In the title compound, C
26H
20ClN
3O
3, the central pyrrolidine ring adopts an envelope conformation. In the crystal structure, the molecules exist as centrosymmetric N—H
O hydrogen-bonded dimers. The dimers are linked
via C—H
O hydrogen bonds, forming a chain along the
b axis.
Supporting information
CCDC reference: 293860
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.108
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.90
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3 ... ?
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O3 .. 3.26 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. CG1 .. 2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. CG2 .. 2.90 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
2 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
4'-(4-Chlorobenzoyl)-1'-methyl-dispiro[indole-3(2
H),2'-pyrrolidine-
3',3''(2''
H)-indole]-2,2''-dione
top
Crystal data top
C26H20ClN3O3 | Z = 2 |
Mr = 457.90 | F(000) = 476 |
Triclinic, P1 | Dx = 1.373 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.795 (6) Å | Cell parameters from 6234 reflections |
b = 10.316 (6) Å | θ = 2.1–27.3° |
c = 11.670 (7) Å | µ = 0.21 mm−1 |
α = 104.275 (9)° | T = 293 K |
β = 93.998 (10)° | Block, colourless |
γ = 102.305 (9)° | 0.22 × 0.20 × 0.20 mm |
V = 1107.2 (12) Å3 | |
Data collection top
Bruker SMART APEX area-detector diffractometer | 4491 independent reflections |
Radiation source: fine-focus sealed tube | 3746 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 27.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.955, Tmax = 0.959 | k = −13→13 |
11608 measured reflections | l = −14→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | All H-atom parameters refined |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.2477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4491 reflections | Δρmax = 0.28 e Å−3 |
379 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0105 (18) |
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 | |
H3 | 0.391 (2) | 0.3927 (19) | 0.8816 (17) | 0.065 (5)* | |
H2 | 0.636 (2) | 0.019 (2) | 1.0695 (18) | 0.072 (6)* | |
Cl1 | 0.03103 (6) | 0.24821 (8) | 0.46553 (6) | 0.0998 (2) | |
N3 | 0.46756 (14) | 0.37456 (13) | 0.86284 (12) | 0.0483 (3) | |
O2 | 0.40878 (12) | 0.14756 (12) | 0.86139 (10) | 0.0565 (3) | |
C16 | 0.68904 (15) | 0.40253 (14) | 0.81108 (12) | 0.0406 (3) | |
C17 | 0.58261 (15) | 0.46926 (15) | 0.84269 (12) | 0.0433 (3) | |
C8 | 0.76452 (15) | 0.30381 (15) | 1.02912 (13) | 0.0423 (3) | |
N2 | 0.66605 (15) | 0.08616 (15) | 1.04051 (13) | 0.0551 (3) | |
