The crystal structure of the title compound, C
17H
15BrN
2O
2, has been determined at room temperature. The indole moiety is essentially planar and the structure is stabilized by intra- and intermolecular N—H
O hydrogen bonds.
Supporting information
CCDC reference: 189894
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.084
- Data-to-parameter ratio = 16.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.43
From the CIF: _reflns_number_total 6698
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 7145
Completeness (_total/calc) 93.74%
Alert C: < 95% complete
PLAT_420 Alert C D-H Without Acceptor N(4) - H(4A) ?
PLAT_725 Alert C D-H Calc 0.96991, Rep 0.98000, Dev. 0.01 Ang.
C33 -H33B 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).
Ethyl 5-bromo-3-phenyl indole-2-carbamate
top
Crystal data top
C17H15BrN2O2 | F(000) = 1456 |
Mr = 359.21 | Dx = 1.524 Mg m−3 |
Monoclinic, P21/n | Melting point: 408 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 13.602 (2) Å | Cell parameters from 9585 reflections |
b = 10.1781 (17) Å | θ = 2.2–23.3° |
c = 23.565 (4) Å | µ = 2.63 mm−1 |
β = 106.267 (3)° | T = 293 K |
V = 3131.8 (9) Å3 | Prism, pale brown |
Z = 8 | 0.32 × 0.21 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6698 independent reflections |
Radiation source: fine-focus sealed tube | 4047 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
φ and ω scans | θmax = 27.4°, θmin = 1.6° |
Absorption correction: multi-scan (XPREP; Bruker, 1998) | h = −17→17 |
Tmin = 0.514, Tmax = 0.769 | k = −13→13 |
39464 measured reflections | l = −30→28 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 0.87 | w = 1/[σ2(Fo2) + (0.0456P)2] where P = (Fo2 + 2Fc2)/3 |
6698 reflections | (Δ/σ)max = 0.001 |
399 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.38 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 | |
Br1 | 0.67662 (2) | 1.15732 (3) | 0.154547 (13) | 0.06427 (11) | |
O1 | 0.46579 (13) | 0.55345 (17) | −0.11174 (8) | 0.0547 (5) | |
O2 | 0.32817 (12) | 0.43617 (16) | −0.10689 (7) | 0.0514 (4) | |
C3 | 0.51756 (16) | 0.8510 (2) | 0.05363 (10) | 0.0402 (6) | |
C5 | 0.63207 (18) | 1.0224 (2) | 0.09692 (11) | 0.0444 (6) | |
C9 | 0.34687 (16) | 0.7463 (2) | 0.06361 (10) | 0.0395 (6) | |
N2 | 0.39265 (14) | 0.58025 (19) | −0.03663 (9) | 0.0458 (5) | |
H2 | 0.3480 | 0.5468 | −0.0213 | 0.055* | |
C15 | 0.40183 (18) | 0.5258 (2) | −0.08708 (11) | 0.0435 (6) | |
C2 | 0.43360 (16) | 0.7585 (2) | 0.03809 (10) | 0.0389 (6) | |
