Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028885/ac6076sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028885/ac6076Isup2.hkl |
CCDC reference: 232169
Key indicators
- Single-crystal X-ray study
- T = 173 K
- R factor = 0.040
- wR factor = 0.102
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.00 Deg.
Alert level B PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.89 PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1997-1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
C19H24BNO4S | Z = 2 |
Mr = 373.26 | F(000) = 396 |
Triclinic, P1 | Dx = 1.293 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.699 (1) Å | Cell parameters from 3627 reflections |
b = 9.4253 (15) Å | θ = 2.4–25.2° |
c = 16.492 (3) Å | µ = 0.19 mm−1 |
α = 106.227 (2)° | T = 173 K |
β = 91.189 (2)° | Cube, colourless |
γ = 105.430 (2)° | 0.45 × 0.4 × 0.4 mm |
V = 958.7 (3) Å3 |
Bruker P4/SMART 1000 diffractometer | 2829 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ω scans | h = −7→7 |
4525 measured reflections | k = −11→10 |
2986 independent reflections | l = −19→19 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0406P)2 + 0.7629P] where P = (Fo2 + 2Fc2)/3 |
2986 reflections | (Δ/σ)max < 0.001 |
240 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. |
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 | ||
B | 0.2511 (4) | 0.2667 (3) | 0.01965 (14) | 0.0292 (5) | |
O1 | 0.0441 (2) | 0.24174 (17) | −0.00330 (8) | 0.0353 (3) | |
C2 | 0.0176 (3) | 0.2152 (2) | −0.09532 (12) | 0.0308 (4) | |
C3 | 0.2209 (3) | 0.1712 (2) | −0.12469 (12) | 0.0295 (4) | |
O4 | 0.3666 (2) | 0.24213 (17) | −0.04729 (8) | 0.0339 (3) | |
C5 | −0.1838 (3) | 0.0896 (3) | −0.13119 (16) | 0.0469 (6) | |
H5A | −0.1827 | −0.0018 | −0.1141 | 0.070* | |
H5B | −0.1973 | 0.0631 | −0.1933 | 0.070* | |
H5C | −0.3017 | 0.1263 | −0.1094 | 0.070* | |
C6 | 0.0036 (4) | 0.3658 (3) | −0.10864 (15) | 0.0454 (6) | |
H6A | −0.1137 | 0.3948 | −0.0809 | 0.068* | |
H6B | −0.0176 | 0.3527 | −0.1696 | 0.068* | |
H6C | 0.1330 | 0.4469 | −0.0840 | 0.068* | |
C7 | 0.1967 (4) | −0.0012 (3) | −0.14860 (15) | 0.0422 (5) | |
H7A | 0.3336 | −0.0192 | −0.1556 | 0.063* | |
H7B | 0.1063 | −0.0532 | −0.2020 | 0.063* | |
H7C | 0.1345 | −0.0421 | −0.1036 | 0.063* | |
C8 | 0.3182 (4) | 0.2370 (3) | −0.19373 (14) | 0.0407 (5) | |
H8A | 0.3491 | 0.3495 | −0.1745 | 0.061* | |