O1 | 0.62657 (14) | −0.03960 (11) | 0.84430 (11) | 0.0642 (3) | |
N1 | 0.85893 (14) | 0.20505 (13) | 0.83758 (11) | 0.0490 (3) | |
C11 | 0.49094 (15) | 0.24701 (15) | 0.84700 (12) | 0.0426 (3) | |
O3 | 0.70782 (14) | 0.23271 (16) | 0.52152 (11) | 0.0741 (4) | |
C20 | 0.47083 (17) | 0.20710 (15) | 0.55448 (12) | 0.0481 (3) | |
C19 | 0.61905 (18) | 0.19908 (16) | 0.58304 (13) | 0.0514 (4) | |
C7 | 0.82088 (16) | 0.44351 (16) | 1.07676 (15) | 0.0492 (4) | |
C10 | 0.64044 (15) | 0.25375 (14) | 0.81173 (12) | 0.0404 (3) | |
C15 | 0.81347 (17) | 0.47508 (17) | 0.78572 (15) | 0.0512 (4) | |
C3 | 0.66632 (16) | 0.06898 (15) | 0.92135 (14) | 0.0478 (3) | |
C18 | 0.65428 (18) | 0.15023 (16) | 0.69213 (13) | 0.0481 (4) | |
C9 | 0.71919 (16) | 0.22292 (16) | 1.10575 (13) | 0.0482 (3) | |
C2 | 0.73605 (15) | 0.21217 (14) | 0.90215 (12) | 0.0416 (3) | |
C25 | 0.3562 (2) | 0.12365 (18) | 0.58535 (14) | 0.0576 (4) | |
C12 | 0.5985 (2) | 0.60811 (17) | 0.85248 (15) | 0.0566 (4) | |
C6 | 0.82829 (18) | 0.4998 (2) | 1.19976 (16) | 0.0594 (4) | |
C21 | 0.4466 (2) | 0.30173 (19) | 0.49361 (15) | 0.0583 (4) | |
C4 | 0.72862 (19) | 0.2777 (2) | 1.22824 (15) | 0.0619 (4) | |
C22 | 0.3127 (2) | 0.3159 (2) | 0.46736 (17) | 0.0649 (5) | |
C24 | 0.2208 (2) | 0.1353 (2) | 0.55710 (16) | 0.0655 (5) | |
C14 | 0.8318 (2) | 0.61476 (18) | 0.79736 (16) | 0.0597 (4) | |
C23 | 0.20077 (19) | 0.2316 (2) | 0.49921 (15) | 0.0633 (4) | |
C5 | 0.7836 (2) | 0.4173 (2) | 1.27360 (16) | 0.0664 (5) | |
C26 | 0.8054 (2) | 0.1334 (2) | 0.71131 (15) | 0.0605 (5) | |
C13 | 0.7258 (2) | 0.67970 (18) | 0.83050 (16) | 0.0624 (5) | |
C1 | 0.9658 (2) | 0.1488 (2) | 0.8887 (2) | 0.0647 (5) | |
H18 | 0.5871 (18) | 0.0637 (18) | 0.6842 (14) | 0.051 (4)* | |
H7 | 0.8562 (17) | 0.5013 (17) | 1.0269 (15) | 0.052 (4)* | |
H15 | 0.886 (2) | 0.4296 (18) | 0.7639 (16) | 0.061 (5)* | |
H26A | 0.803 (2) | 0.030 (2) | 0.6935 (17) | 0.074 (6)* | |
H1C | 0.996 (2) | 0.199 (2) | 0.974 (2) | 0.090 (7)* | |
H26B | 0.865 (2) | 0.1748 (19) | 0.6611 (18) | 0.069 (5)* | |
H1B | 0.933 (2) | 0.051 (2) | 0.8828 (19) | 0.079 (6)* | |
H21 | 0.528 (2) | 0.360 (2) | 0.4716 (18) | 0.076 (6)* | |
H25 | 0.3706 (19) | 0.0558 (19) | 0.6282 (17) | 0.064 (5)* | |
H24 | 0.141 (2) | 0.077 (2) | 0.5779 (18) | 0.076 (6)* | |
H6 | 0.8676 (19) | 0.598 (2) | 1.2335 (17) | 0.064 (5)* | |
H4 | 0.698 (2) | 0.2179 (19) | 1.2785 (18) | 0.068 (5)* | |
H12 | 0.525 (2) | 0.6519 (19) | 0.8710 (16) | 0.065 (5)* | |
H1A | 1.050 (2) | 0.158 (2) | 0.8435 (19) | 0.079 (6)* | |
H14 | 0.921 (2) | 0.6698 (19) | 0.7817 (17) | 0.068 (5)* | |
