In the title compound, C
18H
14N
2, the carbazole and pyridine ring systems are each essentially planar. The asymmetric unit contains three independent molecules. The molecular structure is stabilized by an intermolecular C—H
N hydrogen bond.
Supporting information
CCDC reference: 294140
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.131
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C40 - C41 .. 5.84 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C50
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.
9-(2-pyridylmethyl)carbazole
top
Crystal data top
C18H14N2 | Z = 6 |
Mr = 258.31 | F(000) = 816 |
Triclinic, P1 | Dx = 1.243 Mg m−3 |
Hall symbol: -P 1 | Melting point = 392–393.3 K |
a = 9.8420 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.501 (2) Å | Cell parameters from 3015 reflections |
c = 17.696 (3) Å | θ = 2.4–22.3° |
α = 80.269 (3)° | µ = 0.07 mm−1 |
β = 81.207 (3)° | T = 294 K |
γ = 76.412 (3)° | Block, colourless |
V = 2071.2 (6) Å3 | 0.30 × 0.22 × 0.16 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 7266 independent reflections |
Radiation source: fine-focus sealed tube | 4202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.960, Tmax = 0.988 | k = −13→14 |
10635 measured reflections | l = −18→21 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1491P] where P = (Fo2 + 2Fc2)/3 |
7266 reflections | (Δ/σ)max < 0.001 |
541 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 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 | |
N1 | 1.02427 (18) | 0.19600 (16) | 0.95996 (11) | 0.0623 (5) | |
N2 | 1.34245 (19) | 0.27838 (15) | 0.99386 (10) | 0.0642 (5) | |
N3 | 0.15877 (19) | 0.49046 (16) | 0.66581 (10) | 0.0622 (5) | |
N4 | 0.08656 (19) | 0.64208 (14) | 0.47500 (10) | 0.0619 (5) | |
N5 | 0.19810 (17) | 0.14161 (14) | 0.37409 (9) | 0.0532 (4) | |
N6 | 0.1341 (2) | 0.02681 (17) | 0.57677 (11) | 0.0718 (6) | |
C1 | 0.9452 (2) | 0.14273 (17) | 1.01929 (12) | 0.0560 (6) | |
C2 | 0.9864 (3) | 0.0763 (2) | 1.08644 (14) | 0.0731 (7) | |
H2 | 1.0787 | 0.0627 | 1.0978 | 0.088* | |
C3 | 0.8855 (3) | 0.0314 (2) | 1.13569 (14) | 0.0792 (7) | |
H3 | 0.9109 | −0.0142 | 1.1808 | 0.095* | |
C4 | 0.7476 (3) | 0.0520 (2) | 1.12024 (14) | 0.0763 (7) | |
H4 | 0.6819 | 0.0210 | 1.1552 | 0.092* | |
C5 | 0.7065 (2) | 0.11803 (17) | 1.05345 (13) | 0.0615 (6) | |
H5 | 0.6138 | 0.1314 | 1.0429 | 0.074* | |
C6 | 0.8055 (2) | 0.16416 (16) | 1.00222 (11) | 0.0505 (5) | |
C7 | 0.8010 (2) | 0.23387 (16) | 0.92870 (11) | 0.0483 (5) | |
C8 | 0.6954 (2) | 0.28168 (17) | 0.88186 (12) | 0.0582 (6) | |
H8 | 0.6043 | 0.2708 | 0.8971 | 0.070* | |
C9 | 0.7265 (3) | 0.3453 (2) | 0.81276 (13) | 0.0705 (7) | |
H9 | 0.6564 | 0.3772 | 0.7810 | 0.085* | |
C10 | 0.8616 (3) | 0.3620 (2) | 0.79043 (14) | 0.0782 (7) | |
H10 | 0.8803 | 0.4058 | 0.7437 | 0.094* | |
C11 | 0.9686 (3) | 0.3162 (2) | 0.83484 (14) | 0.0724 (7) | |
H11 | 1.0592 | 0.3277 | 0.8189 | 0.087* | |
