.52 (16) |
C21—C16—C17—C18 | −0.4 (3) | C25—C24—N3—C26 | −79.6 (2) |
C15—C16—C17—C18 | 178.7 (2) | C25—C24—N3—C23 | 154.77 (17) |
C16—C17—C18—C19 | −1.5 (3) | C27—C26—N3—C24 | 165.67 (16) |
C16—C17—C18—C22 | 178.06 (18) | C27—C26—N3—C23 | −68.4 (2) |
C17—C18—C19—O4 | −176.47 (16) | C20—C23—N3—C24 | −72.1 (2) |
C22—C18—C19—O4 | 4.0 (3) | C20—C23—N3—C26 | 161.39 (16) |
C17—C18—C19—C20 | 2.3 (2) | C25ii—C28—N4—C27 | −171.55 (16) |
C22—C18—C19—C20 | −177.30 (16) | C26—C27—N4—C28 | −179.16 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.90 (2) | 1.71 (2) | 2.605 (2) | 169 (2) |
N2—H2B···N1i | 0.90 (2) | 2.26 (2) | 2.909 (2) | 128 (2) |
N4—H4A···O4 | 0.90 (2) | 1.85 (2) | 2.741 (2) | 171 (2) |
N4—H4B···O4ii | 0.90 (2) | 2.01 (2) | 2.883 (2) | 163 (2) |
N4—H4B···N3ii | 0.90 (2) | 2.47 (2) | 2.984 (2) | 117 (2) |
C8—H8···O2 | 0.93 | 2.46 | 2.808 (3) | 102 |
C11—H11A···O2i | 0.97 | 2.50 | 3.231 (3) | 133 |
C14—H14B···O4iii | 0.97 | 2.59 | 3.557 (3) | 172 |
C22—H22···O4 | 0.93 | 2.49 | 2.828 (3) | 102 |
C26—H26A···O4ii | 0.97 | 2.56 | 3.213 (2) | 125 |
C27—H27B···O1ii | 0.97 | 2.39 | 3.317 (3) | 161 |
C29—H29···O1i | 0.98 | 2.46 | 3.326 (3) | 148 |
C13—H13A···Cg1iii | 0.97 | 2.58 | 3.483 (2) | 154 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) x, y−1, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.