Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026790/hg6096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026790/hg6096Isup2.hkl |
CCDC reference: 255950
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
C20H23N2O2+·Cl− | F(000) = 760 |
Mr = 358.85 | Dx = 1.232 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 43202 reflections |
a = 15.6095 (8) Å | θ = 2.6–27.3° |
b = 6.8297 (4) Å | µ = 0.21 mm−1 |
c = 18.6854 (9) Å | T = 173 K |
β = 103.739 (4)° | Plate, colourless |
V = 1935.02 (18) Å3 | 0.33 × 0.27 × 0.19 mm |
Z = 4 |
STOE IPDS II two-circle diffractometer | 8739 independent reflections |
Radiation source: fine-focus sealed tube | 7170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
ω scans | θmax = 27.4°, θmin = 2.7° |
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995) | h = −20→20 |
Tmin = 0.871, Tmax = 0.981 | k = −8→8 |
56436 measured reflections | l = −22→24 |
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)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max = 0.001 |
8739 reflections | Δρmax = 0.14 e Å−3 |
467 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Absolute structure: 3990 Friedel pairs, Flack H. D. (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (3) |
Experimental. Elemental analysis was carried out using Vario EL III CHN-OS elemental analyser |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.46000 (3) | 0.64149 (5) | 0.42837 (2) | 0.04043 (10) | |
C1 | 0.60157 (10) | 0.6467 (3) | 0.60922 (8) | 0.0344 (3) | |
H1A | 0.6292 | 0.5685 | 0.5761 | 0.041* | |
H1B | 0.6024 | 0.7855 | 0.5942 | 0.041* | |
N2 | 0.50693 (8) | 0.5823 (2) | 0.59880 (7) | 0.0325 (3) | |
H2A | 0.5070 (14) | 0.450 (3) | 0.6033 (11) | 0.053 (6)* | |
H2B | 0.4788 (12) | 0.607 (3) | 0.5505 (11) | 0.041 (5)* | |
C3 | 0.45804 (11) | 0.6761 (2) | 0.64993 (8) | 0.0375 (4) | |
H3 | 0.4811 | 0.8124 | 0.6602 | 0.045* | |
C31 | 0.35758 (11) | 0.6899 (3) | 0.61595 (10) | 0.0457 (4) | |
H31 | 0.3295 | 0.7309 | 0.6564 | 0.055* | |
C32 | 0.33606 (13) | 0.8467 (3) | 0.55697 (12) | 0.0557 (5) | |
H32A | 0.3623 | 0.9712 | 0.5771 | 0.084* | |
H32B | 0.2719 | 0.8614 | 0.5406 | 0.084* | |
H32C | 0.3600 | 0.8087 | 0.5151 | 0.084* | |
C33 | 0.31803 (13) | 0.4941 (3) | 0.58815 (13) | 0.0610 (5) | |
H33A | 0.3328 | 0.3973 | 0.6279 | 0.092* | |
H33B | 0.3418 | 0.4516 | 0.5467 | 0.092* | |
H33C | 0.2538 | 0.5067 | 0.5719 | 0.092* | |
C4 | 0.47319 (11) | 0.5694 (3) | 0.72256 (9) | 0.0420 (4) | |
O41 | 0.48967 (8) | 0.38078 (17) | 0.71526 (6) | 0.0449 (3) | |
C41 | 0.50258 (14) | 0.2607 (3) | 0.78061 (10) | 0.0590 (5) | |
