The pyrrolidine ring of the title compound, C
27H
21Br
2N
3O
4·CH
4O, adopts an envelope conformation. The methanol solvent molecule is involved in intermolecular hydrogen bonds. The molecular structure is stabilized by C—H
O interactions, and the packing is stabilized by N—H
O, O—H
O and O—H
N intermolecular interactions.
Supporting information
CCDC reference: 238781
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.048
- wR factor = 0.141
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 28.01
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 6201
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 6692
Completeness (_total/calc) 92.66%
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 1
PLAT432_ALERT_2_C Short Inter X...Y Contact Br1 .. C8 .. 3.33 Ang.
PLAT757_ALERT_4_C D...A Calc 2.80169, Rep 2.802(4) ...... Senseless su
N1 -O36 1.555 1.555
PLAT757_ALERT_4_C D...A Calc 3.05257, Rep 3.053(3) ...... Senseless su
O36 -O17 1.555 4.565
PLAT757_ALERT_4_C D...A Calc 3.18300, Rep 3.183(4) ...... Senseless su
O36 -N14 1.555 4.565
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
3 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
5,7-Dibromo-1'-methyl-2'-(4-methoxybenzoyl)-1
H-indole-3-spiro-2'-pyrrolidine- 3'-spiro-3''-1
H-indole-2,2''(3
H,3''H)-dione
methanol solvate
top
Crystal data top
C27H21Br2N3O4·CH4O | F(000) = 1296 |
Mr = 643.33 | Dx = 1.544 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3283 reflections |
a = 23.285 (2) Å | θ = 2.7–21.4° |
b = 7.8966 (7) Å | µ = 2.97 mm−1 |
c = 15.1669 (14) Å | T = 293 K |
β = 96.979 (2)° | Needles, colourles |
V = 2768.1 (4) Å3 | 0.23 × 0.21 × 0.17 mm |
Z = 4 | |
Data collection top
Bruker Smart APEX CCD area-detector diffractometer | 6201 independent reflections |
Radiation source: fine-focus sealed tube | 3759 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −25→29 |
Tmin = 0.548, Tmax = 0.632 | k = −10→9 |
16394 measured reflections | l = −19→20 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0726P)2 + 0.703P] where P = (Fo2 + 2Fc2)/3 |
6201 reflections | (Δ/σ)max = 0.001 |
343 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −0.47 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 | 0.47663 (2) | −0.27814 (7) | 0.71842 (4) | 0.0883 (2) | |
Br2 | 0.45157 (2) | 0.30348 (6) | 0.50148 (3) | 0.07141 (18) | |
N1 | 0.32940 (12) | 0.3148 (3) | 0.58636 (18) | 0.0433 (7) | |