H22 | 0.301 (2) | 0.383 (2) | 0.4250 (18) | 0.077 (6)* | |
H13 | 0.737 (2) | 0.772 (2) | 0.8369 (18) | 0.075 (6)* | |
H5 | 0.792 (2) | 0.456 (2) | 1.3556 (19) | 0.071 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0582 (3) | 0.1542 (6) | 0.0942 (4) | 0.0262 (3) | 0.0033 (3) | 0.0479 (4) |
N3 | 0.0477 (7) | 0.0552 (8) | 0.0503 (7) | 0.0249 (6) | 0.0158 (6) | 0.0159 (6) |
O2 | 0.0558 (6) | 0.0582 (7) | 0.0593 (7) | 0.0095 (5) | 0.0102 (5) | 0.0253 (5) |
C16 | 0.0495 (8) | 0.0418 (7) | 0.0359 (7) | 0.0191 (6) | 0.0075 (6) | 0.0127 (6) |
C17 | 0.0524 (8) | 0.0462 (8) | 0.0358 (7) | 0.0213 (6) | 0.0071 (6) | 0.0110 (6) |
C8 | 0.0410 (7) | 0.0477 (8) | 0.0417 (7) | 0.0171 (6) | 0.0072 (6) | 0.0120 (6) |
N2 | 0.0655 (9) | 0.0509 (8) | 0.0533 (8) | 0.0098 (6) | 0.0064 (6) | 0.0257 (7) |
O1 | 0.0898 (9) | 0.0394 (6) | 0.0633 (7) | 0.0195 (6) | 0.0023 (6) | 0.0120 (5) |
N1 | 0.0544 (7) | 0.0541 (7) | 0.0484 (7) | 0.0288 (6) | 0.0147 (6) | 0.0163 (6) |
C11 | 0.0481 (8) | 0.0488 (8) | 0.0337 (7) | 0.0153 (6) | 0.0057 (6) | 0.0130 (6) |
O3 | 0.0730 (8) | 0.1138 (11) | 0.0566 (7) | 0.0413 (8) | 0.0265 (6) | 0.0403 (7) |
C20 | 0.0625 (9) | 0.0485 (8) | 0.0318 (7) | 0.0145 (7) | 0.0052 (6) | 0.0071 (6) |
C19 | 0.0674 (10) | 0.0529 (9) | 0.0375 (8) | 0.0236 (7) | 0.0127 (7) | 0.0091 (7) |
C7 | 0.0460 (8) | 0.0500 (8) | 0.0512 (9) | 0.0143 (7) | 0.0059 (7) | 0.0102 (7) |
C10 | 0.0495 (8) | 0.0403 (7) | 0.0369 (7) | 0.0182 (6) | 0.0097 (6) | 0.0127 (6) |
C15 | 0.0528 (9) | 0.0546 (9) | 0.0554 (9) | 0.0197 (7) | 0.0128 (7) | 0.0243 (7) |
C3 | 0.0548 (9) | 0.0431 (8) | 0.0508 (9) | 0.0187 (7) | 0.0049 (7) | 0.0169 (7) |
C18 | 0.0643 (9) | 0.0461 (8) | 0.0388 (8) | 0.0247 (7) | 0.0107 (7) | 0.0092 (6) |
C9 | 0.0458 (8) | 0.0575 (9) | 0.0453 (8) | 0.0157 (7) | 0.0066 (6) | 0.0181 (7) |
C2 | 0.0489 (8) | 0.0399 (7) | 0.0414 (7) | 0.0179 (6) | 0.0084 (6) | 0.0136 (6) |
C25 | 0.0718 (11) | 0.0534 (9) | 0.0413 (8) | 0.0061 (8) | −0.0011 (7) | 0.0110 (7) |
C12 | 0.0753 (11) | 0.0504 (9) | 0.0531 (9) | 0.0343 (8) | 0.0109 (8) | 0.0135 (7) |
C6 | 0.0506 (9) | 0.0609 (10) | 0.0575 (10) | 0.0154 (8) | 0.0025 (7) | −0.0018 (8) |
C21 | 0.0610 (10) | 0.0685 (11) | 0.0517 (9) | 0.0165 (8) | 0.0109 (8) | 0.0257 (8) |
C4 | 0.0600 (10) | 0.0851 (13) | 0.0452 (9) | 0.0180 (9) | 0.0113 (7) | 0.0241 (9) |
C22 | 0.0660 (11) | 0.0797 (12) | 0.0589 (11) | 0.0240 (9) | 0.0080 (8) | 0.0311 (10) |
C24 | 0.0635 (11) | 0.0737 (12) | 0.0481 (9) | −0.0034 (9) | 0.0006 (8) | 0.0148 (9) |
C14 | 0.0658 (11) | 0.0546 (9) | 0.0628 (10) | 0.0096 (8) | 0.0064 (8) | 0.0280 (8) |