C12 | 0.9373 (2) | 0.25181 (18) | 0.90464 (12) | 0.0553 (5) | |
C13 | 1.1733 (2) | 0.1935 (2) | 0.95712 (14) | 0.0723 (7) | |
H13A | 1.2131 | 0.2043 | 0.9035 | 0.087* | |
H13B | 1.2195 | 0.1203 | 0.9799 | 0.087* | |
C14 | 1.2059 (2) | 0.27943 (18) | 0.99812 (12) | 0.0556 (5) | |
C15 | 1.1043 (3) | 0.3515 (2) | 1.03761 (14) | 0.0819 (8) | |
H15 | 1.0097 | 0.3501 | 1.0396 | 0.098* | |
C16 | 1.1435 (4) | 0.4258 (2) | 1.07420 (17) | 0.1003 (9) | |
H16 | 1.0760 | 0.4751 | 1.1016 | 0.120* | |
C17 | 1.2830 (4) | 0.4265 (2) | 1.06986 (16) | 0.0880 (8) | |
H17 | 1.3128 | 0.4761 | 1.0939 | 0.106* | |
C18 | 1.3773 (3) | 0.3523 (2) | 1.02925 (14) | 0.0755 (7) | |
H18 | 1.4722 | 0.3533 | 1.0260 | 0.091* | |
C19 | 0.1823 (2) | 0.5425 (2) | 0.72423 (13) | 0.0653 (6) | |
C20 | 0.1286 (3) | 0.6508 (2) | 0.73881 (19) | 0.0985 (10) | |
H20 | 0.0690 | 0.7012 | 0.7070 | 0.118* | |
C21 | 0.1680 (4) | 0.6809 (3) | 0.8034 (2) | 0.1189 (13) | |
H21 | 0.1344 | 0.7529 | 0.8152 | 0.143* | |
C22 | 0.2563 (4) | 0.6050 (4) | 0.8501 (2) | 0.1122 (12) | |
H22 | 0.2796 | 0.6270 | 0.8933 | 0.135* | |
C23 | 0.3101 (3) | 0.4998 (3) | 0.83534 (14) | 0.0811 (8) | |
H23 | 0.3701 | 0.4504 | 0.8674 | 0.097* | |
C24 | 0.2741 (2) | 0.4667 (2) | 0.77114 (12) | 0.0591 (6) | |
C25 | 0.3104 (2) | 0.36477 (18) | 0.73840 (11) | 0.0512 (5) | |
C26 | 0.3953 (2) | 0.2597 (2) | 0.75725 (13) | 0.0656 (6) | |
H26 | 0.4449 | 0.2452 | 0.7999 | 0.079* | |
C27 | 0.4049 (3) | 0.1784 (2) | 0.71257 (16) | 0.0777 (7) | |
H27 | 0.4622 | 0.1088 | 0.7248 | 0.093* | |
C28 | 0.3313 (3) | 0.1983 (2) | 0.65002 (16) | 0.0790 (7) | |
H28 | 0.3395 | 0.1415 | 0.6207 | 0.095* | |
C29 | 0.2459 (2) | 0.2995 (2) | 0.62961 (13) | 0.0678 (6) | |
H29 | 0.1953 | 0.3118 | 0.5875 | 0.081* | |
C30 | 0.2375 (2) | 0.38279 (18) | 0.67362 (11) | 0.0518 (5) | |
C31 | 0.0789 (2) | 0.5425 (2) | 0.60225 (12) | 0.0728 (7) | |
H31A | 0.0000 | 0.5983 | 0.6207 | 0.087* | |
H31B | 0.0410 | 0.4868 | 0.5854 | 0.087* | |
C32 | 0.1617 (2) | 0.59688 (16) | 0.53362 (11) | 0.0536 (5) | |
C33 | 0.3003 (2) | 0.60065 (19) | 0.53101 (14) | 0.0695 (6) | |
H33 | 0.3496 | 0.5689 | 0.5730 | 0.083* | |
C34 | 0.3652 (3) | 0.6520 (2) | 0.46540 (16) | 0.0812 (7) | |
H34 | 0.4594 | 0.6550 | 0.4622 | 0.097* | |
C35 | 0.2905 (3) | 0.6984 (2) | 0.40513 (15) | 0.0796 (7) | |
H35 | 0.3324 | 0.7334 | 0.3600 | 0.095* | |
C36 | 0.1527 (3) | 0.69234 (19) | 0.41257 (13) | 0.0738 (7) | |
H36 | 0.1015 | 0.7253 | 0.3715 | 0.089* | |
C37 | 0.2695 (2) | 0.22739 (17) | 0.35920 (12) | 0.0515 (5) | |
C38 | 0.2739 (2) | 0.30399 (19) | 0.40598 (14) | 0.0651 (6) | |
H38 | 0.2247 | 0.3034 | 0.4552 | 0.078* | |
C39 | 0.3550 (3) | 0.3820 (2) | 0.37631 (19) | 0.0816 (8) | |
H39 | 0.3599 | 0.4351 | 0.4062 | 0.098* | |
C40 | 0.4288 (3) | 0.3820 (2) | 0.30314 (19) | 0.0890 (9) | |
H40 | 0.4836 | 0.4344 | 0.2851 | 0.107* | |
C41 | 0.4223 (3) | 0.3065 (2) | 0.25709 (15) | 0.0765 (7) | |