H1 | 0.3337 | 0.3903 | 0.5468 | 0.052* | |
C2 | 0.28469 (15) | 0.3103 (4) | 0.6350 (2) | 0.0389 (7) | |
O3 | 0.24617 (11) | 0.4141 (3) | 0.63318 (16) | 0.0504 (6) | |
C4 | 0.29214 (14) | 0.1531 (4) | 0.6981 (2) | 0.0369 (7) | |
C5 | 0.34817 (14) | 0.0799 (4) | 0.67274 (19) | 0.0373 (7) | |
C6 | 0.38078 (15) | −0.0545 (4) | 0.7076 (2) | 0.0449 (8) | |
H6 | 0.3687 | −0.1208 | 0.7526 | 0.054* | |
C7 | 0.43225 (16) | −0.0884 (4) | 0.6738 (2) | 0.0509 (9) | |
C8 | 0.45273 (15) | 0.0121 (4) | 0.6110 (2) | 0.0520 (9) | |
H8 | 0.4877 | −0.0125 | 0.5902 | 0.062* | |
C9 | 0.42042 (15) | 0.1507 (4) | 0.5792 (2) | 0.0459 (8) | |
C10 | 0.36791 (15) | 0.1815 (4) | 0.6083 (2) | 0.0390 (7) | |
C11 | 0.23649 (14) | 0.0369 (3) | 0.68488 (19) | 0.0341 (7) | |
C12 | 0.20112 (14) | 0.0960 (4) | 0.7617 (2) | 0.0423 (8) | |
H12 | 0.2011 | 0.0018 | 0.8037 | 0.051* | |
C13 | 0.23666 (17) | 0.2372 (5) | 0.8085 (2) | 0.0530 (9) | |
H13A | 0.2241 | 0.3467 | 0.7844 | 0.064* | |
H13B | 0.2336 | 0.2362 | 0.8717 | 0.064* | |
N14 | 0.29568 (13) | 0.2005 (3) | 0.79143 (18) | 0.0446 (7) | |
C15 | 0.33617 (18) | 0.3382 (5) | 0.8187 (3) | 0.0638 (11) | |
H15A | 0.3226 | 0.4410 | 0.7895 | 0.096* | |
H15B | 0.3737 | 0.3106 | 0.8026 | 0.096* | |
H15C | 0.3388 | 0.3531 | 0.8819 | 0.096* | |
C16 | 0.25442 (15) | −0.1495 (4) | 0.7002 (2) | 0.0428 (8) | |
O17 | 0.27371 (12) | −0.2101 (3) | 0.77222 (17) | 0.0585 (7) | |
N18 | 0.24414 (14) | −0.2311 (3) | 0.6228 (2) | 0.0518 (8) | |
H18 | 0.2550 | −0.3332 | 0.6144 | 0.062* | |
C19 | 0.21358 (16) | −0.1305 (4) | 0.5572 (2) | 0.0449 (8) | |
C20 | 0.1904 (2) | −0.1769 (5) | 0.4726 (3) | 0.0683 (12) | |
H20 | 0.1962 | −0.2847 | 0.4507 | 0.082* | |
C21 | 0.1586 (2) | −0.0579 (6) | 0.4219 (3) | 0.0689 (12) | |
H21 | 0.1427 | −0.0858 | 0.3646 | 0.083* | |
C22 | 0.14988 (17) | 0.1005 (5) | 0.4539 (2) | 0.0557 (10) | |
H22 | 0.1276 | 0.1779 | 0.4184 | 0.067* | |
C23 | 0.17359 (14) | 0.1470 (4) | 0.5380 (2) | 0.0420 (8) | |
H23 | 0.1676 | 0.2552 | 0.5594 | 0.050* | |
C24 | 0.20627 (13) | 0.0307 (4) | 0.59014 (19) | 0.0337 (7) | |
C25 | 0.13864 (16) | 0.1382 (4) | 0.7300 (2) | 0.0465 (8) | |
O26 | 0.12185 (12) | 0.2856 (3) | 0.72948 (19) | 0.0636 (7) | |
C27 | 0.09846 (15) | −0.0002 (4) | 0.6987 (2) | 0.0447 (8) | |
C28 | 0.04563 (18) | 0.0415 (5) | 0.6521 (3) | 0.0660 (11) | |
H28 | 0.0361 | 0.1550 | 0.6425 | 0.079* | |