H8B | 0.2209 | 0.1953 | −0.2455 | 0.061* | |
H8C | 0.4474 | 0.2086 | −0.2056 | 0.061* | |
C9 | 0.3418 (3) | 0.3161 (2) | 0.11451 (12) | 0.0284 (4) | |
C10 | 0.2229 (3) | 0.3655 (2) | 0.17991 (12) | 0.0301 (4) | |
H10 | 0.0890 | 0.3735 | 0.1657 | 0.036* | |
C11 | 0.2958 (3) | 0.4030 (2) | 0.26483 (12) | 0.0300 (4) | |
H11 | 0.2115 | 0.4343 | 0.3081 | 0.036* | |
C12 | 0.4940 (3) | 0.3943 (2) | 0.28613 (12) | 0.0266 (4) | |
C13 | 0.6161 (3) | 0.3459 (2) | 0.22247 (12) | 0.0292 (4) | |
H13 | 0.7510 | 0.3399 | 0.2369 | 0.035* | |
C14 | 0.5392 (3) | 0.3067 (2) | 0.13781 (12) | 0.0297 (4) | |
H14 | 0.6224 | 0.2727 | 0.0947 | 0.036* | |
N | 0.5682 (3) | 0.44014 (18) | 0.37433 (10) | 0.0288 (4) | |
H0 | 0.5631 | 0.5308 | 0.4064 | 0.035* | |
S | 0.66164 (7) | 0.33328 (6) | 0.41843 (3) | 0.02776 (16) | |
O5 | 0.8379 (2) | 0.29993 (17) | 0.37809 (9) | 0.0353 (3) | |
O6 | 0.6892 (2) | 0.41461 (17) | 0.50803 (8) | 0.0351 (3) | |
C15 | 0.4642 (3) | 0.1568 (2) | 0.40130 (12) | 0.0277 (4) | |
C16 | 0.2619 (3) | 0.1591 (2) | 0.41651 (14) | 0.0355 (5) | |
H16 | 0.2261 | 0.2535 | 0.4316 | 0.043* | |
C17 | 0.1134 (3) | 0.0212 (3) | 0.40925 (14) | 0.0382 (5) | |
H17 | −0.0255 | 0.0222 | 0.4192 | 0.046* | |
C18 | 0.1607 (3) | −0.1191 (2) | 0.38780 (12) | 0.0336 (5) | |
C19 | 0.3643 (4) | −0.1174 (3) | 0.37149 (14) | 0.0394 (5) | |
H19 | 0.4004 | −0.2116 | 0.3559 | 0.047* | |
C20 | 0.5152 (3) | 0.0194 (2) | 0.37757 (13) | 0.0354 (5) | |
H20 | 0.6530 | 0.0185 | 0.3655 | 0.043* | |
C21 | −0.0020 (4) | −0.2681 (3) | 0.38253 (15) | 0.0437 (6) | |
H21A | −0.1365 | −0.2478 | 0.3934 | 0.066* | |
H21B | 0.0388 | −0.3127 | 0.4250 | 0.066* | |
H21C | −0.0138 | −0.3405 | 0.3257 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
B | 0.0327 (12) | 0.0245 (11) | 0.0319 (12) | 0.0078 (9) | 0.0033 (9) | 0.0107 (9) |
O1 | 0.0334 (8) | 0.0480 (9) | 0.0276 (7) | 0.0150 (7) | 0.0034 (6) | 0.0128 (6) |
C2 | 0.0343 (11) | 0.0347 (11) | 0.0250 (10) | 0.0124 (9) | 0.0000 (8) | 0.0091 (8) |
C3 | 0.0324 (11) | 0.0289 (10) | 0.0246 (10) | 0.0077 (8) | −0.0030 (8) | 0.0053 (8) |
O4 | 0.0307 (7) | 0.0432 (8) | 0.0250 (7) | 0.0099 (6) | −0.0007 (6) | 0.0065 (6) |
C5 | 0.0331 (12) | 0.0518 (14) | 0.0515 (14) | 0.0114 (11) | −0.0029 (10) | 0.0095 (12) |
C6 | 0.0628 (16) | 0.0465 (14) | 0.0399 (13) | 0.0313 (12) | 0.0106 (11) | 0.0175 (11) |
C7 | 0.0401 (12) | 0.0324 (12) | 0.0513 (14) | 0.0125 (10) | 0.0013 (10) | 0.0060 (10) |
