Crystal structures of (H2m4na)NO
3 (1), (H2m4na)HSO
4 (2), (H2m4na)
2SiF
6 (3) and (H2m4na)
2SiF
6·2H
2O (4), where 2m4na = 2-methyl-4-nitroaniline, are presented. Two layers of interactions occur in the structures, N—H
O/F hydrogen bonds and interactions with the nitro group. Although diverse, hydrogen-bonding patterns are compared with each other by means of interrelations among elementary graph-set descriptors and descriptors of hydrogen-bonding patterns. Using mathematical relations, the gradual expansion of the ring patterns was shown in the crystal structures. Parallel and perpendicular arranged nitro groups form weak π(N)
NO2π(O)
NO2 and π(N)
NO2O
NO2 interactions, respectively. The π
NO2π
ring interaction has an impact to the stabilization of parallel oriented nitro groups. Generally, weak interactions constructed by the nitro group occur in the studied crystals as follows: π(N)
NO2π(O)
NO2, π
ringπ
ring, C—H
O (1); π(N)
NO2π(O)
NO2, π(N)
NO2O
NO2 (2); π(N)
NO2π(O)
NO2, π(N)
NO2O
NO2 (3); C—H
O (4).
Supporting information
CCDC references: 1439197; 1439198; 1439199; 1482755
Data collection: CrysAlis 1.171.38.34a for M156, M2151, 1652; CrysAlis 1.171.33.42 for M155. For all compounds, cell refinement: CrysAlis 1.171.38.34a; data reduction: CrysAlis 1.171.38.34a; program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).
Crystal data top
C7H9N2O2·NO3 | F(000) = 896 |
Mr = 215.17 | Dx = 1.509 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9356 (4) Å | Cell parameters from 3268 reflections |
b = 7.48389 (15) Å | θ = 2.4–25.4° |
c = 17.1390 (4) Å | µ = 0.13 mm−1 |
β = 112.052 (3)° | T = 295 K |
V = 1894.48 (9) Å3 | Plate, brown |
Z = 8 | 0.37 × 0.32 × 0.11 mm |
Data collection top
KUMA KM-4 with area CCD detector diffractometer | 2785 reflections with I > 2σ(I) |
ω–scan | Rint = 0.032 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 25.4°, θmin = 2.4° |
Tmin = 0.873, Tmax = 1.000 | h = −19→19 |
56168 measured reflections | k = −8→8 |
3268 independent reflections | l = −20→19 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | Only H-atom coordinates refined |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.5514P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = <0.001 |
3268 reflections | Δρmax = 0.16 e Å−3 |
275 parameters | Δρmin = −0.18 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1A | 0.37336 (8) | 0.95522 (17) | 0.42470 (8) | 0.0398 (3) | |
H1A1 | 0.4231 | 0.9200 | 0.4171 | 0.060* | |
H1A2 | 0.3718 | 0.9053 | 0.4713 | 0.060* | |
H1A3 | 0.3738 | 1.0736 | 0.4297 | 0.060* | |
C1A | 0.29349 (10) | 0.90065 (19) | 0.35250 (9) | 0.0348 (3) | |
C2A | 0.20785 (10) | 0.9414 (2) | 0.35122 (10) | 0.0394 (4) | |
C3A | 0.13458 (11) | 0.8897 (2) | 0.27989 (11) | 0.0490 (4) | |
H3A | 0.0758 | 0.9131 | 0.2759 | 0.059* | |
C4A | 0.14942 (12) | 0.8038 (2) | 0.21523 (10) | 0.0508 (4) | |
N2A | 0.07047 (14) | 0.7571 (3) | 0.13897 (12) | 0.0766 (5) | |
O1A | −0.00372 (12) | 0.8004 (3) | 0.13528 (13) | 0.1185 (7) | |
O2A | 0.08473 (14) | 0.6771 (3) | 0.08302 (11) | 0.1113 (7) | |
C5A | 0.23451 (12) | 0.7629 (2) | 0.21755 (10) | 0.0494 (4) | |
H5A | 0.2423 | 0.7033 | 0.1731 | 0.059* | |
C6A | 0.30766 (11) | 0.8129 (2) | 0.28766 (10) | 0.0412 (4) | |
H6A | 0.3662 | 0.7879 | 0.2914 | 0.049* | |
C7A | 0.19334 (12) | 1.0394 (3) | 0.42176 (12) | 0.0551 (5) | |
H7A1 | 0.1336 | 1.0900 | 0.4016 | 0.083* | 0.5 |
H7A2 | 0.2374 | 1.1331 | 0.4419 | 0.083* | 0.5 |
H7A3 | 0.1997 | 0.9576 | 0.4668 | 0.083* | 0.5 |
H7A4 | 0.2469 | 1.0305 | 0.4720 | 0.083* | 0.5 |
H7A5 | 0.1431 | 0.9874 | 0.4316 | 0.083* | 0.5 |
H7A6 | 0.1808 | 1.1629 | 0.4067 | 0.083* | 0.5 |
N1B | 0.38892 (8) | 0.46147 (18) | 0.61102 (8) | 0.0412 (3) | |
H1B1 | 0.3932 | 0.4186 | 0.5642 | 0.062* | |
H1B2 | 0.4375 | 0.4293 | 0.6553 | 0.062* | |
H1B3 | 0.3854 | 0.5801 | 0.6081 | 0.062* | |
C1B | 0.30749 (10) | 0.38959 (19) | 0.62003 (9) | 0.0349 (3) | |
C2B | 0.22252 (10) | 0.4310 (2) | 0.56037 (9) | 0.0386 (4) | |
C3B | 0.14804 (11) | 0.3626 (2) | 0.57446 (10) | 0.0450 (4) | |
H3B | 0.0898 | 0.3852 | 0.5361 | 0.054* | |
C4B | 0.16069 (11) | 0.2620 (2) | 0.64503 (11) | 0.0452 (4) | |
N2B | 0.08023 (12) | 0.2023 (2) | 0.66110 (12) | 0.0643 (4) | |
O1B | 0.00655 (10) | 0.2516 (3) | 0.61346 (13) | 0.1026 (6) | |