C29 | 0.00712 (19) | −0.0801 (5) | 0.6198 (3) | 0.0729 (13) | |
H29 | −0.0275 | −0.0488 | 0.5866 | 0.087* | |
C30 | 0.01913 (18) | −0.2500 (5) | 0.6360 (3) | 0.0573 (10) | |
O31 | −0.02239 (13) | −0.3597 (4) | 0.6019 (2) | 0.0748 (8) | |
C32 | −0.0113 (2) | −0.5362 (5) | 0.6132 (3) | 0.0770 (13) | |
H32A | 0.0226 | −0.5658 | 0.5862 | 0.116* | |
H32B | −0.0438 | −0.5994 | 0.5857 | 0.116* | |
H32C | −0.0050 | −0.5625 | 0.6755 | 0.116* | |
C33 | 0.07166 (18) | −0.2946 (5) | 0.6822 (3) | 0.0560 (10) | |
H33 | 0.0807 | −0.4081 | 0.6927 | 0.067* | |
C34 | 0.11092 (16) | −0.1696 (4) | 0.7128 (2) | 0.0503 (9) | |
H34 | 0.1464 | −0.2006 | 0.7434 | 0.060* | |
C35 | 0.35184 (13) | 0.7135 (3) | 0.46256 (16) | 0.0942 (16) | |
H35A | 0.3642 | 0.7321 | 0.5245 | 0.141* | |
H35B | 0.3271 | 0.8047 | 0.4397 | 0.141* | |
H35C | 0.3851 | 0.7086 | 0.4309 | 0.141* | |
O36 | 0.32130 (13) | 0.5596 (3) | 0.45171 (16) | 0.0778 (9) | |
H36 | 0.3199 | 0.5283 | 0.3999 | 0.117* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0765 (4) | 0.0925 (4) | 0.0976 (4) | 0.0491 (3) | 0.0173 (3) | 0.0313 (3) |
Br2 | 0.0652 (3) | 0.0755 (3) | 0.0779 (3) | −0.0035 (2) | 0.0263 (2) | 0.0123 (2) |
N1 | 0.0477 (18) | 0.0355 (14) | 0.0473 (15) | 0.0005 (12) | 0.0076 (13) | 0.0063 (11) |
C2 | 0.044 (2) | 0.0260 (15) | 0.0448 (18) | −0.0008 (14) | −0.0020 (15) | −0.0042 (12) |
O3 | 0.0523 (16) | 0.0287 (11) | 0.0695 (16) | 0.0064 (11) | 0.0045 (12) | 0.0019 (10) |
C4 | 0.042 (2) | 0.0308 (15) | 0.0369 (16) | 0.0028 (13) | 0.0016 (14) | −0.0009 (12) |
C5 | 0.042 (2) | 0.0330 (16) | 0.0358 (16) | 0.0000 (13) | 0.0011 (14) | −0.0040 (12) |
C6 | 0.047 (2) | 0.0443 (18) | 0.0423 (18) | 0.0051 (15) | −0.0006 (16) | 0.0026 (14) |
C7 | 0.050 (2) | 0.050 (2) | 0.051 (2) | 0.0162 (17) | −0.0032 (18) | 0.0002 (16) |
C8 | 0.041 (2) | 0.059 (2) | 0.056 (2) | 0.0054 (18) | 0.0044 (17) | −0.0098 (18) |
C9 | 0.044 (2) | 0.0498 (19) | 0.0441 (19) | −0.0048 (16) | 0.0049 (16) | −0.0050 (15) |
C10 | 0.0386 (19) | 0.0390 (17) | 0.0385 (17) | 0.0017 (14) | 0.0005 (14) | −0.0031 (13) |
C11 | 0.0398 (19) | 0.0269 (14) | 0.0351 (16) | 0.0041 (12) | 0.0023 (14) | 0.0008 (11) |
C12 | 0.044 (2) | 0.0457 (18) | 0.0381 (17) | 0.0093 (15) | 0.0077 (15) | 0.0031 (14) |
C13 | 0.061 (3) | 0.057 (2) | 0.0410 (19) | 0.0129 (18) | 0.0045 (18) | −0.0111 (15) |
N14 | 0.0451 (18) | 0.0469 (16) | 0.0405 (15) | 0.0030 (13) | 0.0000 (13) | −0.0134 (12) |