H41A | 0.5141 | 0.1253 | 0.7683 | 0.088* | |
H41B | 0.4495 | 0.2651 | 0.7999 | 0.088* | |
H41C | 0.5530 | 0.3103 | 0.8180 | 0.088* | |
O42 | 0.46480 (10) | 0.6476 (3) | 0.77756 (7) | 0.0640 (4) | |
C11 | 0.65634 (10) | 0.6262 (2) | 0.68679 (8) | 0.0314 (3) | |
C12 | 0.67327 (11) | 0.7870 (2) | 0.73320 (9) | 0.0373 (3) | |
H12 | 0.6484 | 0.9104 | 0.7163 | 0.045* | |
C13 | 0.72605 (11) | 0.7704 (2) | 0.80391 (9) | 0.0373 (4) | |
H13 | 0.7365 | 0.8823 | 0.8350 | 0.045* | |
C14 | 0.76397 (10) | 0.5923 (2) | 0.83005 (9) | 0.0341 (3) | |
C15 | 0.74818 (11) | 0.4307 (3) | 0.78286 (9) | 0.0357 (3) | |
H15 | 0.7746 | 0.3083 | 0.7991 | 0.043* | |
C16 | 0.69484 (11) | 0.4472 (2) | 0.71310 (9) | 0.0342 (3) | |
H16 | 0.6839 | 0.3350 | 0.6822 | 0.041* | |
C21 | 0.81981 (11) | 0.5780 (2) | 0.90632 (9) | 0.0364 (3) | |
C22 | 0.81281 (11) | 0.4232 (3) | 0.95412 (9) | 0.0375 (3) | |
C23 | 0.86363 (12) | 0.4177 (3) | 1.02620 (9) | 0.0431 (4) | |
H23 | 0.8577 | 0.3116 | 1.0575 | 0.052* | |
C24 | 0.92239 (12) | 0.5656 (3) | 1.05212 (10) | 0.0471 (4) | |
H24 | 0.9567 | 0.5627 | 1.1014 | 0.057* | |
C25 | 0.93129 (12) | 0.7182 (3) | 1.00630 (10) | 0.0493 (4) | |
H25 | 0.9724 | 0.8198 | 1.0241 | 0.059* | |
C26 | 0.88083 (11) | 0.7253 (3) | 0.93444 (9) | 0.0436 (4) | |
H26 | 0.8878 | 0.8321 | 0.9037 | 0.052* | |
C27 | 0.74803 (12) | 0.2712 (2) | 0.93125 (9) | 0.0402 (4) | |
N27 | 0.69670 (12) | 0.1489 (2) | 0.91460 (9) | 0.0526 (4) | |
Cl1A | 0.95713 (3) | −0.06928 (5) | 0.42820 (2) | 0.04269 (10) | |
C1A | 0.88459 (11) | 0.4322 (3) | 0.39888 (9) | 0.0352 (3) | |
H1A1 | 0.8846 | 0.5562 | 0.4263 | 0.042* | |
H1A2 | 0.8555 | 0.3315 | 0.4231 | 0.042* | |
N2A | 0.97833 (8) | 0.37139 (19) | 0.40492 (7) | 0.0310 (3) | |
H2C | 0.9810 (13) | 0.232 (3) | 0.3977 (10) | 0.048 (5)* | |
H2D | 1.0067 (12) | 0.387 (2) | 0.4525 (10) | 0.036 (4)* | |
C3A | 1.02892 (11) | 0.4824 (2) | 0.35974 (8) | 0.0346 (3) | |
H3A | 1.0055 | 0.6192 | 0.3532 | 0.042* | |
C31A | 1.12703 (12) | 0.4906 (3) | 0.40162 (10) | 0.0450 (4) | |
H31A | 1.1289 | 0.5423 | 0.4520 | 0.054* | |
C32A | 1.17824 (15) | 0.6339 (4) | 0.36527 (12) | 0.0715 (6) | |
H32D | 1.1487 | 0.7615 | 0.3599 | 0.107* | |
H32E | 1.1808 | 0.5843 | 0.3166 | 0.107* | |
H32F | 1.2383 | 0.6482 | 0.3959 | 0.107* | |
C33A | 1.17081 (12) | 0.2889 (4) | 0.41145 (12) | 0.0591 (5) | |
H33D | 1.1367 | 0.2006 | 0.4355 | 0.089* | |
H33E | 1.2310 | 0.3009 | 0.4421 | 0.089* | |
H33F | 1.1728 | 0.2358 | 0.3631 | 0.089* | |
C4A | 1.01912 (10) | 0.3914 (3) | 0.28449 (8) | 0.0402 (4) | |