O2B | 0.09245 (12) | 0.1064 (2) | 0.72232 (12) | 0.0891 (5) | |
C5B | 0.24501 (11) | 0.2192 (2) | 0.70280 (11) | 0.0462 (4) | |
H5B | 0.2516 | 0.1491 | 0.7495 | 0.055* | |
C6B | 0.31965 (11) | 0.2836 (2) | 0.68932 (10) | 0.0404 (4) | |
H6B | 0.3777 | 0.2557 | 0.7267 | 0.048* | |
C7B | 0.20846 (12) | 0.5475 (3) | 0.48495 (11) | 0.0529 (4) | |
H7B1 | 0.1486 | 0.5288 | 0.4438 | 0.079* | 0.5 |
H7B2 | 0.2523 | 0.5175 | 0.4610 | 0.079* | 0.5 |
H7B3 | 0.2155 | 0.6706 | 0.5019 | 0.079* | 0.5 |
H7B4 | 0.2623 | 0.6158 | 0.4940 | 0.079* | 0.5 |
H7B5 | 0.1586 | 0.6271 | 0.4768 | 0.079* | 0.5 |
H7B6 | 0.1954 | 0.4740 | 0.4359 | 0.079* | 0.5 |
N3A | 0.43449 (8) | 0.93022 (18) | 0.64185 (8) | 0.0400 (3) | |
O3A | 0.46600 (9) | 1.06503 (16) | 0.62025 (9) | 0.0595 (4) | |
O4A | 0.37615 (8) | 0.83862 (16) | 0.58543 (7) | 0.0533 (3) | |
O5A | 0.45677 (9) | 0.8842 (2) | 0.71559 (7) | 0.0640 (4) | |
N3B | 0.41246 (8) | 0.42160 (19) | 0.42050 (8) | 0.0412 (3) | |
O3B | 0.37669 (10) | 0.31629 (17) | 0.45690 (9) | 0.0627 (4) | |
O4B | 0.41868 (9) | 0.57972 (16) | 0.44007 (8) | 0.0626 (4) | |
O5B | 0.43959 (10) | 0.3602 (2) | 0.36834 (8) | 0.0751 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0396 (7) | 0.0387 (7) | 0.0405 (7) | −0.0024 (6) | 0.0142 (6) | −0.0035 (6) |
C1A | 0.0390 (8) | 0.0302 (7) | 0.0341 (8) | −0.0025 (6) | 0.0124 (6) | 0.0046 (6) |
C2A | 0.0399 (8) | 0.0357 (8) | 0.0433 (9) | 0.0002 (7) | 0.0166 (7) | 0.0071 (7) |
C3A | 0.0387 (9) | 0.0516 (10) | 0.0528 (10) | −0.0027 (7) | 0.0125 (8) | 0.0121 (8) |
C4A | 0.0513 (10) | 0.0502 (10) | 0.0387 (9) | −0.0126 (8) | 0.0031 (8) | 0.0073 (8) |
N2A | 0.0730 (13) | 0.0831 (13) | 0.0510 (11) | −0.0221 (10) | −0.0027 (9) | 0.0070 (10) |
O1A | 0.0589 (11) | 0.1549 (19) | 0.1006 (14) | −0.0057 (11) | −0.0172 (10) | −0.0142 (13) |
O2A | 0.1175 (15) | 0.1452 (18) | 0.0486 (9) | −0.0439 (13) | 0.0054 (9) | −0.0204 (11) |
C5A | 0.0654 (11) | 0.0457 (9) | 0.0352 (9) | −0.0063 (8) | 0.0168 (8) | −0.0009 (7) |
C6A | 0.0469 (9) | 0.0386 (8) | 0.0404 (9) | 0.0008 (7) | 0.0192 (7) | 0.0033 (7) |
C7A | 0.0528 (10) | 0.0570 (11) | 0.0632 (12) | 0.0035 (8) | 0.0306 (9) | −0.0033 (9) |
N1B | 0.0400 (7) | 0.0431 (7) | 0.0420 (7) | −0.0016 (6) | 0.0171 (6) | 0.0016 (6) |
C1B | 0.0385 (8) | 0.0331 (7) | 0.0352 (8) | −0.0023 (6) | 0.0163 (6) | −0.0055 (6) |
C2B | 0.0409 (8) | 0.0381 (8) | 0.0362 (8) | 0.0018 (7) | 0.0136 (7) | −0.0039 (6) |
C3B | 0.0367 (8) | 0.0504 (10) | 0.0454 (9) | 0.0007 (7) | 0.0125 (7) | −0.0078 (8) |
C4B | 0.0432 (9) | 0.0457 (9) | 0.0534 (10) | −0.0063 (7) | 0.0260 (8) | −0.0080 (8) |
N2B | 0.0571 (10) | 0.0686 (11) | 0.0796 (12) | −0.0092 (8) | 0.0399 (9) | −0.0064 (9) |
O1B | 0.0459 (9) | 0.1501 (18) | 0.1164 (14) | −0.0025 (10) | 0.0356 (9) | 0.0233 (13) |
O2B | 0.0874 (11) | 0.0959 (12) | 0.1089 (13) | −0.0093 (9) | 0.0652 (10) | 0.0201 (11) |
C5B | 0.0550 (10) | 0.0448 (9) | 0.0449 (9) | −0.0020 (8) | 0.0256 (8) | 0.0033 (7) |
C6B | 0.0404 (8) | 0.0426 (9) | 0.0368 (8) | 0.0023 (7) | 0.0129 (7) | 0.0010 (7) |
C7B | 0.0503 (10) | 0.0585 (11) | 0.0441 (10) | 0.0047 (8) | 0.0111 (8) | 0.0095 (8) |
N3A | 0.0381 (7) | 0.0430 (8) | 0.0407 (8) | −0.0010 (6) | 0.0167 (6) | −0.0045 (6) |
O3A | 0.0598 (8) | 0.0469 (7) | 0.0829 (9) | −0.0120 (6) | 0.0395 (7) | −0.0071 (6) |
O4A | 0.0563 (7) | 0.0482 (7) | 0.0435 (7) | −0.0108 (6) | 0.0053 (6) | −0.0013 (5) |
O5A | 0.0625 (8) | 0.0915 (10) | 0.0353 (7) | 0.0028 (7) | 0.0153 (6) | −0.0002 (6) |
N3B | 0.0392 (7) | 0.0472 (8) | 0.0334 (7) | −0.0034 (6) | 0.0093 (6) | −0.0034 (6) |
O3B | 0.0862 (9) | 0.0478 (7) | 0.0749 (9) | −0.0217 (7) | 0.0541 (8) | −0.0149 (6) |
O4B | 0.0696 (8) | 0.0357 (7) | 0.0663 (8) | 0.0009 (6) | 0.0072 (7) | 0.0066 (6) |
O5B | 0.0733 (9) | 0.1139 (12) | 0.0493 (8) | −0.0205 (8) | 0.0361 (7) | −0.0279 (8) |
Geometric parameters (Å, º) top
N1A—C1A | 1.4613 (19) | N1B—H1B3 | 0.8900 |
N1A—H1A1 | 0.8900 | C1B—C6B | 1.380 (2) |
N1A—H1A2 | 0.8900 | C1B—C2B | 1.391 (2) |
N1A—H1A3 | 0.8900 | C2B—C3B | 1.394 (2) |
C1A—C6A | 1.380 (2) | C2B—C7B | 1.505 (2) |
C1A—C2A | 1.391 (2) | C3B—C4B | 1.374 (2) |
C2A—C3A | 1.391 (2) | C3B—H3B | 0.9300 |
C2A—C7A | 1.504 (2) | C4B—C5B | 1.375 (2) |
C3A—C4A | 1.377 (3) | C4B—N2B | 1.478 (2) |
C3A—H3A | 0.9300 | N2B—O1B | 1.209 (2) |
C4A—C5A | 1.376 (3) | N2B—O2B | 1.225 (2) |