C15 | 0.063 (3) | 0.060 (2) | 0.066 (2) | −0.002 (2) | −0.005 (2) | −0.0241 (19) |
C16 | 0.041 (2) | 0.0325 (16) | 0.056 (2) | 0.0025 (14) | 0.0087 (16) | 0.0093 (15) |
O17 | 0.0636 (18) | 0.0478 (14) | 0.0626 (17) | 0.0105 (12) | 0.0016 (13) | 0.0236 (12) |
N18 | 0.061 (2) | 0.0246 (13) | 0.069 (2) | 0.0060 (13) | 0.0043 (16) | −0.0066 (13) |
C19 | 0.050 (2) | 0.0374 (17) | 0.0475 (19) | 0.0024 (15) | 0.0075 (16) | −0.0062 (14) |
C20 | 0.084 (3) | 0.058 (2) | 0.061 (3) | −0.003 (2) | 0.003 (2) | −0.027 (2) |
C21 | 0.071 (3) | 0.091 (3) | 0.042 (2) | −0.009 (2) | −0.005 (2) | −0.011 (2) |
C22 | 0.054 (2) | 0.070 (3) | 0.041 (2) | −0.007 (2) | 0.0005 (17) | 0.0117 (18) |
C23 | 0.041 (2) | 0.0422 (17) | 0.0423 (18) | −0.0036 (15) | 0.0054 (15) | 0.0073 (14) |
C24 | 0.0331 (18) | 0.0315 (15) | 0.0367 (16) | −0.0035 (13) | 0.0055 (13) | −0.0005 (12) |
C25 | 0.052 (2) | 0.050 (2) | 0.0387 (18) | 0.0103 (17) | 0.0103 (16) | 0.0022 (15) |
O26 | 0.0580 (18) | 0.0532 (16) | 0.0790 (19) | 0.0149 (13) | 0.0054 (14) | −0.0070 (13) |
C27 | 0.041 (2) | 0.0469 (19) | 0.0477 (19) | 0.0076 (16) | 0.0105 (16) | 0.0086 (15) |
C28 | 0.055 (3) | 0.043 (2) | 0.098 (3) | 0.0104 (19) | 0.000 (2) | 0.010 (2) |
C29 | 0.054 (3) | 0.056 (2) | 0.103 (4) | 0.008 (2) | −0.014 (2) | 0.013 (2) |
C30 | 0.055 (3) | 0.052 (2) | 0.065 (2) | 0.0034 (19) | 0.007 (2) | 0.0050 (18) |
O31 | 0.069 (2) | 0.0512 (16) | 0.100 (2) | 0.0009 (15) | −0.0064 (17) | 0.0019 (15) |
C32 | 0.096 (4) | 0.048 (2) | 0.087 (3) | −0.006 (2) | 0.011 (3) | 0.001 (2) |
C33 | 0.057 (3) | 0.049 (2) | 0.063 (2) | 0.0111 (19) | 0.012 (2) | 0.0169 (17) |
C34 | 0.040 (2) | 0.051 (2) | 0.060 (2) | 0.0053 (16) | 0.0063 (17) | 0.0162 (16) |
C35 | 0.114 (5) | 0.083 (3) | 0.084 (3) | −0.021 (3) | 0.004 (3) | 0.008 (3) |
O36 | 0.100 (2) | 0.0772 (19) | 0.0528 (16) | −0.0111 (17) | −0.0059 (16) | 0.0165 (14) |
Geometric parameters (Å, º) top
Br1—C7 | 1.897 (3) | N18—H18 | 0.8600 |
Br2—C9 | 1.892 (3) | C19—C20 | 1.380 (5) |
N1—C2 | 1.348 (4) | C19—C24 | 1.385 (4) |
N1—C10 | 1.397 (4) | C20—C21 | 1.372 (6) |
N1—H1 | 0.8600 | C20—H20 | 0.9300 |
C2—O3 | 1.213 (4) | C21—C22 | 1.366 (6) |
C2—C4 | 1.564 (4) | C21—H21 | 0.9300 |
C4—N14 | 1.456 (4) | C22—C23 | 1.378 (5) |
C4—C5 | 1.519 (4) | C22—H22 | 0.9300 |
C4—C11 | 1.581 (4) | C23—C24 | 1.379 (4) |
C5—C6 | 1.373 (4) | C23—H23 | 0.9300 |
C5—C10 | 1.386 (4) | C25—O26 | 1.228 (4) |
