Buy article online - an online subscription or single-article purchase is required to access this article.
In the crystal structure of the title compound, C
24H
22BrClN
4O
3, there are C—H
O and C—H
Br intermolecular hydrogen bonds, and also C—H
O, C—H
Br and C—H
N intramolecular hydrogen bonds.
Supporting information
CCDC reference: 628430
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.050
- wR factor = 0.155
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
| Author Response: ...We have collected data on kappa IP diffractometer and
processed using Denzo; and the DENZO image processing
package is known to have problems with certain strong reflections.
They are often excluded from the data set leading to a lower value for
the above parameter.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H14 .. H29B .. 2.13 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
2 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
0 ALERT type 5 Informative message, check
Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski and Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) ; ORTEP-II (Johnson, 1976); software used to prepare material for publication: PLATON.
10-(2-Bromo-4,5-dimethoxy-benzyl)
-7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo
[
a,d]cyclohepten-11-one
top
Crystal data top
C24H22BrClN4O3 | F(000) = 1080 |
Mr = 529.82 | Dx = 1.495 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7627 reflections |
a = 9.0680 (9) Å | θ = 2.4–25.0° |
b = 16.7840 (9) Å | µ = 1.89 mm−1 |
c = 16.1960 (16) Å | T = 295 K |
β = 107.260 (2)° | Block, pale yellow |
V = 2354.0 (4) Å3 | 0.30 × 0.25 × 0.25 mm |
Z = 4 | |
Data collection top
MacScience DIPLabo 32001 diffractometer | 2933 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
Detector resolution: 10.0 pixels mm-1 | h = −10→10 |
ω scans | k = −19→19 |
7627 measured reflections | l = −19→19 |
4048 independent reflections | |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0944P)2 + 0.2553P] where P = (Fo2 + 2Fc2)/3 |
4048 reflections | (Δ/σ)max < 0.001 |
301 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
Special details top
Experimental. Melting points were determined using SELACO-650 hot-stage melting-point
apparatus and are uncorrected. Infrared (IR) spectra were recorded using a