C4A—N2A | 1.476 (2) | C5B—C6B | 1.381 (2) |
N2A—O1A | 1.205 (3) | C5B—H5B | 0.9300 |
N2A—O2A | 1.222 (3) | C6B—H6B | 0.9300 |
C5A—C6A | 1.375 (2) | C7B—H7B1 | 0.9600 |
C5A—H5A | 0.9300 | C7B—H7B2 | 0.9600 |
C6A—H6A | 0.9300 | C7B—H7B3 | 0.9600 |
C7A—H7A1 | 0.9600 | C7B—H7B4 | 0.9600 |
C7A—H7A2 | 0.9600 | C7B—H7B5 | 0.9600 |
C7A—H7A3 | 0.9600 | C7B—H7B6 | 0.9600 |
C7A—H7A4 | 0.9600 | N3A—O5A | 1.2270 (17) |
C7A—H7A5 | 0.9600 | N3A—O3A | 1.2436 (17) |
C7A—H7A6 | 0.9600 | N3A—O4A | 1.2626 (17) |
N1B—C1B | 1.4655 (19) | N3B—O5B | 1.2196 (18) |
N1B—H1B1 | 0.8900 | N3B—O4B | 1.2238 (18) |
N1B—H1B2 | 0.8900 | N3B—O3B | 1.2658 (18) |
| | | |
C1A—N1A—H1A1 | 109.5 | C1B—N1B—H1B3 | 109.5 |
C1A—N1A—H1A2 | 109.5 | H1B1—N1B—H1B3 | 109.5 |
H1A1—N1A—H1A2 | 109.5 | H1B2—N1B—H1B3 | 109.5 |
C1A—N1A—H1A3 | 109.5 | C6B—C1B—C2B | 122.96 (14) |
H1A1—N1A—H1A3 | 109.5 | C6B—C1B—N1B | 117.25 (13) |
H1A2—N1A—H1A3 | 109.5 | C2B—C1B—N1B | 119.78 (13) |
C6A—C1A—C2A | 123.22 (14) | C1B—C2B—C3B | 116.60 (14) |
C6A—C1A—N1A | 117.45 (13) | C1B—C2B—C7B | 123.40 (14) |
C2A—C1A—N1A | 119.32 (13) | C3B—C2B—C7B | 119.97 (14) |
C1A—C2A—C3A | 116.61 (15) | C4B—C3B—C2B | 120.04 (15) |
C1A—C2A—C7A | 122.71 (14) | C4B—C3B—H3B | 120.0 |
C3A—C2A—C7A | 120.68 (15) | C2B—C3B—H3B | 120.0 |
C4A—C3A—C2A | 119.75 (16) | C3B—C4B—C5B | 122.84 (15) |
C4A—C3A—H3A | 120.1 | C3B—C4B—N2B | 118.61 (16) |
C2A—C3A—H3A | 120.1 | C5B—C4B—N2B | 118.52 (16) |
C5A—C4A—C3A | 123.09 (15) | O1B—N2B—O2B | 124.00 (17) |
C5A—C4A—N2A | 118.43 (18) | O1B—N2B—C4B | 118.20 (18) |
C3A—C4A—N2A | 118.46 (18) | O2B—N2B—C4B | 117.81 (18) |
O1A—N2A—O2A | 124.0 (2) | C4B—C5B—C6B | 117.96 (15) |
O1A—N2A—C4A | 118.4 (2) | C4B—C5B—H5B | 121.0 |
O2A—N2A—C4A | 117.6 (2) | C6B—C5B—H5B | 121.0 |
C6A—C5A—C4A | 117.87 (16) | C1B—C6B—C5B | 119.54 (15) |
C6A—C5A—H5A | 121.1 | C1B—C6B—H6B | 120.2 |
C4A—C5A—H5A | 121.1 | C5B—C6B—H6B | 120.2 |
C5A—C6A—C1A | 119.46 (15) | C2B—C7B—H7B1 | 109.5 |
C5A—C6A—H6A | 120.3 | C2B—C7B—H7B2 | 109.5 |
C1A—C6A—H6A | 120.3 | H7B1—C7B—H7B2 | 109.5 |
C2A—C7A—H7A1 | 109.5 | C2B—C7B—H7B3 | 109.5 |
C2A—C7A—H7A2 | 109.5 | H7B1—C7B—H7B3 | 109.5 |
H7A1—C7A—H7A2 | 109.5 | H7B2—C7B—H7B3 | 109.5 |
C2A—C7A—H7A3 | 109.5 | C2B—C7B—H7B4 | 109.5 |
H7A1—C7A—H7A3 | 109.5 | H7B1—C7B—H7B4 | 141.1 |
H7A2—C7A—H7A3 | 109.5 | H7B2—C7B—H7B4 | 56.3 |
C2A—C7A—H7A4 | 109.5 | H7B3—C7B—H7B4 | 56.3 |
H7A1—C7A—H7A4 | 141.1 | C2B—C7B—H7B5 | 109.5 |
H7A2—C7A—H7A4 | 56.3 | H7B1—C7B—H7B5 | 56.3 |
H7A3—C7A—H7A4 | 56.3 | H7B2—C7B—H7B5 | 141.1 |
C2A—C7A—H7A5 | 109.5 | H7B3—C7B—H7B5 | 56.3 |
H7A1—C7A—H7A5 | 56.3 | H7B4—C7B—H7B5 | 109.5 |
H7A2—C7A—H7A5 | 141.1 | C2B—C7B—H7B6 | 109.5 |
H7A3—C7A—H7A5 | 56.3 | H7B1—C7B—H7B6 | 56.3 |
H7A4—C7A—H7A5 | 109.5 | H7B2—C7B—H7B6 | 56.3 |
C2A—C7A—H7A6 | 109.5 | H7B3—C7B—H7B6 | 141.1 |
H7A1—C7A—H7A6 | 56.3 | H7B4—C7B—H7B6 | 109.5 |
H7A2—C7A—H7A6 | 56.3 | H7B5—C7B—H7B6 | 109.5 |
H7A3—C7A—H7A6 | 141.1 | O5A—N3A—O3A | 122.79 (14) |
H7A4—C7A—H7A6 | 109.5 | O5A—N3A—O4A | 118.78 (14) |
H7A5—C7A—H7A6 | 109.5 | O3A—N3A—O4A | 118.42 (13) |
C1B—N1B—H1B1 | 109.5 | O5B—N3B—O4B | 123.39 (15) |
C1B—N1B—H1B2 | 109.5 | O5B—N3B—O3B | 118.43 (14) |
H1B1—N1B—H1B2 | 109.5 | O4B—N3B—O3B | 118.17 (14) |
| | | |
C6A—C1A—C2A—C3A | −0.3 (2) | C6B—C1B—C2B—C3B | 1.3 (2) |
N1A—C1A—C2A—C3A | 178.49 (13) | N1B—C1B—C2B—C3B | −178.00 (13) |
C6A—C1A—C2A—C7A | −179.11 (15) | C6B—C1B—C2B—C7B | 179.53 (15) |
N1A—C1A—C2A—C7A | −0.3 (2) | N1B—C1B—C2B—C7B | 0.2 (2) |
C1A—C2A—C3A—C4A | −0.3 (2) | C1B—C2B—C3B—C4B | 0.8 (2) |
C7A—C2A—C3A—C4A | 178.52 (15) | C7B—C2B—C3B—C4B | −177.46 (15) |
C2A—C3A—C4A—C5A | 0.9 (3) | C2B—C3B—C4B—C5B | −2.1 (3) |
C2A—C3A—C4A—N2A | −177.58 (15) | C2B—C3B—C4B—N2B | 175.74 (15) |
C5A—C4A—N2A—O1A | −176.5 (2) | C3B—C4B—N2B—O1B | −3.4 (3) |
C3A—C4A—N2A—O1A | 2.0 (3) | C5B—C4B—N2B—O1B | 174.51 (19) |
C5A—C4A—N2A—O2A | 3.1 (3) | C3B—C4B—N2B—O2B | 176.98 (17) |
C3A—C4A—N2A—O2A | −178.32 (19) | C5B—C4B—N2B—O2B | −5.1 (3) |
C3A—C4A—C5A—C6A | −0.8 (3) | C3B—C4B—C5B—C6B | 1.1 (3) |
N2A—C4A—C5A—C6A | 177.66 (15) | N2B—C4B—C5B—C6B | −176.69 (15) |
C4A—C5A—C6A—C1A | 0.2 (2) | C2B—C1B—C6B—C5B | −2.3 (2) |
C2A—C1A—C6A—C5A | 0.3 (2) | N1B—C1B—C6B—C5B | 177.06 (14) |
N1A—C1A—C6A—C5A | −178.45 (14) | C4B—C5B—C6B—C1B | 1.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···O3Ai | 0.89 | 2.10 | 2.9412 (17) | 158 |