C23 | 0.0575 (10) | 0.0836 (12) | 0.0447 (9) | 0.0154 (9) | 0.0016 (7) | 0.0125 (8) |
C5 | 0.0618 (10) | 0.0879 (14) | 0.0417 (9) | 0.0192 (9) | 0.0068 (8) | 0.0021 (9) |
C26 | 0.0759 (12) | 0.0718 (11) | 0.0476 (9) | 0.0443 (10) | 0.0183 (8) | 0.0154 (8) |
C13 | 0.0868 (13) | 0.0417 (9) | 0.0626 (11) | 0.0181 (8) | 0.0059 (9) | 0.0195 (8) |
C1 | 0.0622 (11) | 0.0753 (13) | 0.0688 (12) | 0.0381 (10) | 0.0111 (9) | 0.0225 (10) |
Geometric parameters (Å, º) top
Cl1—C23 | 1.735 (2) | C15—C14 | 1.384 (3) |
N3—C11 | 1.354 (2) | C15—H15 | 0.947 (19) |
N3—C17 | 1.400 (2) | C3—C2 | 1.566 (2) |
N3—H3 | 0.84 (2) | C18—C26 | 1.534 (2) |
O2—C11 | 1.2166 (18) | C18—H18 | 0.969 (17) |
C16—C15 | 1.380 (2) | C9—C4 | 1.390 (2) |
C16—C17 | 1.390 (2) | C25—C24 | 1.381 (3) |
C16—C10 | 1.509 (2) | C25—H25 | 0.982 (19) |
C17—C12 | 1.382 (2) | C12—C13 | 1.382 (3) |
C8—C7 | 1.383 (2) | C12—H12 | 0.939 (19) |
C8—C9 | 1.400 (2) | C6—C5 | 1.384 (3) |
C8—C2 | 1.519 (2) | C6—H6 | 0.970 (19) |
N2—C3 | 1.358 (2) | C21—C22 | 1.372 (3) |
N2—C9 | 1.394 (2) | C21—H21 | 0.98 (2) |
N2—H2 | 0.85 (2) | C4—C5 | 1.377 (3) |
O1—C3 | 1.218 (2) | C4—H4 | 0.97 (2) |
N1—C1 | 1.460 (2) | C22—C23 | 1.381 (3) |
N1—C2 | 1.469 (2) | C22—H22 | 0.96 (2) |
N1—C26 | 1.477 (2) | C24—C23 | 1.370 (3) |
C11—C10 | 1.541 (2) | C24—H24 | 0.96 (2) |
O3—C19 | 1.214 (2) | C14—C13 | 1.379 (3) |
C20—C25 | 1.389 (2) | C14—H14 | 0.99 (2) |
C20—C21 | 1.390 (2) | C5—H5 | 0.93 (2) |
C20—C19 | 1.491 (2) | C26—H26A | 1.03 (2) |
C19—C18 | 1.524 (2) | C26—H26B | 0.97 (2) |
C7—C6 | 1.400 (3) | C13—H13 | 0.92 (2) |
C7—H7 | 0.961 (17) | C1—H1C | 0.99 (2) |
C10—C2 | 1.559 (2) | C1—H1B | 0.97 (2) |
C10—C18 | 1.568 (2) | C1—H1A | 1.01 (2) |
| | | |
C11—N3—C17 | 112.62 (13) | N1—C2—C8 | 116.50 (13) |
C11—N3—H3 | 122.5 (13) | N1—C2—C10 | 99.76 (11) |
C17—N3—H3 | 124.9 (13) | C8—C2—C10 | 116.31 (11) |
C15—C16—C17 | 119.62 (14) | N1—C2—C3 | 111.39 (11) |
C15—C16—C10 | 131.53 (13) | C8—C2—C3 | 101.54 (12) |
C17—C16—C10 | 108.85 (13) | C10—C2—C3 | 111.79 (12) |
C12—C17—C16 | 121.93 (15) | C24—C25—C20 | 120.69 (17) |
C12—C17—N3 | 129.09 (14) | C24—C25—H25 | 119.1 (11) |
C16—C17—N3 | 108.96 (13) | C20—C25—H25 | 120.2 (11) |
C7—C8—C9 | 118.93 (15) | C17—C12—C13 | 117.42 (15) |
C7—C8—C2 | 132.50 (14) | C17—C12—H12 | 121.5 (12) |
C9—C8—C2 | 108.55 (13) | C13—C12—H12 | 121.0 (11) |
C3—N2—C9 | 112.40 (13) | C5—C6—C7 | 120.90 (17) |
C3—N2—H2 | 122.0 (14) | C5—C6—H6 | 119.9 (11) |
C9—N2—H2 | 125.6 (14) | C7—C6—H6 | 119.2 (11) |
C1—N1—C2 | 115.58 (14) | C22—C21—C20 | 120.98 (17) |
