In the title molecule, C
34H
35N
5O
2, all bond lengths and angles are within normal ranges. The crystal packing is stabilized by weak intermolecular C—H
O hydrogen bonds and π–π interactions.
Supporting information
CCDC reference: 642960
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.164
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C6 .. 5.28 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C33 - C34 .. 6.34 su
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H28 .. H34B .. 2.14 Ang.
PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... O2A
H25 O2A
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... O2A
C25 O2A
PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... O2A
C25 H25 O2A
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
2-Dipropylamino-6-methyl-5-(4-methylphenyl)-3,8-diphenyl-5,8-
dihydropyrazolo[4',3':5,6]pyrano[2,3-
d]pyrimidin-4(3
H)-one
top
Crystal data top
C34H35N5O2 | Z = 2 |
Mr = 545.67 | F(000) = 580 |
Triclinic, P1 | Dx = 1.231 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9705 (8) Å | Cell parameters from 1636 reflections |
b = 13.5961 (12) Å | θ = 3.2–24.5° |
c = 14.3869 (12) Å | µ = 0.08 mm−1 |
α = 111.213 (2)° | T = 292 K |
β = 98.877 (2)° | Block, colourless |
γ = 108.884 (2)° | 0.30 × 0.20 × 0.20 mm |
V = 1472.6 (3) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5128 independent reflections |
Radiation source: fine-focus sealed tube | 2947 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
Tmin = 0.977, Tmax = 0.985 | k = −15→16 |
8509 measured reflections | l = −17→12 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0723P)2] where P = (Fo2 + 2Fc2)/3 |
5128 reflections | (Δ/σ)max < 0.001 |
374 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.19 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 | |
C1 | 0.2253 (4) | 0.9232 (3) | 0.2588 (2) | 0.0662 (8) | |
H1 | 0.2946 | 0.9113 | 0.3047 | 0.079* | |
C2 | 0.1999 (4) | 0.8703 (3) | 0.1541 (2) | 0.0823 (10) | |
H2 | 0.2536 | 0.8228 | 0.1290 | 0.099* | |
C3 | 0.0973 (4) | 0.8851 (3) | 0.0846 (2) | 0.0837 (10) | |
H3 | 0.0810 | 0.8481 | 0.0131 | 0.100* | |