C8 | 0.0451 (13) | 0.0464 (13) | 0.0328 (11) | 0.0147 (11) | 0.0070 (10) | 0.0135 (10) |
C9 | 0.0320 (10) | 0.0240 (10) | 0.0296 (10) | 0.0064 (8) | 0.0033 (8) | 0.0098 (8) |
C10 | 0.0295 (10) | 0.0311 (11) | 0.0317 (11) | 0.0099 (8) | 0.0019 (8) | 0.0113 (9) |
C11 | 0.0313 (10) | 0.0318 (11) | 0.0290 (10) | 0.0109 (8) | 0.0073 (8) | 0.0103 (8) |
C12 | 0.0299 (10) | 0.0225 (9) | 0.0264 (10) | 0.0042 (8) | 0.0028 (8) | 0.0085 (8) |
C13 | 0.0266 (10) | 0.0300 (10) | 0.0310 (10) | 0.0070 (8) | 0.0021 (8) | 0.0098 (8) |
C14 | 0.0336 (11) | 0.0278 (10) | 0.0280 (10) | 0.0079 (8) | 0.0066 (8) | 0.0091 (8) |
N | 0.0350 (9) | 0.0234 (8) | 0.0241 (8) | 0.0065 (7) | 0.0002 (7) | 0.0027 (7) |
S | 0.0258 (3) | 0.0315 (3) | 0.0239 (3) | 0.0076 (2) | −0.00044 (19) | 0.0057 (2) |
O5 | 0.0271 (7) | 0.0414 (8) | 0.0356 (8) | 0.0094 (6) | 0.0024 (6) | 0.0089 (6) |
O6 | 0.0344 (8) | 0.0410 (8) | 0.0270 (7) | 0.0115 (6) | −0.0038 (6) | 0.0053 (6) |
C15 | 0.0294 (10) | 0.0323 (11) | 0.0225 (9) | 0.0099 (8) | 0.0008 (8) | 0.0090 (8) |
C16 | 0.0329 (11) | 0.0340 (11) | 0.0437 (12) | 0.0133 (9) | 0.0055 (9) | 0.0145 (9) |
C17 | 0.0280 (11) | 0.0426 (13) | 0.0483 (13) | 0.0102 (9) | 0.0044 (9) | 0.0200 (10) |
C18 | 0.0373 (11) | 0.0353 (11) | 0.0272 (10) | 0.0062 (9) | −0.0026 (8) | 0.0121 (9) |
C19 | 0.0455 (13) | 0.0331 (12) | 0.0415 (13) | 0.0157 (10) | 0.0045 (10) | 0.0094 (10) |
C20 | 0.0315 (11) | 0.0358 (12) | 0.0400 (12) | 0.0130 (9) | 0.0050 (9) | 0.0093 (9) |
C21 | 0.0450 (13) | 0.0408 (13) | 0.0431 (13) | 0.0036 (10) | −0.0030 (10) | 0.0177 (10) |
B—O4 | 1.364 (3) | C11—C12 | 1.396 (3) |
B—O1 | 1.370 (3) | C11—H11 | 0.9500 |
B—C9 | 1.561 (3) | C12—C13 | 1.395 (3) |
O1—C2 | 1.466 (2) | C12—N | 1.433 (2) |
C2—C5 | 1.516 (3) | C13—C14 | 1.390 (3) |
C2—C6 | 1.522 (3) | C13—H13 | 0.9500 |
C2—C3 | 1.574 (3) | C14—H14 | 0.9500 |
C3—O4 | 1.467 (2) | N—S | 1.6311 (17) |
C3—C8 | 1.522 (3) | N—H0 | 0.8800 |
C3—C7 | 1.523 (3) | S—O5 | 1.4316 (15) |
C5—H5A | 0.9800 | S—O6 | 1.4441 (14) |
C5—H5B | 0.9800 | S—C15 | 1.774 (2) |
C5—H5C | 0.9800 | C15—C20 | 1.380 (3) |
C6—H6A | 0.9800 | C15—C16 | 1.388 (3) |
C6—H6B | 0.9800 | C16—C17 | 1.383 (3) |
C6—H6C | 0.9800 | C16—H16 | 0.9500 |
C7—H7A | 0.9800 | C17—C18 | 1.393 (3) |
C7—H7B | 0.9800 | C17—H17 | 0.9500 |
C7—H7C | 0.9800 | C18—C19 | 1.392 (3) |
C8—H8A | 0.9800 | C18—C21 | 1.510 (3) |