H41 | 0.4713 | 0.3081 | 0.2078 | 0.092* | |
C42 | 0.3423 (2) | 0.22744 (18) | 0.28435 (12) | 0.0555 (6) | |
C43 | 0.3141 (2) | 0.13639 (18) | 0.25352 (11) | 0.0559 (6) | |
C44 | 0.3559 (2) | 0.0932 (2) | 0.18360 (12) | 0.0728 (7) | |
H44 | 0.4125 | 0.1268 | 0.1442 | 0.087* | |
C45 | 0.3117 (3) | 0.0002 (2) | 0.17401 (15) | 0.0805 (8) | |
H45 | 0.3404 | −0.0299 | 0.1281 | 0.097* | |
C46 | 0.2254 (3) | −0.0493 (2) | 0.23167 (15) | 0.0762 (7) | |
H46 | 0.1967 | −0.1118 | 0.2236 | 0.091* | |
C47 | 0.1814 (2) | −0.00806 (19) | 0.30024 (13) | 0.0639 (6) | |
H47 | 0.1230 | −0.0414 | 0.3387 | 0.077* | |
C48 | 0.2267 (2) | 0.08497 (17) | 0.31056 (11) | 0.0521 (5) | |
C49 | 0.1175 (2) | 0.11155 (18) | 0.44667 (11) | 0.0554 (5) | |
H49A | 0.0430 | 0.0790 | 0.4364 | 0.066* | |
H49B | 0.0731 | 0.1788 | 0.4690 | 0.066* | |
C50 | 0.2002 (2) | 0.03139 (16) | 0.50548 (12) | 0.0509 (5) | |
C51 | 0.3291 (3) | −0.0339 (2) | 0.48731 (15) | 0.0817 (8) | |
H51 | 0.3728 | −0.0287 | 0.4368 | 0.098* | |
C52 | 0.3933 (3) | −0.1072 (2) | 0.5442 (2) | 0.1087 (10) | |
H52 | 0.4813 | −0.1522 | 0.5328 | 0.130* | |
C53 | 0.3285 (4) | −0.1137 (3) | 0.6168 (2) | 0.1053 (11) | |
H53 | 0.3704 | −0.1631 | 0.6564 | 0.126* | |
C54 | 0.2005 (4) | −0.0465 (3) | 0.63079 (15) | 0.0965 (9) | |
H54 | 0.1558 | −0.0515 | 0.6811 | 0.116* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0442 (10) | 0.0801 (13) | 0.0678 (13) | −0.0180 (10) | −0.0009 (9) | −0.0235 (10) |
N2 | 0.0534 (12) | 0.0759 (13) | 0.0696 (12) | −0.0191 (10) | −0.0112 (9) | −0.0165 (10) |
N3 | 0.0603 (11) | 0.0679 (13) | 0.0505 (11) | −0.0043 (10) | −0.0121 (9) | 0.0052 (9) |
N4 | 0.0644 (12) | 0.0627 (12) | 0.0525 (11) | −0.0067 (10) | −0.0113 (10) | 0.0035 (9) |
N5 | 0.0555 (10) | 0.0591 (11) | 0.0429 (10) | −0.0162 (9) | 0.0020 (8) | −0.0025 (8) |
N6 | 0.0672 (12) | 0.0979 (15) | 0.0499 (12) | −0.0281 (11) | −0.0085 (10) | 0.0070 (10) |
C1 | 0.0532 (14) | 0.0603 (14) | 0.0562 (14) | −0.0074 (11) | −0.0050 (11) | −0.0208 (11) |
C2 | 0.0731 (17) | 0.0753 (17) | 0.0710 (17) | 0.0012 (14) | −0.0216 (14) | −0.0230 (14) |
C3 | 0.104 (2) | 0.0685 (17) | 0.0599 (16) | −0.0039 (16) | −0.0146 (16) | −0.0087 (13) |
C4 | 0.090 (2) | 0.0696 (16) | 0.0651 (16) | −0.0194 (15) | 0.0018 (14) | −0.0037 (13) |
C5 | 0.0585 (14) | 0.0593 (14) | 0.0650 (15) | −0.0149 (12) | 0.0010 (12) | −0.0085 (12) |
C6 | 0.0486 (12) | 0.0514 (12) | 0.0529 (13) | −0.0109 (10) | −0.0022 (10) | −0.0140 (10) |
C7 | 0.0470 (12) | 0.0521 (12) | 0.0491 (12) | −0.0146 (10) | 0.0015 (10) | −0.0172 (10) |
C8 | 0.0583 (14) | 0.0621 (14) | 0.0580 (14) | −0.0149 (12) | −0.0075 (11) | −0.0159 (11) |
C9 | 0.0849 (18) | 0.0720 (16) | 0.0572 (15) | −0.0197 (14) | −0.0120 (13) | −0.0087 (12) |
C10 | 0.103 (2) | 0.0837 (18) | 0.0515 (15) | −0.0349 (17) | 0.0004 (15) | −0.0072 (13) |
C11 | 0.0750 (17) | 0.0871 (18) | 0.0631 (16) | −0.0403 (15) | 0.0161 (14) | −0.0220 (14) |
