The title molecule, C33H37N2O, as a dicondensed spiropyran (DC), contains a benzopyran and two indoline ring systems. Each of the three systems is nearly planar. While both indolines are almost perpendicular to the benzopyran, they make a dihedral angle of 33.6 (4)° with each other. The two chiral C atoms have the same chirality (RR or SS).
Supporting information
CCDC reference: 294028
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.004 Å
- R factor = 0.057
- wR factor = 0.124
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label ..........
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
1 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 215
tertiary C and 0.95\%A for aromatic sp2~ C atoms, and were treated as riding,
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
6-Bromo-1'-ethyl-4-(1-ethyl-3,3-dimethyl-2,3-dimethyl-1
H-indolin-2-
ylidenemethyl)-3',3'-dimethylspiro[3,4-dihydro-2
H-1-benzopyran-2,2'(3'H)- 1
H-indoline]
top
Crystal data top
C33H37BrN2O | F(000) = 1168 |
Mr = 557.56 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/n | Melting point: 457(1) K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71070 Å |
a = 12.4808 (15) Å | Cell parameters from 9054 reflections |
b = 12.0528 (15) Å | θ = 3.1–25.3° |
c = 20.146 (3) Å | µ = 1.45 mm−1 |
β = 107.031 (4)° | T = 193 K |
V = 2897.7 (7) Å3 | Block, colorless |
Z = 4 | 0.32 × 0.30 × 0.19 mm |
Data collection top
Rigaku Mercury diffractometer | 5291 independent reflections |
Radiation source: fine-focus sealed tube | 4270 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.1° |
ω scans | h = −14→15 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −13→14 |
Tmin = 0.648, Tmax = 0.763 | l = −24→24 |
28220 measured 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0445P)2 + 1.8582P] where P = (Fo2 + 2Fc2)/3 |
5291 reflections | (Δ/σ)max = 0.003 |
341 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.44 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 >
2σ(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 | 0.83197 (4) | 0.62034 (4) | 1.132891 (19) | 0.07103 (18) | |
O1 | 0.70680 (15) | 0.49790 (16) | 0.83010 (10) | 0.0359 (5) | |