C4 | 0.0203 (4) | 0.9539 (3) | 0.1213 (3) | 0.0800 (10) | |
H4 | −0.0496 | 0.9643 | 0.0745 | 0.096* | |
C5 | 0.0429 (4) | 1.0094 (3) | 0.2272 (2) | 0.0703 (8) | |
H5 | −0.0119 | 1.0563 | 0.2515 | 0.084* | |
C6 | 0.1478 (3) | 0.9944 (2) | 0.2963 (2) | 0.0567 (7) | |
C7 | 0.1197 (4) | 1.2723 (3) | 0.6082 (2) | 0.0844 (10) | |
H7A | 0.2206 | 1.3410 | 0.6464 | 0.127* | |
H7B | 0.0694 | 1.2518 | 0.6566 | 0.127* | |
H7C | 0.0452 | 1.2862 | 0.5643 | 0.127* | |
C8 | 0.1570 (3) | 1.1760 (2) | 0.5423 (2) | 0.0584 (7) | |
C9 | 0.2313 (3) | 1.1129 (2) | 0.5752 (2) | 0.0527 (7) | |
C10 | 0.2369 (3) | 1.0382 (2) | 0.4875 (2) | 0.0499 (7) | |
C11 | 0.3336 (3) | 0.9413 (2) | 0.5652 (2) | 0.0491 (6) | |
C12 | 0.3312 (3) | 1.0118 (2) | 0.65795 (19) | 0.0462 (6) | |
C13 | 0.2892 (3) | 1.1153 (2) | 0.67953 (19) | 0.0516 (7) | |
H13 | 0.1963 | 1.1041 | 0.7084 | 0.062* | |
C14 | 0.4327 (4) | 1.2271 (2) | 0.7584 (2) | 0.0552 (7) | |
C15 | 0.4240 (4) | 1.2851 (3) | 0.8570 (2) | 0.0681 (8) | |
H15 | 0.3294 | 1.2549 | 0.8743 | 0.082* | |
C16 | 0.5525 (5) | 1.3864 (3) | 0.9297 (2) | 0.0771 (10) | |
H16 | 0.5431 | 1.4228 | 0.9957 | 0.093* | |
C17 | 0.6951 (5) | 1.4359 (3) | 0.9085 (3) | 0.0742 (9) | |
C18 | 0.7041 (4) | 1.3779 (3) | 0.8112 (3) | 0.0730 (9) | |
H18 | 0.7989 | 1.4081 | 0.7940 | 0.088* | |
C19 | 0.5751 (4) | 1.2748 (2) | 0.7375 (2) | 0.0617 (8) | |
H19 | 0.5858 | 1.2373 | 0.6722 | 0.074* | |
C20 | 0.8320 (5) | 1.5499 (3) | 0.9875 (3) | 0.1051 (13) | |
H20A | 0.9213 | 1.5696 | 0.9592 | 0.158* | |
H20B | 0.8712 | 1.5437 | 1.0503 | 0.158* | |
H20C | 0.7908 | 1.6090 | 1.0036 | 0.158* | |
C21 | 0.3526 (3) | 0.9781 (2) | 0.7403 (2) | 0.0490 (6) | |
C22 | 0.4085 (3) | 0.8254 (2) | 0.62213 (19) | 0.0481 (6) | |
C23 | 0.3473 (3) | 0.8202 (2) | 0.78193 (19) | 0.0497 (7) | |
C24 | 0.4497 (4) | 0.8615 (2) | 0.8807 (2) | 0.0619 (8) | |
H24 | 0.5476 | 0.9280 | 0.9079 | 0.074* | |
C25 | 0.4042 (5) | 0.8019 (3) | 0.9397 (2) | 0.0764 (9) | |
H25 | 0.4729 | 0.8283 | 1.0069 | 0.092* | |
C26 | 0.2594 (5) | 0.7049 (3) | 0.8998 (3) | 0.0805 (10) | |
H26 | 0.2308 | 0.6651 | 0.9396 | 0.097* | |
C27 | 0.1576 (4) | 0.6666 (3) | 0.8027 (3) | 0.0812 (10) | |