N1A—H1A2···O4A | 0.89 | 2.00 | 2.8741 (17) | 169 |
N1A—H1A3···N3Bii | 0.89 | 2.69 | 3.5509 (19) | 162 |
N1A—H1A3···O3Bii | 0.89 | 1.87 | 2.7545 (18) | 171 |
C6A—H6A···O5Aiii | 0.93 | 2.61 | 3.399 (2) | 142 |
N1B—H1B1···N3B | 0.89 | 2.59 | 3.4367 (18) | 158 |
N1B—H1B1···O3B | 0.89 | 1.92 | 2.7944 (18) | 168 |
N1B—H1B1···O4B | 0.89 | 2.61 | 3.2612 (19) | 131 |
N1B—H1B2···O5Aiv | 0.89 | 2.25 | 3.1186 (18) | 166 |
N1B—H1B3···O4A | 0.89 | 1.97 | 2.8519 (18) | 172 |
C6B—H6B···O5Aiv | 0.93 | 2.63 | 3.400 (2) | 141 |
C6B—H6B···O5Bv | 0.93 | 2.41 | 3.134 (2) | 134 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y+1, z; (iii) x, −y+3/2, z−1/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
C7H9N2O2·HO4S | F(000) = 520 |
Mr = 250.23 | Dx = 1.639 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9394 (4) Å | Cell parameters from 1970 reflections |
b = 5.01801 (11) Å | θ = 2.6–26.7° |
c = 12.9310 (3) Å | µ = 0.34 mm−1 |
β = 101.367 (2)° | T = 295 K |
V = 1013.99 (4) Å3 | Plate, brown |
Z = 4 | 0.36 × 0.34 × 0.06 mm |
Data collection top
KUMA KM-4 with area CCD detector diffractometer | 1814 reflections with I > 2σ(I) |
ω–scan | Rint = 0.017 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.7°, θmin = 2.6° |
Tmin = 0.894, Tmax = 1.000 | h = −19→19 |
8813 measured reflections | k = −6→5 |
1970 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0381P)2 + 0.4906P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = <0.001 |
1970 reflections | Δρmax = 0.27 e Å−3 |
151 parameters | Δρmin = −0.49 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.06794 (2) | 0.49901 (7) | 0.15921 (3) | 0.01989 (13) | |
O3 | 0.13034 (7) | 0.4330 (3) | 0.25257 (9) | 0.0330 (3) | |
O4 | 0.06022 (8) | 0.8094 (2) | 0.15316 (9) | 0.0323 (3) | |
H4A | 0.0459 (16) | 0.863 (5) | 0.206 (2) | 0.062 (8)* | |
O5 | −0.01632 (7) | 0.3965 (2) | 0.16409 (8) | 0.0305 (3) | |
O6 | 0.09488 (7) | 0.4334 (2) | 0.06186 (8) | 0.0267 (3) | |
C1 | 0.23391 (10) | 0.5726 (3) | 0.51408 (11) | 0.0231 (3) | |
N1 | 0.14196 (8) | 0.5558 (3) | 0.46950 (10) | 0.0249 (3) | |
H1A | 0.1186 | 0.4278 | 0.5022 | 0.037* | |
H1B | 0.1343 | 0.5185 | 0.4010 | 0.037* | |
H1C | 0.1172 | 0.7110 | 0.4783 | 0.037* | |
C2 | 0.28394 (10) | 0.7502 (3) | 0.46987 (12) | 0.0263 (3) | |
C3 | 0.37091 (10) | 0.7522 (3) | 0.51214 (12) | 0.0296 (4) | |
H3 | 0.4067 | 0.8697 | 0.4859 | 0.036* | |
C4 | 0.40429 (10) | 0.5808 (3) | 0.59284 (12) | 0.0282 (3) | |
N2 | 0.49761 (9) | 0.5778 (3) | 0.63155 (11) | 0.0343 (3) | |
O1 | 0.54059 (8) | 0.7464 (3) | 0.59825 (12) | 0.0514 (4) | |
O2 | 0.52842 (8) | 0.4055 (3) | 0.69338 (12) | 0.0499 (4) | |
C5 | 0.35434 (11) | 0.4082 (4) | 0.63746 (13) | 0.0337 (4) | |
H5 | 0.3784 | 0.2960 | 0.6926 | 0.040* | |
C6 | 0.26746 (11) | 0.4075 (4) | 0.59757 (13) | 0.0317 (4) | |
H6 | 0.2316 | 0.2964 | 0.6267 | 0.038* | |
C7 | 0.24754 (12) | 0.9305 (4) | 0.37924 (15) | 0.0398 (4) | |
H7A | 0.1929 | 0.9965 | 0.3882 | 0.060* | |
H7B | 0.2408 | 0.8327 | 0.3143 | 0.060* | |
H7C | 0.2857 | 1.0776 | 0.3773 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0235 (2) | 0.0198 (2) | 0.0169 (2) | 0.00053 (14) | 0.00529 (15) | 0.00030 (13) |
O3 | 0.0331 (7) | 0.0412 (7) | 0.0223 (6) | 0.0060 (5) | −0.0006 (5) | 0.0009 (5) |
O4 | 0.0504 (8) | 0.0205 (6) | 0.0307 (6) | 0.0018 (5) | 0.0194 (6) | −0.0002 (5) |
O5 | 0.0291 (6) | 0.0390 (7) | 0.0247 (6) | −0.0089 (5) | 0.0083 (5) | 0.0009 (5) |
O6 | 0.0320 (6) | 0.0288 (6) | 0.0210 (5) | 0.0041 (5) | 0.0097 (4) | −0.0015 (4) |
C1 | 0.0228 (8) | 0.0260 (8) | 0.0206 (7) | −0.0013 (6) | 0.0041 (6) | −0.0026 (6) |
N1 | 0.0244 (7) | 0.0291 (7) | 0.0213 (6) | 0.0010 (5) | 0.0049 (5) | 0.0019 (5) |
C2 | 0.0317 (8) | 0.0245 (8) | 0.0232 (7) | −0.0006 (6) | 0.0063 (6) | 0.0013 (6) |
C3 | 0.0298 (9) | 0.0305 (8) | 0.0295 (8) | −0.0061 (7) | 0.0080 (7) | 0.0025 (7) |
C4 | 0.0236 (8) | 0.0337 (9) | 0.0265 (8) | −0.0029 (7) | 0.0030 (6) | −0.0023 (7) |
N2 | 0.0269 (7) | 0.0418 (8) | 0.0335 (8) | −0.0035 (6) | 0.0046 (6) | −0.0016 (7) |
O1 | 0.0313 (7) | 0.0636 (10) | 0.0588 (9) | −0.0153 (7) | 0.0074 (6) | 0.0121 (7) |
O2 | 0.0325 (7) | 0.0577 (9) | 0.0553 (8) | 0.0046 (6) | −0.0020 (6) | 0.0174 (7) |
C5 | 0.0303 (9) | 0.0392 (10) | 0.0289 (8) | −0.0026 (7) | −0.0005 (7) | 0.0107 (7) |