N1 | 0.4475 (2) | 0.93270 (19) | 0.91665 (12) | 0.0350 (6) | |
N2 | 0.6294 (2) | 0.5369 (2) | 0.71310 (12) | 0.0353 (6) | |
C1 | 0.7285 (2) | 0.5288 (2) | 0.89797 (15) | 0.0325 (6) | |
C2 | 0.6624 (2) | 0.6031 (2) | 0.92190 (14) | 0.0303 (6) | |
C3 | 0.6950 (2) | 0.6293 (2) | 0.99215 (15) | 0.0368 (7) | |
H3 | 0.6511 | 0.6794 | 1.0096 | 0.044* | |
C4 | 0.7904 (3) | 0.5833 (3) | 1.03696 (16) | 0.0434 (8) | |
C5 | 0.8561 (3) | 0.5100 (3) | 1.01294 (17) | 0.0457 (8) | |
H5 | 0.9217 | 0.4787 | 1.0439 | 0.055* | |
C6 | 0.8247 (2) | 0.4833 (2) | 0.94345 (16) | 0.0380 (7) | |
H6 | 0.8692 | 0.4333 | 0.9264 | 0.046* | |
C7 | 0.5589 (2) | 0.6548 (2) | 0.87177 (14) | 0.0301 (6) | |
H7 | 0.4918 | 0.6109 | 0.8734 | 0.036* | |
C8 | 0.5705 (2) | 0.6472 (2) | 0.79841 (15) | 0.0339 (7) | |
H8A | 0.4983 | 0.6689 | 0.7649 | 0.041* | |
H8B | 0.6276 | 0.7017 | 0.7942 | 0.041* | |
C9 | 0.6029 (2) | 0.5346 (2) | 0.77829 (14) | 0.0310 (6) | |
C10 | 0.5415 (2) | 0.7729 (2) | 0.88818 (15) | 0.0332 (6) | |
H10 | 0.5986 | 0.8229 | 0.8849 | 0.040* | |
C11 | 0.4570 (2) | 0.8185 (2) | 0.90678 (14) | 0.0297 (6) | |
C12 | 0.3570 (2) | 0.7611 (2) | 0.92228 (14) | 0.0335 (6) | |
C13 | 0.2930 (2) | 0.8603 (2) | 0.93758 (15) | 0.0355 (7) | |
C14 | 0.1933 (3) | 0.8647 (3) | 0.95438 (16) | 0.0467 (8) | |
H14 | 0.1551 | 0.7984 | 0.9592 | 0.056* | |
C15 | 0.1495 (3) | 0.9681 (3) | 0.96410 (17) | 0.0522 (9) | |
H15 | 0.0814 | 0.9722 | 0.9760 | 0.063* | |
C16 | 0.2043 (3) | 1.0637 (3) | 0.95657 (17) | 0.0517 (9) | |
H16 | 0.1730 | 1.1333 | 0.9629 | 0.062* | |
C17 | 0.3053 (3) | 1.0610 (3) | 0.93987 (17) | 0.0456 (8) | |
H17 | 0.3431 | 1.1274 | 0.9347 | 0.055* | |
C18 | 0.3481 (2) | 0.9575 (3) | 0.93111 (14) | 0.0349 (7) | |
C19 | 0.5146 (2) | 0.4386 (2) | 0.76736 (14) | 0.0320 (6) | |
C20 | 0.5492 (2) | 0.3671 (2) | 0.71496 (14) | 0.0331 (7) | |
C21 | 0.5233 (2) | 0.2592 (2) | 0.69451 (15) | 0.0384 (7) | |
H21 | 0.4801 | 0.2150 | 0.7162 | 0.046* | |
C22 | 0.5615 (3) | 0.2155 (3) | 0.64142 (16) | 0.0450 (8) | |
H22 | 0.5448 | 0.1407 | 0.6271 | 0.054* | |
C23 | 0.6231 (3) | 0.2797 (3) | 0.60988 (16) | 0.0460 (8) | |
H23 | 0.6478 | 0.2490 | 0.5735 | 0.055* | |
C24 | 0.6498 (3) | 0.3888 (3) | 0.63025 (16) | 0.0426 (8) | |