H27 | 0.0584 | 0.6012 | 0.7761 | 0.097* | |
C28 | 0.2009 (4) | 0.7244 (2) | 0.7433 (2) | 0.0661 (8) | |
H28 | 0.1305 | 0.6984 | 0.6767 | 0.079* | |
C29 | 0.5913 (3) | 0.7502 (2) | 0.6910 (2) | 0.0601 (7) | |
H29A | 0.6179 | 0.8202 | 0.7536 | 0.072* | |
H29B | 0.6894 | 0.7593 | 0.6685 | 0.072* | |
C30 | 0.5500 (4) | 0.6491 (2) | 0.7187 (2) | 0.0733 (9) | |
H30A | 0.4519 | 0.6389 | 0.7413 | 0.088* | |
H30B | 0.5264 | 0.5787 | 0.6572 | 0.088* | |
C31 | 0.6929 (5) | 0.6701 (3) | 0.8051 (3) | 0.1115 (14) | |
H31A | 0.7914 | 0.6847 | 0.7843 | 0.167* | |
H31B | 0.6681 | 0.6031 | 0.8182 | 0.167* | |
H31C | 0.7099 | 0.7359 | 0.8678 | 0.167* | |
C32 | 0.4459 (4) | 0.6668 (2) | 0.5019 (2) | 0.0634 (8) | |
H32A | 0.5166 | 0.6261 | 0.5038 | 0.076* | |
H32B | 0.4863 | 0.7163 | 0.4687 | 0.076* | |
C33 | 0.2740 (4) | 0.5807 (3) | 0.4374 (2) | 0.0853 (10) | |
H33A | 0.2725 | 0.5417 | 0.3657 | 0.102* | |
H33B | 0.2029 | 0.6214 | 0.4374 | 0.102* | |
C34 | 0.2049 (5) | 0.4916 (3) | 0.4756 (3) | 0.1092 (13) | |
H34A | 0.2654 | 0.4438 | 0.4668 | 0.164* | |
H34B | 0.0903 | 0.4443 | 0.4359 | 0.164* | |
H34C | 0.2149 | 0.5296 | 0.5484 | 0.164* | |
N1 | 0.1719 (3) | 1.05304 (19) | 0.40463 (17) | 0.0555 (6) | |
N2 | 0.1234 (3) | 1.1412 (2) | 0.4399 (2) | 0.0647 (7) | |
N3 | 0.3796 (3) | 0.85344 (17) | 0.54570 (15) | 0.0499 (5) | |
N4 | 0.3846 (2) | 0.87842 (17) | 0.71643 (15) | 0.0466 (5) | |
N5 | 0.4585 (3) | 0.73848 (17) | 0.60854 (15) | 0.0517 (6) | |
O1 | 0.2925 (2) | 0.95372 (14) | 0.47477 (13) | 0.0560 (5) | |
O2 | 0.3373 (2) | 1.02535 (16) | 0.82603 (14) | 0.0596 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.064 (2) | 0.085 (2) | 0.059 (2) | 0.0361 (18) | 0.0170 (15) | 0.0385 (17) |
C2 | 0.087 (3) | 0.101 (3) | 0.060 (2) | 0.043 (2) | 0.0169 (18) | 0.0366 (19) |
C3 | 0.084 (3) | 0.102 (3) | 0.058 (2) | 0.032 (2) | 0.0148 (19) | 0.037 (2) |
C4 | 0.066 (2) | 0.108 (3) | 0.066 (2) | 0.028 (2) | 0.0069 (17) | 0.051 (2) |
C5 | 0.059 (2) | 0.087 (2) | 0.074 (2) | 0.0262 (17) | 0.0138 (16) | 0.0506 (19) |
C6 | 0.0464 (17) | 0.0666 (18) | 0.0553 (18) | 0.0114 (14) | 0.0071 (14) | 0.0387 (15) |
C7 | 0.101 (3) | 0.081 (2) | 0.093 (2) | 0.057 (2) | 0.029 (2) | 0.045 (2) |