C6—C7 | 1.386 (5) | C25—C27 | 1.479 (5) |
C6—H6 | 0.9300 | C27—C34 | 1.380 (5) |
C7—C8 | 1.369 (5) | C27—C28 | 1.382 (5) |
C8—C9 | 1.382 (5) | C28—C29 | 1.364 (6) |
C8—H8 | 0.9300 | C28—H28 | 0.9300 |
C9—C10 | 1.371 (5) | C29—C30 | 1.386 (5) |
C11—C24 | 1.522 (4) | C29—H29 | 0.9300 |
C11—C16 | 1.540 (4) | C30—O31 | 1.353 (5) |
C11—C12 | 1.576 (4) | C30—C33 | 1.379 (5) |
C12—C25 | 1.513 (5) | O31—C32 | 1.424 (5) |
C12—C13 | 1.513 (5) | C32—H32A | 0.9600 |
C12—H12 | 0.9800 | C32—H32B | 0.9600 |
C13—N14 | 1.458 (5) | C32—H32C | 0.9600 |
C13—H13A | 0.9700 | C33—C34 | 1.386 (5) |
C13—H13B | 0.9700 | C33—H33 | 0.9300 |
N14—C15 | 1.466 (5) | C34—H34 | 0.9300 |
C15—H15A | 0.9600 | C35—O36 | 1.4074 |
C15—H15B | 0.9600 | C35—H35A | 0.9600 |
C15—H15C | 0.9600 | C35—H35B | 0.9600 |
C16—O17 | 1.227 (4) | C35—H35C | 0.9600 |
C16—N18 | 1.334 (5) | O36—H36 | 0.8200 |
N18—C19 | 1.399 (4) | | |
| | | |
C2—N1—C10 | 111.5 (3) | O17—C16—C11 | 124.8 (3) |
C2—N1—H1 | 124.3 | N18—C16—C11 | 108.2 (3) |
C10—N1—H1 | 124.3 | C16—N18—C19 | 111.9 (3) |
O3—C2—N1 | 126.0 (3) | C16—N18—H18 | 124.0 |
O3—C2—C4 | 125.3 (3) | C19—N18—H18 | 124.0 |
N1—C2—C4 | 108.7 (3) | C20—C19—C24 | 121.9 (3) |
N14—C4—C5 | 113.3 (3) | C20—C19—N18 | 128.2 (3) |
N14—C4—C2 | 112.3 (2) | C24—C19—N18 | 109.8 (3) |
C5—C4—C2 | 100.5 (2) | C21—C20—C19 | 117.6 (4) |
N14—C4—C11 | 102.8 (2) | C21—C20—H20 | 121.2 |
C5—C4—C11 | 117.6 (2) | C19—C20—H20 | 121.2 |
C2—C4—C11 | 110.8 (2) | C22—C21—C20 | 121.5 (4) |
C6—C5—C10 | 120.2 (3) | C22—C21—H21 | 119.3 |
C6—C5—C4 | 130.4 (3) | C20—C21—H21 | 119.3 |
C10—C5—C4 | 109.1 (3) | C21—C22—C23 | 120.8 (4) |
C5—C6—C7 | 118.0 (3) | C21—C22—H22 | 119.6 |
C5—C6—H6 | 121.0 | C23—C22—H22 | 119.6 |
C7—C6—H6 | 121.0 | C22—C23—C24 | 119.0 (3) |
C8—C7—C6 | 122.3 (3) | C22—C23—H23 | 120.5 |
C8—C7—Br1 | 119.0 (3) | C24—C23—H23 | 120.5 |
C6—C7—Br1 | 118.6 (3) | C23—C24—C19 | 119.3 (3) |
C7—C8—C9 | 118.8 (3) | C23—C24—C11 | 132.8 (3) |
C7—C8—H8 | 120.6 | C19—C24—C11 | 107.9 (3) |
C9—C8—H8 | 120.6 | O26—C25—C27 | 120.7 (3) |
C10—C9—C8 | 119.8 (3) | O26—C25—C12 | 120.3 (3) |
C10—C9—Br2 | 120.8 (3) | C27—C25—C12 | 119.1 (3) |
C8—C9—Br2 | 119.3 (3) | C34—C27—C28 | 117.9 (3) |
C9—C10—C5 | 120.6 (3) | C34—C27—C25 | 123.6 (3) |
C9—C10—N1 | 129.0 (3) | C28—C27—C25 | 118.5 (3) |
C5—C10—N1 | 110.2 (3) | C29—C28—C27 | 121.5 (4) |
C24—C11—C16 | 101.4 (2) | C29—C28—H28 | 119.3 |