O41A | 1.00829 (8) | 0.19806 (17) | 0.28657 (6) | 0.0422 (3) | |
C41A | 1.00293 (14) | 0.0910 (4) | 0.21888 (11) | 0.0619 (5) | |
H41D | 0.9948 | −0.0486 | 0.2274 | 0.093* | |
H41E | 1.0575 | 0.1098 | 0.2025 | 0.093* | |
H41F | 0.9528 | 0.1394 | 0.1809 | 0.093* | |
O42A | 1.02639 (10) | 0.4820 (2) | 0.23129 (7) | 0.0600 (4) | |
C11A | 0.83081 (10) | 0.4609 (2) | 0.32136 (9) | 0.0336 (3) | |
C12A | 0.80834 (10) | 0.3040 (2) | 0.27272 (9) | 0.0366 (3) | |
H12A | 0.8278 | 0.1755 | 0.2881 | 0.044* | |
C13A | 0.75787 (11) | 0.3354 (3) | 0.20230 (9) | 0.0385 (4) | |
H13A | 0.7436 | 0.2278 | 0.1694 | 0.046* | |
C14A | 0.72740 (10) | 0.5220 (2) | 0.17841 (9) | 0.0351 (3) | |
C15A | 0.74858 (11) | 0.6767 (2) | 0.22772 (9) | 0.0389 (4) | |
H15A | 0.7276 | 0.8046 | 0.2130 | 0.047* | |
C16A | 0.80003 (11) | 0.6462 (3) | 0.29807 (9) | 0.0377 (3) | |
H16A | 0.8145 | 0.7539 | 0.3309 | 0.045* | |
C21A | 0.67499 (11) | 0.5491 (2) | 0.10145 (9) | 0.0367 (3) | |
C22A | 0.68915 (11) | 0.7055 (2) | 0.05681 (9) | 0.0364 (3) | |
C23A | 0.64110 (11) | 0.7222 (3) | −0.01645 (9) | 0.0407 (4) | |
H23A | 0.6510 | 0.8297 | −0.0457 | 0.049* | |
C24A | 0.57941 (12) | 0.5819 (3) | −0.04581 (10) | 0.0444 (4) | |
H24A | 0.5472 | 0.5916 | −0.0957 | 0.053* | |
C25A | 0.56438 (12) | 0.4275 (3) | −0.00303 (10) | 0.0465 (4) | |
H25A | 0.5219 | 0.3310 | −0.0237 | 0.056* | |
C26A | 0.61069 (12) | 0.4117 (3) | 0.06988 (9) | 0.0436 (4) | |
H26A | 0.5985 | 0.3057 | 0.0989 | 0.052* | |
C27A | 0.75617 (12) | 0.8517 (2) | 0.08259 (9) | 0.0400 (4) | |
N27A | 0.80821 (12) | 0.9709 (2) | 0.09955 (9) | 0.0529 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0550 (2) | 0.03156 (18) | 0.0319 (2) | 0.00088 (17) | 0.00472 (17) | 0.00091 (16) |
C1 | 0.0394 (8) | 0.0331 (7) | 0.0307 (7) | −0.0016 (7) | 0.0080 (6) | 0.0011 (6) |
N2 | 0.0333 (7) | 0.0349 (7) | 0.0270 (6) | 0.0008 (5) | 0.0027 (5) | −0.0004 (5) |
C3 | 0.0353 (8) | 0.0417 (9) | 0.0347 (8) | 0.0023 (6) | 0.0071 (6) | −0.0048 (6) |
C31 | 0.0350 (8) | 0.0610 (11) | 0.0415 (9) | 0.0084 (7) | 0.0101 (7) | 0.0065 (8) |
C32 | 0.0391 (9) | 0.0672 (12) | 0.0621 (12) | 0.0149 (9) | 0.0145 (9) | 0.0157 (10) |
C33 | 0.0378 (10) | 0.0770 (14) | 0.0633 (13) | −0.0121 (9) | 0.0022 (9) | 0.0133 (10) |
C4 | 0.0325 (8) | 0.0602 (10) | 0.0319 (8) | 0.0041 (7) | 0.0048 (6) | −0.0035 (7) |
O41 | 0.0499 (7) | 0.0516 (7) | 0.0327 (6) | −0.0011 (5) | 0.0091 (5) | 0.0041 (5) |
C41 | 0.0612 (12) | 0.0723 (14) | 0.0421 (10) | −0.0012 (10) | 0.0097 (9) | 0.0170 (9) |
O42 | 0.0734 (9) | 0.0867 (10) | 0.0311 (6) | 0.0261 (8) | 0.0105 (6) | −0.0055 (7) |
