Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002048/lh2284sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002048/lh2284Isup2.hkl |
CCDC reference: 638508
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.069
- wR factor = 0.200
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 1.538 Test value = 1.275 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.05 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 1.54 e/A PLAT213_ALERT_2_C Atom O6# has ADP max/min Ratio ............. 3.50 prola PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1A PLAT245_ALERT_2_C U(iso) H15C Smaller than U(eq) C15A by ... 0.01 AngSq PLAT245_ALERT_2_C U(iso) H15E Smaller than U(eq) C15B by ... 0.01 AngSq PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1A .. O3A .. 3.17 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1B .. O3BB .. 3.05 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1B .. O3BA .. 3.25 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C15 H16 N O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C15H16NO+·C6H4ClO3S− | F(000) = 1744 |
Mr = 417.91 | Dx = 1.440 Mg m−3 |
Monoclinic, P21/c | Melting point = 470–471 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.2016 (5) Å | Cell parameters from 7521 reflections |
b = 13.7923 (4) Å | θ = 1.6–26.0° |
c = 22.0003 (7) Å | µ = 0.34 mm−1 |
β = 123.274 (2)° | T = 100 K |
V = 3856.5 (2) Å3 | Needle, yellow |
Z = 8 | 0.56 × 0.18 × 0.16 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 7521 independent reflections |
Radiation source: fine-focus sealed tube | 5951 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −17→17 |
Tmin = 0.836, Tmax = 0.947 | l = −27→27 |
47660 measured reflections |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0999P)2 + 9.2696P] where P = (Fo2 + 2Fc2)/3 |
7521 reflections | (Δ/σ)max = 0.001 |
563 parameters | Δρmax = 1.54 e Å−3 |
18 restraints | Δρmin = −0.75 e Å−3 |
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 | Occ. (<1) | |
S1A | 0.74122 (6) | 0.53963 (6) | 0.74950 (5) | 0.0232 (2) | |
Cl1A | 0.99232 (9) | 0.85893 (7) | 0.70408 (5) | 0.0407 (3) | |
O1A | −0.1752 (2) | 1.3836 (2) | 0.02739 (13) | 0.0388 (7) | |
O2A | 0.7049 (2) | 0.5861 (2) | 0.79108 (17) | 0.0428 (7) | |
O3A | 0.8170 (2) | 0.4641 (2) | 0.78949 (17) | 0.0439 (7) | |
O4A | 0.6564 (3) | 0.5082 (2) | 0.67841 (16) | 0.0513 (8) | |
N1A | −0.1479 (3) | 0.7638 (2) | −0.05484 (17) | 0.0335 (7) | |
C1A | −0.1286 (4) | 0.6664 (3) | −0.0488 (2) | 0.0411 (10) | |
H1A | −0.1746 | 0.6256 | −0.0869 | 0.049* | |
C2A | −0.0429 (4) | 0.6280 (3) | 0.0121 (3) | 0.0462 (11) | |
H2A | −0.0310 | 0.5614 | 0.0157 | 0.055* | |
C3A | 0.0260 (4) | 0.6882 (3) | 0.0684 (3) | 0.0454 (10) | |
H3A | 0.0848 | 0.6629 | 0.1102 | 0.054* | |
C4A | 0.0068 (3) | 0.7857 (3) | 0.0621 (2) | 0.0398 (10) | |
H4A | 0.0539 | 0.8265 | 0.0998 | 0.048* | |
C5A | −0.0820 (3) | 0.8255 (3) | 0.0005 (2) | 0.0348 (9) | |
C6A | −0.1123 (3) | 0.9255 (3) | −0.0086 (2) | 0.0382 (9) | |