C4 | 0.54488 (17) | 0.9524 (2) | 0.09527 (11) | 0.0446 (6) | |
H4 | 0.5056 | 0.9716 | 0.1208 | 0.054* | |
C1 | 0.44969 (16) | 0.6863 (2) | −0.00733 (10) | 0.0408 (6) | |
N1 | 0.53542 (14) | 0.7262 (2) | −0.02121 (9) | 0.0451 (5) | |
H1 | 0.5587 | 0.6933 | −0.0485 | 0.054* | |
C8 | 0.57866 (16) | 0.8280 (2) | 0.01574 (10) | 0.0421 (6) | |
C7 | 0.66524 (18) | 0.9013 (3) | 0.01738 (11) | 0.0494 (6) | |
H7 | 0.7038 | 0.8851 | −0.0088 | 0.059* | |
C14 | 0.36170 (18) | 0.7435 (2) | 0.12431 (11) | 0.0472 (6) | |
H14 | 0.4276 | 0.7513 | 0.1495 | 0.057* | |
C6 | 0.69212 (18) | 0.9994 (3) | 0.05932 (11) | 0.0490 (6) | |
H6 | 0.7504 | 1.0498 | 0.0623 | 0.059* | |
C10 | 0.24711 (17) | 0.7351 (2) | 0.02745 (11) | 0.0461 (6) | |
H10 | 0.2350 | 0.7375 | −0.0134 | 0.055* | |
C13 | 0.2802 (2) | 0.7292 (3) | 0.14777 (12) | 0.0542 (7) | |
H13 | 0.2914 | 0.7283 | 0.1886 | 0.065* | |
C12 | 0.1827 (2) | 0.7164 (3) | 0.11124 (13) | 0.0553 (7) | |
H12 | 0.1281 | 0.7048 | 0.1272 | 0.066* | |
C11 | 0.16562 (18) | 0.7205 (3) | 0.05113 (12) | 0.0535 (7) | |
H11 | 0.0993 | 0.7135 | 0.0263 | 0.064* | |
C16 | 0.32765 (19) | 0.3715 (3) | −0.16147 (11) | 0.0559 (7) | |
H16A | 0.3937 | 0.3311 | −0.1579 | 0.067* | |
H16B | 0.3143 | 0.4348 | −0.1935 | 0.067* | |
C17 | 0.2461 (2) | 0.2695 (3) | −0.17407 (11) | 0.0600 (7) | |
H17A | 0.2594 | 0.2079 | −0.1420 | 0.090* | |
H17B | 0.2455 | 0.2242 | −0.2099 | 0.090* | |
H17C | 0.1809 | 0.3105 | −0.1785 | 0.090* | |
Br2 | −0.00498 (2) | 1.05496 (4) | 0.075163 (13) | 0.07498 (13) | |
O3 | 0.21149 (13) | 0.90039 (19) | 0.45332 (7) | 0.0588 (5) | |
N3 | 0.13685 (14) | 0.9018 (2) | 0.32998 (8) | 0.0474 (5) | |
H3 | 0.1067 | 0.8847 | 0.3567 | 0.057* | |
O4 | 0.37786 (12) | 0.8434 (2) | 0.48626 (7) | 0.0654 (5) | |
N4 | 0.30944 (14) | 0.8667 (2) | 0.39108 (9) | 0.0511 (6) | |
H4A | 0.3693 | 0.8410 | 0.3902 | 0.061* | |
C18 | 0.24032 (17) | 0.8981 (2) | 0.33697 (10) | 0.0431 (6) | |
C26 | 0.36517 (17) | 0.9391 (2) | 0.27647 (10) | 0.0416 (6) | |
C20 | 0.16623 (17) | 0.9546 (2) | 0.24343 (10) | 0.0401 (6) | |
C21 | 0.13790 (17) | 0.9886 (2) | 0.18364 (10) | 0.0435 (6) | |
H21 | 0.1866 | 1.0002 | 0.1632 | 0.052* | |
C22 | 0.03519 (19) | 1.0043 (3) | 0.15614 (11) | 0.0486 (6) | |
C27 | 0.39178 (18) | 1.0505 (3) | 0.25046 (11) | 0.0488 (6) | |
H27 | 0.3452 | 1.1192 | 0.2396 | 0.059* | |
C25 | 0.08992 (17) | 0.9379 (2) | 0.27223 (11) | 0.0435 (6) | |
C32 | 0.29212 (18) | 0.8725 (3) | 0.44470 (11) | 0.0461 (6) | |
C31 | 0.43626 (17) | 0.8379 (3) | 0.29185 (11) | 0.0497 (6) | |