Jasco FTIR-4100 series. Nuclear magnetic resonance (1H NMR) spectra were
recorded on Shimadzu AMX 400-Bruker, 400 MHz s pectrometer using CDCl3 as
solvent and TMS as an internal standard. Elemental analyses (CHNS) were
performed on a Vario EL III Elementar. Silica gel column chromatography was
performed using Merck 7734 silica gel (60–120 mesh) and Merck-made TLC
plates. Melting point: 461–463 K. IR (KBr, cm-1) ν: 1222, 1640, 2926,
3000, 3073 1H NMR (CDCl3, 400 MHz) δ: 8.45 (1H, m), 8.06
(1H, m), 7.02 (1H, s), 7.08 (1H, m), 6.95 (1H, m),
7.0 (1H, s), 4.25 (1H, d), 5.85 (1H, d), 2.32 (5H,
s), 1.65 (3H, s), 3.80 (3H, s), 3.84 (3H, s). Elemental
analysis data in (%) for C24H22BrClN4O3; Calculated: C 54.41, H 4.19,
N 10.57. Found: C 54.43, H 4.17, N 10.54. |
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | |
Br29 | 0.4986 (5) | 0.59422 (3) | 0.25969 (3) | 0.0653 (2) | |
Cl1 | 0.32343 (16) | 0.42506 (8) | −0.04134 (8) | 0.0751 (5) | |
O18 | −0.0942 (4) | 0.50473 (19) | 0.3195 (2) | 0.0680 (12) | |
O30 | 0.6757 (4) | 0.35892 (18) | 0.4785 (2) | 0.0710 (12) | |
O32 | 0.4100 (4) | 0.33985 (18) | 0.5024 (2) | 0.0712 (12) | |
N3 | 0.2026 (4) | 0.39674 (18) | 0.0827 (2) | 0.0464 (11) | |
N5 | 0.0908 (4) | 0.35607 (16) | 0.1890 (2) | 0.0429 (10) | |
N7 | −0.1413 (4) | 0.28578 (19) | 0.1416 (2) | 0.0597 (14) | |
N13 | 0.0640 (4) | 0.51688 (17) | 0.23551 (19) | 0.0423 (10) | |
C2 | 0.2354 (5) | 0.4551 (3) | 0.0358 (3) | 0.0528 (16) | |
C4 | 0.1380 (4) | 0.4182 (2) | 0.1435 (2) | 0.0426 (12) | |
C6 | −0.0690 (5) | 0.3527 (2) | 0.1766 (2) | 0.0455 (12) | |
C8 | −0.2938 (6) | 0.2832 (3) | 0.1273 (3) | 0.0687 (17) | |
C9 | −0.3788 (6) | 0.3443 (3) | 0.1452 (3) | 0.0640 (17) | |
C10 | −0.3020 (5) | 0.4116 (2) | 0.1843 (3) | 0.0548 (17) | |
C11 | −0.1448 (5) | 0.4175 (2) | 0.2006 (3) | 0.0456 (12) | |
C12 | −0.0573 (5) | 0.4835 (2) | 0.2555 (3) | 0.0472 (12) | |
C14 | 0.1086 (4) | 0.4973 (2) | 0.1605 (2) | 0.0405 (12) | |
C15 | 0.1360 (5) | 0.5565 (2) | 0.1063 (2) | 0.0480 (14) | |
C16 | 0.2010 (5) | 0.5339 (2) | 0.0426 (3) | 0.0543 (14) | |
C17 | 0.0957 (6) | 0.6434 (2) | 0.1145 (3) | 0.0651 (16) | |
C19 | 0.1711 (5) | 0.2815 (2) | 0.1934 (3) | 0.0535 (16) | |
C20 | 0.2053 (6) | 0.2374 (3) | 0.2763 (3) | 0.078 (2) | |