H6A | −0.1665 | 0.9466 | −0.0543 | 0.046* | |
C7A | −0.0659 (3) | 0.9901 (3) | 0.0461 (2) | 0.0367 (9) | |
H7A | −0.0121 | 0.9675 | 0.0914 | 0.044* | |
C8A | −0.0929 (3) | 1.0930 (3) | 0.04017 (19) | 0.0314 (8) | |
C9A | −0.1851 (3) | 1.1323 (3) | −0.02010 (19) | 0.0312 (8) | |
H9A | −0.2300 | 1.0923 | −0.0592 | 0.037* | |
C10A | −0.2102 (3) | 1.2282 (3) | −0.02254 (18) | 0.0315 (8) | |
H10A | −0.2719 | 1.2525 | −0.0628 | 0.040 (12)* | |
C11A | −0.1437 (3) | 1.2896 (3) | 0.03504 (18) | 0.0281 (8) | |
C12A | −0.0512 (3) | 1.2537 (3) | 0.09550 (18) | 0.0288 (8) | |
H12A | −0.0060 | 1.2944 | 0.1340 | 0.040 (12)* | |
C13A | −0.0278 (3) | 1.1565 (3) | 0.09709 (18) | 0.0283 (8) | |
H13A | 0.0336 | 1.1323 | 0.1377 | 0.031 (10)* | |
C14A | −0.1189 (3) | 1.4458 (3) | 0.0895 (2) | 0.0391 (9) | |
H14A | −0.1497 | 1.5093 | 0.0772 | 0.037 (11)* | |
H14B | −0.0467 | 1.4498 | 0.1044 | 0.049 (13)* | |
H14C | −0.1226 | 1.4198 | 0.1286 | 0.047 (13)* | |
C15A | −0.2420 (3) | 0.8002 (3) | −0.1219 (2) | 0.0371 (9) | |
H15A | −0.2871 | 0.8321 | −0.1103 | 0.045 (12)* | |
H15B | −0.2790 | 0.7469 | −0.1541 | 0.058 (14)* | |
H15C | −0.2213 | 0.8453 | −0.1451 | 0.026 (10)* | |
C16A | 0.8089 (2) | 0.6303 (2) | 0.73332 (16) | 0.0192 (6) | |
C17A | 0.7798 (3) | 0.7271 (2) | 0.72692 (17) | 0.0235 (7) | |
H17A | 0.7232 | 0.7442 | 0.7300 | 0.040 (12)* | |
C18A | 0.8339 (3) | 0.7977 (2) | 0.71629 (17) | 0.0268 (8) | |
H18A | 0.8139 | 0.8624 | 0.7115 | 0.028 (10)* | |
C19A | 0.9179 (3) | 0.7702 (2) | 0.71255 (17) | 0.0259 (7) | |
C20A | 0.9479 (3) | 0.6739 (2) | 0.71674 (16) | 0.0220 (7) | |
H20A | 1.0037 | 0.6572 | 0.7127 | 0.024 (9)* | |
C21A | 0.8921 (2) | 0.6039 (2) | 0.72698 (17) | 0.0200 (7) | |
H21A | 0.9102 | 0.5389 | 0.7297 | 0.024 (9)* | |
S1B | 0.24499 (6) | 0.94356 (6) | 0.24253 (5) | 0.0263 (2) | |
Cl1B | 0.53089 (8) | 0.64984 (6) | 0.20871 (5) | 0.0317 (2) | |
O1B | 0.6735 (2) | 0.8972 (2) | 0.47042 (13) | 0.0372 (6) | |
O2BA | 0.1743 (8) | 0.8841 (6) | 0.2494 (10) | 0.026 (3) | 0.65 (6) |
O3BA | 0.3243 (9) | 0.9936 (8) | 0.3091 (6) | 0.028 (2) | 0.65 (6) |
O4BA | 0.1949 (9) | 1.0047 (8) | 0.1774 (6) | 0.030 (3) | 0.65 (6) |
O2BB | 0.194 (3) | 0.895 (3) | 0.278 (3) | 0.060 (7) | 0.35 (6) |
O3BB | 0.308 (3) | 1.017 (4) | 0.290 (3) | 0.073 (10) | 0.35 (6) |
O4BB | 0.171 (4) | 0.988 (3) | 0.1778 (15) | 0.077 (8) | 0.35 (6) |
N1B | 0.6683 (3) | 0.2791 (2) | 0.57215 (18) | 0.0341 (7) | |
C1B | 0.6496 (3) | 0.1830 (3) | 0.5704 (2) | 0.0410 (10) | |
H1B | 0.6962 | 0.1447 | 0.6101 | 0.049* | |
C2B | 0.5644 (4) | 0.1411 (4) | 0.5118 (3) | 0.0500 (11) | |
H2B | 0.5531 | 0.0747 | 0.5111 | 0.060* | |
C3B | 0.4947 (4) | 0.1982 (4) | 0.4531 (3) | 0.0519 (12) | |
H3B | 0.4357 | 0.1707 | 0.4127 | 0.062* | |
C4B | 0.5135 (3) | 0.2963 (4) | 0.4550 (2) | 0.0430 (10) | |
H4B | 0.4663 | 0.3350 | 0.4158 | 0.052* | |
C5B | 0.6025 (3) | 0.3382 (3) | 0.5152 (2) | 0.0362 (9) | |
C6B | 0.6305 (3) | 0.4397 (3) | 0.5204 (2) | 0.0379 (9) | |