C6 | 0.0290 (9) | 0.0373 (9) | 0.0281 (8) | −0.0065 (7) | 0.0042 (7) | 0.0090 (7) |
C7 | 0.0395 (10) | 0.0389 (10) | 0.0382 (10) | −0.0059 (8) | 0.0010 (8) | 0.0145 (8) |
Geometric parameters (Å, º) top
S1—O3 | 1.4434 (11) | C3—C4 | 1.376 (2) |
S1—O6 | 1.4458 (10) | C3—H3 | 0.9300 |
S1—O5 | 1.4511 (11) | C4—C5 | 1.378 (2) |
S1—O4 | 1.5631 (12) | C4—N2 | 1.473 (2) |
O4—H4A | 0.80 (3) | N2—O2 | 1.214 (2) |
C1—C6 | 1.382 (2) | N2—O1 | 1.220 (2) |
C1—C2 | 1.391 (2) | C5—C6 | 1.379 (2) |
C1—N1 | 1.4679 (19) | C5—H5 | 0.9300 |
N1—H1A | 0.8900 | C6—H6 | 0.9300 |
N1—H1B | 0.8900 | C7—H7A | 0.9600 |
N1—H1C | 0.8900 | C7—H7B | 0.9600 |
C2—C3 | 1.386 (2) | C7—H7C | 0.9600 |
C2—C7 | 1.504 (2) | | |
| | | |
O3—S1—O6 | 113.70 (7) | C4—C3—H3 | 120.0 |
O3—S1—O5 | 111.92 (7) | C2—C3—H3 | 120.0 |
O6—S1—O5 | 113.16 (7) | C3—C4—C5 | 122.79 (15) |
O3—S1—O4 | 107.76 (7) | C3—C4—N2 | 118.55 (14) |
O6—S1—O4 | 102.55 (6) | C5—C4—N2 | 118.65 (15) |
O5—S1—O4 | 106.92 (7) | O2—N2—O1 | 122.99 (15) |
S1—O4—H4A | 109.0 (18) | O2—N2—C4 | 118.79 (15) |
C6—C1—C2 | 122.67 (15) | O1—N2—C4 | 118.21 (15) |
C6—C1—N1 | 118.37 (14) | C4—C5—C6 | 117.75 (16) |
C2—C1—N1 | 118.95 (14) | C4—C5—H5 | 121.1 |
C1—N1—H1A | 109.5 | C6—C5—H5 | 121.1 |
C1—N1—H1B | 109.5 | C5—C6—C1 | 119.74 (15) |
H1A—N1—H1B | 109.5 | C5—C6—H6 | 120.1 |
C1—N1—H1C | 109.5 | C1—C6—H6 | 120.1 |
H1A—N1—H1C | 109.5 | C2—C7—H7A | 109.5 |
H1B—N1—H1C | 109.5 | C2—C7—H7B | 109.5 |
C3—C2—C1 | 116.89 (14) | H7A—C7—H7B | 109.5 |
C3—C2—C7 | 120.32 (14) | C2—C7—H7C | 109.5 |
C1—C2—C7 | 122.77 (15) | H7A—C7—H7C | 109.5 |
C4—C3—C2 | 120.10 (15) | H7B—C7—H7C | 109.5 |
| | | |
C6—C1—C2—C3 | 1.2 (2) | C5—C4—N2—O2 | 7.6 (2) |
N1—C1—C2—C3 | −177.76 (13) | C3—C4—N2—O1 | 7.6 (2) |
C6—C1—C2—C7 | −179.81 (16) | C5—C4—N2—O1 | −173.75 (17) |
N1—C1—C2—C7 | 1.2 (2) | C3—C4—C5—C6 | 0.9 (3) |
C1—C2—C3—C4 | 1.0 (2) | N2—C4—C5—C6 | −177.75 (16) |
C7—C2—C3—C4 | −177.94 (16) | C4—C5—C6—C1 | 1.4 (3) |
C2—C3—C4—C5 | −2.1 (3) | C2—C1—C6—C5 | −2.5 (3) |
C2—C3—C4—N2 | 176.49 (14) | N1—C1—C6—C5 | 176.50 (15) |
C3—C4—N2—O2 | −171.08 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O5i | 0.80 (3) | 1.84 (3) | 2.6301 (15) | 165 (3) |
N1—H1A···O6ii | 0.89 | 2.03 | 2.8929 (17) | 162 |
N1—H1B···O3 | 0.89 | 1.96 | 2.8423 (17) | 174 |
N1—H1C···O5i | 0.89 | 2.38 | 2.9246 (17) | 120 |
N1—H1C···O6iii | 0.89 | 2.15 | 2.9853 (17) | 156 |
C3—H3···O1iv | 0.93 | 2.44 | 3.339 (2) | 162 |
C6—H6···O6ii | 0.93 | 2.46 | 3.195 (2) | 136 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+2, −z+1. |
Crystal data top
2(C7H9N2O2)·F6Si | F(000) = 920 |
Mr = 448.41 | Dx = 1.588 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1643 (3) Å | Cell parameters from 4034 reflections |
b = 10.2128 (4) Å | θ = 2.1–26.9° |
c = 29.8240 (16) Å | µ = 0.21 mm−1 |
β = 92.439 (4)° | T = 295 K |
V = 1875.85 (16) Å3 | Plate, yellow |
Z = 4 | 0.79 × 0.45 × 0.02 mm |
Data collection top
KUMA KM-4 with area CCD detector diffractometer | 2877 reflections with I > 2σ(I) |
ω–scan | Rint = 0.040 |
Absorption correction: gaussian CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.9°, θmin = 2.1° |
Tmin = 0.906, Tmax = 0.997 | h = −7→7 |
24281 measured reflections | k = −12→13 |
4034 independent reflections | l = −37→37 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | Only H-atom coordinates refined |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.9712P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = <0.001 |
4034 reflections | Δρmax = 0.35 e Å−3 |
269 parameters | Δρmin = −0.29 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Si1A | 0.5000 | 1.0000 | 0.0000 | 0.0309 (2) | |
F1A | 0.6859 (2) | 1.09680 (14) | 0.02530 (5) | 0.0529 (4) | |
F2A | 0.4057 (2) | 0.96016 (15) | 0.05019 (4) | 0.0519 (4) | |
F3A | 0.6738 (2) | 0.87212 (14) | 0.00348 (5) | 0.0600 (4) | |
Si1B | 0.0000 | 0.5000 | 0.0000 | 0.0318 (2) | |
F1B | −0.0409 (3) | 0.36342 (14) | 0.02863 (6) | 0.0666 (5) | |
F2B | 0.2081 (3) | 0.42663 (15) | −0.02408 (5) | 0.0652 (5) | |
F3B | 0.1695 (3) | 0.55403 (17) | 0.04110 (6) | 0.0847 (6) | |
C1A | 0.9953 (3) | 0.8479 (2) | 0.10697 (7) | 0.0349 (5) | |
N1A | 1.0368 (3) | 0.81848 (19) | 0.05964 (6) | 0.0408 (4) | |
H1A1 | 0.9240 | 0.8445 | 0.0423 | 0.061* | |
H1A2 | 1.0558 | 0.7327 | 0.0564 | 0.061* | |
H1A3 | 1.1557 | 0.8606 | 0.0517 | 0.061* | |