C8 | 0.0536 (18) | 0.0610 (18) | 0.073 (2) | 0.0280 (15) | 0.0215 (15) | 0.0385 (16) |
C9 | 0.0543 (17) | 0.0543 (16) | 0.0596 (18) | 0.0253 (13) | 0.0165 (13) | 0.0333 (15) |
C10 | 0.0484 (17) | 0.0548 (16) | 0.0577 (17) | 0.0247 (13) | 0.0178 (13) | 0.0331 (15) |
C11 | 0.0478 (16) | 0.0536 (16) | 0.0477 (16) | 0.0194 (13) | 0.0103 (12) | 0.0272 (14) |
C12 | 0.0473 (16) | 0.0467 (15) | 0.0478 (16) | 0.0214 (12) | 0.0148 (12) | 0.0223 (13) |
C13 | 0.0519 (17) | 0.0555 (16) | 0.0576 (17) | 0.0275 (14) | 0.0201 (13) | 0.0296 (14) |
C14 | 0.069 (2) | 0.0498 (16) | 0.0583 (18) | 0.0329 (15) | 0.0197 (15) | 0.0282 (14) |
C15 | 0.091 (2) | 0.0594 (19) | 0.066 (2) | 0.0423 (18) | 0.0350 (18) | 0.0267 (17) |
C16 | 0.110 (3) | 0.0554 (19) | 0.064 (2) | 0.045 (2) | 0.021 (2) | 0.0174 (17) |
C17 | 0.093 (3) | 0.0510 (18) | 0.068 (2) | 0.0329 (18) | −0.0001 (19) | 0.0231 (17) |
C18 | 0.065 (2) | 0.073 (2) | 0.081 (2) | 0.0228 (17) | 0.0109 (18) | 0.0432 (19) |
C19 | 0.065 (2) | 0.0625 (18) | 0.0556 (17) | 0.0241 (16) | 0.0150 (15) | 0.0274 (15) |
C20 | 0.114 (3) | 0.065 (2) | 0.098 (3) | 0.030 (2) | −0.012 (2) | 0.020 (2) |
C21 | 0.0498 (17) | 0.0488 (15) | 0.0479 (16) | 0.0201 (13) | 0.0118 (13) | 0.0222 (13) |
C22 | 0.0500 (16) | 0.0443 (15) | 0.0454 (16) | 0.0151 (13) | 0.0103 (12) | 0.0207 (13) |
C23 | 0.0589 (18) | 0.0494 (15) | 0.0454 (15) | 0.0229 (14) | 0.0144 (13) | 0.0256 (13) |
C24 | 0.076 (2) | 0.0535 (16) | 0.0487 (17) | 0.0237 (15) | 0.0083 (15) | 0.0215 (14) |
C25 | 0.104 (3) | 0.084 (2) | 0.0515 (18) | 0.047 (2) | 0.0188 (18) | 0.0356 (18) |
C26 | 0.107 (3) | 0.082 (2) | 0.073 (2) | 0.039 (2) | 0.037 (2) | 0.051 (2) |
C27 | 0.076 (2) | 0.080 (2) | 0.086 (2) | 0.0143 (18) | 0.0260 (19) | 0.050 (2) |
C28 | 0.062 (2) | 0.0680 (19) | 0.0612 (18) | 0.0143 (16) | 0.0112 (15) | 0.0349 (16) |
C29 | 0.0600 (19) | 0.0612 (17) | 0.0627 (18) | 0.0283 (15) | 0.0124 (14) | 0.0310 (15) |
C30 | 0.092 (2) | 0.072 (2) | 0.073 (2) | 0.0461 (18) | 0.0226 (17) | 0.0405 (17) |
C31 | 0.135 (3) | 0.124 (3) | 0.093 (3) | 0.079 (3) | 0.006 (2) | 0.056 (2) |
C32 | 0.081 (2) | 0.0657 (18) | 0.0552 (18) | 0.0438 (17) | 0.0239 (16) | 0.0251 (15) |