H6B | 0.6847 | 0.4633 | 0.5652 | 0.045* | |
C7B | 0.5823 (3) | 0.5015 (3) | 0.4640 (2) | 0.0380 (9) | |
H7B | 0.5288 | 0.4763 | 0.4196 | 0.046* | |
C8B | 0.6062 (3) | 0.6042 (3) | 0.46605 (19) | 0.0328 (8) | |
C9B | 0.6964 (3) | 0.6480 (3) | 0.52469 (19) | 0.0348 (9) | |
H9B | 0.7436 | 0.6105 | 0.5648 | 0.042* | |
C10B | 0.7163 (3) | 0.7446 (3) | 0.52416 (19) | 0.0344 (9) | |
H10B | 0.7766 | 0.7720 | 0.5636 | 0.047 (13)* | |
C11B | 0.6469 (3) | 0.8019 (3) | 0.46507 (18) | 0.0302 (8) | |
C12B | 0.5564 (3) | 0.7614 (3) | 0.40565 (18) | 0.0292 (8) | |
H12B | 0.5095 | 0.7995 | 0.3659 | 0.047 (13)* | |
C13B | 0.5373 (3) | 0.6633 (3) | 0.40685 (18) | 0.0297 (8) | |
H13B | 0.4772 | 0.6360 | 0.3671 | 0.030 (10)* | |
C14B | 0.6112 (3) | 0.9589 (3) | 0.40879 (19) | 0.0349 (9) | |
H14D | 0.6400 | 1.0232 | 0.4201 | 0.050 (13)* | |
H14E | 0.5402 | 0.9604 | 0.3968 | 0.049 (13)* | |
H14F | 0.6116 | 0.9343 | 0.3681 | 0.028 (10)* | |
C15B | 0.7638 (3) | 0.3176 (3) | 0.6382 (2) | 0.0381 (9) | |
H15D | 0.8027 | 0.2652 | 0.6708 | 0.048 (13)* | |
H15E | 0.7439 | 0.3629 | 0.6618 | 0.027 (10)* | |
H15F | 0.8069 | 0.3499 | 0.6249 | 0.044 (12)* | |
C16B | 0.3204 (2) | 0.8590 (2) | 0.22814 (17) | 0.0220 (7) | |
C17B | 0.3022 (3) | 0.7599 (2) | 0.22535 (17) | 0.0254 (7) | |
H17B | 0.2477 | 0.7367 | 0.2288 | 0.036 (11)* | |
C18B | 0.3653 (3) | 0.6955 (2) | 0.21722 (17) | 0.0247 (7) | |
H18B | 0.3527 | 0.6292 | 0.2146 | 0.017 (8)* | |
C19B | 0.4466 (3) | 0.7306 (2) | 0.21328 (17) | 0.0237 (7) | |
C20B | 0.4645 (3) | 0.8299 (2) | 0.21383 (17) | 0.0224 (7) | |
H20B | 0.5181 | 0.8529 | 0.2092 | 0.041 (12)* | |
C21B | 0.4003 (2) | 0.8935 (2) | 0.22133 (17) | 0.0217 (7) | |
H21B | 0.4110 | 0.9600 | 0.2218 | 0.026 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0167 (4) | 0.0222 (4) | 0.0286 (4) | −0.0017 (3) | 0.0111 (4) | −0.0039 (3) |
Cl1A | 0.0565 (6) | 0.0275 (5) | 0.0310 (5) | −0.0199 (4) | 0.0196 (5) | −0.0012 (4) |
O1A | 0.0395 (15) | 0.0365 (15) | 0.0221 (13) | 0.0036 (12) | 0.0052 (12) | 0.0053 (11) |
O2A | 0.0429 (16) | 0.0388 (16) | 0.065 (2) | −0.0076 (13) | 0.0417 (16) | −0.0125 (14) |
O3A | 0.0359 (15) | 0.0373 (16) | 0.066 (2) | 0.0091 (12) | 0.0327 (15) | 0.0244 (14) |
O4A | 0.0491 (18) | 0.0525 (19) | 0.0359 (16) | −0.0301 (15) | 0.0128 (14) | −0.0082 (14) |
N1A | 0.0335 (17) | 0.0403 (19) | 0.0357 (17) | −0.0044 (14) | 0.0247 (15) | −0.0049 (14) |
C1A | 0.050 (3) | 0.037 (2) | 0.054 (3) | −0.0098 (19) | 0.040 (2) | −0.0092 (19) |
C2A | 0.048 (3) | 0.042 (2) | 0.059 (3) | 0.005 (2) | 0.035 (2) | 0.008 (2) |
C3A | 0.041 (2) | 0.053 (3) | 0.053 (3) | 0.006 (2) | 0.033 (2) | 0.009 (2) |
C4A | 0.036 (2) | 0.054 (3) | 0.035 (2) | 0.0011 (19) | 0.0234 (19) | −0.0015 (19) |
C5A | 0.039 (2) | 0.041 (2) | 0.036 (2) | −0.0033 (17) | 0.0279 (19) | −0.0063 (17) |
C6A | 0.040 (2) | 0.044 (2) | 0.032 (2) | −0.0075 (18) | 0.0207 (18) | −0.0051 (17) |
C7A | 0.035 (2) | 0.046 (2) | 0.032 (2) | −0.0030 (18) | 0.0196 (18) | −0.0033 (17) |