H24 | 0.6922 | 0.4332 | 0.6081 | 0.051* | |
C25 | 0.6131 (2) | 0.4313 (2) | 0.68364 (14) | 0.0336 (7) | |
C26 | 0.5150 (3) | 1.0155 (3) | 0.89537 (17) | 0.0417 (7) | |
H26A | 0.5940 | 0.9904 | 0.9088 | 0.050* | |
H26B | 0.5118 | 1.0857 | 0.9202 | 0.050* | |
C27 | 0.4760 (3) | 1.0366 (3) | 0.8181 (2) | 0.0648 (11) | |
H27A | 0.4821 | 0.9680 | 0.7933 | 0.097* | |
H27B | 0.5227 | 1.0942 | 0.8063 | 0.097* | |
H27C | 0.3977 | 1.0612 | 0.8044 | 0.097* | |
C28 | 0.3948 (3) | 0.6840 (3) | 0.98545 (17) | 0.0449 (8) | |
H28A | 0.4366 | 0.6214 | 0.9744 | 0.067* | |
H28B | 0.3289 | 0.6563 | 0.9973 | 0.067* | |
H28C | 0.4429 | 0.7252 | 1.0249 | 0.067* | |
C29 | 0.2824 (3) | 0.6967 (3) | 0.85981 (17) | 0.0433 (8) | |
H29A | 0.2657 | 0.7436 | 0.8183 | 0.065* | |
H29B | 0.2124 | 0.6757 | 0.8692 | 0.065* | |
H29C | 0.3217 | 0.6297 | 0.8522 | 0.065* | |
C30 | 0.7137 (3) | 0.6120 (3) | 0.70176 (19) | 0.0505 (9) | |
H30A | 0.7723 | 0.5681 | 0.6895 | 0.061* | |
H30B | 0.7498 | 0.6523 | 0.7454 | 0.061* | |
C31 | 0.6646 (4) | 0.6950 (4) | 0.6446 (2) | 0.0799 (13) | |
H31A | 0.6303 | 0.6555 | 0.6011 | 0.120* | |
H31B | 0.7241 | 0.7438 | 0.6390 | 0.120* | |
H31C | 0.6075 | 0.7395 | 0.6569 | 0.120* | |
C32 | 0.5168 (3) | 0.3747 (3) | 0.83336 (16) | 0.0411 (7) | |
H32A | 0.4621 | 0.3141 | 0.8217 | 0.062* | |
H32B | 0.4978 | 0.4250 | 0.8664 | 0.062* | |
H32C | 0.5919 | 0.3441 | 0.8542 | 0.062* | |
C33 | 0.3960 (2) | 0.4828 (3) | 0.73230 (17) | 0.0422 (8) | |
H33A | 0.3957 | 0.5246 | 0.6905 | 0.063* | |
H33B | 0.3729 | 0.5316 | 0.7646 | 0.063* | |
H33C | 0.3436 | 0.4204 | 0.7195 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0876 (3) | 0.0788 (3) | 0.0327 (2) | −0.0062 (2) | −0.00406 (18) | −0.00030 (18) |
O1 | 0.0329 (10) | 0.0393 (12) | 0.0339 (11) | 0.0050 (9) | 0.0071 (8) | −0.0023 (9) |
N1 | 0.0395 (14) | 0.0281 (13) | 0.0386 (14) | −0.0006 (11) | 0.0133 (11) | −0.0014 (11) |
N2 | 0.0435 (14) | 0.0352 (14) | 0.0311 (13) | −0.0040 (11) | 0.0169 (11) | −0.0014 (11) |
C1 | 0.0327 (15) | 0.0310 (15) | 0.0328 (16) | −0.0061 (13) | 0.0081 (12) | 0.0028 (12) |
C2 | 0.0314 (14) | 0.0284 (15) | 0.0304 (15) | −0.0053 (12) | 0.0081 (12) | 0.0003 (12) |