C12 | 0.0522 (13) | 0.0649 (14) | 0.0536 (14) | −0.0177 (11) | 0.0019 (11) | −0.0211 (11) |
C13 | 0.0431 (13) | 0.0907 (18) | 0.0899 (18) | −0.0140 (12) | 0.0015 (12) | −0.0407 (14) |
C14 | 0.0491 (13) | 0.0622 (14) | 0.0561 (13) | −0.0108 (11) | −0.0036 (10) | −0.0139 (11) |
C15 | 0.0652 (16) | 0.0883 (19) | 0.096 (2) | −0.0120 (15) | 0.0018 (14) | −0.0410 (16) |
C16 | 0.104 (2) | 0.089 (2) | 0.115 (2) | −0.0130 (19) | −0.0020 (19) | −0.0549 (18) |
C17 | 0.117 (3) | 0.0784 (19) | 0.0846 (19) | −0.0340 (18) | −0.0251 (18) | −0.0251 (15) |
C18 | 0.0777 (17) | 0.0847 (18) | 0.0753 (17) | −0.0293 (15) | −0.0199 (14) | −0.0157 (15) |
C19 | 0.0675 (15) | 0.0638 (16) | 0.0584 (15) | −0.0163 (13) | 0.0090 (12) | −0.0031 (12) |
C20 | 0.108 (2) | 0.074 (2) | 0.097 (2) | −0.0145 (17) | 0.0287 (18) | −0.0081 (17) |
C21 | 0.147 (3) | 0.084 (2) | 0.123 (3) | −0.045 (2) | 0.060 (3) | −0.047 (2) |
C22 | 0.134 (3) | 0.130 (3) | 0.091 (2) | −0.071 (3) | 0.033 (2) | −0.048 (2) |
C23 | 0.0850 (18) | 0.111 (2) | 0.0587 (16) | −0.0473 (18) | 0.0041 (13) | −0.0184 (15) |
C24 | 0.0577 (14) | 0.0783 (16) | 0.0449 (13) | −0.0300 (13) | 0.0003 (11) | −0.0022 (12) |
C25 | 0.0431 (12) | 0.0664 (15) | 0.0437 (12) | −0.0204 (11) | −0.0049 (10) | 0.0052 (11) |
C26 | 0.0506 (13) | 0.0823 (18) | 0.0605 (15) | −0.0193 (13) | −0.0146 (11) | 0.0135 (13) |
C27 | 0.0661 (16) | 0.0641 (17) | 0.096 (2) | −0.0126 (13) | −0.0073 (15) | 0.0053 (15) |
C28 | 0.0776 (18) | 0.0760 (19) | 0.0861 (19) | −0.0220 (15) | −0.0008 (15) | −0.0192 (15) |
C29 | 0.0648 (15) | 0.0868 (19) | 0.0563 (14) | −0.0226 (14) | −0.0121 (12) | −0.0090 (13) |
C30 | 0.0465 (12) | 0.0643 (15) | 0.0426 (12) | −0.0160 (11) | −0.0047 (10) | 0.0036 (10) |
C31 | 0.0538 (14) | 0.0895 (18) | 0.0625 (15) | −0.0075 (13) | −0.0118 (12) | 0.0178 (13) |
C32 | 0.0528 (13) | 0.0515 (13) | 0.0522 (13) | −0.0060 (11) | −0.0077 (11) | −0.0010 (10) |
C33 | 0.0590 (15) | 0.0763 (16) | 0.0731 (16) | −0.0190 (13) | −0.0141 (12) | 0.0024 (13) |
C34 | 0.0677 (16) | 0.0843 (18) | 0.092 (2) | −0.0322 (15) | 0.0000 (15) | −0.0001 (16) |
C35 | 0.097 (2) | 0.0705 (17) | 0.0668 (17) | −0.0300 (16) | 0.0099 (16) | 0.0014 (13) |
C36 | 0.093 (2) | 0.0680 (16) | 0.0551 (15) | −0.0146 (15) | −0.0091 (14) | 0.0033 (12) |
C37 | 0.0444 (12) | 0.0513 (13) | 0.0553 (13) | −0.0072 (10) | −0.0108 (10) | 0.0023 (10) |
C38 | 0.0586 (14) | 0.0633 (15) | 0.0715 (16) | −0.0051 (12) | −0.0163 (12) | −0.0076 (12) |
C39 | 0.0729 (17) | 0.0600 (16) | 0.117 (2) | −0.0133 (14) | −0.0356 (17) | −0.0071 (15) |
C40 | 0.0742 (18) | 0.0738 (19) | 0.117 (3) | −0.0298 (15) | −0.0272 (18) | 0.0275 (18) |
C41 | 0.0676 (16) | 0.0802 (18) | 0.0759 (17) | −0.0245 (15) | −0.0138 (13) | 0.0220 (15) |
C42 | 0.0448 (12) | 0.0604 (14) | 0.0537 (13) | −0.0094 (11) | −0.0084 (10) | 0.0127 (11) |
C43 | 0.0499 (13) | 0.0664 (14) | 0.0442 (13) | −0.0056 (11) | −0.0067 (10) | 0.0043 (11) |
C44 | 0.0612 (15) | 0.098 (2) | 0.0456 (14) | −0.0014 (15) | −0.0036 (11) | 0.0040 (13) |