C8A | 0.0317 (19) | 0.043 (2) | 0.0219 (17) | −0.0011 (16) | 0.0162 (16) | −0.0024 (15) |
C9A | 0.0295 (19) | 0.043 (2) | 0.0189 (17) | −0.0081 (16) | 0.0121 (15) | −0.0058 (15) |
C10A | 0.0216 (17) | 0.049 (2) | 0.0153 (16) | −0.0019 (16) | 0.0045 (14) | 0.0062 (15) |
C11A | 0.0294 (19) | 0.0306 (19) | 0.0215 (17) | −0.0022 (15) | 0.0121 (15) | 0.0048 (14) |
C12A | 0.0254 (18) | 0.040 (2) | 0.0163 (16) | −0.0081 (16) | 0.0088 (14) | −0.0021 (15) |
C13A | 0.0229 (17) | 0.043 (2) | 0.0171 (16) | −0.0012 (15) | 0.0096 (14) | −0.0014 (15) |
C14A | 0.044 (2) | 0.029 (2) | 0.034 (2) | 0.0016 (17) | 0.0157 (19) | 0.0010 (17) |
C15A | 0.041 (2) | 0.042 (2) | 0.037 (2) | −0.0063 (18) | 0.0268 (19) | −0.0099 (18) |
C16A | 0.0151 (15) | 0.0197 (16) | 0.0153 (14) | −0.0003 (12) | 0.0036 (12) | −0.0026 (12) |
C17A | 0.0235 (17) | 0.0213 (17) | 0.0188 (16) | 0.0058 (13) | 0.0072 (14) | −0.0029 (13) |
C18A | 0.037 (2) | 0.0149 (16) | 0.0158 (15) | 0.0058 (14) | 0.0066 (14) | −0.0005 (12) |
C19A | 0.0307 (18) | 0.0204 (17) | 0.0129 (15) | −0.0087 (14) | 0.0033 (14) | 0.0000 (12) |
C20A | 0.0189 (16) | 0.0232 (16) | 0.0173 (15) | −0.0013 (13) | 0.0057 (13) | 0.0000 (13) |
C21A | 0.0158 (15) | 0.0148 (15) | 0.0210 (15) | 0.0020 (12) | 0.0049 (13) | −0.0005 (12) |
S1B | 0.0190 (4) | 0.0228 (4) | 0.0345 (5) | 0.0011 (3) | 0.0130 (4) | 0.0068 (4) |
Cl1B | 0.0403 (5) | 0.0220 (4) | 0.0333 (5) | 0.0037 (4) | 0.0206 (4) | 0.0001 (3) |
O1B | 0.0316 (14) | 0.0447 (16) | 0.0203 (13) | −0.0022 (12) | 0.0046 (11) | −0.0057 (11) |
O2BA | 0.020 (3) | 0.021 (3) | 0.045 (5) | −0.0002 (19) | 0.023 (4) | 0.003 (3) |
O3BA | 0.017 (3) | 0.030 (4) | 0.029 (4) | 0.003 (2) | 0.008 (3) | −0.008 (2) |
O4BA | 0.030 (4) | 0.024 (3) | 0.032 (4) | 0.008 (3) | 0.015 (3) | 0.011 (3) |
O2BB | 0.045 (11) | 0.083 (12) | 0.07 (2) | 0.019 (9) | 0.044 (13) | 0.035 (12) |
O3BB | 0.046 (11) | 0.085 (19) | 0.10 (2) | 0.003 (12) | 0.046 (14) | −0.037 (16) |
O4BB | 0.087 (18) | 0.061 (13) | 0.093 (13) | 0.054 (12) | 0.055 (12) | 0.058 (10) |
N1B | 0.0349 (17) | 0.0407 (19) | 0.0369 (18) | 0.0053 (14) | 0.0261 (15) | 0.0052 (14) |
C1B | 0.042 (2) | 0.042 (2) | 0.053 (3) | 0.0030 (19) | 0.035 (2) | −0.001 (2) |
C2B | 0.058 (3) | 0.046 (3) | 0.064 (3) | −0.004 (2) | 0.045 (3) | −0.004 (2) |
C3B | 0.047 (3) | 0.075 (3) | 0.049 (3) | −0.018 (2) | 0.036 (2) | −0.015 (2) |
C4B | 0.041 (2) | 0.064 (3) | 0.036 (2) | −0.001 (2) | 0.029 (2) | 0.002 (2) |
C5B | 0.035 (2) | 0.050 (2) | 0.032 (2) | 0.0050 (18) | 0.0240 (18) | 0.0044 (18) |
C6B | 0.035 (2) | 0.053 (3) | 0.0272 (19) | 0.0084 (19) | 0.0181 (17) | 0.0057 (18) |
C7B | 0.034 (2) | 0.055 (3) | 0.027 (2) | 0.0026 (19) | 0.0185 (18) | 0.0020 (18) |
C8B | 0.032 (2) | 0.046 (2) | 0.0216 (17) | 0.0059 (17) | 0.0152 (16) | 0.0055 (16) |
C9B | 0.0275 (19) | 0.056 (3) | 0.0180 (17) | 0.0104 (18) | 0.0106 (15) | 0.0083 (16) |
C10B | 0.0215 (18) | 0.057 (3) | 0.0171 (17) | 0.0009 (17) | 0.0059 (15) | −0.0037 (16) |