C3 | 0.0408 (17) | 0.0360 (17) | 0.0325 (16) | −0.0057 (14) | 0.0090 (13) | −0.0012 (13) |
C4 | 0.0466 (18) | 0.0468 (19) | 0.0299 (16) | −0.0104 (16) | 0.0004 (14) | 0.0040 (14) |
C5 | 0.0388 (17) | 0.0459 (19) | 0.045 (2) | −0.0058 (15) | 0.0001 (14) | 0.0118 (15) |
C6 | 0.0310 (15) | 0.0361 (17) | 0.0457 (18) | 0.0000 (13) | 0.0092 (13) | 0.0050 (14) |
C7 | 0.0308 (14) | 0.0283 (14) | 0.0313 (15) | −0.0022 (12) | 0.0092 (12) | −0.0016 (12) |
C8 | 0.0357 (15) | 0.0318 (16) | 0.0320 (16) | −0.0005 (13) | 0.0063 (12) | 0.0012 (12) |
C9 | 0.0324 (15) | 0.0324 (15) | 0.0280 (15) | 0.0036 (12) | 0.0085 (12) | 0.0010 (12) |
C10 | 0.0340 (15) | 0.0284 (15) | 0.0360 (16) | −0.0031 (13) | 0.0084 (12) | −0.0017 (12) |
C11 | 0.0367 (15) | 0.0260 (14) | 0.0254 (14) | −0.0015 (12) | 0.0076 (12) | −0.0011 (11) |
C12 | 0.0347 (15) | 0.0372 (16) | 0.0292 (15) | −0.0016 (13) | 0.0105 (12) | −0.0013 (13) |
C13 | 0.0375 (16) | 0.0409 (17) | 0.0273 (15) | −0.0014 (14) | 0.0083 (12) | −0.0073 (13) |
C14 | 0.0421 (18) | 0.061 (2) | 0.0389 (18) | −0.0079 (16) | 0.0142 (14) | −0.0142 (16) |
C15 | 0.0444 (19) | 0.073 (3) | 0.0420 (19) | 0.0075 (19) | 0.0173 (15) | −0.0185 (18) |
C16 | 0.052 (2) | 0.059 (2) | 0.043 (2) | 0.0126 (18) | 0.0120 (16) | −0.0182 (17) |
C17 | 0.0510 (19) | 0.0416 (18) | 0.0439 (19) | 0.0058 (15) | 0.0132 (15) | −0.0092 (15) |
C18 | 0.0378 (16) | 0.0396 (17) | 0.0263 (15) | 0.0039 (14) | 0.0076 (12) | −0.0036 (12) |
C19 | 0.0348 (15) | 0.0341 (16) | 0.0280 (15) | 0.0003 (13) | 0.0104 (12) | −0.0015 (12) |
C20 | 0.0319 (15) | 0.0374 (16) | 0.0282 (15) | 0.0049 (13) | 0.0061 (12) | 0.0007 (12) |
C21 | 0.0383 (16) | 0.0368 (17) | 0.0361 (17) | −0.0004 (14) | 0.0045 (13) | −0.0018 (13) |
C22 | 0.0482 (19) | 0.0388 (18) | 0.0415 (19) | 0.0083 (15) | 0.0029 (15) | −0.0097 (15) |
C23 | 0.0472 (19) | 0.055 (2) | 0.0336 (17) | 0.0172 (16) | 0.0081 (14) | −0.0084 (15) |
C24 | 0.0451 (18) | 0.051 (2) | 0.0344 (17) | 0.0077 (15) | 0.0156 (14) | 0.0013 (15) |
C25 | 0.0350 (15) | 0.0368 (16) | 0.0285 (15) | 0.0049 (13) | 0.0086 (12) | −0.0016 (13) |
C26 | 0.0476 (18) | 0.0316 (16) | 0.0479 (19) | −0.0034 (14) | 0.0173 (15) | 0.0005 (14) |