C21 | 0.3295 (6) | 0.2800 (3) | 0.2511 (3) | 0.0711 (18) | |
C22 | 0.1787 (5) | 0.5617 (2) | 0.3045 (3) | 0.0500 (14) | |
C23 | 0.3164 (5) | 0.5098 (2) | 0.3490 (2) | 0.0467 (12) | |
C24 | 0.2998 (5) | 0.4502 (2) | 0.4058 (3) | 0.0524 (14) | |
C25 | 0.4187 (5) | 0.4000 (2) | 0.4476 (3) | 0.0546 (14) | |
C26 | 0.5637 (5) | 0.4096 (2) | 0.4337 (3) | 0.0511 (14) | |
C27 | 0.5831 (5) | 0.4673 (2) | 0.3779 (3) | 0.0509 (12) | |
C28 | 0.4587 (5) | 0.5161 (2) | 0.3360 (3) | 0.0483 (14) | |
C31 | 0.8231 (6) | 0.3641 (3) | 0.4658 (4) | 0.085 (2) | |
C33 | 0.2655 (6) | 0.3249 (3) | 0.5151 (4) | 0.081 (2) | |
H10 | 0.2209 | 0.5715 | 0.0051 | 0.0650* | |
H13A | 0.3702 | 0.3286 | 0.2819 | 0.0850* | |
H13B | 0.4046 | 0.2481 | 0.2339 | 0.0850* | |
H14 | 0.1489 | 0.2499 | 0.1403 | 0.0640* | |
H15A | 0.2044 | 0.1797 | 0.2741 | 0.0930* | |
H15B | 0.1700 | 0.2603 | 0.3221 | 0.0930* | |
H18 | −0.3566 | 0.4531 | 0.1996 | 0.0660* | |
H19 | −0.4857 | 0.3406 | 0.1313 | 0.0770* | |
H20 | −0.3455 | 0.2368 | 0.1038 | 0.0820* | |
H22A | 0.1301 | 0.5804 | 0.3468 | 0.0600* | |
H22B | 0.2136 | 0.6078 | 0.2795 | 0.0600* | |
H24 | 0.2046 | 0.4441 | 0.4158 | 0.0630* | |
H27 | 0.6784 | 0.4739 | 0.3681 | 0.0610* | |
H29A | 0.2348 | 0.3703 | 0.5421 | 0.1210* | |
H29B | 0.2731 | 0.2791 | 0.5517 | 0.1210* | |
H29C | 0.1902 | 0.3151 | 0.4603 | 0.1210* | |
H30A | 0.8146 | 0.3522 | 0.4066 | 0.1280* | |
H30B | 0.8916 | 0.3266 | 0.5029 | 0.1280* | |
H30C | 0.8630 | 0.4171 | 0.4793 | 0.1280* | |
H33A | 0.1884 | 0.6730 | 0.1408 | 0.0980* | |
H33B | 0.0276 | 0.6474 | 0.1498 | 0.0980* | |
H33C | 0.0456 | 0.6648 | 0.0582 | 0.0980* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br29 | 0.0683 (4) | 0.0623 (3) | 0.0702 (4) | −0.0057 (2) | 0.0282 (3) | 0.0174 (2) |
Cl1 | 0.0850 (9) | 0.1010 (9) | 0.0526 (7) | 0.0071 (6) | 0.0408 (7) | 0.0055 (6) |
O18 | 0.066 (2) | 0.087 (2) | 0.062 (2) | −0.0144 (16) | 0.0357 (18) | −0.0233 (16) |
O30 | 0.060 (2) | 0.082 (2) | 0.072 (2) | 0.0123 (15) | 0.0210 (17) | 0.0291 (17) |
O32 | 0.068 (2) | 0.083 (2) | 0.068 (2) | −0.0006 (16) | 0.0285 (18) | 0.0299 (16) |
N3 | 0.049 (2) | 0.0530 (18) | 0.0397 (18) | 0.0028 (14) | 0.0172 (15) | 0.0018 (14) |
N5 | 0.053 (2) | 0.0377 (16) | 0.0440 (18) | 0.0039 (13) | 0.0235 (16) | 0.0029 (12) |
N7 | 0.062 (3) | 0.0508 (19) | 0.067 (2) | −0.0112 (16) | 0.020 (2) | −0.0088 (16) |