C24—C11—C12 | 118.9 (3) | C27—C28—H28 | 119.3 |
C16—C11—C12 | 109.1 (2) | C28—C29—C30 | 120.5 (4) |
C24—C11—C4 | 114.6 (2) | C28—C29—H29 | 119.7 |
C16—C11—C4 | 109.4 (3) | C30—C29—H29 | 119.7 |
C12—C11—C4 | 103.2 (2) | O31—C30—C33 | 125.3 (4) |
C25—C12—C13 | 115.9 (3) | O31—C30—C29 | 115.6 (4) |
C25—C12—C11 | 113.5 (3) | C33—C30—C29 | 119.0 (4) |
C13—C12—C11 | 105.1 (3) | C30—O31—C32 | 118.0 (3) |
C25—C12—H12 | 107.3 | O31—C32—H32A | 109.5 |
C13—C12—H12 | 107.3 | O31—C32—H32B | 109.5 |
C11—C12—H12 | 107.3 | H32A—C32—H32B | 109.5 |
N14—C13—C12 | 104.1 (3) | O31—C32—H32C | 109.5 |
N14—C13—H13A | 110.9 | H32A—C32—H32C | 109.5 |
C12—C13—H13A | 110.9 | H32B—C32—H32C | 109.5 |
N14—C13—H13B | 110.9 | C30—C33—C34 | 119.7 (3) |
C12—C13—H13B | 110.9 | C30—C33—H33 | 120.1 |
H13A—C13—H13B | 109.0 | C34—C33—H33 | 120.1 |
C4—N14—C13 | 106.3 (3) | C27—C34—C33 | 121.4 (4) |
C4—N14—C15 | 115.1 (3) | C27—C34—H34 | 119.3 |
C13—N14—C15 | 113.0 (3) | C33—C34—H34 | 119.3 |
N14—C15—H15A | 109.5 | O36—C35—H35A | 109.5 |
N14—C15—H15B | 109.5 | O36—C35—H35B | 109.5 |
H15A—C15—H15B | 109.5 | H35A—C35—H35B | 109.5 |
N14—C15—H15C | 109.5 | O36—C35—H35C | 109.5 |
H15A—C15—H15C | 109.5 | H35A—C35—H35C | 109.5 |
H15B—C15—H15C | 109.5 | H35B—C35—H35C | 109.5 |
O17—C16—N18 | 127.0 (3) | C35—O36—H36 | 109.5 |
| | | |
C10—N1—C2—O3 | 176.4 (3) | C5—C4—N14—C15 | 64.6 (4) |
C10—N1—C2—C4 | −0.8 (4) | C2—C4—N14—C15 | −48.3 (4) |
O3—C2—C4—N14 | −56.6 (4) | C11—C4—N14—C15 | −167.4 (3) |
N1—C2—C4—N14 | 120.7 (3) | C12—C13—N14—C4 | 43.3 (3) |
O3—C2—C4—C5 | −177.3 (3) | C12—C13—N14—C15 | 170.4 (3) |
N1—C2—C4—C5 | 0.0 (3) | C24—C11—C16—O17 | −169.9 (3) |
O3—C2—C4—C11 | 57.7 (4) | C12—C11—C16—O17 | −43.6 (4) |
N1—C2—C4—C11 | −125.0 (3) | C4—C11—C16—O17 | 68.6 (4) |
N14—C4—C5—C6 | 55.6 (4) | C24—C11—C16—N18 | 8.8 (3) |
C2—C4—C5—C6 | 175.6 (3) | C12—C11—C16—N18 | 135.1 (3) |
C11—C4—C5—C6 | −64.2 (4) | C4—C11—C16—N18 | −112.6 (3) |
N14—C4—C5—C10 | −119.2 (3) | O17—C16—N18—C19 | 170.3 (3) |
C2—C4—C5—C10 | 0.8 (3) | C11—C16—N18—C19 | −8.4 (4) |
C11—C4—C5—C10 | 121.0 (3) | C16—N18—C19—C20 | −172.9 (4) |
C10—C5—C6—C7 | −2.6 (5) | C16—N18—C19—C24 | 4.3 (4) |
C4—C5—C6—C7 | −176.8 (3) | C24—C19—C20—C21 | −1.2 (6) |
C5—C6—C7—C8 | 3.6 (5) | N18—C19—C20—C21 | 175.6 (4) |
C5—C6—C7—Br1 | −177.9 (2) | C19—C20—C21—C22 | −0.2 (7) |
C6—C7—C8—C9 | −1.1 (5) | C20—C21—C22—C23 | 1.0 (7) |