C1—N1—C26 | 113.85 (14) | C22—C21—H21 | 120.7 (12) |
C2—N1—C26 | 107.34 (13) | C20—C21—H21 | 118.3 (12) |
O2—C11—N3 | 125.38 (14) | C5—C4—C9 | 117.66 (17) |
O2—C11—C10 | 127.24 (13) | C5—C4—H4 | 122.4 (12) |
N3—C11—C10 | 107.36 (12) | C9—C4—H4 | 119.9 (12) |
C25—C20—C21 | 118.69 (16) | C21—C22—C23 | 119.04 (18) |
C25—C20—C19 | 122.90 (15) | C21—C22—H22 | 118.1 (13) |
C21—C20—C19 | 118.41 (15) | C23—C22—H22 | 122.8 (12) |
O3—C19—C20 | 120.26 (15) | C23—C24—C25 | 119.15 (18) |
O3—C19—C18 | 121.95 (16) | C23—C24—H24 | 119.7 (12) |
C20—C19—C18 | 117.79 (13) | C25—C24—H24 | 121.1 (12) |
C8—C7—C6 | 118.95 (16) | C13—C14—C15 | 120.51 (17) |
C8—C7—H7 | 120.9 (10) | C13—C14—H14 | 118.7 (11) |
C6—C7—H7 | 120.1 (10) | C15—C14—H14 | 120.8 (11) |
C16—C10—C11 | 102.20 (11) | C24—C23—C22 | 121.42 (18) |
C16—C10—C2 | 112.97 (12) | C24—C23—Cl1 | 119.25 (15) |
C11—C10—C2 | 111.61 (11) | C22—C23—Cl1 | 119.33 (15) |
C16—C10—C18 | 113.06 (12) | C4—C5—C6 | 121.11 (17) |
C11—C10—C18 | 116.86 (12) | C4—C5—H5 | 119.1 (12) |
C2—C10—C18 | 100.62 (11) | C6—C5—H5 | 119.8 (12) |
C16—C15—C14 | 119.02 (15) | N1—C26—C18 | 106.04 (12) |
C16—C15—H15 | 119.7 (11) | N1—C26—H26A | 111.1 (11) |
C14—C15—H15 | 121.3 (11) | C18—C26—H26A | 109.0 (11) |
O1—C3—N2 | 126.03 (14) | N1—C26—H26B | 109.1 (12) |
O1—C3—C2 | 126.36 (14) | C18—C26—H26B | 111.9 (12) |
N2—C3—C2 | 107.50 (13) | H26A—C26—H26B | 109.6 (16) |
C19—C18—C26 | 115.33 (14) | C14—C13—C12 | 121.43 (16) |
C19—C18—C10 | 112.52 (12) | C14—C13—H13 | 120.5 (13) |
C26—C18—C10 | 103.37 (13) | C12—C13—H13 | 118.1 (13) |
C19—C18—H18 | 106.9 (10) | N1—C1—H1C | 110.5 (13) |
C26—C18—H18 | 110.4 (10) | N1—C1—H1B | 112.9 (13) |
C10—C18—H18 | 108.2 (10) | H1C—C1—H1B | 108.6 (18) |
C4—C9—N2 | 127.64 (15) | N1—C1—H1A | 109.3 (12) |
C4—C9—C8 | 122.44 (16) | H1C—C1—H1A | 109.1 (18) |
N2—C9—C8 | 109.92 (14) | H1B—C1—H1A | 106.2 (17) |
| | | |
C15—C16—C17—C12 | −1.6 (2) | C26—N1—C2—C10 | −43.39 (14) |
C10—C16—C17—C12 | 178.41 (13) | C1—N1—C2—C3 | −53.49 (19) |
C15—C16—C17—N3 | 179.46 (13) | C26—N1—C2—C3 | 74.76 (15) |
C10—C16—C17—N3 | −0.55 (16) | C7—C8—C2—N1 | 60.9 (2) |
C11—N3—C17—C12 | −178.57 (15) | C9—C8—C2—N1 | −120.49 (13) |
C11—N3—C17—C16 | 0.29 (17) | C7—C8—C2—C10 | −56.3 (2) |
C17—N3—C11—O2 | 178.43 (13) | C9—C8—C2—C10 | 122.27 (14) |
C17—N3—C11—C10 | 0.09 (16) | C7—C8—C2—C3 | −177.89 (15) |
C25—C20—C19—O3 | 153.18 (16) | C9—C8—C2—C3 | 0.69 (14) |
C21—C20—C19—O3 | −26.4 (2) | C16—C10—C2—N1 | −74.52 (13) |
C25—C20—C19—C18 | −27.9 (2) | C11—C10—C2—N1 | 170.98 (11) |
C21—C20—C19—C18 | 152.53 (15) | C18—C10—C2—N1 | 46.31 (13) |