H31 | 0.4198 | 0.7615 | 0.3089 | 0.060* | |
C24 | −0.01346 (18) | 0.9537 (3) | 0.24349 (11) | 0.0506 (7) | |
H24 | −0.0630 | 0.9420 | 0.2633 | 0.061* | |
C19 | 0.26273 (16) | 0.9280 (2) | 0.28583 (10) | 0.0407 (6) | |
C23 | −0.03975 (18) | 0.9869 (3) | 0.18481 (11) | 0.0533 (7) | |
H23 | −0.1083 | 0.9978 | 0.1642 | 0.064* | |
C33 | 0.3759 (2) | 0.8414 (3) | 0.54739 (11) | 0.0649 (8) | |
H33A | 0.4142 | 0.7662 | 0.5673 | 0.078* | |
H33B | 0.3058 | 0.8332 | 0.5492 | 0.078* | |
C29 | 0.5562 (2) | 0.9604 (3) | 0.25614 (12) | 0.0597 (8) | |
H29 | 0.6200 | 0.9676 | 0.2491 | 0.072* | |
C30 | 0.53170 (19) | 0.8502 (3) | 0.28198 (12) | 0.0595 (7) | |
H30 | 0.5793 | 0.7827 | 0.2931 | 0.071* | |
C34 | 0.4210 (3) | 0.9624 (3) | 0.57708 (14) | 0.0844 (10) | |
H34A | 0.4874 | 0.9754 | 0.5713 | 0.127* | |
H34B | 0.4274 | 0.9557 | 0.6186 | 0.127* | |
H34C | 0.3777 | 1.0355 | 0.5608 | 0.127* | |
C28 | 0.4867 (2) | 1.0605 (3) | 0.24051 (12) | 0.0600 (7) | |
H28 | 0.5036 | 1.1359 | 0.2230 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.06387 (18) | 0.05642 (19) | 0.0667 (2) | −0.01506 (14) | 0.00868 (14) | −0.00791 (15) |
O1 | 0.0529 (10) | 0.0624 (12) | 0.0556 (11) | −0.0058 (9) | 0.0263 (9) | −0.0062 (9) |
O2 | 0.0496 (9) | 0.0571 (12) | 0.0488 (11) | −0.0107 (8) | 0.0161 (8) | −0.0131 (9) |
C3 | 0.0367 (12) | 0.0409 (14) | 0.0407 (14) | 0.0030 (11) | 0.0070 (10) | 0.0045 (12) |
C5 | 0.0437 (13) | 0.0385 (15) | 0.0440 (15) | −0.0008 (11) | 0.0010 (11) | 0.0050 (12) |
C9 | 0.0403 (13) | 0.0364 (14) | 0.0423 (15) | 0.0020 (10) | 0.0122 (11) | −0.0007 (11) |
N2 | 0.0474 (11) | 0.0495 (13) | 0.0454 (13) | −0.0105 (10) | 0.0208 (10) | −0.0049 (10) |
C15 | 0.0427 (13) | 0.0439 (16) | 0.0434 (15) | 0.0050 (12) | 0.0113 (12) | 0.0011 (12) |
C2 | 0.0360 (12) | 0.0415 (14) | 0.0381 (14) | 0.0021 (10) | 0.0088 (10) | 0.0006 (12) |
C4 | 0.0426 (13) | 0.0446 (15) | 0.0450 (15) | 0.0020 (11) | 0.0097 (11) | 0.0033 (13) |
C1 | 0.0396 (13) | 0.0417 (15) | 0.0406 (14) | −0.0006 (11) | 0.0107 (11) | 0.0030 (12) |
N1 | 0.0445 (11) | 0.0516 (13) | 0.0434 (12) | 0.0000 (10) | 0.0193 (9) | −0.0013 (10) |
C8 | 0.0369 (12) | 0.0461 (15) | 0.0413 (14) | 0.0024 (11) | 0.0076 (11) | 0.0066 (12) |
C7 | 0.0421 (13) | 0.0556 (16) | 0.0506 (16) | 0.0001 (12) | 0.0131 (12) | 0.0150 (14) |
C14 | 0.0460 (14) | 0.0492 (16) | 0.0446 (16) | −0.0017 (12) | 0.0098 (11) | −0.0051 (13) |
C6 | 0.0395 (13) | 0.0458 (16) | 0.0572 (17) | −0.0055 (11) | 0.0062 (12) | 0.0119 (14) |