Br1—C7—C8—C9 | −179.6 (3) | C21—C22—C23—C24 | −0.3 (5) |
C7—C8—C9—C10 | −2.4 (5) | C22—C23—C24—C19 | −1.1 (5) |
C7—C8—C9—Br2 | 173.7 (3) | C22—C23—C24—C11 | −177.7 (3) |
C8—C9—C10—C5 | 3.4 (5) | C20—C19—C24—C23 | 1.9 (5) |
Br2—C9—C10—C5 | −172.7 (2) | N18—C19—C24—C23 | −175.4 (3) |
C8—C9—C10—N1 | 178.4 (3) | C20—C19—C24—C11 | 179.3 (3) |
Br2—C9—C10—N1 | 2.3 (5) | N18—C19—C24—C11 | 1.9 (4) |
C6—C5—C10—C9 | −0.8 (5) | C16—C11—C24—C23 | 170.6 (3) |
C4—C5—C10—C9 | 174.6 (3) | C12—C11—C24—C23 | 51.0 (5) |
C6—C5—C10—N1 | −176.7 (3) | C4—C11—C24—C23 | −71.7 (4) |
C4—C5—C10—N1 | −1.4 (4) | C16—C11—C24—C19 | −6.3 (3) |
C2—N1—C10—C9 | −174.1 (3) | C12—C11—C24—C19 | −125.9 (3) |
C2—N1—C10—C5 | 1.4 (4) | C4—C11—C24—C19 | 111.5 (3) |
N14—C4—C11—C24 | 154.2 (2) | C13—C12—C25—O26 | 11.9 (4) |
C5—C4—C11—C24 | −80.6 (3) | C11—C12—C25—O26 | −109.9 (3) |
C2—C4—C11—C24 | 34.1 (3) | C13—C12—C25—C27 | −168.9 (3) |
N14—C4—C11—C16 | −92.7 (3) | C11—C12—C25—C27 | 69.3 (4) |
C5—C4—C11—C16 | 32.5 (3) | O26—C25—C27—C34 | −167.2 (3) |
C2—C4—C11—C16 | 147.2 (3) | C12—C25—C27—C34 | 13.6 (5) |
N14—C4—C11—C12 | 23.4 (3) | O26—C25—C27—C28 | 13.3 (5) |
C5—C4—C11—C12 | 148.6 (3) | C12—C25—C27—C28 | −165.9 (3) |
C2—C4—C11—C12 | −96.8 (3) | C34—C27—C28—C29 | −0.9 (6) |
C24—C11—C12—C25 | 1.0 (4) | C25—C27—C28—C29 | 178.6 (4) |
C16—C11—C12—C25 | −114.6 (3) | C27—C28—C29—C30 | 2.5 (7) |
C4—C11—C12—C25 | 129.1 (3) | C28—C29—C30—O31 | 179.1 (4) |
C24—C11—C12—C13 | −126.7 (3) | C28—C29—C30—C33 | −2.6 (7) |
C16—C11—C12—C13 | 117.8 (3) | C33—C30—O31—C32 | −0.8 (6) |
C4—C11—C12—C13 | 1.5 (3) | C29—C30—O31—C32 | 177.3 (4) |
C25—C12—C13—N14 | −152.2 (3) | O31—C30—C33—C34 | 179.2 (4) |
C11—C12—C13—N14 | −26.0 (3) | C29—C30—C33—C34 | 1.1 (6) |
C5—C4—N14—C13 | −169.5 (3) | C28—C27—C34—C33 | −0.7 (5) |
C2—C4—N14—C13 | 77.5 (3) | C25—C27—C34—C33 | 179.9 (3) |
C11—C4—N14—C13 | −41.6 (3) | C30—C33—C34—C27 | 0.5 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O36 | 0.86 | 1.96 | 2.802 (4) | 165 |
C6—H6···O17 | 0.93 | 2.37 | 3.046 (5) | 129 |
C12—H12···O17 | 0.98 | 2.47 | 2.943 (4) | 110 |
C13—H13A···O3 | 0.97 | 2.47 | 3.036 (5) | 117 |
C13—H13A···O26 | 0.97 | 2.47 | 2.820 (5) | 101 |
C23—H23···O3 | 0.93 | 2.38 | 2.966 (4) | 121 |
N18—H18···O3i | 0.86 | 2.03 | 2.806 (3) | 150 |
O36—H36···O17ii | 0.82 | 2.54 | 3.053 (3) | 122 |
O36—H36···N14ii | 0.82 | 2.46 | 3.183 (4) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2. |