C9—C8—C7—C6 | −1.2 (2) | C16—C10—C2—C8 | 51.65 (16) |
C2—C8—C7—C6 | 177.27 (15) | C11—C10—C2—C8 | −62.86 (16) |
C15—C16—C10—C11 | −179.44 (15) | C18—C10—C2—C8 | 172.47 (12) |
C17—C16—C10—C11 | 0.57 (14) | C16—C10—C2—C3 | 167.62 (11) |
C15—C16—C10—C2 | 60.5 (2) | C11—C10—C2—C3 | 53.12 (15) |
C17—C16—C10—C2 | −119.48 (13) | C18—C10—C2—C3 | −71.55 (14) |
C15—C16—C10—C18 | −53.0 (2) | O1—C3—C2—N1 | −53.9 (2) |
C17—C16—C10—C18 | 127.06 (13) | N2—C3—C2—N1 | 122.40 (14) |
O2—C11—C10—C16 | −178.69 (14) | O1—C3—C2—C8 | −178.62 (15) |
N3—C11—C10—C16 | −0.40 (14) | N2—C3—C2—C8 | −2.29 (15) |
O2—C11—C10—C2 | −57.69 (19) | O1—C3—C2—C10 | 56.7 (2) |
N3—C11—C10—C2 | 120.60 (13) | N2—C3—C2—C10 | −126.96 (13) |
O2—C11—C10—C18 | 57.33 (19) | C21—C20—C25—C24 | −0.6 (2) |
N3—C11—C10—C18 | −124.38 (13) | C19—C20—C25—C24 | 179.84 (15) |
C17—C16—C15—C14 | 2.7 (2) | C16—C17—C12—C13 | −0.5 (2) |
C10—C16—C15—C14 | −177.24 (15) | N3—C17—C12—C13 | 178.19 (15) |
C9—N2—C3—O1 | 179.52 (15) | C8—C7—C6—C5 | 1.7 (2) |
C9—N2—C3—C2 | 3.18 (17) | C25—C20—C21—C22 | 1.9 (3) |
O3—C19—C18—C26 | −5.7 (2) | C19—C20—C21—C22 | −178.47 (16) |
C20—C19—C18—C26 | 175.44 (14) | N2—C9—C4—C5 | −179.15 (16) |
O3—C19—C18—C10 | 112.59 (17) | C8—C9—C4—C5 | 0.7 (3) |
C20—C19—C18—C10 | −66.31 (18) | C20—C21—C22—C23 | −1.9 (3) |
C16—C10—C18—C19 | −37.51 (18) | C20—C25—C24—C23 | −0.8 (3) |
C11—C10—C18—C19 | 80.73 (17) | C16—C15—C14—C13 | −1.8 (3) |
C2—C10—C18—C19 | −158.27 (13) | C25—C24—C23—C22 | 0.8 (3) |
C16—C10—C18—C26 | 87.55 (15) | C25—C24—C23—Cl1 | −179.07 (14) |
C11—C10—C18—C26 | −154.20 (13) | C21—C22—C23—C24 | 0.5 (3) |
C2—C10—C18—C26 | −33.20 (15) | C21—C22—C23—Cl1 | −179.61 (15) |
C3—N2—C9—C4 | 177.09 (16) | C9—C4—C5—C6 | −0.3 (3) |
C3—N2—C9—C8 | −2.80 (18) | C7—C6—C5—C4 | −0.9 (3) |
C7—C8—C9—C4 | 0.0 (2) | C1—N1—C26—C18 | 151.80 (15) |
C2—C8—C9—C4 | −178.79 (14) | C2—N1—C26—C18 | 22.55 (17) |
C7—C8—C9—N2 | 179.91 (13) | C19—C18—C26—N1 | 131.25 (15) |
C2—C8—C9—N2 | 1.10 (16) | C10—C18—C26—N1 | 8.02 (17) |
C1—N1—C2—C8 | 62.32 (19) | C15—C14—C13—C12 | −0.3 (3) |
C26—N1—C2—C8 | −169.42 (13) | C17—C12—C13—C14 | 1.5 (3) |
C1—N1—C2—C10 | −171.65 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O1 | 0.97 (2) | 2.42 (2) | 2.936 (3) | 113 (1) |
C26—H26B···O3 | 0.97 (2) | 2.43 (2) | 2.848 (3) | 106 (1) |
N2—H2···O2i | 0.85 (2) | 2.05 (2) | 2.896 (3) | 172 (2) |
C13—H13···O1ii | 0.92 (2) | 2.40 (2) | 3.217 (3) | 148 (2) |
C7—H7···Cg1 | 0.96 (2) | 2.90 (2) | 3.572 (3) | 128 (1) |
C12—H12···Cg2iii | 0.94 (2) | 2.90 (2) | 3.730 (3) | 149 (2) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |