The title compound, C
32H
27N, was synthesized
via the Ullmann reaction. The structure has a pseudo-twofold axis approximately parallel to the
b axis, and hence the pseudo-space group
C2/
c. The crystal packing is stabilized by weak C—H
π and and van der Waals interactions.
Supporting information
CCDC reference: 227881
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.056
- wR factor = 0.154
- Data-to-parameter ratio = 7.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 81 PerFit
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . C2/c
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.10
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 2130
Count of symmetry unique reflns 2131
Completeness (_total/calc) 99.95%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.
{4-[(1-Naphthyl)vinyl]phenyl}di-
p-tolylamine
top
Crystal data top
C32H27N | F(000) = 904 |
Mr = 425.55 | Dx = 1.167 Mg m−3 |
Monoclinic, Cc | Melting point = 383–386 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.482 (7) Å | Cell parameters from 724 reflections |
b = 17.045 (7) Å | θ = 2.4–21.7° |
c = 8.635 (3) Å | µ = 0.07 mm−1 |
β = 117.094 (5)° | T = 293 K |
V = 2421.9 (16) Å3 | Plate, yellow |
Z = 4 | 0.40 × 0.34 × 0.28 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2130 independent reflections |
Radiation source: fine-focus sealed tube | 1453 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −21→21 |
Tmin = 0.973, Tmax = 0.981 | k = −20→10 |
5052 measured reflections | l = −10→7 |
Refinement top
Refinement on F2 | 74 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[σ2(Fo2) + (0.0877P)2 + 0.2832P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.154 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.18 e Å−3 |
2130 reflections | Δρmin = −0.17 e Å−3 |
300 parameters | |
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 | |
N1 | 0.1212 (3) | 0.18419 (18) | 0.4176 (7) | 0.0544 (9) | |
C1 | 0.1941 (3) | 0.1443 (3) | 0.4472 (6) | 0.0491 (12) | |
C2 | 0.2680 (3) | 0.1696 (3) | 0.5739 (7) | 0.0623 (14) | |
H2 | 0.2708 | 0.2120 | 0.6443 | 0.075* | |
C3 | 0.3376 (3) | 0.1319 (4) | 0.5954 (8) | 0.0720 (16) | |
H3 | 0.3873 | 0.1500 | 0.6807 | 0.086* | |
C4 | 0.3367 (3) | 0.0693 (3) | 0.4971 (8) | 0.0643 (15) | |
C5 | 0.2617 (3) | 0.0437 (3) | 0.3715 (7) | 0.0646 (15) | |
H5 | 0.2588 | 0.0006 | 0.3027 | 0.078* | |
C6 | 0.1911 (3) | 0.0811 (3) | 0.3471 (7) | 0.0570 (13) | |
H6 | 0.1413 | 0.0633 | 0.2620 | 0.068* | |
C7 | 0.4135 (4) | 0.0291 (5) | 0.5208 (11) | 0.101 (2) | |
H7A | 0.4543 | 0.0678 | 0.5383 | 0.152* | |
H7B | 0.4029 | −0.0012 | 0.4190 | 0.152* | |
H7C | 0.4325 | −0.0048 | 0.6203 | 0.152* | |
C8 | 0.0517 (3) | 0.1396 (3) | 0.3910 (7) | 0.0517 (13) | |
C9 | 0.0576 (3) | 0.0757 (4) | 0.4948 (8) | 0.0739 (17) | |
H9 | 0.1079 | 0.0621 | 0.5849 | 0.089* | |
C10 | −0.0097 (4) | 0.0320 (4) | 0.4670 (9) | 0.0780 (17) | |
H10 | −0.0039 | −0.0106 | 0.5388 | 0.094* | |
C11 | −0.0845 (3) | 0.0496 (3) | 0.3367 (7) | 0.0608 (14) | |
C12 | −0.0916 (3) | 0.1139 (4) | 0.2354 (7) | 0.0658 (15) | |
H12 | −0.1425 | 0.1280 | 0.1483 | 0.079* | |
C13 | −0.0241 (3) | 0.1584 (3) | 0.2602 (7) | 0.0592 (14) | |
H13 | −0.0302 | 0.2011 | 0.1882 | 0.071* | |
C14 | −0.1582 (4) | 0.0004 (4) | 0.3066 (9) | 0.090 (2) | |
H14A | −0.2065 | 0.0257 | 0.2221 | 0.135* | |
H14B | −0.1614 | −0.0052 | 0.4140 | 0.135* | |
H14C | −0.1534 | −0.0505 | 0.2645 | 0.135* | |
C15 | 0.1190 (3) | 0.2659 (2) | 0.4240 (7) | 0.0477 (10) | |
C16 | 0.0721 (3) | 0.3039 (3) | 0.4874 (7) | 0.0539 (13) | |
H16 | 0.0416 | 0.2744 | 0.5270 | 0.065* | |
C17 | 0.0694 (3) | 0.3846 (3) | 0.4937 (7) | 0.0595 (13) | |
H17 | 0.0364 | 0.4081 | 0.5354 | 0.071* | |
C18 | 0.1148 (3) | 0.4313 (3) | 0.4393 (7) | 0.0540 (12) | |
C19 | 0.1629 (3) | 0.3932 (3) | 0.3758 (6) | 0.0554 (13) | |
H19 | 0.1943 | 0.4227 | 0.3386 | 0.066* | |
C20 | 0.1642 (3) | 0.3126 (3) | 0.3677 (6) | 0.0530 (13) | |
H20 | 0.1962 | 0.2887 | 0.3235 | 0.064* | |
C21 | 0.1092 (3) | 0.5166 (3) | 0.4529 (7) | 0.0614 (13) | |
H21 | 0.0739 | 0.5345 | 0.4948 | 0.074* | |
C22 | 0.1483 (3) | 0.5707 (3) | 0.4125 (7) | 0.0672 (15) | |
H22 | 0.1846 | 0.5540 | 0.3721 | 0.081* | |
C23 | 0.1394 (4) | 0.6557 (3) | 0.4263 (8) | 0.0688 (18) | |
C24 | 0.0682 (5) | 0.6879 (4) | 0.4052 (9) | 0.092 (2) | |
H24 | 0.0247 | 0.6548 | 0.3845 | 0.111* | |
C25 | 0.0578 (7) | 0.7689 (6) | 0.4132 (11) | 0.114 (3) | |
H25 | 0.0082 | 0.7888 | 0.3980 | 0.137* | |
C26 | 0.1182 (9) | 0.8166 (5) | 0.4421 (13) | 0.118 (3) | |
H26 | 0.1102 | 0.8703 | 0.4452 | 0.141* | |
C27 | 0.1936 (7) | 0.7895 (4) | 0.4682 (10) | 0.100 (2) | |
C28 | 0.2058 (5) | 0.7066 (3) | 0.4607 (8) | 0.0794 (18) | |
C29 | 0.2826 (5) | 0.6806 (4) | 0.4872 (9) | 0.094 (2) | |
H29 | 0.2899 | 0.6271 | 0.4786 | 0.112* | |
C30 | 0.3481 (6) | 0.7299 (5) | 0.5254 (11) | 0.127 (3) | |
H30 | 0.3981 | 0.7107 | 0.5415 | 0.152* | |
C31 | 0.3353 (7) | 0.8110 (6) | 0.5387 (13) | 0.140 (3) | |
H31 | 0.3782 | 0.8458 | 0.5679 | 0.168* | |
C32 | 0.2614 (8) | 0.8386 (5) | 0.5097 (12) | 0.125 (3) | |
H32 | 0.2552 | 0.8924 | 0.5175 | 0.150* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0410 (18) | 0.0349 (18) | 0.087 (3) | 0.000 (2) | 0.0293 (17) | 0.001 (2) |
C1 | 0.042 (3) | 0.043 (3) | 0.060 (3) | 0.002 (2) | 0.020 (3) | 0.003 (2) |
C2 | 0.054 (3) | 0.055 (3) | 0.072 (4) | 0.000 (3) | 0.024 (3) | −0.010 (3) |
C3 | 0.044 (3) | 0.067 (4) | 0.085 (4) | −0.001 (3) | 0.012 (3) | −0.001 (3) |
C4 | 0.050 (3) | 0.065 (4) | 0.082 (4) | 0.014 (3) | 0.034 (3) | 0.013 (3) |
C5 | 0.063 (4) | 0.056 (3) | 0.076 (4) | 0.011 (3) | 0.033 (3) | 0.000 (3) |
C6 | 0.046 (3) | 0.044 (3) | 0.070 (3) | −0.005 (2) | 0.017 (3) | −0.006 (2) |
C7 | 0.068 (4) | 0.105 (5) | 0.136 (6) | 0.025 (4) | 0.051 (4) | 0.006 (4) |
C8 | 0.047 (3) | 0.040 (3) | 0.073 (4) | 0.001 (2) | 0.031 (3) | 0.000 (3) |
C9 | 0.044 (3) | 0.075 (4) | 0.091 (4) | −0.001 (3) | 0.021 (3) | 0.024 (3) |
C10 | 0.064 (4) | 0.068 (4) | 0.096 (4) | −0.004 (3) | 0.031 (3) | 0.022 (3) |
C11 | 0.054 (3) | 0.063 (3) | 0.068 (4) | −0.010 (3) | 0.030 (3) | −0.008 (3) |
C12 | 0.045 (3) | 0.078 (4) | 0.064 (3) | −0.002 (3) | 0.016 (3) | −0.012 (3) |
C13 | 0.054 (3) | 0.056 (3) | 0.064 (4) | 0.006 (3) | 0.023 (3) | 0.005 (2) |
C14 | 0.068 (4) | 0.097 (5) | 0.107 (5) | −0.030 (4) | 0.041 (4) | −0.019 (4) |
C15 | 0.042 (2) | 0.042 (2) | 0.058 (2) | 0.000 (2) | 0.0220 (19) | 0.001 (3) |
C16 | 0.059 (3) | 0.047 (3) | 0.065 (3) | 0.001 (2) | 0.036 (3) | 0.001 (2) |
C17 | 0.061 (3) | 0.055 (3) | 0.066 (3) | 0.006 (3) | 0.032 (3) | −0.002 (3) |
C18 | 0.044 (3) | 0.045 (3) | 0.059 (3) | −0.002 (3) | 0.011 (2) | −0.006 (2) |
C19 | 0.051 (3) | 0.048 (3) | 0.063 (3) | −0.007 (2) | 0.022 (3) | 0.013 (3) |
C20 | 0.049 (3) | 0.053 (3) | 0.061 (3) | −0.001 (2) | 0.029 (3) | −0.002 (2) |
C21 | 0.052 (3) | 0.062 (3) | 0.069 (3) | 0.003 (3) | 0.026 (2) | 0.002 (3) |
C22 | 0.077 (4) | 0.056 (3) | 0.064 (3) | 0.000 (3) | 0.029 (3) | −0.002 (3) |
C23 | 0.107 (6) | 0.043 (3) | 0.055 (3) | 0.015 (3) | 0.035 (3) | 0.000 (3) |
C24 | 0.133 (6) | 0.058 (4) | 0.087 (5) | 0.023 (4) | 0.051 (4) | 0.006 (3) |
C25 | 0.146 (7) | 0.103 (6) | 0.097 (5) | 0.038 (5) | 0.059 (5) | −0.001 (4) |
C26 | 0.174 (7) | 0.073 (4) | 0.101 (5) | 0.013 (6) | 0.058 (5) | 0.002 (4) |
C27 | 0.159 (6) | 0.069 (4) | 0.075 (4) | −0.024 (5) | 0.057 (4) | −0.004 (4) |
C28 | 0.140 (6) | 0.046 (3) | 0.056 (3) | −0.007 (4) | 0.047 (4) | −0.003 (3) |
C29 | 0.119 (6) | 0.072 (4) | 0.091 (5) | −0.019 (4) | 0.049 (4) | −0.009 (4) |
C30 | 0.166 (7) | 0.105 (5) | 0.110 (5) | −0.046 (5) | 0.064 (5) | −0.016 (4) |
C31 | 0.177 (7) | 0.114 (6) | 0.125 (6) | −0.061 (6) | 0.064 (6) | −0.015 (5) |
C32 | 0.193 (8) | 0.074 (4) | 0.103 (5) | −0.027 (5) | 0.063 (5) | −0.012 (4) |
Geometric parameters (Å, º) top
N1—C15 | 1.395 (5) | C15—C20 | 1.393 (7) |
N1—C8 | 1.417 (6) | C16—C17 | 1.377 (7) |
N1—C1 | 1.425 (6) | C16—H16 | 0.93 |
C1—C6 | 1.367 (7) | C17—C18 | 1.384 (7) |
C1—C2 | 1.374 (7) | C17—H17 | 0.93 |
C2—C3 | 1.373 (8) | C18—C19 | 1.398 (7) |
C2—H2 | 0.93 | C18—C21 | 1.467 (7) |
C3—C4 | 1.360 (8) | C19—C20 | 1.377 (7) |
C3—H3 | 0.93 | C19—H19 | 0.93 |
C4—C5 | 1.386 (8) | C20—H20 | 0.93 |
C4—C7 | 1.503 (8) | C21—C22 | 1.314 (7) |
C5—C6 | 1.378 (7) | C21—H21 | 0.93 |
C5—H5 | 0.93 | C22—C23 | 1.469 (7) |
C6—H6 | 0.93 | C22—H22 | 0.93 |
C7—H7A | 0.96 | C23—C24 | 1.358 (9) |
C7—H7B | 0.96 | C23—C28 | 1.419 (9) |
C7—H7C | 0.96 | C24—C25 | 1.401 (11) |
C8—C13 | 1.378 (7) | C24—H24 | 0.93 |
C8—C9 | 1.384 (8) | C25—C26 | 1.309 (13) |
C9—C10 | 1.374 (8) | C25—H25 | 0.93 |
C9—H9 | 0.93 | C26—C27 | 1.386 (14) |
C10—C11 | 1.361 (8) | C26—H26 | 0.93 |
C10—H10 | 0.93 | C27—C32 | 1.412 (13) |
C11—C12 | 1.370 (8) | C27—C28 | 1.435 (9) |
C11—C14 | 1.518 (7) | C28—C29 | 1.403 (10) |
C12—C13 | 1.391 (7) | C29—C30 | 1.385 (10) |
C12—H12 | 0.93 | C29—H29 | 0.93 |
C13—H13 | 0.93 | C30—C31 | 1.415 (13) |
C14—H14A | 0.96 | C30—H30 | 0.93 |
C14—H14B | 0.96 | C31—C32 | 1.355 (12) |
C14—H14C | 0.96 | C31—H31 | 0.93 |
C15—C16 | 1.379 (7) | C32—H32 | 0.93 |
| | | |
C15—N1—C8 | 120.1 (4) | C20—C15—N1 | 121.5 (4) |
C15—N1—C1 | 120.8 (4) | C17—C16—C15 | 121.7 (5) |
C8—N1—C1 | 119.1 (3) | C17—C16—H16 | 119.1 |
C6—C1—C2 | 119.4 (5) | C15—C16—H16 | 119.1 |
C6—C1—N1 | 120.0 (5) | C16—C17—C18 | 121.4 (5) |
C2—C1—N1 | 120.6 (4) | C16—C17—H17 | 119.3 |
C3—C2—C1 | 119.4 (5) | C18—C17—H17 | 119.3 |
C3—C2—H2 | 120.3 | C17—C18—C19 | 117.2 (4) |
C1—C2—H2 | 120.3 | C17—C18—C21 | 117.9 (5) |
C4—C3—C2 | 122.6 (6) | C19—C18—C21 | 124.9 (4) |
C4—C3—H3 | 118.7 | C20—C19—C18 | 120.9 (4) |
C2—C3—H3 | 118.7 | C20—C19—H19 | 119.6 |
C3—C4—C5 | 117.3 (5) | C18—C19—H19 | 119.6 |
C3—C4—C7 | 122.0 (6) | C19—C20—C15 | 121.6 (4) |
C5—C4—C7 | 120.7 (6) | C19—C20—H20 | 119.2 |
C6—C5—C4 | 120.9 (5) | C15—C20—H20 | 119.2 |
C6—C5—H5 | 119.5 | C22—C21—C18 | 127.4 (5) |
C4—C5—H5 | 119.5 | C22—C21—H21 | 116.3 |
C1—C6—C5 | 120.3 (5) | C18—C21—H21 | 116.3 |
C1—C6—H6 | 119.8 | C21—C22—C23 | 125.1 (5) |
C5—C6—H6 | 119.8 | C21—C22—H22 | 117.5 |
C4—C7—H7A | 109.5 | C23—C22—H22 | 117.5 |
C4—C7—H7B | 109.5 | C24—C23—C28 | 118.3 (6) |
H7A—C7—H7B | 109.5 | C24—C23—C22 | 121.7 (6) |
C4—C7—H7C | 109.5 | C28—C23—C22 | 120.1 (6) |
H7A—C7—H7C | 109.5 | C23—C24—C25 | 122.5 (8) |
H7B—C7—H7C | 109.5 | C23—C24—H24 | 118.8 |
C13—C8—C9 | 117.6 (5) | C25—C24—H24 | 118.8 |
C13—C8—N1 | 121.1 (5) | C26—C25—C24 | 119.8 (9) |
C9—C8—N1 | 121.3 (5) | C26—C25—H25 | 120.1 |
C10—C9—C8 | 121.1 (5) | C24—C25—H25 | 120.1 |
C10—C9—H9 | 119.5 | C25—C26—C27 | 122.0 (8) |
C8—C9—H9 | 119.5 | C25—C26—H26 | 119.0 |
C11—C10—C9 | 121.6 (6) | C27—C26—H26 | 119.0 |
C11—C10—H10 | 119.2 | C26—C27—C32 | 123.7 (9) |
C9—C10—H10 | 119.2 | C26—C27—C28 | 119.1 (8) |
C10—C11—C12 | 118.0 (5) | C32—C27—C28 | 117.1 (9) |
C10—C11—C14 | 121.0 (6) | C29—C28—C23 | 123.7 (5) |
C12—C11—C14 | 121.0 (6) | C29—C28—C27 | 118.1 (7) |
C11—C12—C13 | 121.3 (5) | C23—C28—C27 | 118.2 (7) |
C11—C12—H12 | 119.3 | C30—C29—C28 | 123.9 (7) |
C13—C12—H12 | 119.3 | C30—C29—H29 | 118.1 |
C8—C13—C12 | 120.4 (5) | C28—C29—H29 | 118.1 |
C8—C13—H13 | 119.8 | C29—C30—C31 | 116.8 (9) |
C12—C13—H13 | 119.8 | C29—C30—H30 | 121.6 |
C11—C14—H14A | 109.5 | C31—C30—H30 | 121.6 |
C11—C14—H14B | 109.5 | C32—C31—C30 | 121.1 (9) |
H14A—C14—H14B | 109.5 | C32—C31—H31 | 119.4 |
C11—C14—H14C | 109.5 | C30—C31—H31 | 119.4 |
H14A—C14—H14C | 109.5 | C31—C32—C27 | 122.9 (9) |
H14B—C14—H14C | 109.5 | C31—C32—H32 | 118.5 |
C16—C15—C20 | 117.2 (4) | C27—C32—H32 | 118.5 |
C16—C15—N1 | 121.3 (5) | | |
| | | |