N13 | 0.0436 (19) | 0.0464 (17) | 0.0386 (18) | 0.0002 (13) | 0.0147 (15) | −0.0034 (13) |
C2 | 0.056 (3) | 0.070 (3) | 0.036 (2) | 0.000 (2) | 0.019 (2) | 0.0006 (18) |
C4 | 0.043 (2) | 0.050 (2) | 0.035 (2) | 0.0023 (15) | 0.0121 (17) | 0.0016 (15) |
C6 | 0.048 (2) | 0.052 (2) | 0.038 (2) | 0.0005 (16) | 0.0151 (18) | 0.0052 (16) |
C8 | 0.064 (3) | 0.067 (3) | 0.073 (3) | −0.018 (2) | 0.017 (3) | −0.009 (2) |
C9 | 0.048 (3) | 0.078 (3) | 0.065 (3) | −0.013 (2) | 0.015 (2) | 0.002 (2) |
C10 | 0.050 (3) | 0.065 (3) | 0.052 (3) | 0.0030 (19) | 0.019 (2) | 0.0024 (19) |
C11 | 0.047 (2) | 0.051 (2) | 0.043 (2) | −0.0016 (16) | 0.0200 (18) | 0.0012 (16) |
C12 | 0.045 (2) | 0.055 (2) | 0.043 (2) | 0.0048 (17) | 0.0152 (19) | −0.0010 (17) |
C14 | 0.039 (2) | 0.047 (2) | 0.035 (2) | 0.0023 (15) | 0.0104 (17) | 0.0019 (15) |
C15 | 0.052 (3) | 0.049 (2) | 0.041 (2) | −0.0014 (17) | 0.0105 (19) | 0.0073 (17) |
C16 | 0.062 (3) | 0.062 (2) | 0.039 (2) | −0.003 (2) | 0.015 (2) | 0.0123 (18) |
C17 | 0.080 (3) | 0.048 (2) | 0.065 (3) | 0.006 (2) | 0.018 (3) | 0.0133 (19) |
C19 | 0.064 (3) | 0.043 (2) | 0.061 (3) | 0.0074 (18) | 0.030 (2) | 0.0010 (18) |
C20 | 0.100 (4) | 0.060 (3) | 0.087 (4) | 0.024 (3) | 0.049 (3) | 0.024 (2) |
C21 | 0.067 (3) | 0.054 (2) | 0.095 (4) | 0.019 (2) | 0.028 (3) | 0.010 (2) |
C22 | 0.055 (3) | 0.050 (2) | 0.048 (2) | −0.0005 (18) | 0.020 (2) | −0.0044 (18) |
C23 | 0.050 (2) | 0.050 (2) | 0.041 (2) | −0.0047 (17) | 0.0151 (19) | −0.0067 (16) |
C24 | 0.045 (2) | 0.068 (3) | 0.047 (2) | −0.0066 (19) | 0.018 (2) | 0.0010 (19) |
C25 | 0.060 (3) | 0.061 (2) | 0.045 (2) | −0.002 (2) | 0.019 (2) | 0.0114 (19) |
C26 | 0.052 (3) | 0.057 (2) | 0.044 (2) | 0.0002 (18) | 0.0136 (19) | 0.0065 (18) |
C27 | 0.045 (2) | 0.063 (2) | 0.047 (2) | −0.0029 (18) | 0.017 (2) | 0.0014 (19) |
C28 | 0.054 (3) | 0.048 (2) | 0.044 (2) | −0.0062 (17) | 0.0160 (19) | −0.0011 (16) |
C31 | 0.064 (4) | 0.103 (4) | 0.096 (4) | 0.020 (3) | 0.034 (3) | 0.024 (3) |
C33 | 0.076 (4) | 0.101 (4) | 0.072 (3) | −0.014 (3) | 0.031 (3) | 0.028 (3) |
Geometric parameters (Å, º) top
Br29—C28 | 1.909 (4) | C22—C23 | 1.518 (6) |
Cl1—C2 | 1.745 (5) | C23—C24 | 1.397 (5) |
O18—C12 | 1.233 (6) | C23—C28 | 1.372 (7) |
O30—C26 | 1.358 (5) | C24—C25 | 1.378 (6) |