C45 | 0.0789 (18) | 0.097 (2) | 0.0583 (16) | 0.0104 (17) | −0.0194 (14) | −0.0219 (15) |
C46 | 0.0783 (18) | 0.0740 (17) | 0.0754 (18) | 0.0005 (14) | −0.0238 (15) | −0.0185 (14) |
C47 | 0.0624 (15) | 0.0630 (15) | 0.0641 (15) | −0.0093 (12) | −0.0096 (12) | −0.0064 (12) |
C48 | 0.0497 (12) | 0.0573 (13) | 0.0450 (12) | −0.0065 (11) | −0.0062 (10) | −0.0015 (10) |
C49 | 0.0477 (12) | 0.0636 (14) | 0.0489 (12) | −0.0092 (11) | 0.0009 (10) | −0.0009 (10) |
C50 | 0.0516 (13) | 0.0514 (13) | 0.0530 (13) | −0.0205 (11) | −0.0082 (10) | −0.0013 (10) |
C51 | 0.0718 (17) | 0.0815 (18) | 0.0789 (18) | 0.0083 (15) | −0.0141 (14) | −0.0051 (15) |
C52 | 0.095 (2) | 0.086 (2) | 0.130 (3) | 0.0107 (18) | −0.040 (2) | 0.010 (2) |
C53 | 0.107 (3) | 0.097 (2) | 0.114 (3) | −0.034 (2) | −0.060 (2) | 0.040 (2) |
C54 | 0.102 (2) | 0.128 (3) | 0.0628 (18) | −0.048 (2) | −0.0278 (17) | 0.0250 (17) |
Geometric parameters (Å, º) top
N1—C1 | 1.382 (3) | C23—H23 | 0.9300 |
N1—C12 | 1.387 (3) | C24—C25 | 1.435 (3) |
N1—C13 | 1.453 (3) | C25—C26 | 1.399 (3) |
N2—C14 | 1.331 (3) | C25—C30 | 1.403 (3) |
N2—C18 | 1.331 (3) | C26—C27 | 1.367 (3) |
N3—C30 | 1.382 (3) | C26—H26 | 0.9300 |
N3—C19 | 1.384 (3) | C27—C28 | 1.371 (3) |
N3—C31 | 1.445 (3) | C27—H27 | 0.9300 |
N4—C36 | 1.333 (3) | C28—C29 | 1.370 (3) |
N4—C32 | 1.335 (2) | C28—H28 | 0.9300 |
N5—C37 | 1.384 (3) | C29—C30 | 1.382 (3) |
N5—C48 | 1.387 (2) | C29—H29 | 0.9300 |
N5—C49 | 1.444 (2) | C31—C32 | 1.510 (3) |
N6—C50 | 1.327 (2) | C31—H31A | 0.9700 |
N6—C54 | 1.339 (3) | C31—H31B | 0.9700 |
C1—C2 | 1.386 (3) | C32—C33 | 1.369 (3) |
C1—C6 | 1.408 (3) | C33—C34 | 1.372 (3) |
C2—C3 | 1.376 (3) | C33—H33 | 0.9300 |
C2—H2 | 0.9300 | C34—C35 | 1.358 (3) |
C3—C4 | 1.382 (4) | C34—H34 | 0.9300 |
C3—H3 | 0.9300 | C35—C36 | 1.362 (3) |
C4—C5 | 1.379 (3) | C35—H35 | 0.9300 |
C4—H4 | 0.9300 | C36—H36 | 0.9300 |
C5—C6 | 1.386 (3) | C37—C38 | 1.379 (3) |
C5—H5 | 0.9300 | C37—C42 | 1.406 (3) |
C6—C7 | 1.439 (3) | C38—C39 | 1.388 (3) |
C7—C8 | 1.389 (3) | C38—H38 | 0.9300 |
C7—C12 | 1.402 (3) | C39—C40 | 1.384 (4) |
C8—C9 | 1.376 (3) | C39—H39 | 0.9300 |
C8—H8 | 0.9300 | C40—C41 | 1.366 (4) |
C9—C10 | 1.382 (3) | C40—H40 | 0.9300 |
C9—H9 | 0.9300 | C41—C42 | 1.385 (3) |
C10—C11 | 1.368 (3) | C41—H41 | 0.9300 |
C10—H10 | 0.9300 | C42—C43 | 1.440 (3) |
C11—C12 | 1.390 (3) | C43—C48 | 1.396 (3) |
C11—H11 | 0.9300 | C43—C44 | 1.399 (3) |
C13—C14 | 1.510 (3) | C44—C45 | 1.378 (4) |
C13—H13A | 0.9700 | C44—H44 | 0.9300 |
C13—H13B | 0.9700 | C45—C46 | 1.383 (3) |
C14—C15 | 1.370 (3) | C45—H45 | 0.9300 |
C15—C16 | 1.371 (3) | C46—C47 | 1.368 (3) |
C15—H15 | 0.9300 | C46—H46 | 0.9300 |
C16—C17 | 1.366 (4) | C47—C48 | 1.387 (3) |
C16—H16 | 0.9300 | C47—H47 | 0.9300 |
C17—C18 | 1.362 (3) | C49—C50 | 1.508 (3) |
C17—H17 | 0.9300 | C49—H49A | 0.9700 |
C18—H18 | 0.9300 | C49—H49B | 0.9700 |
C19—C20 | 1.386 (3) | C50—C51 | 1.363 (3) |