C11 | 0.0293 (7) | 0.0343 (7) | 0.0306 (7) | −0.0019 (6) | 0.0070 (6) | 0.0000 (6) |
C12 | 0.0411 (8) | 0.0307 (7) | 0.0388 (8) | 0.0003 (6) | 0.0071 (7) | 0.0009 (6) |
C13 | 0.0431 (9) | 0.0319 (8) | 0.0357 (8) | −0.0038 (6) | 0.0070 (7) | −0.0047 (6) |
C14 | 0.0320 (8) | 0.0390 (8) | 0.0320 (8) | −0.0008 (6) | 0.0091 (6) | −0.0032 (6) |
C15 | 0.0368 (8) | 0.0349 (7) | 0.0347 (8) | 0.0051 (7) | 0.0070 (6) | 0.0009 (7) |
C16 | 0.0360 (8) | 0.0316 (8) | 0.0349 (8) | 0.0020 (6) | 0.0083 (6) | −0.0032 (6) |
C21 | 0.0344 (8) | 0.0430 (8) | 0.0321 (8) | 0.0035 (7) | 0.0087 (6) | −0.0021 (6) |
C22 | 0.0370 (8) | 0.0405 (8) | 0.0359 (8) | 0.0065 (7) | 0.0106 (6) | −0.0021 (7) |
C23 | 0.0445 (9) | 0.0491 (9) | 0.0357 (8) | 0.0105 (8) | 0.0093 (7) | 0.0044 (8) |
C24 | 0.0417 (10) | 0.0647 (11) | 0.0318 (8) | 0.0071 (8) | 0.0024 (7) | −0.0027 (8) |
C25 | 0.0425 (9) | 0.0634 (11) | 0.0393 (9) | −0.0064 (9) | 0.0042 (8) | −0.0078 (8) |
C26 | 0.0408 (9) | 0.0525 (10) | 0.0361 (8) | −0.0050 (8) | 0.0064 (7) | −0.0003 (7) |
C27 | 0.0502 (9) | 0.0361 (8) | 0.0342 (8) | 0.0077 (8) | 0.0101 (7) | 0.0037 (6) |
N27 | 0.0680 (11) | 0.0401 (8) | 0.0485 (8) | −0.0042 (8) | 0.0114 (8) | 0.0025 (7) |
Cl1A | 0.0619 (3) | 0.03245 (19) | 0.0297 (2) | −0.00554 (18) | 0.00287 (18) | −0.00058 (16) |
C1A | 0.0328 (8) | 0.0391 (8) | 0.0339 (8) | −0.0008 (7) | 0.0082 (6) | −0.0003 (7) |
N2A | 0.0318 (6) | 0.0333 (7) | 0.0270 (6) | −0.0023 (5) | 0.0050 (5) | 0.0004 (5) |
C3A | 0.0347 (8) | 0.0379 (8) | 0.0313 (7) | −0.0044 (6) | 0.0081 (6) | 0.0024 (6) |
C31A | 0.0371 (9) | 0.0615 (10) | 0.0362 (8) | −0.0152 (8) | 0.0082 (7) | −0.0042 (7) |
C32A | 0.0586 (12) | 0.0999 (17) | 0.0568 (12) | −0.0421 (13) | 0.0150 (10) | 0.0014 (12) |
C33A | 0.0332 (9) | 0.0852 (15) | 0.0552 (11) | 0.0053 (10) | 0.0032 (8) | −0.0038 (11) |
C4A | 0.0314 (8) | 0.0565 (10) | 0.0316 (8) | −0.0042 (7) | 0.0051 (6) | 0.0061 (7) |
O41A | 0.0445 (6) | 0.0512 (7) | 0.0316 (5) | −0.0019 (5) | 0.0105 (5) | −0.0062 (5) |
C41A | 0.0603 (12) | 0.0835 (15) | 0.0426 (10) | −0.0070 (10) | 0.0137 (9) | −0.0241 (10) |
O42A | 0.0674 (9) | 0.0801 (10) | 0.0319 (7) | −0.0150 (7) | 0.0103 (7) | 0.0102 (6) |
C11A | 0.0288 (7) | 0.0386 (8) | 0.0339 (8) | −0.0010 (6) | 0.0085 (6) | −0.0039 (6) |
C12A | 0.0352 (8) | 0.0340 (8) | 0.0401 (8) | −0.0022 (7) | 0.0082 (7) | −0.0025 (7) |
C13A | 0.0378 (8) | 0.0385 (8) | 0.0383 (8) | −0.0052 (7) | 0.0072 (7) | −0.0074 (7) |
C14A | 0.0307 (8) | 0.0396 (8) | 0.0347 (8) | 0.0001 (6) | 0.0072 (7) | −0.0042 (6) |
C15A | 0.0389 (9) | 0.0364 (9) | 0.0391 (8) | 0.0053 (6) | 0.0050 (7) | −0.0046 (6) |