C10 | 0.0430 (13) | 0.0504 (16) | 0.0451 (15) | −0.0032 (11) | 0.0125 (11) | 0.0024 (12) |
C13 | 0.0614 (17) | 0.0608 (18) | 0.0457 (16) | −0.0051 (14) | 0.0238 (13) | −0.0124 (14) |
C12 | 0.0522 (16) | 0.0564 (17) | 0.066 (2) | −0.0054 (13) | 0.0304 (14) | −0.0061 (15) |
C11 | 0.0410 (14) | 0.0585 (18) | 0.0608 (19) | −0.0041 (12) | 0.0139 (13) | 0.0009 (15) |
C16 | 0.0601 (16) | 0.064 (2) | 0.0432 (16) | −0.0029 (14) | 0.0141 (13) | −0.0091 (14) |
C17 | 0.0686 (18) | 0.0530 (18) | 0.0505 (17) | −0.0048 (14) | 0.0038 (13) | −0.0044 (14) |
Br2 | 0.0711 (2) | 0.1016 (3) | 0.04400 (18) | 0.00474 (17) | 0.00264 (14) | 0.01354 (17) |
O3 | 0.0444 (10) | 0.0853 (14) | 0.0488 (11) | −0.0027 (9) | 0.0164 (8) | 0.0076 (10) |
N3 | 0.0416 (11) | 0.0637 (14) | 0.0391 (12) | −0.0035 (10) | 0.0151 (9) | 0.0039 (11) |
O4 | 0.0438 (9) | 0.1117 (16) | 0.0373 (10) | 0.0039 (10) | 0.0060 (8) | 0.0001 (10) |
N4 | 0.0403 (11) | 0.0737 (16) | 0.0396 (12) | 0.0062 (10) | 0.0118 (9) | 0.0031 (11) |
C18 | 0.0404 (13) | 0.0496 (15) | 0.0366 (14) | −0.0017 (11) | 0.0063 (11) | −0.0013 (12) |
C26 | 0.0432 (13) | 0.0478 (16) | 0.0330 (13) | −0.0027 (11) | 0.0092 (10) | −0.0050 (12) |
C20 | 0.0432 (12) | 0.0391 (14) | 0.0388 (14) | 0.0013 (11) | 0.0125 (11) | −0.0025 (11) |
C21 | 0.0492 (14) | 0.0436 (15) | 0.0394 (15) | 0.0009 (11) | 0.0153 (11) | −0.0038 (12) |
C22 | 0.0548 (15) | 0.0475 (16) | 0.0386 (15) | 0.0023 (12) | 0.0049 (12) | 0.0000 (12) |
C27 | 0.0488 (14) | 0.0491 (16) | 0.0506 (16) | 0.0040 (12) | 0.0171 (12) | 0.0016 (13) |
C25 | 0.0438 (13) | 0.0452 (15) | 0.0399 (14) | −0.0005 (11) | 0.0092 (11) | −0.0017 (12) |
C32 | 0.0421 (14) | 0.0560 (17) | 0.0409 (15) | −0.0064 (12) | 0.0128 (12) | 0.0047 (13) |
C31 | 0.0469 (14) | 0.0507 (16) | 0.0503 (16) | 0.0011 (13) | 0.0117 (12) | 0.0023 (13) |
C24 | 0.0411 (13) | 0.0612 (18) | 0.0512 (17) | −0.0013 (12) | 0.0155 (12) | −0.0039 (14) |
C19 | 0.0399 (12) | 0.0459 (15) | 0.0362 (14) | −0.0014 (11) | 0.0105 (10) | −0.0022 (12) |
C23 | 0.0409 (13) | 0.0639 (18) | 0.0494 (17) | 0.0031 (12) | 0.0032 (12) | 0.0018 (14) |
C33 | 0.0572 (16) | 0.094 (2) | 0.0415 (16) | −0.0023 (16) | 0.0105 (13) | 0.0056 (16) |
C29 | 0.0433 (14) | 0.073 (2) | 0.067 (2) | −0.0102 (15) | 0.0225 (13) | −0.0095 (16) |
C30 | 0.0471 (15) | 0.065 (2) | 0.0644 (19) | 0.0099 (14) | 0.0128 (13) | −0.0081 (16) |
C34 | 0.088 (2) | 0.102 (3) | 0.060 (2) | −0.010 (2) | 0.0156 (17) | −0.0146 (19) |
C28 | 0.0625 (17) | 0.0614 (19) | 0.0595 (18) | −0.0107 (15) | 0.0224 (14) | 0.0002 (15) |