O30—C31 | 1.414 (7) | C25—C26 | 1.408 (7) |
O32—C25 | 1.362 (5) | C26—C27 | 1.371 (6) |
O32—C33 | 1.408 (7) | C27—C28 | 1.396 (6) |
N3—C2 | 1.326 (6) | C8—H20 | 0.9302 |
N3—C4 | 1.336 (5) | C9—H19 | 0.9299 |
N5—C4 | 1.415 (5) | C10—H18 | 0.9298 |
N5—C6 | 1.404 (6) | C16—H10 | 0.9299 |
N5—C19 | 1.439 (5) | C17—H33A | 0.9604 |
N7—C6 | 1.339 (5) | C17—H33B | 0.9603 |
N7—C8 | 1.333 (7) | C17—H33C | 0.9597 |
N13—C12 | 1.356 (6) | C19—H14 | 0.9791 |
N13—C14 | 1.428 (5) | C20—H15A | 0.9690 |
N13—C22 | 1.485 (5) | C20—H15B | 0.9702 |
C2—C16 | 1.371 (6) | C21—H13A | 0.9701 |
C4—C14 | 1.397 (5) | C21—H13B | 0.9699 |
C6—C11 | 1.402 (5) | C22—H22A | 0.9702 |
C8—C9 | 1.365 (7) | C22—H22B | 0.9689 |
C9—C10 | 1.378 (6) | C24—H24 | 0.9300 |
C10—C11 | 1.374 (7) | C27—H27 | 0.9304 |
C11—C12 | 1.493 (6) | C31—H30A | 0.9598 |
C14—C15 | 1.396 (5) | C31—H30B | 0.9600 |
C15—C16 | 1.384 (6) | C31—H30C | 0.9608 |
C15—C17 | 1.519 (5) | C33—H29A | 0.9600 |
C19—C20 | 1.483 (6) | C33—H29B | 0.9606 |
C19—C21 | 1.463 (7) | C33—H29C | 0.9599 |
C20—C21 | 1.490 (8) | | |
| | | |
Br29···C15 | 3.541 (4) | C27···H30C | 2.7158 |
Br29···C21i | 3.514 (5) | C31···H27 | 2.5278 |
Br29···H22B | 2.7067 | C31···H22Aviii | 3.0815 |
Br29···H33A | 3.1866 | C33···H24 | 2.5233 |
Br29···H18ii | 3.0066 | C33···H14x | 2.8422 |
Br29···H13Bi | 2.7199 | H10···H33C | 2.5554 |
Br29···H15Ai | 3.2382 | H13A···C4 | 2.9864 |
Cl1···C10iii | 3.556 (4) | H13A···C24 | 3.0594 |
O18···C27iv | 3.390 (6) | H13A···C25 | 2.8515 |
O30···O32 | 2.571 (5) | H13A···C26 | 2.9003 |
O30···C8v | 3.343 (6) | H13B···Br29vii | 2.7199 |
O32···O30 | 2.571 (5) | H14···N3 | 2.7297 |
O18···H27iv | 2.4703 | H14···N7 | 2.7057 |
O18···H22A | 2.3263 | H14···C33ix | 2.8422 |
O18···H24 | 2.8813 | H14···H29Bix | 2.1269 |
O18···H18 | 2.7279 | H15A···Br29vii | 3.2382 |
O30···H20v | 2.6397 | H15B···H29C | 2.3762 |
O32···H20v | 2.6659 | H18···Br29iv | 3.0066 |
N3···C21 | 3.277 (6) | H18···O18 | 2.7279 |
N5···N13 | 2.832 (4) | H19···N3iv | 2.8594 |
N7···C20 | 3.351 (6) | H19···C21iv | 3.0882 |
N13···N5 | 2.832 (4) | H20···O30vi | 2.6397 |
N3···H33Ciii | 2.8796 | H20···O32vi | 2.6659 |
N3···H19ii | 2.8594 | H22A···O18 | 2.3263 |
N3···H14 | 2.7297 | H22A···H24 | 2.5477 |
N7···H14 | 2.7057 | H22A···C31viii | 3.0815 |