C27 | 0.078 (3) | 0.060 (2) | 0.059 (2) | 0.002 (2) | 0.026 (2) | 0.0232 (19) |
C28 | 0.0497 (19) | 0.0430 (18) | 0.0433 (18) | −0.0034 (15) | 0.0159 (15) | 0.0101 (15) |
C29 | 0.0364 (17) | 0.0436 (18) | 0.0491 (19) | −0.0010 (14) | 0.0112 (14) | −0.0110 (15) |
C30 | 0.054 (2) | 0.052 (2) | 0.055 (2) | −0.0172 (17) | 0.0293 (17) | −0.0081 (17) |
C31 | 0.112 (4) | 0.062 (3) | 0.075 (3) | −0.017 (2) | 0.043 (3) | 0.022 (2) |
C32 | 0.0531 (19) | 0.0362 (17) | 0.0363 (17) | −0.0080 (15) | 0.0165 (14) | −0.0016 (14) |
C33 | 0.0361 (16) | 0.0442 (18) | 0.0456 (19) | −0.0014 (14) | 0.0110 (14) | −0.0097 (15) |
Geometric parameters (Å, º) top
Br1—C4 | 1.902 (3) | C17—C18 | 1.389 (4) |
O1—C1 | 1.366 (3) | C17—H17 | 0.9500 |
O1—C9 | 1.474 (3) | C19—C20 | 1.520 (4) |
N1—C18 | 1.388 (4) | C19—C32 | 1.530 (4) |
N1—C11 | 1.401 (4) | C19—C33 | 1.537 (4) |
N1—C26 | 1.449 (4) | C20—C21 | 1.373 (4) |
N2—C25 | 1.394 (4) | C20—C25 | 1.389 (4) |
N2—C9 | 1.446 (4) | C21—C22 | 1.396 (4) |
N2—C30 | 1.455 (4) | C21—H21 | 0.9500 |
C1—C6 | 1.392 (4) | C22—C23 | 1.370 (5) |
C1—C2 | 1.396 (4) | C22—H22 | 0.9500 |
C2—C3 | 1.389 (4) | C23—C24 | 1.389 (5) |
C2—C7 | 1.520 (4) | C23—H23 | 0.9500 |
C3—C4 | 1.382 (4) | C24—C25 | 1.385 (4) |
C3—H3 | 0.9500 | C24—H24 | 0.9500 |
C4—C5 | 1.385 (5) | C26—C27 | 1.511 (5) |
C5—C6 | 1.377 (4) | C26—H26A | 0.9900 |
C5—H5 | 0.9500 | C26—H26B | 0.9900 |
C6—H6 | 0.9500 | C27—H27A | 0.9800 |
C7—C10 | 1.492 (4) | C27—H27B | 0.9800 |
C7—C8 | 1.529 (4) | C27—H27C | 0.9800 |
C7—H7 | 1.0000 | C28—H28A | 0.9800 |
C8—C9 | 1.506 (4) | C28—H28B | 0.9800 |
C8—H8A | 0.9900 | C28—H28C | 0.9800 |
C8—H8B | 0.9900 | C29—H29A | 0.9800 |
C9—C19 | 1.569 (4) | C29—H29B | 0.9800 |
C10—C11 | 1.337 (4) | C29—H29C | 0.9800 |
C10—H10 | 0.9500 | C30—C31 | 1.513 (5) |
C11—C12 | 1.536 (4) | C30—H30A | 0.9900 |
C12—C13 | 1.519 (4) | C30—H30B | 0.9900 |
C12—C28 | 1.534 (4) | C31—H31A | 0.9800 |
C12—C29 | 1.539 (4) | C31—H31B | 0.9800 |
C13—C14 | 1.383 (4) | C31—H31C | 0.9800 |
C13—C18 | 1.385 (4) | C32—H32A | 0.9800 |
C14—C15 | 1.397 (5) | C32—H32B | 0.9800 |
C14—H14 | 0.9500 | C32—H32C | 0.9800 |
C15—C16 | 1.371 (5) | C33—H33A | 0.9800 |
C15—H15 | 0.9500 | C33—H33B | 0.9800 |