Geometric parameters (Å, º) top
Br1—C5 | 1.906 (2) | Br2—C22 | 1.903 (2) |
O1—C15 | 1.207 (3) | O3—C32 | 1.204 (3) |
O2—C15 | 1.339 (3) | N3—C18 | 1.371 (3) |
O2—C16 | 1.443 (3) | N3—C25 | 1.381 (3) |
C3—C8 | 1.400 (3) | N3—H3 | 0.860 |
C3—C4 | 1.401 (3) | O4—C32 | 1.329 (3) |
C3—C2 | 1.446 (3) | O4—C33 | 1.448 (3) |
C5—C4 | 1.375 (3) | N4—C32 | 1.350 (3) |
C5—C6 | 1.383 (3) | N4—C18 | 1.393 (3) |
C9—C14 | 1.388 (3) | N4—H4A | 0.860 |
C9—C10 | 1.390 (3) | C18—C19 | 1.358 (3) |
C9—C2 | 1.472 (3) | C26—C27 | 1.385 (3) |
N2—C15 | 1.349 (3) | C26—C31 | 1.390 (3) |
N2—C1 | 1.394 (3) | C26—C19 | 1.475 (3) |
N2—H2 | 0.860 | C20—C21 | 1.396 (3) |
C2—C1 | 1.366 (3) | C20—C25 | 1.401 (3) |
C4—H4 | 0.930 | C20—C19 | 1.435 (3) |
C1—N1 | 1.358 (3) | C21—C22 | 1.375 (3) |
N1—C8 | 1.375 (3) | C21—H21 | 0.930 |
N1—H1 | 0.860 | C22—C23 | 1.383 (3) |
C8—C7 | 1.386 (3) | C27—C28 | 1.379 (3) |
C7—C6 | 1.380 (4) | C27—H27 | 0.930 |
C7—H7 | 0.930 | C25—C24 | 1.389 (3) |
C14—C13 | 1.379 (3) | C31—C30 | 1.387 (3) |
C14—H14 | 0.930 | C31—H31 | 0.930 |
C6—H6 | 0.930 | C24—C23 | 1.370 (3) |
C10—C11 | 1.381 (3) | C24—H24 | 0.930 |
C10—H10 | 0.930 | C23—H23 | 0.930 |
C13—C12 | 1.370 (3) | C33—C34 | 1.464 (4) |
C13—H13 | 0.930 | C33—H33A | 0.970 |
C12—C11 | 1.370 (3) | C33—H33B | 0.970 |
C12—H12 | 0.930 | C29—C30 | 1.361 (4) |
C11—H11 | 0.930 | C29—C28 | 1.368 (4) |
C16—C17 | 1.487 (4) | C29—H29 | 0.930 |
C16—H16A | 0.970 | C30—H30 | 0.930 |
C16—H16B | 0.970 | C34—H34A | 0.960 |
C17—H17A | 0.960 | C34—H34B | 0.960 |
C17—H17B | 0.960 | C34—H34C | 0.960 |
C17—H17C | 0.960 | C28—H28 | 0.930 |
| | | |
C15—O2—C16 | 115.97 (19) | C18—N3—C25 | 107.52 (19) |
C8—C3—C4 | 118.8 (2) | C18—N3—H3 | 126.2 |
C8—C3—C2 | 107.3 (2) | C25—N3—H3 | 126.2 |
C4—C3—C2 | 133.9 (2) | C32—O4—C33 | 118.7 (2) |
C4—C5—C6 | 123.6 (2) | C32—N4—C18 | 126.7 (2) |
C4—C5—Br1 | 119.5 (2) | C32—N4—H4A | 116.7 |
C6—C5—Br1 | 116.85 (18) | C18—N4—H4A | 116.7 |
C14—C9—C10 | 117.7 (2) | C19—C18—N3 | 111.4 (2) |
C14—C9—C2 | 121.4 (2) | C19—C18—N4 | 127.0 (2) |
C10—C9—C2 | 120.9 (2) | N3—C18—N4 | 121.5 (2) |
C15—N2—C1 | 125.3 (2) | C27—C26—C31 | 118.3 (2) |
C15—N2—H2 | 117.3 | C27—C26—C19 | 120.2 (2) |
C1—N2—H2 | 117.3 | C31—C26—C19 | 121.5 (2) |
O1—C15—O2 | 124.1 (2) | C21—C20—C25 | 119.1 (2) |
O1—C15—N2 | 125.9 (2) | C21—C20—C19 | 133.6 (2) |
O2—C15—N2 | 110.0 (2) | C25—C20—C19 | 107.3 (2) |
C1—C2—C3 | 105.1 (2) | C22—C21—C20 | 117.5 (2) |
C1—C2—C9 | 126.7 (2) | C22—C21—H21 | 121.3 |