N13···H33B | 2.5618 | H22B···Br29 | 2.7067 |
C2···C15iii | 3.475 (6) | H22B···C15 | 2.8167 |
C4···C23 | 3.587 (5) | H22B···C17 | 2.6355 |
C8···O30vi | 3.343 (6) | H22B···H33A | 2.4477 |
C10···Cl1iii | 3.556 (4) | H22B···H33B | 2.3657 |
C12···C24 | 3.471 (7) | H24···O18 | 2.8813 |
C14···C28 | 3.592 (6) | H24···C12 | 3.0264 |
C15···Br29 | 3.541 (4) | H24···C33 | 2.5233 |
C15···C2iii | 3.475 (6) | H24···H22A | 2.5477 |
C17···C22 | 3.247 (6) | H24···H29A | 2.3369 |
C20···N7 | 3.351 (6) | H24···H29C | 2.2979 |
C21···N3 | 3.277 (6) | H27···O18ii | 2.4703 |
C21···Br29vii | 3.514 (5) | H27···C31 | 2.5278 |
C22···C17 | 3.247 (6) | H27···H30A | 2.3726 |
C23···C4 | 3.587 (5) | H27···H30C | 2.2728 |
C24···C12 | 3.471 (7) | H29A···C24 | 2.7912 |
C24···C26viii | 3.452 (6) | H29A···H24 | 2.3369 |
C26···C24viii | 3.452 (6) | H29B···C19x | 2.9011 |
C27···O18ii | 3.390 (6) | H29B···H14x | 2.1269 |
C28···C14 | 3.592 (6) | H29C···C24 | 2.7256 |
C4···H13A | 2.9864 | H29C···H15B | 2.3762 |
C12···H24 | 3.0264 | H29C···H24 | 2.2979 |
C15···H22B | 2.8167 | H30A···C27 | 2.7885 |
C17···H22B | 2.6355 | H30A···H27 | 2.3726 |
C19···H29Bix | 2.9011 | H30C···C27 | 2.7158 |
C21···H19ii | 3.0882 | H30C···H27 | 2.2728 |
C22···H33B | 2.8613 | H33A···Br29 | 3.1866 |
C24···H29C | 2.7256 | H33A···H22B | 2.4477 |
C24···H29A | 2.7912 | H33B···N13 | 2.5618 |
C24···H13A | 3.0594 | H33B···C22 | 2.8613 |
C25···H13A | 2.8515 | H33B···H22B | 2.3657 |
C26···H13A | 2.9003 | H33C···H10 | 2.5554 |
C27···H30A | 2.7885 | H33C···N3iii | 2.8796 |
| | | |
C26—O30—C31 | 118.2 (4) | Br29—C28—C23 | 121.3 (3) |
C25—O32—C33 | 117.6 (4) | Br29—C28—C27 | 115.9 (3) |
C2—N3—C4 | 116.4 (3) | C23—C28—C27 | 122.8 (4) |
C4—N5—C6 | 114.5 (3) | N7—C8—H20 | 117.98 |
C4—N5—C19 | 116.1 (3) | C9—C8—H20 | 117.92 |
C6—N5—C19 | 117.2 (3) | C8—C9—H19 | 120.82 |
C6—N7—C8 | 116.9 (4) | C10—C9—H19 | 120.94 |
C12—N13—C14 | 124.2 (3) | C9—C10—H18 | 119.99 |
C12—N13—C22 | 117.8 (3) | C11—C10—H18 | 119.93 |
C14—N13—C22 | 116.4 (3) | C2—C16—H10 | 120.63 |
Cl1—C2—N3 | 115.1 (4) | C15—C16—H10 | 120.59 |
Cl1—C2—C16 | 120.0 (4) | C15—C17—H33A | 109.50 |
N3—C2—C16 | 124.9 (4) | C15—C17—H33B | 109.45 |
N3—C4—N5 | 116.9 (3) | C15—C17—H33C | 109.55 |
N3—C4—C14 | 123.5 (3) | H33A—C17—H33B | 109.43 |
N5—C4—C14 | 119.5 (3) | H33A—C17—H33C | 109.46 |