C33 | 0.101 (3) | 0.073 (2) | 0.067 (2) | 0.044 (2) | 0.0088 (19) | 0.0147 (18) |
C34 | 0.090 (3) | 0.076 (2) | 0.113 (3) | 0.019 (2) | 0.006 (2) | 0.015 (2) |
N1 | 0.0535 (14) | 0.0668 (15) | 0.0609 (15) | 0.0301 (12) | 0.0170 (11) | 0.0389 (13) |
N2 | 0.0689 (17) | 0.0706 (16) | 0.0730 (17) | 0.0382 (14) | 0.0218 (13) | 0.0424 (14) |
N3 | 0.0591 (14) | 0.0526 (13) | 0.0486 (13) | 0.0296 (11) | 0.0178 (10) | 0.0272 (11) |
N4 | 0.0527 (14) | 0.0474 (12) | 0.0456 (13) | 0.0224 (10) | 0.0164 (10) | 0.0245 (10) |
N5 | 0.0630 (15) | 0.0494 (13) | 0.0497 (13) | 0.0294 (11) | 0.0158 (11) | 0.0243 (11) |
O1 | 0.0689 (13) | 0.0619 (11) | 0.0500 (11) | 0.0341 (10) | 0.0176 (9) | 0.0319 (9) |
O2 | 0.0732 (13) | 0.0655 (12) | 0.0500 (11) | 0.0374 (10) | 0.0227 (10) | 0.0264 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.357 (4) | C20—H20B | 0.9600 |
C1—C6 | 1.374 (4) | C20—H20C | 0.9600 |
C1—H1 | 0.9300 | C21—O2 | 1.221 (3) |
C2—C3 | 1.366 (4) | C21—N4 | 1.408 (3) |
C2—H2 | 0.9300 | C22—N3 | 1.304 (3) |
C3—C4 | 1.343 (4) | C22—N5 | 1.356 (3) |
C3—H3 | 0.9300 | C22—N4 | 1.374 (3) |
C4—C5 | 1.380 (4) | C23—C24 | 1.366 (4) |
C4—H4 | 0.9300 | C23—C28 | 1.369 (4) |
C5—C6 | 1.377 (4) | C23—N4 | 1.447 (3) |
C5—H5 | 0.9300 | C24—C25 | 1.390 (4) |
C6—N1 | 1.413 (4) | C24—H24 | 0.9300 |
C7—C8 | 1.486 (4) | C25—C26 | 1.368 (4) |
C7—H7A | 0.9600 | C25—H25 | 0.9300 |
C7—H7B | 0.9600 | C26—C27 | 1.352 (4) |
C7—H7C | 0.9600 | C26—H26 | 0.9300 |
C8—N2 | 1.324 (4) | C27—C28 | 1.374 (4) |
C8—C9 | 1.404 (4) | C27—H27 | 0.9300 |
C9—C10 | 1.324 (3) | C28—H28 | 0.9300 |
C9—C13 | 1.495 (4) | C29—N5 | 1.469 (3) |
C10—N1 | 1.355 (3) | C29—C30 | 1.516 (4) |
C10—O1 | 1.359 (3) | C29—H29A | 0.9700 |
C11—N3 | 1.337 (3) | C29—H29B | 0.9700 |
C11—C12 | 1.341 (3) | C30—C31 | 1.512 (4) |
C11—O1 | 1.381 (3) | C30—H30A | 0.9700 |
C12—C21 | 1.424 (3) | C30—H30B | 0.9700 |
C12—C13 | 1.510 (4) | C31—H31A | 0.9600 |
C13—C14 | 1.513 (4) | C31—H31B | 0.9600 |
C13—H13 | 0.9800 | C31—H31C | 0.9600 |
C14—C19 | 1.366 (4) | C32—N5 | 1.453 (3) |
C14—C15 | 1.380 (4) | C32—C33 | 1.488 (4) |
C15—C16 | 1.370 (4) | C32—H32A | 0.9700 |