C3—C2—C9 | 128.2 (2) | C20—C21—H21 | 121.3 |
C5—C4—C3 | 117.3 (2) | C21—C22—C23 | 123.1 (2) |
C5—C4—H4 | 121.3 | C21—C22—Br2 | 118.2 (2) |
C3—C4—H4 | 121.3 | C23—C22—Br2 | 118.73 (18) |
N1—C1—C2 | 111.4 (2) | C28—C27—C26 | 120.6 (2) |
N1—C1—N2 | 120.6 (2) | C28—C27—H27 | 119.7 |
C2—C1—N2 | 128.0 (2) | C26—C27—H27 | 119.7 |
C1—N1—C8 | 108.46 (19) | N3—C25—C24 | 129.5 (2) |
C1—N1—H1 | 125.8 | N3—C25—C20 | 108.00 (19) |
C8—N1—H1 | 125.8 | C24—C25—C20 | 122.4 (2) |
N1—C8—C7 | 129.3 (2) | O3—C32—O4 | 125.5 (2) |
N1—C8—C3 | 107.8 (2) | O3—C32—N4 | 125.0 (2) |
C7—C8—C3 | 122.9 (2) | O4—C32—N4 | 109.4 (2) |
C6—C7—C8 | 117.5 (2) | C30—C31—C26 | 120.3 (3) |
C6—C7—H7 | 121.2 | C30—C31—H31 | 119.8 |
C8—C7—H7 | 121.2 | C26—C31—H31 | 119.8 |
C13—C14—C9 | 121.0 (2) | C23—C24—C25 | 117.6 (2) |
C13—C14—H14 | 119.5 | C23—C24—H24 | 121.2 |
C9—C14—H14 | 119.5 | C25—C24—H24 | 121.2 |
C7—C6—C5 | 119.7 (2) | C18—C19—C20 | 105.74 (19) |
C7—C6—H6 | 120.1 | C18—C19—C26 | 127.3 (2) |
C5—C6—H6 | 120.1 | C20—C19—C26 | 126.8 (2) |
C11—C10—C9 | 121.1 (2) | C24—C23—C22 | 120.3 (2) |
C11—C10—H10 | 119.4 | C24—C23—H23 | 119.8 |
C9—C10—H10 | 119.4 | C22—C23—H23 | 119.8 |
C12—C13—C14 | 120.2 (2) | O4—C33—C34 | 110.0 (2) |
C12—C13—H13 | 119.9 | O4—C33—H33A | 109.7 |
C14—C13—H13 | 119.9 | C34—C33—H33A | 109.7 |
C13—C12—C11 | 120.1 (2) | O4—C33—H33B | 109.7 |
C13—C12—H12 | 120.0 | C34—C33—H33B | 109.7 |
C11—C12—H12 | 120.0 | H33A—C33—H33B | 108.2 |
C12—C11—C10 | 119.9 (2) | C30—C29—C28 | 119.7 (2) |
C12—C11—H11 | 120.1 | C30—C29—H29 | 120.1 |
C10—C11—H11 | 120.1 | C28—C29—H29 | 120.1 |
O2—C16—C17 | 108.3 (2) | C29—C30—C31 | 120.5 (3) |
O2—C16—H16A | 110.0 | C29—C30—H30 | 119.8 |
C17—C16—H16A | 110.0 | C31—C30—H30 | 119.8 |
O2—C16—H16B | 110.0 | C33—C34—H34A | 109.5 |
C17—C16—H16B | 110.0 | C33—C34—H34B | 109.5 |
H16A—C16—H16B | 108.4 | H34A—C34—H34B | 109.5 |
C16—C17—H17A | 109.5 | C33—C34—H34C | 109.5 |
C16—C17—H17B | 109.5 | H34A—C34—H34C | 109.5 |
H17A—C17—H17B | 109.5 | H34B—C34—H34C | 109.5 |
C16—C17—H17C | 109.5 | C29—C28—C27 | 120.6 (3) |
H17A—C17—H17C | 109.5 | C29—C28—H28 | 119.7 |
H17B—C17—H17C | 109.5 | C27—C28—H28 | 119.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 2.19 | 2.722 (3) | 120 |
N1—H1···O3i | 0.86 | 2.28 | 2.926 (3) | 132 |
N2—H2···O3ii | 0.86 | 2.48 | 3.282 (3) | 155 |
N3—H3···O3 | 0.86 | 2.33 | 2.797 (2) | 114 |
N3—H3···O1iii | 0.86 | 2.33 | 3.049 (3) | 142 |
C33—H33B···O3 | 0.98 | 2.37 | 2.739 (3) | 102 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, −y+3/2, z+1/2. |