C11B | 0.0242 (18) | 0.048 (2) | 0.0166 (16) | 0.0014 (16) | 0.0098 (15) | −0.0037 (15) |
C12B | 0.0236 (17) | 0.044 (2) | 0.0146 (16) | 0.0030 (16) | 0.0072 (14) | −0.0004 (15) |
C13B | 0.0227 (17) | 0.047 (2) | 0.0174 (16) | 0.0001 (16) | 0.0098 (15) | −0.0009 (15) |
C14B | 0.034 (2) | 0.039 (2) | 0.0249 (18) | −0.0006 (17) | 0.0120 (16) | −0.0054 (16) |
C15B | 0.038 (2) | 0.042 (2) | 0.037 (2) | 0.0047 (18) | 0.0227 (19) | 0.0059 (18) |
C16B | 0.0160 (15) | 0.0217 (16) | 0.0192 (15) | 0.0000 (12) | 0.0039 (13) | 0.0055 (13) |
C17B | 0.0227 (17) | 0.0263 (18) | 0.0173 (15) | −0.0074 (14) | 0.0046 (13) | 0.0044 (13) |
C18B | 0.0309 (18) | 0.0170 (16) | 0.0171 (15) | −0.0056 (14) | 0.0073 (14) | −0.0004 (12) |
C19B | 0.0264 (17) | 0.0218 (16) | 0.0167 (15) | 0.0018 (13) | 0.0079 (14) | 0.0001 (13) |
C20B | 0.0210 (16) | 0.0194 (16) | 0.0204 (16) | −0.0023 (13) | 0.0073 (14) | 0.0012 (13) |
C21B | 0.0194 (16) | 0.0172 (16) | 0.0216 (16) | −0.0039 (12) | 0.0068 (13) | 0.0008 (12) |
S1A—O3A | 1.440 (3) | S1B—O2BA | 1.425 (10) |
S1A—O4A | 1.444 (3) | S1B—O3BA | 1.462 (11) |
S1A—O2A | 1.452 (3) | S1B—O4BA | 1.465 (12) |
S1A—C16A | 1.775 (3) | S1B—O2BB | 1.53 (2) |
Cl1A—C19A | 1.744 (3) | S1B—C16B | 1.782 (3) |
O1A—C11A | 1.361 (5) | Cl1B—C19B | 1.742 (3) |
O1A—C14A | 1.433 (5) | O1B—C11B | 1.361 (5) |
N1A—C1A | 1.366 (5) | O1B—C14B | 1.432 (5) |
N1A—C5A | 1.368 (5) | N1B—C1B | 1.353 (5) |
N1A—C15A | 1.469 (5) | N1B—C5B | 1.364 (5) |
C1A—C2A | 1.363 (6) | N1B—C15B | 1.479 (5) |
C1A—H1A | 0.9300 | C1B—C2B | 1.357 (6) |
C2A—C3A | 1.378 (7) | C1B—H1B | 0.9300 |
C2A—H2A | 0.9300 | C2B—C3B | 1.381 (7) |
C3A—C4A | 1.366 (6) | C2B—H2B | 0.9300 |
C3A—H3A | 0.9300 | C3B—C4B | 1.379 (7) |
C4A—C5A | 1.398 (6) | C3B—H3B | 0.9300 |
C4A—H4A | 0.9300 | C4B—C5B | 1.397 (6) |
C5A—C6A | 1.433 (6) | C4B—H4B | 0.9300 |
C6A—C7A | 1.344 (6) | C5B—C6B | 1.449 (6) |
C6A—H6A | 0.9300 | C6B—C7B | 1.343 (6) |
C7A—C8A | 1.464 (6) | C6B—H6B | 0.9300 |
C7A—H7A | 0.9300 | C7B—C8B | 1.457 (6) |
C8A—C13A | 1.398 (5) | C7B—H7B | 0.9300 |
C8A—C9A | 1.406 (5) | C8B—C13B | 1.401 (5) |
C9A—C10A | 1.369 (6) | C8B—C9B | 1.403 (5) |
C9A—H9A | 0.9300 | C9B—C10B | 1.368 (6) |
C10A—C11A | 1.392 (5) | C9B—H9B | 0.9300 |
C10A—H10A | 0.9301 | C10B—C11B | 1.386 (5) |
C11A—C12A | 1.392 (5) | C10B—H10B | 0.9300 |
C12A—C13A | 1.383 (5) | C11B—C12B | 1.393 (5) |
C12A—H12A | 0.9299 | C12B—C13B | 1.386 (5) |
C13A—H13A | 0.9299 | C12B—H12B | 0.9302 |
C14A—H14A | 0.9600 | C13B—H13B | 0.9301 |
C14A—H14B | 0.9600 | C14B—H14D | 0.9600 |
C14A—H14C | 0.9600 | C14B—H14E | 0.9600 |
C15A—H15A | 0.9600 | C14B—H14F | 0.9600 |
C15A—H15B | 0.9600 | C15B—H15D | 0.9600 |
C15A—H15C | 0.9600 | C15B—H15E | 0.9600 |
C16A—C17A | 1.390 (4) | C15B—H15F | 0.9600 |
C16A—C21A | 1.395 (4) | C16B—C21B | 1.386 (5) |
C17A—C18A | 1.375 (5) | C16B—C17B | 1.389 (5) |
C17A—H17A | 0.9299 | C17B—C18B | 1.389 (5) |
C18A—C19A | 1.378 (5) | C17B—H17B | 0.9302 |