C15—H15 | 0.9300 | C32—H32B | 0.9700 |
C16—C17 | 1.377 (5) | C33—C34 | 1.502 (5) |
C16—H16 | 0.9300 | C33—H33A | 0.9700 |
C17—C18 | 1.366 (4) | C33—H33B | 0.9700 |
C17—C20 | 1.505 (4) | C34—H34A | 0.9600 |
C18—C19 | 1.387 (4) | C34—H34B | 0.9600 |
C18—H18 | 0.9300 | C34—H34C | 0.9600 |
C19—H19 | 0.9300 | N1—N2 | 1.360 (3) |
C20—H20A | 0.9600 | | |
| | | |
C2—C1—C6 | 119.4 (3) | N4—C21—C12 | 116.0 (2) |
C2—C1—H1 | 120.3 | N3—C22—N5 | 119.9 (2) |
C6—C1—H1 | 120.3 | N3—C22—N4 | 122.2 (2) |
C1—C2—C3 | 121.6 (3) | N5—C22—N4 | 117.8 (2) |
C1—C2—H2 | 119.2 | C24—C23—C28 | 120.7 (3) |
C3—C2—H2 | 119.2 | C24—C23—N4 | 121.7 (2) |
C4—C3—C2 | 118.9 (3) | C28—C23—N4 | 117.6 (2) |
C4—C3—H3 | 120.5 | C23—C24—C25 | 118.4 (3) |
C2—C3—H3 | 120.5 | C23—C24—H24 | 120.8 |
C3—C4—C5 | 121.4 (3) | C25—C24—H24 | 120.8 |
C3—C4—H4 | 119.3 | C26—C25—C24 | 120.6 (3) |
C5—C4—H4 | 119.3 | C26—C25—H25 | 119.7 |
C6—C5—C4 | 119.0 (3) | C24—C25—H25 | 119.7 |
C6—C5—H5 | 120.5 | C27—C26—C25 | 120.2 (3) |
C4—C5—H5 | 120.5 | C27—C26—H26 | 119.9 |
C1—C6—C5 | 119.7 (3) | C25—C26—H26 | 119.9 |
C1—C6—N1 | 121.7 (2) | C26—C27—C28 | 119.9 (3) |
C5—C6—N1 | 118.6 (3) | C26—C27—H27 | 120.0 |
C8—C7—H7A | 109.5 | C28—C27—H27 | 120.0 |
C8—C7—H7B | 109.5 | C23—C28—C27 | 120.2 (3) |
H7A—C7—H7B | 109.5 | C23—C28—H28 | 119.9 |
C8—C7—H7C | 109.5 | C27—C28—H28 | 119.9 |
H7A—C7—H7C | 109.5 | N5—C29—C30 | 114.5 (2) |
H7B—C7—H7C | 109.5 | N5—C29—H29A | 108.6 |
N2—C8—C9 | 111.4 (2) | C30—C29—H29A | 108.6 |
N2—C8—C7 | 120.9 (2) | N5—C29—H29B | 108.6 |
C9—C8—C7 | 127.7 (3) | C30—C29—H29B | 108.6 |
C10—C9—C8 | 103.9 (2) | H29A—C29—H29B | 107.6 |
C10—C9—C13 | 122.9 (2) | C31—C30—C29 | 110.5 (3) |
C8—C9—C13 | 133.1 (3) | C31—C30—H30A | 109.6 |
C9—C10—N1 | 110.4 (2) | C29—C30—H30A | 109.6 |
C9—C10—O1 | 128.1 (2) | C31—C30—H30B | 109.6 |
N1—C10—O1 | 121.4 (2) | C29—C30—H30B | 109.6 |
N3—C11—C12 | 126.9 (2) | H30A—C30—H30B | 108.1 |
N3—C11—O1 | 110.1 (2) | C30—C31—H31A | 109.5 |
C12—C11—O1 | 123.0 (2) | C30—C31—H31B | 109.5 |
C11—C12—C21 | 116.4 (2) | H31A—C31—H31B | 109.5 |
C11—C12—C13 | 126.0 (2) | C30—C31—H31C | 109.5 |
C21—C12—C13 | 117.2 (2) | H31A—C31—H31C | 109.5 |
