Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501843X/cv6529sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680501843X/cv6529Isup2.hkl |
CCDC reference: 277241
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.002 Å
- R factor = 0.023
- wR factor = 0.057
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N5 - N6 .. 9.06 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N8 - N9 .. 8.28 su
Alert level C PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.57 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 C7 -N5 -N6 -N7 -178.20 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 31 C8 -N8 -N9 -N10 18.00 0.00 1.555 1.555 1.555 1.555
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 26.21 From the CIF: _reflns_number_total 3765 Count of symmetry unique reflns 2163 Completeness (_total/calc) 174.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1602 Fraction of Friedel pairs measured 0.741 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2003; cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H17N7O7S | F(000) = 888 |
Mr = 427.41 | Dx = 1.514 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 26411 reflections |
a = 8.6418 (4) Å | θ = 2–26° |
b = 11.8765 (6) Å | µ = 0.23 mm−1 |
c = 18.2755 (12) Å | T = 193 K |
V = 1875.69 (18) Å3 | Plate, colourless |
Z = 4 | 0.6 × 0.3 × 0.2 mm |
STOE IPDS-II diffractometer | Rint = 0.031 |
ω scans | θmax = 26.2°, θmin = 2.1° |
27463 measured reflections | h = −10→10 |
3765 independent reflections | k = −14→14 |
3473 reflections with I > 2σ(I) | l = −22→22 |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0405P)2] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max = 0.001 |
R[F2 > 2σ(F2)] = 0.023 | Δρmax = 0.18 e Å−3 |
wR(F2) = 0.057 | Δρmin = −0.15 e Å−3 |
S = 1.03 | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3765 reflections | Extinction coefficient: 0.0035 (8) |
298 parameters | Absolute structure: Flack (1983), 1222 Friedel pairs |
0 restraints | Absolute structure parameter: −0.02 (5) |
H atoms treated by a mixture of independent and constrained refinement |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.93658 (4) | 0.78105 (3) | 0.932394 (19) | 0.02993 (9) | |
O1 | 0.72097 (14) | 1.02073 (9) | 0.84038 (6) | 0.0422 (3) | |
O2 | 0.77775 (13) | 1.07408 (9) | 0.95457 (6) | 0.0387 (3) | |
C2 | 0.79249 (18) | 0.84106 (13) | 0.99221 (7) | 0.0303 (3) | |