C16A | 0.0378 (8) | 0.0378 (8) | 0.0356 (8) | 0.0017 (7) | 0.0047 (7) | −0.0089 (7) |
C21A | 0.0337 (8) | 0.0410 (8) | 0.0347 (8) | 0.0000 (7) | 0.0066 (7) | −0.0053 (7) |
C22A | 0.0350 (8) | 0.0379 (8) | 0.0361 (8) | 0.0026 (6) | 0.0083 (7) | −0.0059 (7) |
C23A | 0.0412 (9) | 0.0423 (8) | 0.0385 (8) | 0.0038 (7) | 0.0094 (7) | −0.0021 (7) |
C24A | 0.0432 (10) | 0.0551 (10) | 0.0330 (8) | 0.0035 (8) | 0.0055 (7) | −0.0027 (7) |
C25A | 0.0404 (9) | 0.0565 (10) | 0.0389 (8) | −0.0100 (8) | 0.0021 (7) | −0.0073 (8) |
C26A | 0.0427 (9) | 0.0495 (9) | 0.0372 (8) | −0.0077 (8) | 0.0067 (7) | −0.0012 (7) |
C27A | 0.0441 (9) | 0.0371 (8) | 0.0385 (8) | 0.0027 (7) | 0.0093 (7) | −0.0047 (7) |
N27A | 0.0584 (10) | 0.0458 (9) | 0.0531 (9) | −0.0074 (7) | 0.0106 (8) | −0.0087 (7) |
C1—C11 | 1.504 (2) | C1A—N2A | 1.499 (2) |
C1—N2 | 1.509 (2) | C1A—C11A | 1.505 (2) |
C1—H1A | 0.9900 | C1A—H1A1 | 0.9900 |
C1—H1B | 0.9900 | C1A—H1A2 | 0.9900 |
N2—C3 | 1.5005 (19) | N2A—C3A | 1.4926 (19) |
N2—H2A | 0.91 (2) | N2A—H2C | 0.96 (2) |
N2—H2B | 0.920 (19) | N2A—H2D | 0.901 (19) |
C3—C4 | 1.509 (2) | C3A—C4A | 1.512 (2) |
C3—C31 | 1.549 (2) | C3A—C31A | 1.546 (2) |
C3—H3 | 1.0000 | C3A—H3A | 1.0000 |
C31—C33 | 1.512 (3) | C31A—C32A | 1.522 (3) |
C31—C32 | 1.516 (3) | C31A—C33A | 1.529 (3) |
C31—H31 | 1.0000 | C31A—H31A | 1.0000 |
C32—H32A | 0.9800 | C32A—H32D | 0.9800 |
C32—H32B | 0.9800 | C32A—H32E | 0.9800 |
C32—H32C | 0.9800 | C32A—H32F | 0.9800 |
C33—H33A | 0.9800 | C33A—H33D | 0.9800 |
C33—H33B | 0.9800 | C33A—H33E | 0.9800 |
C33—H33C | 0.9800 | C33A—H33F | 0.9800 |
C4—O42 | 1.193 (2) | C4A—O42A | 1.199 (2) |
C4—O41 | 1.327 (2) | C4A—O41A | 1.333 (2) |
O41—C41 | 1.445 (2) | O41A—C41A | 1.446 (2) |
C41—H41A | 0.9800 | C41A—H41D | 0.9800 |
C41—H41B | 0.9800 | C41A—H41E | 0.9800 |
C41—H41C | 0.9800 | C41A—H41F | 0.9800 |
C11—C12 | 1.386 (2) | C11A—C16A | 1.387 (2) |
C11—C16 | 1.399 (2) | C11A—C12A | 1.395 (2) |
C12—C13 | 1.386 (2) | C12A—C13A | 1.380 (2) |
C12—H12 | 0.9500 | C12A—H12A | 0.9500 |
C13—C14 | 1.390 (2) | C13A—C14A | 1.396 (2) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C14—C15 | 1.398 (2) | C14A—C15A | 1.390 (2) |
C14—C21 | 1.487 (2) | C14A—C21A | 1.488 (2) |
C15—C16 | 1.374 (2) | C15A—C16A | 1.384 (2) |
C15—H15 | 0.9500 | C15A—H15A | 0.9500 |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
C21—C26 | 1.399 (2) | C21A—C26A | 1.398 (2) |
C21—C22 | 1.405 (2) | C21A—C22A | 1.405 (2) |
C22—C23 | 1.392 (2) | C22A—C23A | 1.401 (2) |
C22—C27 | 1.441 (3) | C22A—C27A | 1.444 (2) |