C9—C13—C12 | 106.0 (2) | H31B—C31—H31C | 109.5 |
C9—C13—C14 | 114.1 (2) | N5—C32—C33 | 113.1 (3) |
C12—C13—C14 | 112.2 (2) | N5—C32—H32A | 109.0 |
C9—C13—H13 | 108.1 | C33—C32—H32A | 109.0 |
C12—C13—H13 | 108.1 | N5—C32—H32B | 109.0 |
C14—C13—H13 | 108.1 | C33—C32—H32B | 109.0 |
C19—C14—C15 | 117.0 (3) | H32A—C32—H32B | 107.8 |
C19—C14—C13 | 123.0 (3) | C32—C33—C34 | 113.6 (3) |
C15—C14—C13 | 120.0 (3) | C32—C33—H33A | 108.8 |
C16—C15—C14 | 121.1 (3) | C34—C33—H33A | 108.8 |
C16—C15—H15 | 119.5 | C32—C33—H33B | 108.8 |
C14—C15—H15 | 119.5 | C34—C33—H33B | 108.8 |
C15—C16—C17 | 122.2 (3) | H33A—C33—H33B | 107.7 |
C15—C16—H16 | 118.9 | C33—C34—H34A | 109.5 |
C17—C16—H16 | 118.9 | C33—C34—H34B | 109.5 |
C18—C17—C16 | 116.6 (3) | H34A—C34—H34B | 109.5 |
C18—C17—C20 | 121.8 (4) | C33—C34—H34C | 109.5 |
C16—C17—C20 | 121.6 (3) | H34A—C34—H34C | 109.5 |
C17—C18—C19 | 121.5 (3) | H34B—C34—H34C | 109.5 |
C17—C18—H18 | 119.3 | C10—N1—N2 | 108.7 (2) |
C19—C18—H18 | 119.3 | C10—N1—C6 | 131.8 (2) |
C14—C19—C18 | 121.6 (3) | N2—N1—C6 | 119.4 (2) |
C14—C19—H19 | 119.2 | C8—N2—N1 | 105.5 (2) |
C18—C19—H19 | 119.2 | C22—N3—C11 | 116.7 (2) |
C17—C20—H20A | 109.5 | C22—N4—C21 | 120.5 (2) |
C17—C20—H20B | 109.5 | C22—N4—C23 | 121.8 (2) |
H20A—C20—H20B | 109.5 | C21—N4—C23 | 115.8 (2) |
C17—C20—H20C | 109.5 | C22—N5—C32 | 116.5 (2) |
H20A—C20—H20C | 109.5 | C22—N5—C29 | 120.8 (2) |
H20B—C20—H20C | 109.5 | C32—N5—C29 | 115.5 (2) |
O2—C21—N4 | 118.9 (2) | C10—O1—C11 | 113.4 (2) |
O2—C21—C12 | 125.0 (2) | | |
| | | |
C6—C1—C2—C3 | −0.8 (5) | C23—C24—C25—C26 | −0.6 (4) |
C1—C2—C3—C4 | 0.1 (5) | C24—C25—C26—C27 | −0.8 (5) |
C2—C3—C4—C5 | 0.0 (5) | C25—C26—C27—C28 | 0.9 (5) |
C3—C4—C5—C6 | 0.6 (5) | C24—C23—C28—C27 | −1.9 (4) |
C2—C1—C6—C5 | 1.3 (4) | N4—C23—C28—C27 | −179.0 (3) |
C2—C1—C6—N1 | −179.0 (3) | C26—C27—C28—C23 | 0.4 (5) |
C4—C5—C6—C1 | −1.2 (4) | N5—C29—C30—C31 | −179.1 (3) |
C4—C5—C6—N1 | 179.1 (3) | N5—C32—C33—C34 | −64.5 (4) |
N2—C8—C9—C10 | −1.2 (3) | C9—C10—N1—N2 | 0.4 (3) |
C7—C8—C9—C10 | −179.8 (3) | O1—C10—N1—N2 | 178.6 (2) |
N2—C8—C9—C13 | −178.4 (3) | C9—C10—N1—C6 | −178.8 (3) |
C7—C8—C9—C13 | 2.9 (5) | O1—C10—N1—C6 | −0.7 (4) |