O3 | 0.41574 (12) | 0.87437 (10) | 0.85470 (7) | 0.0445 (3) | |
C3 | 0.67490 (16) | 0.89081 (11) | 0.93976 (8) | 0.0274 (3) | |
O4 | 0.65824 (11) | 0.79216 (9) | 0.72530 (5) | 0.0343 (2) | |
N4 | 0.65314 (13) | 0.80757 (9) | 0.88205 (6) | 0.0257 (2) | |
O5 | 0.52800 (18) | 0.79360 (19) | 0.62079 (7) | 0.0835 (6) | |
C5 | 0.52719 (16) | 0.81647 (12) | 0.83818 (8) | 0.0297 (3) | |
N5 | 0.40742 (14) | 0.59176 (12) | 0.82761 (7) | 0.0356 (3) | |
O6 | 0.69789 (10) | 0.58136 (8) | 0.92982 (5) | 0.0274 (2) | |
N6 | 0.27310 (15) | 0.61778 (11) | 0.81167 (7) | 0.0363 (3) | |
C6 | 0.52657 (15) | 0.75261 (12) | 0.76574 (8) | 0.0302 (3) | |
O7 | 0.88241 (16) | 0.45006 (11) | 0.94269 (9) | 0.0635 (4) | |
C7 | 0.52604 (15) | 0.62456 (12) | 0.77305 (8) | 0.0286 (3) | |
N7 | 0.14630 (16) | 0.63567 (16) | 0.80547 (9) | 0.0527 (4) | |
N8 | 0.78018 (14) | 0.56883 (11) | 0.73145 (7) | 0.0349 (3) | |
C8 | 0.67658 (16) | 0.56820 (12) | 0.79691 (8) | 0.0286 (3) | |
N9 | 0.86548 (15) | 0.48517 (13) | 0.72995 (7) | 0.0415 (3) | |
C9 | 0.76799 (15) | 0.61597 (11) | 0.86206 (7) | 0.0251 (3) | |
C9A | 0.79345 (14) | 0.74260 (11) | 0.86352 (7) | 0.0246 (3) | |
C10 | 0.72686 (15) | 1.00102 (12) | 0.90444 (8) | 0.0295 (3) | |
N10 | 0.9475 (2) | 0.41203 (16) | 0.72358 (9) | 0.0617 (4) | |
C11 | 0.8232 (2) | 1.18381 (13) | 0.92716 (12) | 0.0501 (4) | |
H11A | 0.8943 | 1.1744 | 0.8858 | 0.075* | |
H11B | 0.8748 | 1.2262 | 0.9662 | 0.075* | |
H11C | 0.7311 | 1.225 | 0.911 | 0.075* | |
C12 | 0.6455 (2) | 0.80834 (14) | 0.65298 (8) | 0.0389 (4) | |
C13 | 0.7961 (2) | 0.84535 (16) | 0.62221 (9) | 0.0455 (4) | |
H13A | 0.8478 | 0.7812 | 0.599 | 0.068* | |
H13B | 0.8615 | 0.8749 | 0.6616 | 0.068* | |
H13C | 0.7784 | 0.9044 | 0.5857 | 0.068* | |
C14 | 0.76862 (17) | 0.49567 (12) | 0.96557 (8) | 0.0326 (3) | |
C15 | 0.6889 (2) | 0.46680 (14) | 1.03475 (9) | 0.0422 (4) | |
H15A | 0.744 | 0.405 | 1.059 | 0.063* | |
H15B | 0.5825 | 0.4435 | 1.0241 | 0.063* | |
H15C | 0.6876 | 0.5328 | 1.067 | 0.063* | |
H21 | 0.8441 (19) | 0.8953 (14) | 1.0223 (9) | 0.033 (4)* | |
H22 | 0.7459 (18) | 0.7858 (14) | 1.0232 (9) | 0.030 (4)* | |
H3 | 0.5795 (19) | 0.9057 (14) | 0.9626 (9) | 0.031 (4)* | |
H6 | 0.4343 (18) | 0.7751 (13) | 0.7410 (8) | 0.026 (4)* | |
H7 | 0.4978 (18) | 0.5928 (15) | 0.7221 (9) | 0.036 (4)* | |
H81 | 0.6503 (18) | 0.4896 (14) | 0.8091 (8) | 0.025 (4)* | |
H9 | 0.8721 (18) | 0.5806 (13) | 0.8601 (8) | 0.029 (4)* | |