C2A | 1.1240 (4) | 0.7907 (2) | 0.14093 (7) | 0.0389 (5) | |
C3A | 1.0796 (4) | 0.8239 (2) | 0.18484 (7) | 0.0406 (5) | |
H3A | 1.1593 | 0.7861 | 0.2087 | 0.049* | |
C4A | 0.9181 (4) | 0.9126 (2) | 0.19305 (7) | 0.0385 (5) | |
N2A | 0.8829 (3) | 0.9517 (2) | 0.23979 (7) | 0.0475 (5) | |
O1A | 0.9724 (3) | 0.8876 (2) | 0.26990 (6) | 0.0578 (5) | |
O2A | 0.7681 (3) | 1.0461 (2) | 0.24623 (7) | 0.0716 (6) | |
C5A | 0.7916 (4) | 0.9686 (3) | 0.15919 (8) | 0.0497 (6) | |
H5A | 0.6819 | 1.0275 | 0.1655 | 0.060* | |
C6A | 0.8326 (4) | 0.9347 (2) | 0.11562 (8) | 0.0478 (6) | |
H6A | 0.7495 | 0.9709 | 0.0920 | 0.057* | |
C7A | 1.3064 (5) | 0.6981 (3) | 0.13207 (9) | 0.0682 (8) | |
H7A1 | 1.2480 | 0.6176 | 0.1201 | 0.102* | |
H7A2 | 1.3876 | 0.6807 | 0.1596 | 0.102* | |
H7A3 | 1.4001 | 0.7367 | 0.1108 | 0.102* | |
N1B | 0.5134 (3) | 0.34784 (18) | 0.05360 (6) | 0.0413 (4) | |
H1B1 | 0.4205 | 0.4100 | 0.0445 | 0.062* | |
H1B2 | 0.4936 | 0.2770 | 0.0365 | 0.062* | |
H1B3 | 0.6487 | 0.3768 | 0.0514 | 0.062* | |
C1B | 0.4761 (3) | 0.3143 (2) | 0.10070 (7) | 0.0351 (5) | |
C2B | 0.5978 (4) | 0.3735 (2) | 0.13517 (7) | 0.0380 (5) | |
C3B | 0.5565 (4) | 0.3347 (2) | 0.17880 (7) | 0.0400 (5) | |
H3B | 0.6315 | 0.3734 | 0.2031 | 0.048* | |
C4B | 0.4045 (3) | 0.2392 (2) | 0.18591 (7) | 0.0371 (5) | |
N2B | 0.3732 (3) | 0.1952 (2) | 0.23243 (7) | 0.0465 (5) | |
O1B | 0.4557 (3) | 0.25986 (19) | 0.26303 (5) | 0.0528 (4) | |
O2B | 0.2690 (3) | 0.0962 (2) | 0.23778 (7) | 0.0745 (6) | |
C5B | 0.2831 (4) | 0.1819 (2) | 0.15133 (8) | 0.0465 (6) | |
H5B | 0.1796 | 0.1185 | 0.1570 | 0.056* | |
C6B | 0.3194 (4) | 0.2213 (2) | 0.10815 (8) | 0.0442 (5) | |
H6B | 0.2386 | 0.1855 | 0.0841 | 0.053* | |
C7B | 0.7692 (5) | 0.4754 (3) | 0.12784 (9) | 0.0598 (7) | |
H7B1 | 0.8921 | 0.4350 | 0.1148 | 0.090* | |
H7B2 | 0.8136 | 0.5141 | 0.1561 | 0.090* | |
H7B3 | 0.7112 | 0.5419 | 0.1080 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1A | 0.0311 (4) | 0.0315 (4) | 0.0300 (4) | −0.0014 (3) | −0.0012 (3) | 0.0005 (3) |
F1A | 0.0536 (8) | 0.0572 (8) | 0.0469 (8) | −0.0194 (7) | −0.0102 (6) | −0.0016 (7) |
F2A | 0.0517 (8) | 0.0703 (9) | 0.0339 (7) | −0.0141 (7) | 0.0028 (6) | 0.0058 (6) |
F3A | 0.0651 (9) | 0.0558 (9) | 0.0579 (9) | 0.0264 (7) | −0.0101 (7) | −0.0063 (7) |
Si1B | 0.0363 (4) | 0.0282 (4) | 0.0312 (4) | −0.0015 (3) | 0.0025 (3) | −0.0009 (3) |
F1B | 0.0843 (11) | 0.0439 (8) | 0.0739 (11) | 0.0074 (8) | 0.0286 (9) | 0.0221 (7) |
F2B | 0.0688 (10) | 0.0559 (9) | 0.0733 (11) | 0.0188 (8) | 0.0321 (8) | 0.0060 (8) |
F3B | 0.0956 (13) | 0.0616 (10) | 0.0921 (13) | 0.0131 (9) | −0.0518 (11) | −0.0289 (10) |
C1A | 0.0366 (11) | 0.0377 (11) | 0.0303 (11) | −0.0062 (9) | −0.0008 (9) | −0.0018 (9) |
N1A | 0.0450 (11) | 0.0445 (11) | 0.0325 (10) | −0.0051 (8) | −0.0016 (8) | −0.0035 (8) |
C2A | 0.0406 (12) | 0.0385 (12) | 0.0370 (12) | 0.0032 (9) | −0.0045 (9) | −0.0039 (10) |
C3A | 0.0452 (13) | 0.0422 (12) | 0.0334 (12) | 0.0034 (10) | −0.0069 (9) | 0.0020 (10) |
C4A | 0.0372 (12) | 0.0459 (12) | 0.0326 (11) | −0.0042 (10) | 0.0022 (9) | −0.0029 (10) |
N2A | 0.0407 (11) | 0.0641 (14) | 0.0377 (11) | −0.0061 (10) | 0.0030 (9) | −0.0061 (10) |
O1A | 0.0512 (10) | 0.0868 (14) | 0.0353 (9) | −0.0074 (10) | −0.0006 (8) | 0.0033 (9) |
O2A | 0.0703 (13) | 0.0864 (15) | 0.0583 (12) | 0.0219 (11) | 0.0045 (10) | −0.0235 (11) |
C5A | 0.0427 (13) | 0.0616 (16) | 0.0442 (14) | 0.0158 (11) | −0.0038 (11) | −0.0033 (12) |
C6A | 0.0481 (14) | 0.0570 (15) | 0.0371 (13) | 0.0101 (11) | −0.0101 (10) | 0.0006 (11) |
C7A | 0.0741 (19) | 0.078 (2) | 0.0514 (16) | 0.0353 (16) | −0.0146 (14) | −0.0168 (15) |
N1B | 0.0501 (11) | 0.0422 (10) | 0.0316 (10) | 0.0021 (9) | 0.0032 (8) | 0.0009 (8) |
C1B | 0.0376 (11) | 0.0365 (11) | 0.0315 (11) | 0.0070 (9) | 0.0043 (9) | 0.0028 (9) |
C2B | 0.0377 (12) | 0.0400 (12) | 0.0362 (12) | −0.0016 (9) | 0.0016 (9) | 0.0001 (9) |
C3B | 0.0399 (12) | 0.0466 (13) | 0.0333 (12) | −0.0030 (10) | −0.0003 (9) | −0.0039 (10) |
C4B | 0.0361 (11) | 0.0434 (12) | 0.0321 (11) | 0.0010 (9) | 0.0040 (9) | 0.0015 (9) |
N2B | 0.0428 (11) | 0.0575 (13) | 0.0395 (11) | 0.0002 (10) | 0.0050 (9) | 0.0057 (10) |
O1B | 0.0516 (10) | 0.0731 (12) | 0.0333 (9) | 0.0028 (9) | −0.0013 (7) | −0.0019 (8) |