C23—C24 | 1.373 (3) | C23A—C24A | 1.377 (3) |
C23—H23 | 0.9500 | C23A—H23A | 0.9500 |
C24—C25 | 1.377 (3) | C24A—C25A | 1.376 (3) |
C24—H24 | 0.9500 | C24A—H24A | 0.9500 |
C25—C26 | 1.387 (2) | C25A—C26A | 1.387 (2) |
C25—H25 | 0.9500 | C25A—H25A | 0.9500 |
C26—H26 | 0.9500 | C26A—H26A | 0.9500 |
C27—N27 | 1.148 (2) | C27A—N27A | 1.140 (2) |
C11—C1—N2 | 114.34 (12) | N2A—C1A—C11A | 114.83 (13) |
C11—C1—H1A | 108.7 | N2A—C1A—H1A1 | 108.6 |
N2—C1—H1A | 108.7 | C11A—C1A—H1A1 | 108.6 |
C11—C1—H1B | 108.7 | N2A—C1A—H1A2 | 108.6 |
N2—C1—H1B | 108.7 | C11A—C1A—H1A2 | 108.6 |
H1A—C1—H1B | 107.6 | H1A1—C1A—H1A2 | 107.5 |
C3—N2—C1 | 115.09 (12) | C3A—N2A—C1A | 117.04 (12) |
C3—N2—H2A | 110.8 (13) | C3A—N2A—H2C | 112.1 (12) |
C1—N2—H2A | 107.3 (14) | C1A—N2A—H2C | 109.7 (12) |
C3—N2—H2B | 110.5 (11) | C3A—N2A—H2D | 107.1 (11) |
C1—N2—H2B | 107.4 (11) | C1A—N2A—H2D | 106.4 (11) |
H2A—N2—H2B | 105.1 (17) | H2C—N2A—H2D | 103.4 (16) |
N2—C3—C4 | 111.82 (13) | N2A—C3A—C4A | 111.52 (13) |
N2—C3—C31 | 112.55 (13) | N2A—C3A—C31A | 108.99 (12) |
C4—C3—C31 | 108.99 (13) | C4A—C3A—C31A | 110.78 (13) |
N2—C3—H3 | 107.8 | N2A—C3A—H3A | 108.5 |
C4—C3—H3 | 107.8 | C4A—C3A—H3A | 108.5 |
C31—C3—H3 | 107.8 | C31A—C3A—H3A | 108.5 |
C33—C31—C32 | 111.89 (16) | C32A—C31A—C33A | 111.45 (18) |
C33—C31—C3 | 112.21 (15) | C32A—C31A—C3A | 111.05 (15) |
C32—C31—C3 | 111.66 (15) | C33A—C31A—C3A | 112.89 (14) |
C33—C31—H31 | 106.9 | C32A—C31A—H31A | 107.0 |
C32—C31—H31 | 106.9 | C33A—C31A—H31A | 107.0 |
C3—C31—H31 | 106.9 | C3A—C31A—H31A | 107.0 |
C31—C32—H32A | 109.5 | C31A—C32A—H32D | 109.5 |
C31—C32—H32B | 109.5 | C31A—C32A—H32E | 109.5 |
H32A—C32—H32B | 109.5 | H32D—C32A—H32E | 109.5 |
C31—C32—H32C | 109.5 | C31A—C32A—H32F | 109.5 |
H32A—C32—H32C | 109.5 | H32D—C32A—H32F | 109.5 |
H32B—C32—H32C | 109.5 | H32E—C32A—H32F | 109.5 |
C31—C33—H33A | 109.5 | C31A—C33A—H33D | 109.5 |
C31—C33—H33B | 109.5 | C31A—C33A—H33E | 109.5 |
H33A—C33—H33B | 109.5 | H33D—C33A—H33E | 109.5 |
C31—C33—H33C | 109.5 | C31A—C33A—H33F | 109.5 |
H33A—C33—H33C | 109.5 | H33D—C33A—H33F | 109.5 |
H33B—C33—H33C | 109.5 | H33E—C33A—H33F | 109.5 |
O42—C4—O41 | 125.94 (17) | O42A—C4A—O41A | 124.96 (17) |
O42—C4—C3 | 122.19 (17) | O42A—C4A—C3A | 123.39 (17) |
O41—C4—C3 | 111.68 (13) | O41A—C4A—C3A | 111.47 (13) |
C4—O41—C41 | 117.10 (14) | C4A—O41A—C41A | 117.17 (15) |
O41—C41—H41A | 109.5 | O41A—C41A—H41D | 109.5 |
O41—C41—H41B | 109.5 | O41A—C41A—H41E | 109.5 |
H41A—C41—H41B | 109.5 | H41D—C41A—H41E | 109.5 |
O41—C41—H41C | 109.5 | O41A—C41A—H41F | 109.5 |
H41A—C41—H41C | 109.5 | H41D—C41A—H41F | 109.5 |