H9A | 0.8322 (17) | 0.7637 (12) | 0.8156 (8) | 0.021 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02403 (16) | 0.03384 (18) | 0.03193 (16) | −0.00140 (14) | −0.00650 (14) | −0.00153 (14) |
O1 | 0.0503 (7) | 0.0405 (6) | 0.0359 (6) | −0.0046 (5) | −0.0076 (5) | 0.0092 (5) |
O2 | 0.0464 (6) | 0.0277 (5) | 0.0419 (6) | −0.0049 (5) | −0.0049 (5) | −0.0047 (4) |
C2 | 0.0331 (8) | 0.0327 (8) | 0.0250 (6) | −0.0040 (6) | −0.0030 (6) | 0.0005 (6) |
O3 | 0.0287 (6) | 0.0514 (7) | 0.0534 (7) | 0.0124 (5) | −0.0087 (5) | −0.0144 (5) |
C3 | 0.0264 (7) | 0.0295 (7) | 0.0264 (7) | −0.0006 (5) | 0.0022 (6) | −0.0028 (5) |
O4 | 0.0280 (5) | 0.0451 (6) | 0.0297 (5) | −0.0064 (4) | −0.0024 (4) | 0.0082 (5) |
N4 | 0.0231 (5) | 0.0257 (6) | 0.0282 (6) | 0.0001 (4) | −0.0023 (4) | −0.0028 (4) |
O5 | 0.0585 (8) | 0.1550 (17) | 0.0369 (7) | −0.0463 (10) | −0.0175 (6) | 0.0212 (9) |
C5 | 0.0236 (6) | 0.0303 (7) | 0.0352 (7) | 0.0005 (5) | −0.0019 (5) | 0.0000 (6) |
N5 | 0.0229 (6) | 0.0473 (8) | 0.0365 (6) | −0.0038 (5) | 0.0019 (5) | 0.0012 (6) |
O6 | 0.0258 (5) | 0.0289 (5) | 0.0276 (5) | 0.0015 (4) | 0.0029 (4) | 0.0038 (4) |
N6 | 0.0294 (7) | 0.0430 (8) | 0.0364 (7) | −0.0074 (5) | 0.0044 (5) | −0.0056 (6) |
C6 | 0.0201 (6) | 0.0388 (8) | 0.0318 (7) | −0.0010 (5) | −0.0042 (5) | 0.0008 (6) |
O7 | 0.0610 (8) | 0.0524 (8) | 0.0771 (9) | 0.0306 (6) | 0.0298 (7) | 0.0284 (7) |
C7 | 0.0220 (6) | 0.0371 (8) | 0.0267 (6) | −0.0062 (5) | 0.0013 (5) | −0.0028 (6) |
N7 | 0.0256 (7) | 0.0708 (11) | 0.0616 (9) | 0.0009 (7) | 0.0050 (7) | −0.0050 (8) |
N8 | 0.0313 (6) | 0.0421 (7) | 0.0313 (6) | 0.0027 (6) | 0.0054 (5) | −0.0080 (5) |
C8 | 0.0262 (7) | 0.0293 (7) | 0.0305 (7) | −0.0016 (6) | 0.0033 (5) | −0.0041 (6) |
N9 | 0.0350 (7) | 0.0543 (9) | 0.0353 (7) | 0.0035 (7) | 0.0020 (6) | −0.0142 (6) |
C9 | 0.0208 (6) | 0.0292 (7) | 0.0252 (6) | 0.0000 (5) | 0.0032 (5) | −0.0008 (5) |
C9A | 0.0199 (6) | 0.0287 (7) | 0.0252 (6) | −0.0012 (5) | −0.0004 (5) | 0.0011 (5) |
C10 | 0.0241 (6) | 0.0296 (7) | 0.0347 (7) | 0.0018 (6) | −0.0017 (6) | −0.0016 (6) |
N10 | 0.0537 (9) | 0.0721 (11) | 0.0593 (9) | 0.0247 (9) | 0.0065 (8) | −0.0198 (8) |
C11 | 0.0485 (10) | 0.0265 (7) | 0.0754 (12) | −0.0043 (7) | −0.0123 (9) | 0.0046 (8) |
C12 | 0.0421 (8) | 0.0453 (9) | 0.0292 (7) | −0.0085 (7) | −0.0059 (6) | 0.0042 (6) |
C13 | 0.0463 (10) | 0.0534 (10) | 0.0369 (8) | −0.0097 (8) | 0.0040 (7) | 0.0048 (7) |