C18A—H18A | 0.9301 | C18B—C19B | 1.374 (5) |
C19A—C20A | 1.391 (5) | C18B—H18B | 0.9300 |
C20A—C21A | 1.383 (5) | C19B—C20B | 1.395 (5) |
C20A—H20A | 0.9300 | C20B—C21B | 1.389 (5) |
C21A—H21A | 0.9301 | C20B—H20B | 0.9301 |
S1B—O4BB | 1.38 (3) | C21B—H21B | 0.9298 |
S1B—O3BB | 1.39 (3) | ||
O3A—S1A—O4A | 112.6 (2) | O2BA—S1B—O4BA | 114.6 (6) |
O3A—S1A—O2A | 112.83 (19) | O3BA—S1B—O4BA | 114.1 (5) |
O4A—S1A—O2A | 113.1 (2) | O4BB—S1B—O2BB | 111.7 (16) |
O3A—S1A—C16A | 105.92 (15) | O3BB—S1B—O2BB | 105.5 (14) |
O4A—S1A—C16A | 105.44 (16) | O3BA—S1B—O2BB | 94 (2) |
O2A—S1A—C16A | 106.16 (16) | O4BA—S1B—O2BB | 128.3 (12) |
C11A—O1A—C14A | 117.8 (3) | O4BB—S1B—C16B | 110.4 (13) |
C1A—N1A—C5A | 120.8 (4) | O3BB—S1B—C16B | 111.3 (14) |
C1A—N1A—C15A | 118.2 (3) | O2BA—S1B—C16B | 103.8 (4) |
C5A—N1A—C15A | 121.0 (3) | O3BA—S1B—C16B | 103.3 (5) |
C2A—C1A—N1A | 121.1 (4) | O4BA—S1B—C16B | 104.0 (5) |
C2A—C1A—H1A | 119.5 | O2BB—S1B—C16B | 111.0 (14) |
N1A—C1A—H1A | 119.5 | C11B—O1B—C14B | 118.8 (3) |
C1A—C2A—C3A | 119.6 (4) | C1B—N1B—C5B | 121.5 (4) |
C1A—C2A—H2A | 120.2 | C1B—N1B—C15B | 117.2 (3) |
C3A—C2A—H2A | 120.2 | C5B—N1B—C15B | 121.2 (3) |
C4A—C3A—C2A | 119.2 (4) | N1B—C1B—C2B | 121.4 (4) |
C4A—C3A—H3A | 120.4 | N1B—C1B—H1B | 119.3 |
C2A—C3A—H3A | 120.4 | C2B—C1B—H1B | 119.3 |
C3A—C4A—C5A | 121.6 (4) | C1B—C2B—C3B | 119.2 (5) |
C3A—C4A—H4A | 119.2 | C1B—C2B—H2B | 120.4 |
C5A—C4A—H4A | 119.2 | C3B—C2B—H2B | 120.4 |
N1A—C5A—C4A | 117.7 (4) | C4B—C3B—C2B | 119.4 (5) |
N1A—C5A—C6A | 116.9 (4) | C4B—C3B—H3B | 120.3 |
C4A—C5A—C6A | 125.3 (4) | C2B—C3B—H3B | 120.3 |
C7A—C6A—C5A | 122.9 (4) | C3B—C4B—C5B | 120.8 (4) |
C7A—C6A—H6A | 118.6 | C3B—C4B—H4B | 119.6 |
C5A—C6A—H6A | 118.6 | C5B—C4B—H4B | 119.6 |
C6A—C7A—C8A | 125.4 (4) | N1B—C5B—C4B | 117.7 (4) |
C6A—C7A—H7A | 117.3 | N1B—C5B—C6B | 117.9 (4) |
C8A—C7A—H7A | 117.3 | C4B—C5B—C6B | 124.4 (4) |
C13A—C8A—C9A | 116.9 (4) | C7B—C6B—C5B | 123.5 (4) |
C13A—C8A—C7A | 120.1 (3) | C7B—C6B—H6B | 118.3 |
C9A—C8A—C7A | 122.9 (3) | C5B—C6B—H6B | 118.3 |
C10A—C9A—C8A | 121.4 (3) | C6B—C7B—C8B | 126.0 (4) |
C10A—C9A—H9A | 119.3 | C6B—C7B—H7B | 117.0 |
C8A—C9A—H9A | 119.3 | C8B—C7B—H7B | 117.0 |
C9A—C10A—C11A | 120.2 (3) | C13B—C8B—C9B | 117.3 (4) |
C9A—C10A—H10A | 119.9 | C13B—C8B—C7B | 119.5 (4) |
C11A—C10A—H10A | 119.9 | C9B—C8B—C7B | 123.2 (4) |
O1A—C11A—C10A | 115.8 (3) | C10B—C9B—C8B | 121.4 (4) |
O1A—C11A—C12A | 124.0 (3) | C10B—C9B—H9B | 119.3 |
C10A—C11A—C12A | 120.2 (3) | C8B—C9B—H9B | 119.3 |
C13A—C12A—C11A | 118.6 (3) | C9B—C10B—C11B | 120.3 (4) |
C13A—C12A—H12A | 120.7 | C9B—C10B—H10B | 119.8 |
C11A—C12A—H12A | 120.6 | C11B—C10B—H10B | 119.8 |
C12A—C13A—C8A | 122.6 (3) | O1B—C11B—C10B | 115.6 (3) |
C12A—C13A—H13A | 118.7 | O1B—C11B—C12B | 124.2 (3) |
C8A—C13A—H13A | 118.7 | C10B—C11B—C12B | 120.2 (4) |
O1A—C14A—H14A | 109.5 | C13B—C12B—C11B | 118.8 (3) |
O1A—C14A—H14B | 109.5 | C13B—C12B—H12B | 120.6 |
H14A—C14A—H14B | 109.5 | C11B—C12B—H12B | 120.6 |