C19—C24 | 1.401 (3) | C51—C52 | 1.365 (3) |
C20—C21 | 1.397 (4) | C51—H51 | 0.9300 |
C20—H20 | 0.9300 | C52—C53 | 1.343 (4) |
C21—C22 | 1.381 (5) | C52—H52 | 0.9300 |
C21—H21 | 0.9300 | C53—C54 | 1.354 (4) |
C22—C23 | 1.351 (4) | C53—H53 | 0.9300 |
C22—H22 | 0.9300 | C54—H54 | 0.9300 |
C23—C24 | 1.392 (3) | | |
| | | |
C1—N1—C12 | 108.47 (17) | C25—C26—H26 | 120.2 |
C1—N1—C13 | 125.1 (2) | C26—C27—C28 | 120.8 (2) |
C12—N1—C13 | 126.4 (2) | C26—C27—H27 | 119.6 |
C14—N2—C18 | 117.0 (2) | C28—C27—H27 | 119.6 |
C30—N3—C19 | 108.28 (18) | C29—C28—C27 | 121.8 (2) |
C30—N3—C31 | 125.2 (2) | C29—C28—H28 | 119.1 |
C19—N3—C31 | 126.2 (2) | C27—C28—H28 | 119.1 |
C36—N4—C32 | 116.8 (2) | C28—C29—C30 | 117.8 (2) |
C37—N5—C48 | 108.72 (16) | C28—C29—H29 | 121.1 |
C37—N5—C49 | 124.83 (17) | C30—C29—H29 | 121.1 |
C48—N5—C49 | 126.25 (18) | C29—C30—N3 | 129.0 (2) |
C50—N6—C54 | 116.4 (2) | C29—C30—C25 | 121.8 (2) |
N1—C1—C2 | 129.4 (2) | N3—C30—C25 | 109.11 (19) |
N1—C1—C6 | 109.14 (19) | N3—C31—C32 | 114.64 (18) |
C2—C1—C6 | 121.5 (2) | N3—C31—H31A | 108.6 |
C3—C2—C1 | 117.4 (2) | C32—C31—H31A | 108.6 |
C3—C2—H2 | 121.3 | N3—C31—H31B | 108.6 |
C1—C2—H2 | 121.3 | C32—C31—H31B | 108.6 |
C2—C3—C4 | 122.1 (2) | H31A—C31—H31B | 107.6 |
C2—C3—H3 | 119.0 | N4—C32—C33 | 122.6 (2) |
C4—C3—H3 | 119.0 | N4—C32—C31 | 113.53 (19) |
C5—C4—C3 | 120.6 (2) | C33—C32—C31 | 123.88 (19) |
C5—C4—H4 | 119.7 | C32—C33—C34 | 118.9 (2) |
C3—C4—H4 | 119.7 | C32—C33—H33 | 120.6 |
C4—C5—C6 | 119.0 (2) | C34—C33—H33 | 120.6 |
C4—C5—H5 | 120.5 | C35—C34—C33 | 119.4 (2) |
C6—C5—H5 | 120.5 | C35—C34—H34 | 120.3 |
C5—C6—C1 | 119.5 (2) | C33—C34—H34 | 120.3 |
C5—C6—C7 | 134.0 (2) | C34—C35—C36 | 118.2 (2) |
C1—C6—C7 | 106.50 (18) | C34—C35—H35 | 120.9 |
C8—C7—C12 | 119.2 (2) | C36—C35—H35 | 120.9 |
C8—C7—C6 | 133.88 (19) | N4—C36—C35 | 124.1 (2) |
C12—C7—C6 | 106.90 (18) | N4—C36—H36 | 117.9 |
C9—C8—C7 | 119.5 (2) | C35—C36—H36 | 117.9 |
C9—C8—H8 | 120.3 | C38—C37—N5 | 129.1 (2) |
C7—C8—H8 | 120.3 | C38—C37—C42 | 122.3 (2) |
C8—C9—C10 | 120.2 (2) | N5—C37—C42 | 108.65 (19) |
C8—C9—H9 | 119.9 | C37—C38—C39 | 117.1 (2) |
C10—C9—H9 | 119.9 | C37—C38—H38 | 121.5 |
C11—C10—C9 | 122.1 (2) | C39—C38—H38 | 121.5 |
C11—C10—H10 | 118.9 | C40—C39—C38 | 121.3 (3) |
C9—C10—H10 | 118.9 | C40—C39—H39 | 119.4 |
C10—C11—C12 | 117.7 (2) | C38—C39—H39 | 119.4 |
C10—C11—H11 | 121.1 | C41—C40—C39 | 121.1 (3) |
C12—C11—H11 | 121.1 | C41—C40—H40 | 119.5 |
N1—C12—C11 | 129.7 (2) | C39—C40—H40 | 119.5 |
N1—C12—C7 | 108.99 (18) | C40—C41—C42 | 119.5 (2) |
C11—C12—C7 | 121.3 (2) | C40—C41—H41 | 120.2 |
N1—C13—C14 | 114.65 (18) | C42—C41—H41 | 120.2 |
N1—C13—H13A | 108.6 | C41—C42—C37 | 118.7 (2) |
C14—C13—H13A | 108.6 | C41—C42—C43 | 134.5 (2) |
N1—C13—H13B | 108.6 | C37—C42—C43 | 106.73 (18) |
C14—C13—H13B | 108.6 | C48—C43—C44 | 118.8 (2) |
H13A—C13—H13B | 107.6 | C48—C43—C42 | 106.95 (18) |
N2—C14—C15 | 122.5 (2) | C44—C43—C42 | 134.3 (2) |