N5—C6—N7 | 116.7 (3) | H33B—C17—H33C | 109.43 |
N5—C6—C11 | 120.0 (3) | N5—C19—H14 | 117.29 |
N7—C6—C11 | 123.3 (4) | C20—C19—H14 | 117.26 |
N7—C8—C9 | 124.1 (5) | C21—C19—H14 | 117.31 |
C8—C9—C10 | 118.2 (5) | C19—C20—H15A | 117.92 |
C9—C10—C11 | 120.1 (4) | C19—C20—H15B | 117.82 |
C6—C11—C10 | 117.2 (4) | C21—C20—H15A | 117.93 |
C6—C11—C12 | 121.5 (4) | C21—C20—H15B | 117.85 |
C10—C11—C12 | 120.4 (4) | H15A—C20—H15B | 115.02 |
O18—C12—N13 | 121.5 (4) | C19—C21—H13A | 117.75 |
O18—C12—C11 | 119.1 (4) | C19—C21—H13B | 117.77 |
N13—C12—C11 | 119.3 (4) | C20—C21—H13A | 117.77 |
N13—C14—C4 | 120.3 (3) | C20—C21—H13B | 117.78 |
N13—C14—C15 | 121.3 (3) | H13A—C21—H13B | 114.80 |
C4—C14—C15 | 118.2 (3) | N13—C22—H22A | 109.37 |
C14—C15—C16 | 117.9 (3) | N13—C22—H22B | 109.43 |
C14—C15—C17 | 122.4 (4) | C23—C22—H22A | 109.42 |
C16—C15—C17 | 119.7 (3) | C23—C22—H22B | 109.39 |
C2—C16—C15 | 118.8 (4) | H22A—C22—H22B | 108.05 |
N5—C19—C20 | 116.5 (4) | C23—C24—H24 | 118.71 |
N5—C19—C21 | 115.7 (4) | C25—C24—H24 | 118.60 |
C20—C19—C21 | 60.7 (3) | C26—C27—H27 | 120.26 |
C19—C20—C21 | 59.0 (3) | C28—C27—H27 | 120.30 |
C19—C21—C20 | 60.3 (3) | O30—C31—H30A | 109.47 |
N13—C22—C23 | 111.1 (3) | O30—C31—H30B | 109.43 |
C22—C23—C24 | 119.3 (4) | O30—C31—H30C | 109.40 |
C22—C23—C28 | 124.2 (3) | H30A—C31—H30B | 109.52 |
C24—C23—C28 | 116.5 (4) | H30A—C31—H30C | 109.46 |
C23—C24—C25 | 122.7 (4) | H30B—C31—H30C | 109.55 |
O32—C25—C24 | 125.8 (4) | O32—C33—H29A | 109.47 |
O32—C25—C26 | 115.3 (4) | O32—C33—H29B | 109.47 |
C24—C25—C26 | 118.9 (4) | O32—C33—H29C | 109.45 |
O30—C26—C25 | 115.4 (4) | H29A—C33—H29B | 109.36 |
O30—C26—C27 | 124.9 (4) | H29A—C33—H29C | 109.53 |
C25—C26—C27 | 119.7 (4) | H29B—C33—H29C | 109.54 |
C26—C27—C28 | 119.4 (4) | | |
| | | |
C31—O30—C26—C25 | 178.4 (4) | N7—C6—C11—C12 | 167.2 (4) |
C31—O30—C26—C27 | −1.6 (6) | N7—C6—C11—C10 | −2.0 (6) |
C33—O32—C25—C26 | −176.8 (4) | N5—C6—C11—C12 | −12.8 (6) |
C33—O32—C25—C24 | 2.9 (6) | N5—C6—C11—C10 | 178.0 (4) |
C4—N3—C2—C16 | −3.4 (7) | N7—C8—C9—C10 | −3.2 (7) |
C4—N3—C2—Cl1 | 178.7 (3) | C8—C9—C10—C11 | 3.0 (7) |
C2—N3—C4—N5 | 174.9 (4) | C9—C10—C11—C12 | −169.9 (4) |
C2—N3—C4—C14 | −1.8 (6) | C9—C10—C11—C6 | −0.6 (6) |
C19—N5—C4—N3 | 25.5 (5) | C10—C11—C12—N13 | −143.5 (4) |