C14 | 0.0325 (8) | 0.0240 (7) | 0.0412 (8) | 0.0005 (6) | 0.0007 (6) | 0.0044 (6) |
C15 | 0.0478 (9) | 0.0384 (9) | 0.0406 (8) | 0.0041 (7) | 0.0048 (7) | 0.0105 (7) |
S1—C2 | 1.8038 (15) | C6—H6 | 0.954 (16) |
S1—C9A | 1.8228 (13) | O7—C14 | 1.1980 (19) |
O1—C10 | 1.1950 (18) | C7—C8 | 1.527 (2) |
O2—C10 | 1.3362 (18) | C7—H7 | 1.034 (17) |
O2—C11 | 1.450 (2) | N8—N9 | 1.2375 (19) |
C2—C3 | 1.517 (2) | N8—C8 | 1.4941 (18) |
C2—H21 | 0.957 (18) | C8—C9 | 1.5374 (19) |
C2—H22 | 0.955 (17) | C8—H81 | 0.986 (16) |
O3—C5 | 1.2213 (17) | N9—N10 | 1.127 (2) |
C3—N4 | 1.4577 (17) | C9—C9A | 1.5202 (19) |
C3—C10 | 1.527 (2) | C9—H9 | 0.994 (16) |
C3—H3 | 0.941 (17) | C9A—H9A | 0.971 (15) |
O4—C12 | 1.3401 (18) | C11—H11A | 0.98 |
O4—C6 | 1.4359 (17) | C11—H11B | 0.98 |
N4—C5 | 1.3559 (18) | C11—H11C | 0.98 |
N4—C9A | 1.4766 (17) | C12—C13 | 1.484 (2) |
O5—C12 | 1.187 (2) | C13—H13A | 0.98 |
C5—C6 | 1.526 (2) | C13—H13B | 0.98 |
N5—N6 | 1.2361 (18) | C13—H13C | 0.98 |
N5—C7 | 1.4822 (18) | C14—C15 | 1.480 (2) |
O6—C14 | 1.3550 (17) | C15—H15A | 0.98 |
O6—C9 | 1.4386 (16) | C15—H15B | 0.98 |
N6—N7 | 1.1219 (19) | C15—H15C | 0.98 |
C6—C7 | 1.527 (2) | ||
C2—S1—C9A | 92.81 (6) | C9—C8—H81 | 107.0 (9) |
C10—O2—C11 | 115.84 (13) | N10—N9—N8 | 174.66 (19) |
C3—C2—S1 | 103.49 (9) | O6—C9—C9A | 109.17 (10) |
C3—C2—H21 | 114.4 (10) | O6—C9—C8 | 110.18 (11) |
S1—C2—H21 | 107.0 (10) | C9A—C9—C8 | 116.94 (11) |
C3—C2—H22 | 111.1 (10) | O6—C9—H9 | 107.0 (9) |
S1—C2—H22 | 112.2 (10) | C9A—C9—H9 | 106.7 (9) |
H21—C2—H22 | 108.5 (13) | C8—C9—H9 | 106.3 (9) |
N4—C3—C2 | 106.24 (11) | N4—C9A—C9 | 113.72 (10) |
N4—C3—C10 | 108.27 (11) | N4—C9A—S1 | 105.54 (9) |
C2—C3—C10 | 113.83 (12) | C9—C9A—S1 | 110.99 (9) |
N4—C3—H3 | 109.6 (10) | N4—C9A—H9A | 110.8 (9) |
C2—C3—H3 | 112.3 (10) | C9—C9A—H9A | 106.8 (9) |
C10—C3—H3 | 106.5 (10) | S1—C9A—H9A | 108.9 (8) |
C12—O4—C6 | 119.31 (11) | O1—C10—O2 | 123.95 (14) |
C5—N4—C3 | 118.59 (11) | O1—C10—C3 | 124.71 (13) |
C5—N4—C9A | 124.36 (11) | O2—C10—C3 | 111.33 (12) |
C3—N4—C9A | 114.48 (10) | O2—C11—H11A | 109.5 |
O3—C5—N4 | 122.06 (13) | O2—C11—H11B | 109.5 |
O3—C5—C6 | 119.44 (13) | H11A—C11—H11B | 109.5 |
N4—C5—C6 | 118.50 (12) | O2—C11—H11C | 109.5 |
N6—N5—C7 | 115.16 (13) | H11A—C11—H11C | 109.5 |
C14—O6—C9 | 116.08 (10) | H11B—C11—H11C | 109.5 |
N7—N6—N5 | 171.25 (17) | O5—C12—O4 | 122.56 (15) |
O4—C6—C5 | 106.33 (11) | O5—C12—C13 | 127.31 (15) |
O4—C6—C7 | 111.92 (11) | O4—C12—C13 | 110.13 (13) |