O1A—C14A—H14C | 109.5 | C12B—C13B—C8B | 121.9 (3) |
H14A—C14A—H14C | 109.5 | C12B—C13B—H13B | 119.1 |
H14B—C14A—H14C | 109.5 | C8B—C13B—H13B | 119.0 |
N1A—C15A—H15A | 109.5 | O1B—C14B—H14D | 109.5 |
N1A—C15A—H15B | 109.5 | O1B—C14B—H14E | 109.5 |
H15A—C15A—H15B | 109.5 | H14D—C14B—H14E | 109.5 |
N1A—C15A—H15C | 109.5 | O1B—C14B—H14F | 109.5 |
H15A—C15A—H15C | 109.5 | H14D—C14B—H14F | 109.5 |
H15B—C15A—H15C | 109.5 | H14E—C14B—H14F | 109.5 |
C17A—C16A—C21A | 119.8 (3) | N1B—C15B—H15D | 109.5 |
C17A—C16A—S1A | 120.6 (3) | N1B—C15B—H15E | 109.5 |
C21A—C16A—S1A | 119.6 (2) | H15D—C15B—H15E | 109.5 |
C18A—C17A—C16A | 120.7 (3) | N1B—C15B—H15F | 109.5 |
C18A—C17A—H17A | 119.8 | H15D—C15B—H15F | 109.5 |
C16A—C17A—H17A | 119.5 | H15E—C15B—H15F | 109.5 |
C17A—C18A—C19A | 118.4 (3) | C21B—C16B—C17B | 119.9 (3) |
C17A—C18A—H18A | 120.7 | C21B—C16B—S1B | 118.8 (2) |
C19A—C18A—H18A | 120.9 | C17B—C16B—S1B | 121.3 (3) |
C18A—C19A—C20A | 122.7 (3) | C16B—C17B—C18B | 120.0 (3) |
C18A—C19A—Cl1A | 119.4 (3) | C16B—C17B—H17B | 120.0 |
C20A—C19A—Cl1A | 117.9 (3) | C18B—C17B—H17B | 120.0 |
C21A—C20A—C19A | 118.0 (3) | C19B—C18B—C17B | 119.4 (3) |
C21A—C20A—H20A | 121.1 | C19B—C18B—H18B | 120.3 |
C19A—C20A—H20A | 120.9 | C17B—C18B—H18B | 120.2 |
C20A—C21A—C16A | 120.4 (3) | C18B—C19B—C20B | 121.6 (3) |
C20A—C21A—H21A | 119.9 | C18B—C19B—Cl1B | 119.6 (3) |
C16A—C21A—H21A | 119.8 | C20B—C19B—Cl1B | 118.8 (3) |
O4BB—S1B—O3BB | 106.7 (18) | C21B—C20B—C19B | 118.3 (3) |
O4BB—S1B—O2BA | 97 (2) | C21B—C20B—H20B | 120.8 |
O3BB—S1B—O2BA | 126.0 (17) | C19B—C20B—H20B | 120.8 |
O4BB—S1B—O3BA | 125.5 (18) | C16B—C21B—C20B | 120.7 (3) |
O2BA—S1B—O3BA | 114.9 (8) | C16B—C21B—H21B | 119.7 |
O3BB—S1B—O4BA | 95 (3) | C20B—C21B—H21B | 119.6 |
C5A—N1A—C1A—C2A | −0.5 (6) | C1B—C2B—C3B—C4B | 0.5 (6) |
C15A—N1A—C1A—C2A | −179.7 (4) | C2B—C3B—C4B—C5B | 0.7 (6) |
N1A—C1A—C2A—C3A | −0.5 (6) | C1B—N1B—C5B—C4B | 1.2 (5) |
C1A—C2A—C3A—C4A | 0.2 (6) | C15B—N1B—C5B—C4B | −179.5 (3) |
C2A—C3A—C4A—C5A | 1.2 (6) | C1B—N1B—C5B—C6B | −177.6 (3) |
C1A—N1A—C5A—C4A | 1.8 (5) | C15B—N1B—C5B—C6B | 1.7 (5) |
C15A—N1A—C5A—C4A | −179.0 (3) | C3B—C4B—C5B—N1B | −1.5 (6) |
C1A—N1A—C5A—C6A | −175.8 (3) | C3B—C4B—C5B—C6B | 177.3 (4) |
C15A—N1A—C5A—C6A | 3.3 (5) | N1B—C5B—C6B—C7B | 168.8 (4) |
C3A—C4A—C5A—N1A | −2.1 (6) | C4B—C5B—C6B—C7B | −10.0 (6) |
C3A—C4A—C5A—C6A | 175.3 (4) | C5B—C6B—C7B—C8B | 179.3 (4) |
N1A—C5A—C6A—C7A | 167.7 (4) | C6B—C7B—C8B—C13B | −168.4 (4) |
C4A—C5A—C6A—C7A | −9.8 (6) | C6B—C7B—C8B—C9B | 12.3 (6) |
C5A—C6A—C7A—C8A | 179.7 (4) | C13B—C8B—C9B—C10B | 0.1 (5) |
C6A—C7A—C8A—C13A | −169.0 (4) | C7B—C8B—C9B—C10B | 179.4 (4) |
C6A—C7A—C8A—C9A | 13.3 (6) | C8B—C9B—C10B—C11B | 0.1 (6) |
C13A—C8A—C9A—C10A | −0.5 (5) | C14B—O1B—C11B—C10B | 174.1 (3) |
C7A—C8A—C9A—C10A | 177.3 (4) | C14B—O1B—C11B—C12B | −6.6 (5) |
C8A—C9A—C10A—C11A | 0.5 (6) | C9B—C10B—C11B—O1B | 179.3 (3) |
C14A—O1A—C11A—C10A | 170.1 (3) | C9B—C10B—C11B—C12B | −0.1 (5) |