N2—C14—C13 | 114.40 (18) | C45—C44—C43 | 118.9 (2) |
C15—C14—C13 | 123.1 (2) | C45—C44—H44 | 120.5 |
C14—C15—C16 | 119.2 (3) | C43—C44—H44 | 120.5 |
C14—C15—H15 | 120.4 | C44—C45—C46 | 121.0 (2) |
C16—C15—H15 | 120.4 | C44—C45—H45 | 119.5 |
C17—C16—C15 | 119.0 (3) | C46—C45—H45 | 119.5 |
C17—C16—H16 | 120.5 | C47—C46—C45 | 121.3 (3) |
C15—C16—H16 | 120.5 | C47—C46—H46 | 119.3 |
C18—C17—C16 | 118.0 (3) | C45—C46—H46 | 119.3 |
C18—C17—H17 | 121.0 | C46—C47—C48 | 117.9 (2) |
C16—C17—H17 | 121.0 | C46—C47—H47 | 121.0 |
N2—C18—C17 | 124.3 (2) | C48—C47—H47 | 121.0 |
N2—C18—H18 | 117.9 | N5—C48—C47 | 129.08 (19) |
C17—C18—H18 | 117.9 | N5—C48—C43 | 108.93 (19) |
N3—C19—C20 | 129.1 (3) | C47—C48—C43 | 122.0 (2) |
N3—C19—C24 | 109.1 (2) | N5—C49—C50 | 115.34 (16) |
C20—C19—C24 | 121.8 (3) | N5—C49—H49A | 108.4 |
C19—C20—C21 | 117.0 (3) | C50—C49—H49A | 108.4 |
C19—C20—H20 | 121.5 | N5—C49—H49B | 108.4 |
C21—C20—H20 | 121.5 | C50—C49—H49B | 108.4 |
C22—C21—C20 | 120.7 (3) | H49A—C49—H49B | 107.5 |
C22—C21—H21 | 119.6 | N6—C50—C51 | 122.5 (2) |
C20—C21—H21 | 119.6 | N6—C50—C49 | 113.97 (18) |
C23—C22—C21 | 122.3 (3) | C51—C50—C49 | 123.52 (19) |
C23—C22—H22 | 118.9 | C50—C51—C52 | 119.2 (3) |
C21—C22—H22 | 118.9 | C50—C51—H51 | 120.4 |
C22—C23—C24 | 118.8 (3) | C52—C51—H51 | 120.4 |
C22—C23—H23 | 120.6 | C53—C52—C51 | 119.6 (3) |
C24—C23—H23 | 120.6 | C53—C52—H52 | 120.2 |
C23—C24—C19 | 119.4 (2) | C51—C52—H52 | 120.2 |
C23—C24—C25 | 133.8 (2) | C52—C53—C54 | 118.2 (3) |
C19—C24—C25 | 106.7 (2) | C52—C53—H53 | 120.9 |
C26—C25—C30 | 118.2 (2) | C54—C53—H53 | 120.9 |
C26—C25—C24 | 135.0 (2) | N6—C54—C53 | 124.2 (3) |
C30—C25—C24 | 106.74 (19) | N6—C54—H54 | 117.9 |
C27—C26—C25 | 119.6 (2) | C53—C54—H54 | 117.9 |
C27—C26—H26 | 120.2 | | |
| | | |
C12—N1—C1—C2 | 179.3 (2) | C27—C28—C29—C30 | 1.0 (4) |
C13—N1—C1—C2 | −0.9 (3) | C28—C29—C30—N3 | −179.1 (2) |
C12—N1—C1—C6 | 0.1 (2) | C28—C29—C30—C25 | −1.6 (3) |
C13—N1—C1—C6 | 179.80 (18) | C19—N3—C30—C29 | 178.8 (2) |
N1—C1—C2—C3 | −178.8 (2) | C31—N3—C30—C29 | −7.7 (3) |
C6—C1—C2—C3 | 0.4 (3) | C19—N3—C30—C25 | 1.0 (2) |
C1—C2—C3—C4 | −0.8 (4) | C31—N3—C30—C25 | 174.59 (18) |
C2—C3—C4—C5 | 0.9 (4) | C26—C25—C30—C29 | 1.1 (3) |
C3—C4—C5—C6 | −0.4 (3) | C24—C25—C30—C29 | −178.10 (19) |
C4—C5—C6—C1 | 0.0 (3) | C26—C25—C30—N3 | 179.09 (17) |
C4—C5—C6—C7 | 179.0 (2) | C24—C25—C30—N3 | −0.2 (2) |
N1—C1—C6—C5 | 179.33 (17) | C30—N3—C31—C32 | −86.9 (3) |
C2—C1—C6—C5 | 0.0 (3) | C19—N3—C31—C32 | 85.5 (3) |
N1—C1—C6—C7 | 0.1 (2) | C36—N4—C32—C33 | −0.2 (3) |
C2—C1—C6—C7 | −179.29 (18) | C36—N4—C32—C31 | 179.52 (19) |
C5—C6—C7—C8 | 0.6 (4) | N3—C31—C32—N4 | 178.51 (19) |
C1—C6—C7—C8 | 179.7 (2) | N3—C31—C32—C33 | −1.8 (3) |
C5—C6—C7—C12 | −179.3 (2) | N4—C32—C33—C34 | −0.6 (3) |
C1—C6—C7—C12 | −0.2 (2) | C31—C32—C33—C34 | 179.8 (2) |
C12—C7—C8—C9 | 0.2 (3) | C32—C33—C34—C35 | 0.5 (4) |
C6—C7—C8—C9 | −179.6 (2) | C33—C34—C35—C36 | 0.3 (4) |