C5—C6—C7 | 114.79 (12) | C12—C13—H13A | 109.5 |
O4—C6—H6 | 109.1 (9) | C12—C13—H13B | 109.5 |
C5—C6—H6 | 106.0 (9) | H13A—C13—H13B | 109.5 |
C7—C6—H6 | 108.5 (10) | C12—C13—H13C | 109.5 |
N5—C7—C8 | 106.37 (11) | H13A—C13—H13C | 109.5 |
N5—C7—C6 | 108.83 (12) | H13B—C13—H13C | 109.5 |
C8—C7—C6 | 117.34 (12) | O7—C14—O6 | 122.79 (14) |
N5—C7—H7 | 110.3 (9) | O7—C14—C15 | 125.12 (14) |
C8—C7—H7 | 107.4 (9) | O6—C14—C15 | 112.09 (12) |
C6—C7—H7 | 106.6 (10) | C14—C15—H15A | 109.5 |
N9—N8—C8 | 111.76 (13) | C14—C15—H15B | 109.5 |
N8—C8—C7 | 106.25 (11) | H15A—C15—H15B | 109.5 |
N8—C8—C9 | 108.08 (11) | C14—C15—H15C | 109.5 |
C7—C8—C9 | 119.82 (12) | H15A—C15—H15C | 109.5 |
N8—C8—H81 | 108.8 (9) | H15B—C15—H15C | 109.5 |
C7—C8—H81 | 106.5 (9) | ||
C9A—S1—C2—C3 | −34.03 (10) | C6—C7—C8—C9 | 46.58 (18) |
S1—C2—C3—N4 | 43.01 (12) | C8—N8—N9—N10 | 18E1 (10) |
S1—C2—C3—C10 | −76.03 (13) | C14—O6—C9—C9A | −128.22 (12) |
C2—C3—N4—C5 | 163.42 (12) | C14—O6—C9—C8 | 102.08 (13) |
C10—C3—N4—C5 | −73.95 (15) | N8—C8—C9—O6 | −159.52 (11) |
C2—C3—N4—C9A | −33.98 (15) | C7—C8—C9—O6 | 78.73 (15) |
C10—C3—N4—C9A | 88.66 (13) | N8—C8—C9—C9A | 75.08 (14) |
C3—N4—C5—O3 | −16.7 (2) | C7—C8—C9—C9A | −46.68 (17) |
C9A—N4—C5—O3 | −177.43 (13) | C5—N4—C9A—C9 | −68.54 (16) |
C3—N4—C5—C6 | 162.77 (12) | C3—N4—C9A—C9 | 130.00 (12) |
C9A—N4—C5—C6 | 2.01 (19) | C5—N4—C9A—S1 | 169.57 (11) |
C7—N5—N6—N7 | −178.2 (11) | C3—N4—C9A—S1 | 8.11 (13) |
C12—O4—C6—C5 | −140.65 (13) | O6—C9—C9A—N4 | −52.54 (14) |
C12—O4—C6—C7 | 93.27 (16) | C8—C9—C9A—N4 | 73.36 (15) |
O3—C5—C6—O4 | 120.95 (14) | O6—C9—C9A—S1 | 66.28 (12) |
N4—C5—C6—O4 | −58.52 (15) | C8—C9—C9A—S1 | −167.82 (9) |
O3—C5—C6—C7 | −114.73 (15) | C2—S1—C9A—N4 | 15.90 (9) |
N4—C5—C6—C7 | 65.81 (16) | C2—S1—C9A—C9 | −107.74 (10) |
N6—N5—C7—C8 | −170.85 (13) | C11—O2—C10—O1 | 1.8 (2) |
N6—N5—C7—C6 | 61.86 (16) | C11—O2—C10—C3 | −177.17 (12) |
O4—C6—C7—N5 | 168.32 (10) | N4—C3—C10—O1 | 13.18 (19) |
C5—C6—C7—N5 | 47.00 (15) | C2—C3—C10—O1 | 131.07 (15) |
O4—C6—C7—C8 | 47.55 (16) | N4—C3—C10—O2 | −167.88 (11) |
C5—C6—C7—C8 | −73.77 (15) | C2—C3—C10—O2 | −49.99 (16) |
N9—N8—C8—C7 | −147.21 (13) | C6—O4—C12—O5 | 1.7 (3) |
N9—N8—C8—C9 | 83.00 (15) | C6—O4—C12—C13 | −178.08 (13) |
N5—C7—C8—N8 | 161.89 (11) | C9—O6—C14—O7 | −0.4 (2) |
C6—C7—C8—N8 | −76.07 (15) | C9—O6—C14—C15 | 179.55 (12) |
N5—C7—C8—C9 | −75.46 (15) |
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