C19—N5—C6—N7 | −21.8 (5) | C10—C11—C12—O18 | 38.7 (6) |
C6—N5—C4—N3 | −116.0 (4) | C6—C11—C12—O18 | −130.2 (4) |
C19—N5—C6—C11 | 158.2 (4) | C6—C11—C12—N13 | 47.6 (6) |
C4—N5—C19—C21 | 73.0 (5) | C4—C14—C15—C17 | 174.9 (4) |
C4—N5—C6—C11 | −60.8 (4) | C4—C14—C15—C16 | −4.5 (6) |
C19—N5—C4—C14 | −157.7 (3) | N13—C14—C15—C17 | −10.2 (6) |
C4—N5—C6—N7 | 119.3 (3) | N13—C14—C15—C16 | 170.4 (4) |
C6—N5—C4—C14 | 60.8 (4) | C14—C15—C16—C2 | −0.1 (6) |
C6—N5—C19—C21 | −146.5 (4) | C17—C15—C16—C2 | −179.5 (4) |
C6—N5—C19—C20 | −78.0 (5) | N5—C19—C21—C20 | 107.3 (5) |
C4—N5—C19—C20 | 141.5 (4) | N5—C19—C20—C21 | −106.0 (4) |
C8—N7—C6—C11 | 2.0 (5) | N13—C22—C23—C24 | −73.4 (5) |
C6—N7—C8—C9 | 0.7 (6) | N13—C22—C23—C28 | 105.2 (4) |
C8—N7—C6—N5 | −178.1 (3) | C24—C23—C28—C27 | −1.3 (6) |
C12—N13—C22—C23 | 96.5 (4) | C24—C23—C28—Br29 | 179.6 (3) |
C22—N13—C12—C11 | −160.1 (3) | C28—C23—C24—C25 | 0.3 (6) |
C14—N13—C12—C11 | 4.9 (6) | C22—C23—C28—Br29 | 1.0 (5) |
C14—N13—C22—C23 | −69.8 (4) | C22—C23—C24—C25 | 179.0 (4) |
C12—N13—C14—C4 | −54.6 (5) | C22—C23—C28—C27 | −179.9 (4) |
C22—N13—C14—C4 | 110.7 (4) | C23—C24—C25—C26 | 0.9 (6) |
C22—N13—C12—O18 | 17.7 (6) | C23—C24—C25—O32 | −178.7 (4) |
C12—N13—C14—C15 | 130.6 (4) | C24—C25—C26—O30 | 178.7 (4) |
C14—N13—C12—O18 | −177.3 (4) | O32—C25—C26—O30 | −1.6 (5) |
C22—N13—C14—C15 | −64.1 (5) | C24—C25—C26—C27 | −1.3 (6) |
Cl1—C2—C16—C15 | −177.8 (3) | O32—C25—C26—C27 | 178.4 (4) |
N3—C2—C16—C15 | 4.3 (7) | C25—C26—C27—C28 | 0.4 (6) |
N5—C4—C14—N13 | 14.1 (5) | O30—C26—C27—C28 | −179.6 (4) |
N5—C4—C14—C15 | −170.9 (3) | C26—C27—C28—Br29 | −179.9 (3) |
N3—C4—C14—C15 | 5.7 (6) | C26—C27—C28—C23 | 0.9 (6) |
N3—C4—C14—N13 | −169.3 (3) | | |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z; (iv) x−1, y, z; (v) x+1, −y+1/2, z+1/2; (vi) x−1, −y+1/2, z−1/2; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) x, −y+1/2, z−1/2; (x) x, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H13B···Br29vii | 0.97 | 2.72 | 3.514 (5) | 139 |
C22—H22A···O18 | 0.97 | 2.33 | 2.730 (6) | 104 |
C22—H22B···Br29 | 0.97 | 2.71 | 3.239 (5) | 115 |
C27—H27···O18ii | 0.93 | 2.47 | 3.390 (6) | 170 |
C17—H33B···N13 | 0.96 | 2.56 | 2.961 (5) | 105 |
Symmetry codes: (ii) x+1, y, z; (vii) −x+1, y−1/2, −z+1/2. |
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.