C7—C8—C9—C10 | −0.4 (3) | C32—N4—C36—C35 | 1.0 (3) |
C8—C9—C10—C11 | 0.6 (4) | C34—C35—C36—N4 | −1.1 (4) |
C9—C10—C11—C12 | −0.5 (4) | C48—N5—C37—C38 | −179.0 (2) |
C1—N1—C12—C11 | −179.6 (2) | C49—N5—C37—C38 | −3.8 (3) |
C13—N1—C12—C11 | 0.6 (3) | C48—N5—C37—C42 | 1.4 (2) |
C1—N1—C12—C7 | −0.2 (2) | C49—N5—C37—C42 | 176.56 (17) |
C13—N1—C12—C7 | −179.90 (19) | N5—C37—C38—C39 | 179.92 (19) |
C10—C11—C12—N1 | 179.7 (2) | C42—C37—C38—C39 | −0.5 (3) |
C10—C11—C12—C7 | 0.3 (3) | C37—C38—C39—C40 | −0.4 (3) |
C8—C7—C12—N1 | −179.69 (17) | C38—C39—C40—C41 | 1.1 (4) |
C6—C7—C12—N1 | 0.2 (2) | C39—C40—C41—C42 | −0.9 (4) |
C8—C7—C12—C11 | −0.2 (3) | C40—C41—C42—C37 | 0.0 (3) |
C6—C7—C12—C11 | 179.71 (18) | C40—C41—C42—C43 | −178.6 (2) |
C1—N1—C13—C14 | −85.4 (3) | C38—C37—C42—C41 | 0.7 (3) |
C12—N1—C13—C14 | 94.3 (3) | N5—C37—C42—C41 | −179.63 (17) |
C18—N2—C14—C15 | −0.8 (3) | C38—C37—C42—C43 | 179.66 (18) |
C18—N2—C14—C13 | −179.8 (2) | N5—C37—C42—C43 | −0.7 (2) |
N1—C13—C14—N2 | −178.6 (2) | C41—C42—C43—C48 | 178.5 (2) |
N1—C13—C14—C15 | 2.5 (3) | C37—C42—C43—C48 | −0.2 (2) |
N2—C14—C15—C16 | 0.1 (4) | C41—C42—C43—C44 | −0.7 (4) |
C13—C14—C15—C16 | 179.0 (2) | C37—C42—C43—C44 | −179.4 (2) |
C14—C15—C16—C17 | 0.4 (4) | C48—C43—C44—C45 | −1.3 (3) |
C15—C16—C17—C18 | −0.2 (4) | C42—C43—C44—C45 | 177.8 (2) |
C14—N2—C18—C17 | 1.0 (4) | C43—C44—C45—C46 | 1.2 (4) |
C16—C17—C18—N2 | −0.5 (4) | C44—C45—C46—C47 | −0.3 (4) |
C30—N3—C19—C20 | 178.6 (2) | C45—C46—C47—C48 | −0.3 (3) |
C31—N3—C19—C20 | 5.1 (4) | C37—N5—C48—C47 | 178.1 (2) |
C30—N3—C19—C24 | −1.5 (2) | C49—N5—C48—C47 | 3.0 (3) |
C31—N3—C19—C24 | −175.00 (19) | C37—N5—C48—C43 | −1.6 (2) |
N3—C19—C20—C21 | 178.7 (2) | C49—N5—C48—C43 | −176.64 (17) |
C24—C19—C20—C21 | −1.1 (4) | C46—C47—C48—N5 | −179.5 (2) |
C19—C20—C21—C22 | −0.1 (4) | C46—C47—C48—C43 | 0.1 (3) |
C20—C21—C22—C23 | 1.0 (5) | C44—C43—C48—N5 | −179.56 (18) |
C21—C22—C23—C24 | −0.6 (4) | C42—C43—C48—N5 | 1.1 (2) |
C22—C23—C24—C19 | −0.7 (3) | C44—C43—C48—C47 | 0.7 (3) |
C22—C23—C24—C25 | 179.7 (2) | C42—C43—C48—C47 | −178.61 (18) |
N3—C19—C24—C23 | −178.29 (19) | C37—N5—C49—C50 | −86.8 (2) |
C20—C19—C24—C23 | 1.6 (3) | C48—N5—C49—C50 | 87.5 (2) |
N3—C19—C24—C25 | 1.4 (2) | C54—N6—C50—C51 | −0.4 (3) |
C20—C19—C24—C25 | −178.7 (2) | C54—N6—C50—C49 | 177.4 (2) |
C23—C24—C25—C26 | −0.2 (4) | N5—C49—C50—N6 | 163.81 (18) |
C19—C24—C25—C26 | −179.8 (2) | N5—C49—C50—C51 | −18.5 (3) |
C23—C24—C25—C30 | 178.9 (2) | N6—C50—C51—C52 | 0.1 (4) |
C19—C24—C25—C30 | −0.8 (2) | C49—C50—C51—C52 | −177.4 (2) |
C30—C25—C26—C27 | 0.0 (3) | C50—C51—C52—C53 | 0.1 (5) |
C24—C25—C26—C27 | 179.0 (2) | C51—C52—C53—C54 | 0.0 (5) |
C25—C26—C27—C28 | −0.7 (3) | C50—N6—C54—C53 | 0.5 (4) |
C26—C27—C28—C29 | 0.2 (4) | C52—C53—C54—N6 | −0.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C49—H49A···N6i | 0.97 | 2.48 | 3.445 (3) | 172 |
Symmetry code: (i) −x, −y, −z+1. |