C16—C17 | 1.396 (5) | C33—H33C | 0.9800 |
C16—H16 | 0.9500 | | |
| | | |
C1—O1—C9 | 120.2 (2) | C20—C19—C32 | 112.4 (2) |
C18—N1—C11 | 111.0 (2) | C20—C19—C33 | 108.0 (2) |
C18—N1—C26 | 123.1 (2) | C32—C19—C33 | 110.1 (2) |
C11—N1—C26 | 123.7 (2) | C20—C19—C9 | 100.7 (2) |
C25—N2—C9 | 109.0 (2) | C32—C19—C9 | 114.6 (2) |
C25—N2—C30 | 121.5 (2) | C33—C19—C9 | 110.6 (2) |
C9—N2—C30 | 121.5 (2) | C21—C20—C25 | 120.5 (3) |
O1—C1—C6 | 115.6 (3) | C21—C20—C19 | 131.0 (3) |
O1—C1—C2 | 123.8 (2) | C25—C20—C19 | 108.5 (2) |
C6—C1—C2 | 120.6 (3) | C20—C21—C22 | 119.0 (3) |
C3—C2—C1 | 118.1 (3) | C20—C21—H21 | 120.5 |
C3—C2—C7 | 121.5 (3) | C22—C21—H21 | 120.5 |
C1—C2—C7 | 120.4 (2) | C23—C22—C21 | 120.4 (3) |
C4—C3—C2 | 120.9 (3) | C23—C22—H22 | 119.8 |
C4—C3—H3 | 119.5 | C21—C22—H22 | 119.8 |
C2—C3—H3 | 119.5 | C22—C23—C24 | 121.1 (3) |
C3—C4—C5 | 120.8 (3) | C22—C23—H23 | 119.4 |
C3—C4—Br1 | 119.7 (3) | C24—C23—H23 | 119.4 |
C5—C4—Br1 | 119.4 (2) | C25—C24—C23 | 118.3 (3) |
C6—C5—C4 | 118.9 (3) | C25—C24—H24 | 120.9 |
C6—C5—H5 | 120.6 | C23—C24—H24 | 120.9 |
C4—C5—H5 | 120.6 | C24—C25—C20 | 120.8 (3) |
C5—C6—C1 | 120.7 (3) | C24—C25—N2 | 128.9 (3) |
C5—C6—H6 | 119.6 | C20—C25—N2 | 110.3 (2) |
C1—C6—H6 | 119.6 | N1—C26—C27 | 112.4 (3) |
C10—C7—C2 | 113.2 (2) | N1—C26—H26A | 109.1 |
C10—C7—C8 | 109.4 (2) | C27—C26—H26A | 109.1 |
C2—C7—C8 | 108.4 (2) | N1—C26—H26B | 109.1 |
C10—C7—H7 | 108.6 | C27—C26—H26B | 109.1 |
C2—C7—H7 | 108.6 | H26A—C26—H26B | 107.9 |
C8—C7—H7 | 108.6 | C26—C27—H27A | 109.5 |
C9—C8—C7 | 115.0 (2) | C26—C27—H27B | 109.5 |
C9—C8—H8A | 108.5 | H27A—C27—H27B | 109.5 |
C7—C8—H8A | 108.5 | C26—C27—H27C | 109.5 |
C9—C8—H8B | 108.5 | H27A—C27—H27C | 109.5 |
C7—C8—H8B | 108.5 | H27B—C27—H27C | 109.5 |
H8A—C8—H8B | 107.5 | C12—C28—H28A | 109.5 |
N2—C9—O1 | 105.1 (2) | C12—C28—H28B | 109.5 |
N2—C9—C8 | 112.2 (2) | H28A—C28—H28B | 109.5 |
O1—C9—C8 | 109.3 (2) | C12—C28—H28C | 109.5 |
N2—C9—C19 | 103.0 (2) | H28A—C28—H28C | 109.5 |
O1—C9—C19 | 108.3 (2) | H28B—C28—H28C | 109.5 |
C8—C9—C19 | 118.0 (2) | C12—C29—H29A | 109.5 |
C11—C10—C7 | 129.2 (3) | C12—C29—H29B | 109.5 |
C11—C10—H10 | 115.4 | H29A—C29—H29B | 109.5 |