C14A—O1A—C11A—C12A | −10.1 (5) | O1B—C11B—C12B—C13B | −179.3 (3) |
C9A—C10A—C11A—O1A | 179.8 (3) | C10B—C11B—C12B—C13B | 0.0 (5) |
C9A—C10A—C11A—C12A | 0.0 (5) | C11B—C12B—C13B—C8B | 0.2 (5) |
O1A—C11A—C12A—C13A | 179.7 (3) | C9B—C8B—C13B—C12B | −0.2 (5) |
C10A—C11A—C12A—C13A | −0.5 (5) | C7B—C8B—C13B—C12B | −179.6 (3) |
C11A—C12A—C13A—C8A | 0.6 (5) | O4BB—S1B—C16B—C21B | 79 (3) |
C9A—C8A—C13A—C12A | −0.1 (5) | O3BB—S1B—C16B—C21B | −40 (3) |
C7A—C8A—C13A—C12A | −177.9 (3) | O2BA—S1B—C16B—C21B | −178.1 (8) |
O3A—S1A—C16A—C17A | −150.6 (3) | O3BA—S1B—C16B—C21B | −57.8 (5) |
O4A—S1A—C16A—C17A | 89.8 (3) | O4BA—S1B—C16B—C21B | 61.7 (5) |
O2A—S1A—C16A—C17A | −30.4 (3) | O2BB—S1B—C16B—C21B | −157 (3) |
O3A—S1A—C16A—C21A | 29.4 (3) | O4BB—S1B—C16B—C17B | −103 (3) |
O4A—S1A—C16A—C21A | −90.1 (3) | O3BB—S1B—C16B—C17B | 139 (3) |
O2A—S1A—C16A—C21A | 149.6 (3) | O2BA—S1B—C16B—C17B | 0.5 (8) |
C21A—C16A—C17A—C18A | −1.7 (5) | O3BA—S1B—C16B—C17B | 120.7 (5) |
S1A—C16A—C17A—C18A | 178.3 (2) | O4BA—S1B—C16B—C17B | −119.8 (5) |
C16A—C17A—C18A—C19A | −0.3 (5) | O2BB—S1B—C16B—C17B | 22 (3) |
C17A—C18A—C19A—C20A | 2.1 (5) | C21B—C16B—C17B—C18B | 1.3 (5) |
C17A—C18A—C19A—Cl1A | −176.5 (2) | S1B—C16B—C17B—C18B | −177.2 (2) |
C18A—C19A—C20A—C21A | −1.7 (5) | C16B—C17B—C18B—C19B | 1.1 (5) |
Cl1A—C19A—C20A—C21A | 176.9 (2) | C17B—C18B—C19B—C20B | −3.0 (5) |
C19A—C20A—C21A—C16A | −0.4 (4) | C17B—C18B—C19B—Cl1B | 176.1 (2) |
C17A—C16A—C21A—C20A | 2.1 (5) | C18B—C19B—C20B—C21B | 2.5 (5) |
S1A—C16A—C21A—C20A | −177.9 (2) | Cl1B—C19B—C20B—C21B | −176.7 (2) |
C5B—N1B—C1B—C2B | −0.1 (6) | C17B—C16B—C21B—C20B | −1.9 (5) |
C15B—N1B—C1B—C2B | −179.4 (4) | S1B—C16B—C21B—C20B | 176.7 (2) |
N1B—C1B—C2B—C3B | −0.7 (6) | C19B—C20B—C21B—C16B | 0.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H1A···O2Ai | 0.93 | 2.34 | 3.203 (5) | 155 |
C3A—H3A···O3Aii | 0.93 | 2.56 | 3.420 (6) | 154 |
C6A—H6A···O4BAiii | 0.93 | 2.59 | 3.343 (12) | 139 |
C7B—H7B···O4Aii | 0.93 | 2.44 | 3.244 (6) | 145 |
C15A—H15B···O2Ai | 0.96 | 2.47 | 3.368 (5) | 155 |
C15A—H15C···O4BAiii | 0.96 | 2.29 | 3.194 (13) | 156 |
C15B—H15E···O4A | 0.96 | 2.54 | 3.456 (6) | 159 |
C17B—H17B···O2BA | 0.93 | 2.48 | 2.850 (15) | 104 |
C20A—H20A···O2BAiv | 0.93 | 2.33 | 3.207 (17) | 158 |
C20B—H20B···O2Av | 0.93 | 2.53 | 3.282 (6) | 138 |
C9A—H9A···Cg5iii | 0.93 | 3.36 | 3.857 (4) | 116 |
C9B—H9B···Cg4 | 0.93 | 3.15 | 3.706 (4) | 120 |
C10A—H10A···Cg5iii | 0.93 | 2.97 | 3.652 (4) | 131 |
C10B—H10B···Cg1iv | 0.93 | 3.32 | 3.628 (6) | 102 |
C10B—H10B···Cg4 | 0.93 | 3.14 | 3.695 (4) | 121 |
C12A—H12A···Cg4vi | 0.93 | 2.68 | 3.475 (4) | 144 |
C12B—H12B···Cg5 | 0.93 | 2.69 | 3.470 (4) | 142 |
C15A—H15A···Cg3vii | 0.96 | 2.67 | 3.449 (5) | 138 |
C15B—H15F···Cg2iv | 0.96 | 2.78 | 3.532 (5) | 136 |
Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z; (iv) x+1, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) −x+1, −y+2, −z+1; (vii) x−1, −y+3/2, z−1/2. |
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