H41B—C41—H41C | 109.5 | H41E—C41A—H41F | 109.5 |
C12—C11—C16 | 118.08 (14) | C16A—C11A—C12A | 118.81 (15) |
C12—C11—C1 | 120.64 (15) | C16A—C11A—C1A | 119.56 (14) |
C16—C11—C1 | 121.22 (15) | C12A—C11A—C1A | 121.59 (15) |
C11—C12—C13 | 120.89 (15) | C13A—C12A—C11A | 120.00 (16) |
C11—C12—H12 | 119.6 | C13A—C12A—H12A | 120.0 |
C13—C12—H12 | 119.6 | C11A—C12A—H12A | 120.0 |
C12—C13—C14 | 120.94 (15) | C12A—C13A—C14A | 121.37 (15) |
C12—C13—H13 | 119.5 | C12A—C13A—H13A | 119.3 |
C14—C13—H13 | 119.5 | C14A—C13A—H13A | 119.3 |
C13—C14—C15 | 118.21 (15) | C15A—C14A—C13A | 118.24 (15) |
C13—C14—C21 | 119.90 (14) | C15A—C14A—C21A | 122.39 (15) |
C15—C14—C21 | 121.89 (15) | C13A—C14A—C21A | 119.37 (14) |
C16—C15—C14 | 120.67 (16) | C16A—C15A—C14A | 120.54 (16) |
C16—C15—H15 | 119.7 | C16A—C15A—H15A | 119.7 |
C14—C15—H15 | 119.7 | C14A—C15A—H15A | 119.7 |
C15—C16—C11 | 121.18 (15) | C15A—C16A—C11A | 121.01 (15) |
C15—C16—H16 | 119.4 | C15A—C16A—H16A | 119.5 |
C11—C16—H16 | 119.4 | C11A—C16A—H16A | 119.5 |
C26—C21—C22 | 116.82 (15) | C26A—C21A—C22A | 117.28 (15) |
C26—C21—C14 | 120.28 (15) | C26A—C21A—C14A | 119.92 (16) |
C22—C21—C14 | 122.86 (15) | C22A—C21A—C14A | 122.75 (15) |
C23—C22—C21 | 121.52 (17) | C23A—C22A—C21A | 121.26 (15) |
C23—C22—C27 | 117.80 (16) | C23A—C22A—C27A | 116.57 (15) |
C21—C22—C27 | 120.56 (15) | C21A—C22A—C27A | 122.11 (15) |
C24—C23—C22 | 120.09 (18) | C24A—C23A—C22A | 119.63 (17) |
C24—C23—H23 | 120.0 | C24A—C23A—H23A | 120.2 |
C22—C23—H23 | 120.0 | C22A—C23A—H23A | 120.2 |
C23—C24—C25 | 119.68 (17) | C25A—C24A—C23A | 120.08 (17) |
C23—C24—H24 | 120.2 | C25A—C24A—H24A | 120.0 |
C25—C24—H24 | 120.2 | C23A—C24A—H24A | 120.0 |
C24—C25—C26 | 120.71 (18) | C24A—C25A—C26A | 120.63 (17) |
C24—C25—H25 | 119.6 | C24A—C25A—H25A | 119.7 |
C26—C25—H25 | 119.6 | C26A—C25A—H25A | 119.7 |
C25—C26—C21 | 121.18 (18) | C25A—C26A—C21A | 121.10 (17) |
C25—C26—H26 | 119.4 | C25A—C26A—H26A | 119.5 |
C21—C26—H26 | 119.4 | C21A—C26A—H26A | 119.5 |
N27—C27—C22 | 178.51 (18) | N27A—C27A—C22A | 176.66 (19) |
C11—C1—N2—C3 | 53.57 (18) | C1A—N2A—C3A—C4A | −89.72 (17) |
C1—N2—C3—C4 | −85.06 (16) | C1A—N2A—C3A—C31A | 147.67 (14) |
C1—N2—C3—C31 | 151.87 (14) | N2A—C3A—C31A—C32A | −169.18 (17) |
N2—C3—C31—C33 | 53.11 (19) | C4A—C3A—C31A—C32A | 67.8 (2) |
C4—C3—C31—C33 | −71.53 (19) | N2A—C3A—C31A—C33A | 64.81 (18) |
N2—C3—C31—C32 | −73.44 (19) | C4A—C3A—C31A—C33A | −58.25 (19) |
C4—C3—C31—C32 | 161.91 (16) | N2A—C3A—C4A—O42A | 153.67 (16) |
N2—C3—C4—O42 | 156.10 (16) | C31A—C3A—C4A—O42A | −84.7 (2) |