C7—C10—H10 | 115.4 | C12—C29—H29C | 109.5 |
C10—C11—N1 | 123.3 (3) | H29A—C29—H29C | 109.5 |
C10—C11—C12 | 128.8 (3) | H29B—C29—H29C | 109.5 |
N1—C11—C12 | 107.9 (2) | N2—C30—C31 | 112.3 (3) |
C13—C12—C28 | 111.1 (2) | N2—C30—H30A | 109.1 |
C13—C12—C11 | 101.2 (2) | C31—C30—H30A | 109.1 |
C28—C12—C11 | 111.8 (2) | N2—C30—H30B | 109.1 |
C13—C12—C29 | 109.6 (2) | C31—C30—H30B | 109.1 |
C28—C12—C29 | 109.8 (3) | H30A—C30—H30B | 107.9 |
C11—C12—C29 | 113.2 (2) | C30—C31—H31A | 109.5 |
C14—C13—C18 | 119.9 (3) | C30—C31—H31B | 109.5 |
C14—C13—C12 | 130.2 (3) | H31A—C31—H31B | 109.5 |
C18—C13—C12 | 109.9 (2) | C30—C31—H31C | 109.5 |
C13—C14—C15 | 119.0 (3) | H31A—C31—H31C | 109.5 |
C13—C14—H14 | 120.5 | H31B—C31—H31C | 109.5 |
C15—C14—H14 | 120.5 | C19—C32—H32A | 109.5 |
C16—C15—C14 | 120.4 (3) | C19—C32—H32B | 109.5 |
C16—C15—H15 | 119.8 | H32A—C32—H32B | 109.5 |
C14—C15—H15 | 119.8 | C19—C32—H32C | 109.5 |
C15—C16—C17 | 121.5 (3) | H32A—C32—H32C | 109.5 |
C15—C16—H16 | 119.3 | H32B—C32—H32C | 109.5 |
C17—C16—H16 | 119.3 | C19—C33—H33A | 109.5 |
C18—C17—C16 | 117.4 (3) | C19—C33—H33B | 109.5 |
C18—C17—H17 | 121.3 | H33A—C33—H33B | 109.5 |
C16—C17—H17 | 121.3 | C19—C33—H33C | 109.5 |
C13—C18—N1 | 109.7 (3) | H33A—C33—H33C | 109.5 |
C13—C18—C17 | 121.9 (3) | H33B—C33—H33C | 109.5 |
N1—C18—C17 | 128.4 (3) | | |
| | | |
C9—O1—C1—C6 | 175.6 (2) | C11—C12—C13—C18 | 0.4 (3) |
C9—O1—C1—C2 | −6.1 (4) | C29—C12—C13—C18 | −119.4 (3) |
O1—C1—C2—C3 | −178.8 (3) | C18—C13—C14—C15 | 0.4 (4) |
C6—C1—C2—C3 | −0.6 (4) | C12—C13—C14—C15 | −178.0 (3) |
O1—C1—C2—C7 | 0.3 (4) | C13—C14—C15—C16 | 0.5 (5) |
C6—C1—C2—C7 | 178.5 (3) | C14—C15—C16—C17 | −0.7 (5) |
C1—C2—C3—C4 | 0.3 (4) | C15—C16—C17—C18 | 0.0 (5) |
C7—C2—C3—C4 | −178.8 (3) | C14—C13—C18—N1 | 177.8 (3) |
C2—C3—C4—C5 | 0.1 (5) | C12—C13—C18—N1 | −3.4 (3) |
C2—C3—C4—Br1 | −179.6 (2) | C14—C13—C18—C17 | −1.1 (4) |
C3—C4—C5—C6 | −0.1 (5) | C12—C13—C18—C17 | 177.6 (3) |
Br1—C4—C5—C6 | 179.6 (2) | C11—N1—C18—C13 | 5.4 (3) |
C4—C5—C6—C1 | −0.2 (5) | C26—N1—C18—C13 | 169.2 (3) |
O1—C1—C6—C5 | 178.9 (3) | C11—N1—C18—C17 | −175.8 (3) |
C2—C1—C6—C5 | 0.5 (4) | C26—N1—C18—C17 | −11.9 (5) |
C3—C2—C7—C10 | 36.6 (4) | C16—C17—C18—C13 | 0.9 (5) |
