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
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.068
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 88 PerFit PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . P21/c
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT230_ALERT_2_C Hirshfeld Test Diff for C3A - C4A .. 5.72 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C22 - C27 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C22A - C27A ... 1.44 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 41 C23 -C22 -C27 -N27 11.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42 C21 -C22 -C27 -N27 -165.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 83 C23A-C22A-C27A-N27A -4.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 84 C21A-C22A-C27A-N27A 173.00 3.00 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 27.42 From the CIF: _reflns_number_total 8739 Count of symmetry unique reflns 4768 Completeness (_total/calc) 183.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3971 Fraction of Friedel pairs measured 0.833 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 7 ALERT type 4 Improvement, methodology, query or suggestion
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. |