O2B | 0.0834 (15) | 0.0844 (15) | 0.0556 (12) | −0.0376 (12) | 0.0035 (10) | 0.0193 (11) |
C5B | 0.0480 (14) | 0.0505 (14) | 0.0413 (13) | −0.0139 (11) | 0.0048 (10) | −0.0011 (11) |
C6B | 0.0482 (13) | 0.0492 (13) | 0.0350 (12) | −0.0069 (11) | −0.0014 (10) | −0.0063 (10) |
C7B | 0.0647 (17) | 0.0689 (18) | 0.0460 (15) | −0.0249 (14) | 0.0037 (13) | 0.0053 (13) |
Geometric parameters (Å, º) top
Si1A—F1A | 1.6694 (12) | C5A—C6A | 1.378 (3) |
Si1A—F1Ai | 1.6694 (12) | C5A—H5A | 0.9300 |
Si1A—F2Ai | 1.6786 (13) | C6A—H6A | 0.9300 |
Si1A—F2A | 1.6787 (12) | C7A—H7A1 | 0.9600 |
Si1A—F3A | 1.6894 (13) | C7A—H7A2 | 0.9600 |
Si1A—F3Ai | 1.6895 (13) | C7A—H7A3 | 0.9600 |
Si1B—F1Bii | 1.6603 (14) | N1B—C1B | 1.473 (3) |
Si1B—F1B | 1.6603 (14) | N1B—H1B1 | 0.8900 |
Si1B—F3B | 1.6701 (15) | N1B—H1B2 | 0.8900 |
Si1B—F3Bii | 1.6702 (15) | N1B—H1B3 | 0.8900 |
Si1B—F2B | 1.6739 (13) | C1B—C6B | 1.379 (3) |
Si1B—F2Bii | 1.6739 (13) | C1B—C2B | 1.386 (3) |
C1A—C6A | 1.372 (3) | C2B—C3B | 1.394 (3) |
C1A—C2A | 1.389 (3) | C2B—C7B | 1.505 (3) |
C1A—N1A | 1.476 (3) | C3B—C4B | 1.376 (3) |
N1A—H1A1 | 0.8900 | C3B—H3B | 0.9300 |
N1A—H1A2 | 0.8900 | C4B—C5B | 1.378 (3) |
N1A—H1A3 | 0.8900 | C4B—N2B | 1.478 (3) |
C2A—C3A | 1.391 (3) | N2B—O2B | 1.212 (3) |
C2A—C7A | 1.501 (3) | N2B—O1B | 1.220 (3) |
C3A—C4A | 1.376 (3) | C5B—C6B | 1.376 (3) |
C3A—H3A | 0.9300 | C5B—H5B | 0.9300 |
C4A—C5A | 1.374 (3) | C6B—H6B | 0.9300 |
C4A—N2A | 1.475 (3) | C7B—H7B1 | 0.9600 |
N2A—O2A | 1.215 (3) | C7B—H7B2 | 0.9600 |
N2A—O1A | 1.224 (3) | C7B—H7B3 | 0.9600 |
| | | |
F1A—Si1A—F1Ai | 180.0 | O2A—N2A—O1A | 123.8 (2) |
F1A—Si1A—F2Ai | 90.14 (7) | O2A—N2A—C4A | 118.3 (2) |
F1Ai—Si1A—F2Ai | 89.86 (7) | O1A—N2A—C4A | 117.9 (2) |
F1A—Si1A—F2A | 89.86 (7) | C4A—C5A—C6A | 117.9 (2) |
F1Ai—Si1A—F2A | 90.14 (7) | C4A—C5A—H5A | 121.1 |
F2Ai—Si1A—F2A | 180.0 | C6A—C5A—H5A | 121.1 |
F1A—Si1A—F3A | 90.50 (7) | C1A—C6A—C5A | 120.3 (2) |
F1Ai—Si1A—F3A | 89.50 (7) | C1A—C6A—H6A | 119.9 |
F2Ai—Si1A—F3A | 89.97 (8) | C5A—C6A—H6A | 119.9 |
F2A—Si1A—F3A | 90.03 (8) | C2A—C7A—H7A1 | 109.5 |
F1A—Si1A—F3Ai | 89.50 (7) | C2A—C7A—H7A2 | 109.5 |
F1Ai—Si1A—F3Ai | 90.50 (7) | H7A1—C7A—H7A2 | 109.5 |
F2Ai—Si1A—F3Ai | 90.03 (8) | C2A—C7A—H7A3 | 109.5 |
F2A—Si1A—F3Ai | 89.97 (8) | H7A1—C7A—H7A3 | 109.5 |
F3A—Si1A—F3Ai | 180.0 | H7A2—C7A—H7A3 | 109.5 |
F1Bii—Si1B—F1B | 180.0 | C1B—N1B—H1B1 | 109.5 |
F1Bii—Si1B—F3B | 89.76 (10) | C1B—N1B—H1B2 | 109.5 |
F1B—Si1B—F3B | 90.23 (10) | H1B1—N1B—H1B2 | 109.5 |
F1Bii—Si1B—F3Bii | 90.23 (10) | C1B—N1B—H1B3 | 109.5 |
F1B—Si1B—F3Bii | 89.77 (10) | H1B1—N1B—H1B3 | 109.5 |
F3B—Si1B—F3Bii | 180.0 | H1B2—N1B—H1B3 | 109.5 |
F1Bii—Si1B—F2B | 91.11 (7) | C6B—C1B—C2B | 122.8 (2) |
F1B—Si1B—F2B | 88.89 (7) | C6B—C1B—N1B | 116.91 (19) |
F3B—Si1B—F2B | 89.77 (9) | C2B—C1B—N1B | 120.27 (19) |
F3Bii—Si1B—F2B | 90.23 (9) | C1B—C2B—C3B | 117.0 (2) |
F1Bii—Si1B—F2Bii | 88.89 (7) | C1B—C2B—C7B | 123.7 (2) |
F1B—Si1B—F2Bii | 91.11 (7) | C3B—C2B—C7B | 119.3 (2) |
F3B—Si1B—F2Bii | 90.23 (9) | C4B—C3B—C2B | 119.9 (2) |
F3Bii—Si1B—F2Bii | 89.78 (9) | C4B—C3B—H3B | 120.1 |
F2B—Si1B—F2Bii | 180.0 | C2B—C3B—H3B | 120.1 |
C6A—C1A—C2A | 122.3 (2) | C3B—C4B—C5B | 122.5 (2) |
C6A—C1A—N1A | 118.00 (19) | C3B—C4B—N2B | 118.5 (2) |
C2A—C1A—N1A | 119.66 (19) | C5B—C4B—N2B | 119.0 (2) |
C1A—N1A—H1A1 | 109.5 | O2B—N2B—O1B | 124.0 (2) |
C1A—N1A—H1A2 | 109.5 | O2B—N2B—C4B | 117.9 (2) |
H1A1—N1A—H1A2 | 109.5 | O1B—N2B—C4B | 118.1 (2) |
C1A—N1A—H1A3 | 109.5 | C6B—C5B—C4B | 118.1 (2) |
H1A1—N1A—H1A3 | 109.5 | C6B—C5B—H5B | 120.9 |
H1A2—N1A—H1A3 | 109.5 | C4B—C5B—H5B | 120.9 |
C1A—C2A—C3A | 117.1 (2) | C5B—C6B—C1B | 119.6 (2) |
C1A—C2A—C7A | 123.1 (2) | C5B—C6B—H6B | 120.2 |
C3A—C2A—C7A | 119.9 (2) | C1B—C6B—H6B | 120.2 |
C4A—C3A—C2A | 120.0 (2) | C2B—C7B—H7B1 | 109.5 |
C4A—C3A—H3A | 120.0 | C2B—C7B—H7B2 | 109.5 |
C2A—C3A—H3A | 120.0 | H7B1—C7B—H7B2 | 109.5 |
C5A—C4A—C3A | 122.4 (2) | C2B—C7B—H7B3 | 109.5 |
C5A—C4A—N2A | 118.7 (2) | H7B1—C7B—H7B3 | 109.5 |
C3A—C4A—N2A | 118.9 (2) | H7B2—C7B—H7B3 | 109.5 |
| | | |
C6A—C1A—C2A—C3A | 0.8 (3) | C6B—C1B—C2B—C3B | 0.3 (3) |
N1A—C1A—C2A—C3A | 178.89 (19) | N1B—C1B—C2B—C3B | −178.68 (19) |
C6A—C1A—C2A—C7A | −178.4 (2) | C6B—C1B—C2B—C7B | −179.8 (2) |
N1A—C1A—C2A—C7A | −0.3 (3) | N1B—C1B—C2B—C7B | 1.2 (3) |
C1A—C2A—C3A—C4A | −1.7 (3) | C1B—C2B—C3B—C4B | 1.7 (3) |