C1—C2—C7—C10 | −142.5 (3) | C16—C17—C18—N1 | −177.8 (3) |
C3—C2—C7—C8 | 158.1 (3) | N2—C9—C19—C20 | 27.6 (3) |
C1—C2—C7—C8 | −21.0 (3) | O1—C9—C19—C20 | −83.4 (2) |
C10—C7—C8—C9 | 172.7 (2) | C8—C9—C19—C20 | 151.8 (2) |
C2—C7—C8—C9 | 48.8 (3) | N2—C9—C19—C32 | 148.4 (2) |
C25—N2—C9—O1 | 85.7 (3) | O1—C9—C19—C32 | 37.4 (3) |
C30—N2—C9—O1 | −63.6 (3) | C8—C9—C19—C32 | −87.3 (3) |
C25—N2—C9—C8 | −155.7 (2) | N2—C9—C19—C33 | −86.4 (3) |
C30—N2—C9—C8 | 55.0 (4) | O1—C9—C19—C33 | 162.6 (2) |
C25—N2—C9—C19 | −27.7 (3) | C8—C9—C19—C33 | 37.8 (3) |
C30—N2—C9—C19 | −177.0 (3) | C32—C19—C20—C21 | 41.5 (4) |
C1—O1—C9—N2 | 152.8 (2) | C33—C19—C20—C21 | −80.2 (4) |
C1—O1—C9—C8 | 32.2 (3) | C9—C19—C20—C21 | 163.9 (3) |
C1—O1—C9—C19 | −97.6 (3) | C32—C19—C20—C25 | −141.7 (3) |
C7—C8—C9—N2 | −171.0 (2) | C33—C19—C20—C25 | 96.7 (3) |
C7—C8—C9—O1 | −54.8 (3) | C9—C19—C20—C25 | −19.3 (3) |
C7—C8—C9—C19 | 69.5 (3) | C25—C20—C21—C22 | −0.5 (4) |
C2—C7—C10—C11 | −116.7 (3) | C19—C20—C21—C22 | 176.0 (3) |
C8—C7—C10—C11 | 122.4 (3) | C20—C21—C22—C23 | −0.6 (4) |
C7—C10—C11—N1 | −175.9 (3) | C21—C22—C23—C24 | 0.7 (5) |
C7—C10—C11—C12 | 5.3 (5) | C22—C23—C24—C25 | 0.3 (5) |
C18—N1—C11—C10 | 175.9 (3) | C23—C24—C25—C20 | −1.4 (4) |
C26—N1—C11—C10 | 12.2 (4) | C23—C24—C25—N2 | 179.8 (3) |
C18—N1—C11—C12 | −5.0 (3) | C21—C20—C25—C24 | 1.5 (4) |
C26—N1—C11—C12 | −168.7 (2) | C19—C20—C25—C24 | −175.7 (3) |
C10—C11—C12—C13 | −178.3 (3) | C21—C20—C25—N2 | −179.5 (3) |
N1—C11—C12—C13 | 2.7 (3) | C19—C20—C25—N2 | 3.3 (3) |
C10—C11—C12—C28 | 63.4 (4) | C9—N2—C25—C24 | −164.8 (3) |
N1—C11—C12—C28 | −115.6 (3) | C30—N2—C25—C24 | −15.5 (5) |
C10—C11—C12—C29 | −61.2 (4) | C9—N2—C25—C20 | 16.3 (3) |
N1—C11—C12—C29 | 119.8 (3) | C30—N2—C25—C20 | 165.6 (3) |
C28—C12—C13—C14 | −62.2 (4) | C18—N1—C26—C27 | −85.1 (4) |
C11—C12—C13—C14 | 179.0 (3) | C11—N1—C26—C27 | 76.7 (4) |
C29—C12—C13—C14 | 59.2 (4) | C25—N2—C30—C31 | 97.7 (4) |
C28—C12—C13—C18 | 119.2 (3) | C9—N2—C30—C31 | −116.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31B···01i | 0.98 | 3.19 | 3.960 (3) | 136 |
C23—H23···Cg5ii | 0.95 | 2.82 | 3.629 (3) | 143 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2. |