C8—C9—C10—N1 | 0.4 (3) | C1—C6—N1—C10 | −15.3 (4) |
C13—C9—C10—N1 | 178.0 (2) | C5—C6—N1—C10 | 164.4 (3) |
C8—C9—C10—O1 | −177.5 (2) | C1—C6—N1—N2 | 165.5 (2) |
C13—C9—C10—O1 | 0.1 (4) | C5—C6—N1—N2 | −14.8 (4) |
N3—C11—C12—C21 | −11.5 (4) | C9—C8—N2—N1 | 1.4 (3) |
O1—C11—C12—C21 | 171.0 (2) | C7—C8—N2—N1 | −179.8 (2) |
N3—C11—C12—C13 | 175.8 (2) | C10—N1—N2—C8 | −1.1 (3) |
O1—C11—C12—C13 | −1.7 (4) | C6—N1—N2—C8 | 178.2 (2) |
C10—C9—C13—C12 | −6.1 (3) | N5—C22—N3—C11 | −178.8 (2) |
C8—C9—C13—C12 | 170.8 (3) | N4—C22—N3—C11 | 3.5 (4) |
C10—C9—C13—C14 | 117.8 (3) | C12—C11—N3—C22 | 7.8 (4) |
C8—C9—C13—C14 | −65.4 (4) | O1—C11—N3—C22 | −174.4 (2) |
C11—C12—C13—C9 | 6.9 (3) | N3—C22—N4—C21 | −10.1 (4) |
C21—C12—C13—C9 | −165.7 (2) | N5—C22—N4—C21 | 172.2 (2) |
C11—C12—C13—C14 | −118.1 (3) | N3—C22—N4—C23 | 153.1 (2) |
C21—C12—C13—C14 | 69.2 (3) | N5—C22—N4—C23 | −24.5 (3) |
C9—C13—C14—C19 | −52.0 (3) | O2—C21—N4—C22 | −177.6 (2) |
C12—C13—C14—C19 | 68.5 (3) | C12—C21—N4—C22 | 5.9 (3) |
C9—C13—C14—C15 | 128.8 (3) | O2—C21—N4—C23 | 18.1 (3) |
C12—C13—C14—C15 | −110.8 (3) | C12—C21—N4—C23 | −158.4 (2) |
C19—C14—C15—C16 | 0.6 (4) | C24—C23—N4—C22 | 118.6 (3) |
C13—C14—C15—C16 | 179.9 (2) | C28—C23—N4—C22 | −64.4 (3) |
C14—C15—C16—C17 | 0.6 (4) | C24—C23—N4—C21 | −77.4 (3) |
C15—C16—C17—C18 | −1.2 (4) | C28—C23—N4—C21 | 99.6 (3) |
C15—C16—C17—C20 | 177.2 (3) | N3—C22—N5—C32 | −11.5 (3) |
C16—C17—C18—C19 | 0.7 (4) | N4—C22—N5—C32 | 166.2 (2) |
C20—C17—C18—C19 | −177.8 (3) | N3—C22—N5—C29 | 137.3 (3) |
C15—C14—C19—C18 | −1.1 (4) | N4—C22—N5—C29 | −44.9 (3) |
C13—C14—C19—C18 | 179.6 (2) | C33—C32—N5—C22 | −77.4 (3) |
C17—C18—C19—C14 | 0.5 (4) | C33—C32—N5—C29 | 132.1 (3) |
C11—C12—C21—O2 | −172.3 (3) | C30—C29—N5—C22 | 130.2 (3) |
C13—C12—C21—O2 | 1.1 (4) | C30—C29—N5—C32 | −80.7 (3) |
C11—C12—C21—N4 | 4.0 (3) | C9—C10—O1—C11 | 6.0 (4) |
C13—C12—C21—N4 | 177.3 (2) | N1—C10—O1—C11 | −171.8 (2) |
C28—C23—C24—C25 | 2.0 (4) | N3—C11—O1—C10 | 177.1 (2) |
N4—C23—C24—C25 | 178.9 (2) | C12—C11—O1—C10 | −5.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···O2Ai | 0.93 | 2.39 | 3.253 (7) | 154 |
Symmetry code: (i) −x+1, −y, −z. |