C15—N1—C1—C6 | −139.1 (5) | C15—C16—C17—C18 | −1.2 (8) |
C8—N1—C1—C6 | 44.4 (7) | C16—C17—C18—C19 | 0.7 (8) |
C15—N1—C1—C2 | 39.7 (8) | C16—C17—C18—C21 | −179.1 (5) |
C8—N1—C1—C2 | −136.9 (5) | C17—C18—C19—C20 | 0.3 (8) |
C6—C1—C2—C3 | 1.1 (8) | C21—C18—C19—C20 | −179.9 (5) |
N1—C1—C2—C3 | −177.6 (5) | C18—C19—C20—C15 | −0.8 (8) |
C1—C2—C3—C4 | −0.7 (9) | C16—C15—C20—C19 | 0.4 (8) |
C2—C3—C4—C5 | −0.2 (9) | N1—C15—C20—C19 | −179.2 (5) |
C2—C3—C4—C7 | 179.3 (6) | C17—C18—C21—C22 | 178.3 (6) |
C3—C4—C5—C6 | 0.6 (8) | C19—C18—C21—C22 | −1.5 (10) |
C7—C4—C5—C6 | −178.8 (6) | C18—C21—C22—C23 | 179.0 (5) |
C2—C1—C6—C5 | −0.7 (8) | C21—C22—C23—C24 | −30.6 (10) |
N1—C1—C6—C5 | 178.1 (5) | C21—C22—C23—C28 | 150.1 (5) |
C4—C5—C6—C1 | −0.2 (8) | C28—C23—C24—C25 | 1.1 (10) |
C15—N1—C8—C13 | 48.1 (7) | C22—C23—C24—C25 | −178.3 (6) |
C1—N1—C8—C13 | −135.4 (5) | C23—C24—C25—C26 | 0.0 (12) |
C15—N1—C8—C9 | −132.1 (6) | C24—C25—C26—C27 | −1.0 (14) |
C1—N1—C8—C9 | 44.5 (8) | C25—C26—C27—C32 | −176.2 (7) |
C13—C8—C9—C10 | 0.8 (9) | C25—C26—C27—C28 | 0.9 (13) |
N1—C8—C9—C10 | −179.1 (6) | C24—C23—C28—C29 | 179.2 (6) |
C8—C9—C10—C11 | 0.0 (10) | C22—C23—C28—C29 | −1.5 (9) |
C9—C10—C11—C12 | −1.5 (9) | C24—C23—C28—C27 | −1.1 (8) |
C9—C10—C11—C14 | 179.5 (6) | C22—C23—C28—C27 | 178.2 (5) |
C10—C11—C12—C13 | 2.2 (8) | C26—C27—C28—C29 | 179.9 (8) |
C14—C11—C12—C13 | −178.8 (5) | C32—C27—C28—C29 | −2.8 (9) |
C9—C8—C13—C12 | −0.1 (7) | C26—C27—C28—C23 | 0.2 (9) |
N1—C8—C13—C12 | 179.8 (5) | C32—C27—C28—C23 | 177.5 (7) |
C11—C12—C13—C8 | −1.4 (8) | C23—C28—C29—C30 | −178.2 (6) |
C8—N1—C15—C16 | 31.6 (8) | C27—C28—C29—C30 | 2.1 (10) |
C1—N1—C15—C16 | −144.9 (5) | C28—C29—C30—C31 | 0.4 (11) |
C8—N1—C15—C20 | −148.8 (5) | C29—C30—C31—C32 | −2.1 (13) |
C1—N1—C15—C20 | 34.7 (8) | C30—C31—C32—C27 | 1.2 (14) |
C20—C15—C16—C17 | 0.6 (9) | C26—C27—C32—C31 | 178.4 (9) |
N1—C15—C16—C17 | −179.8 (5) | C28—C27—C32—C31 | 1.3 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg3i | 0.93 | 3.09 | 3.835 (7) | 138 |
C10—H10···Cg1ii | 0.93 | 3.26 | 4.107 (8) | 153 |
C16—H16···Cg2i | 0.93 | 3.15 | 3.586 (6) | 111 |
C20—H20···Cg2iii | 0.93 | 3.03 | 3.592 (6) | 121 |
C30—H30···Cg1iv | 0.93 | 3.30 | 4.079 (11) | 142 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z+1/2; (iii) x, −y+1, z−1/2; (iv) x+1/2, y+1/2, z. |