C31—C3—C4—O42 | −78.8 (2) | N2A—C3A—C4A—O41A | −31.03 (18) |
N2—C3—C4—O41 | −28.61 (19) | C31A—C3A—C4A—O41A | 90.55 (16) |
C31—C3—C4—O41 | 96.46 (16) | O42A—C4A—O41A—C41A | −1.5 (3) |
O42—C4—O41—C41 | −3.0 (3) | C3A—C4A—O41A—C41A | −176.70 (14) |
C3—C4—O41—C41 | −178.07 (14) | N2A—C1A—C11A—C16A | −114.59 (17) |
N2—C1—C11—C12 | −100.07 (17) | N2A—C1A—C11A—C12A | 67.7 (2) |
N2—C1—C11—C16 | 82.85 (18) | C16A—C11A—C12A—C13A | 1.3 (2) |
C16—C11—C12—C13 | −0.7 (2) | C1A—C11A—C12A—C13A | 179.11 (15) |
C1—C11—C12—C13 | −177.88 (16) | C11A—C12A—C13A—C14A | −0.8 (2) |
C11—C12—C13—C14 | 0.5 (3) | C12A—C13A—C14A—C15A | −0.5 (2) |
C12—C13—C14—C15 | 0.6 (2) | C12A—C13A—C14A—C21A | 178.58 (15) |
C12—C13—C14—C21 | −179.55 (15) | C13A—C14A—C15A—C16A | 1.3 (2) |
C13—C14—C15—C16 | −1.5 (2) | C21A—C14A—C15A—C16A | −177.79 (16) |
C21—C14—C15—C16 | 178.68 (15) | C14A—C15A—C16A—C11A | −0.7 (3) |
C14—C15—C16—C11 | 1.3 (2) | C12A—C11A—C16A—C15A | −0.6 (2) |
C12—C11—C16—C15 | −0.2 (2) | C1A—C11A—C16A—C15A | −178.40 (15) |
C1—C11—C16—C15 | 176.98 (15) | C15A—C14A—C21A—C26A | −139.58 (17) |
C13—C14—C21—C26 | −42.3 (2) | C13A—C14A—C21A—C26A | 41.4 (2) |
C15—C14—C21—C26 | 137.52 (17) | C15A—C14A—C21A—C22A | 42.8 (2) |
C13—C14—C21—C22 | 135.64 (16) | C13A—C14A—C21A—C22A | −136.20 (17) |
C15—C14—C21—C22 | −44.5 (2) | C26A—C21A—C22A—C23A | −0.3 (2) |
C26—C21—C22—C23 | 0.5 (2) | C14A—C21A—C22A—C23A | 177.30 (15) |
C14—C21—C22—C23 | −177.47 (15) | C26A—C21A—C22A—C27A | −177.51 (15) |
C26—C21—C22—C27 | 176.30 (15) | C14A—C21A—C22A—C27A | 0.1 (2) |
C14—C21—C22—C27 | −1.7 (2) | C21A—C22A—C23A—C24A | −0.7 (3) |
C21—C22—C23—C24 | −0.1 (3) | C27A—C22A—C23A—C24A | 176.58 (15) |
C27—C22—C23—C24 | −175.94 (16) | C22A—C23A—C24A—C25A | 0.8 (3) |
C22—C23—C24—C25 | −0.6 (3) | C23A—C24A—C25A—C26A | 0.2 (3) |
C23—C24—C25—C26 | 0.7 (3) | C24A—C25A—C26A—C21A | −1.3 (3) |
C24—C25—C26—C21 | −0.2 (3) | C22A—C21A—C26A—C25A | 1.4 (3) |
C22—C21—C26—C25 | −0.4 (3) | C14A—C21A—C26A—C25A | −176.33 (16) |
C14—C21—C26—C25 | 177.67 (17) | C23A—C22A—C27A—N27A | −4 (3) |
C23—C22—C27—N27 | 11 (7) | C21A—C22A—C27A—N27A | 173 (3) |
C21—C22—C27—N27 | −165 (7) | N2—C3—C31—H31 | 169.99 |
C11A—C1A—N2A—C3A | 46.89 (19) | N2A—C3A—C31A—H31A | −52.69 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···Cl1 | 0.920 (19) | 2.243 (19) | 3.1199 (13) | 159.0 (15) |
N2—H2A···Cl1i | 0.91 (2) | 2.28 (2) | 3.1168 (14) | 153.1 (18) |
N2A—H2C···Cl1A | 0.96 (2) | 2.19 (2) | 3.0700 (14) | 151.1 (16) |
N2A—H2D···Cl1Aii | 0.901 (19) | 2.185 (19) | 3.0676 (14) | 166.0 (15) |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1. |