C8—H8B | 0.9800 | C19—C20 | 1.388 (3) |
C8—H8C | 0.9800 | C19—H19 | 0.9500 |
C9—C14 | 1.402 (3) | C20—H20 | 0.9500 |
C9—C10 | 1.402 (3) | C21—H21A | 0.9800 |
C10—C11 | 1.388 (3) | C21—H21B | 0.9800 |
C10—H10 | 0.9500 | C21—H21C | 0.9800 |
O4—B—O1 | 114.03 (18) | C9—C10—H10 | 119.1 |
O4—B—C9 | 123.96 (19) | C10—C11—C12 | 119.44 (18) |
O1—B—C9 | 122.00 (18) | C10—C11—H11 | 120.3 |
B—O1—C2 | 107.52 (15) | C12—C11—H11 | 120.3 |
O1—C2—C5 | 108.35 (17) | C13—C12—C11 | 120.13 (18) |
O1—C2—C6 | 106.62 (16) | C13—C12—N | 121.79 (17) |
C5—C2—C6 | 110.00 (19) | C11—C12—N | 118.06 (17) |
O1—C2—C3 | 102.52 (14) | C14—C13—C12 | 119.58 (18) |
C5—C2—C3 | 114.94 (17) | C14—C13—H13 | 120.2 |
C6—C2—C3 | 113.70 (17) | C12—C13—H13 | 120.2 |
O4—C3—C8 | 107.77 (16) | C13—C14—C9 | 121.56 (18) |
O4—C3—C7 | 106.41 (16) | C13—C14—H14 | 119.2 |
C8—C3—C7 | 110.26 (18) | C9—C14—H14 | 119.2 |
O4—C3—C2 | 102.79 (14) | C12—N—S | 123.50 (13) |
C8—C3—C2 | 115.22 (17) | C12—N—H0 | 118.3 |
C7—C3—C2 | 113.57 (17) | S—N—H0 | 118.3 |
B—O4—C3 | 107.32 (15) | O5—S—O6 | 118.71 (8) |
C2—C5—H5A | 109.5 | O5—S—N | 110.24 (9) |
C2—C5—H5B | 109.5 | O6—S—N | 104.20 (8) |
H5A—C5—H5B | 109.5 | O5—S—C15 | 108.00 (9) |
C2—C5—H5C | 109.5 | O6—S—C15 | 108.10 (9) |
H5A—C5—H5C | 109.5 | N—S—C15 | 107.02 (9) |
H5B—C5—H5C | 109.5 | C20—C15—C16 | 120.69 (19) |
C2—C6—H6A | 109.5 | C20—C15—S | 119.75 (16) |
C2—C6—H6B | 109.5 | C16—C15—S | 119.46 (15) |
H6A—C6—H6B | 109.5 | C17—C16—C15 | 118.66 (19) |
C2—C6—H6C | 109.5 | C17—C16—H16 | 120.7 |
H6A—C6—H6C | 109.5 | C15—C16—H16 | 120.7 |
H6B—C6—H6C | 109.5 | C16—C17—C18 | 122.2 (2) |
C3—C7—H7A | 109.5 | C16—C17—H17 | 118.9 |
C3—C7—H7B | 109.5 | C18—C17—H17 | 118.9 |
H7A—C7—H7B | 109.5 | C19—C18—C17 | 117.61 (19) |
C3—C7—H7C | 109.5 | C19—C18—C21 | 120.9 (2) |
H7A—C7—H7C | 109.5 | C17—C18—C21 | 121.5 (2) |
H7B—C7—H7C | 109.5 | C20—C19—C18 | 121.2 (2) |
C3—C8—H8A | 109.5 | C20—C19—H19 | 119.4 |
C3—C8—H8B | 109.5 | C18—C19—H19 | 119.4 |
H8A—C8—H8B | 109.5 | C15—C20—C19 | 119.7 (2) |
C3—C8—H8C | 109.5 | C15—C20—H20 | 120.2 |
H8A—C8—H8C | 109.5 | C19—C20—H20 | 120.2 |
H8B—C8—H8C | 109.5 | C18—C21—H21A | 109.5 |
C14—C9—C10 | 117.55 (18) | C18—C21—H21B | 109.5 |
C14—C9—B | 121.88 (18) | H21A—C21—H21B | 109.5 |
C10—C9—B | 120.51 (18) | C18—C21—H21C | 109.5 |
C11—C10—C9 | 121.72 (18) | H21A—C21—H21C | 109.5 |
C11—C10—H10 | 119.1 | H21B—C21—H21C | 109.5 |