C7A—C2A—C3A—C4A | 177.5 (2) | C7B—C2B—C3B—C4B | −178.2 (2) |
C2A—C3A—C4A—C5A | 1.8 (4) | C2B—C3B—C4B—C5B | −2.4 (3) |
C2A—C3A—C4A—N2A | −176.5 (2) | C2B—C3B—C4B—N2B | 176.7 (2) |
C5A—C4A—N2A—O2A | −11.3 (3) | C3B—C4B—N2B—O2B | −167.1 (2) |
C3A—C4A—N2A—O2A | 167.1 (2) | C5B—C4B—N2B—O2B | 12.0 (3) |
C5A—C4A—N2A—O1A | 169.2 (2) | C3B—C4B—N2B—O1B | 12.1 (3) |
C3A—C4A—N2A—O1A | −12.4 (3) | C5B—C4B—N2B—O1B | −168.8 (2) |
C3A—C4A—C5A—C6A | −0.9 (4) | C3B—C4B—C5B—C6B | 1.1 (4) |
N2A—C4A—C5A—C6A | 177.5 (2) | N2B—C4B—C5B—C6B | −178.0 (2) |
C2A—C1A—C6A—C5A | 0.1 (4) | C4B—C5B—C6B—C1B | 0.9 (4) |
N1A—C1A—C6A—C5A | −178.0 (2) | C2B—C1B—C6B—C5B | −1.6 (3) |
C4A—C5A—C6A—C1A | −0.1 (4) | N1B—C1B—C6B—C5B | 177.4 (2) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···F3A | 0.89 | 1.91 | 2.792 (2) | 171 |
N1A—H1A2···F2Biii | 0.89 | 2.47 | 3.088 (2) | 127 |
N1A—H1A2···F3Biv | 0.89 | 2.01 | 2.882 (3) | 165 |
N1A—H1A3···F1Av | 0.89 | 2.57 | 3.234 (2) | 132 |
N1A—H1A3···F2Aiv | 0.89 | 1.85 | 2.720 (2) | 166 |
C3A—H3A···O1Bvi | 0.93 | 2.50 | 3.266 (3) | 140 |
C6A—H6A···F1A | 0.93 | 2.39 | 3.256 (3) | 156 |
C6A—H6A···F2A | 0.93 | 2.42 | 3.219 (3) | 145 |
N1B—H1B1···F2B | 0.89 | 2.39 | 3.031 (2) | 130 |
N1B—H1B1···F3B | 0.89 | 2.13 | 3.000 (3) | 164 |
N1B—H1B2···F1Avii | 0.89 | 2.22 | 2.914 (2) | 134 |
N1B—H1B2···F3Aiii | 0.89 | 2.17 | 3.018 (2) | 159 |
N1B—H1B3···F1Biv | 0.89 | 2.06 | 2.881 (2) | 153 |
N1B—H1B3···F2Biii | 0.89 | 2.35 | 3.026 (2) | 133 |
C3B—H3B···O1Aviii | 0.93 | 2.54 | 3.269 (3) | 135 |
Symmetry codes: (iii) −x+1, −y+1, −z; (iv) x+1, y, z; (v) −x+2, −y+2, −z; (vi) −x+2, y+1/2, −z+1/2; (vii) x, y−1, z; (viii) −x+2, y−1/2, −z+1/2. |
Crystal data top
2(C7H9N2O2)·F6Si·2(H2O | F(000) = 500 |
Mr = 242.22 | Dx = 1.536 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.0445 (8) Å | Cell parameters from 1555 reflections |
b = 8.8682 (4) Å | θ = 2.7–23.5° |
c = 8.1133 (4) Å | µ = 0.20 mm−1 |
β = 104.638 (5)° | T = 295 K |
V = 1047.32 (9) Å3 | Plate, yellow |
Z = 4 | 0.32 × 0.29 × 0.01 mm |
Data collection top
KUMA KM-4 with area CCD detector diffractometer | 1117 reflections with I > 2σ(I) |
ω–scan | Rint = 0.046 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 23.5°, θmin = 2.7° |
Tmin = 0.681, Tmax = 1.000 | h = −16→16 |
8200 measured reflections | k = −9→9 |
1555 independent reflections | l = −8→9 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.4536P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = <0.001 |
1555 reflections | Δρmax = 0.28 e Å−3 |
150 parameters | Δρmin = −0.24 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Si1 | 0.0000 | 0.0000 | 0.5000 | 0.0362 (3) | |
F1 | 0.06765 (12) | 0.14276 (19) | 0.5961 (2) | 0.0531 (5) | |
F2 | −0.00753 (12) | 0.0786 (2) | 0.3116 (2) | 0.0572 (6) | |
F3 | 0.09301 (12) | −0.09649 (19) | 0.4815 (2) | 0.0561 (5) | |
C1 | 0.22639 (19) | 0.3269 (3) | 0.4282 (3) | 0.0390 (7) | |
N1 | 0.13715 (16) | 0.3805 (3) | 0.4478 (3) | 0.0445 (7) | |
H1A | 0.1023 | 0.4089 | 0.3468 | 0.067* | |
H1B | 0.1458 | 0.4587 | 0.5189 | 0.067* | |
H1C | 0.1093 | 0.3066 | 0.4894 | 0.067* | |
C2 | 0.2905 (2) | 0.4294 (4) | 0.4027 (4) | 0.0509 (9) | |
C3 | 0.3720 (2) | 0.3692 (5) | 0.3811 (4) | 0.0643 (11) | |
H3 | 0.4183 | 0.4333 | 0.3664 | 0.077* | |
C4 | 0.3847 (2) | 0.2168 (5) | 0.3813 (4) | 0.0571 (10) | |
N2 | 0.4714 (3) | 0.1580 (6) | 0.3516 (5) | 0.0897 (12) | |
O1 | 0.5362 (2) | 0.2402 (5) | 0.3735 (6) | 0.159 (2) | |
O2 | 0.4730 (2) | 0.0260 (5) | 0.3111 (5) | 0.1256 (14) | |
C5 | 0.3205 (2) | 0.1170 (4) | 0.4047 (4) | 0.0625 (10) | |
H5 | 0.3307 | 0.0136 | 0.4042 | 0.075* | |
C6 | 0.2400 (2) | 0.1739 (4) | 0.4290 (4) | 0.0524 (9) | |
H6 | 0.1947 | 0.1088 | 0.4461 | 0.063* | |
C7 | 0.2733 (3) | 0.5961 (4) | 0.3940 (6) | 0.0899 (14) | |
H7A | 0.2141 | 0.6161 | 0.3191 | 0.135* | |
H7B | 0.3199 | 0.6453 | 0.3516 | 0.135* | |
H7C | 0.2750 | 0.6335 | 0.5058 | 0.135* | |
O1W | 0.1241 (3) | 0.6204 (3) | 0.6491 (4) | 0.0857 (10) | |
H1W | 0.108 (3) | 0.701 (3) | 0.603 (6) | 0.128* | |
H2W | 0.111 (3) | 0.615 (6) | 0.741 (4) | 0.128* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0424 (7) | 0.0312 (7) | 0.0370 (6) | −0.0035 (6) | 0.0141 (5) | 0.0008 (5) |
F1 | 0.0622 (12) | 0.0470 (11) | 0.0527 (11) | −0.0182 (9) | 0.0190 (9) | −0.0097 (9) |
F2 | 0.0778 (14) | 0.0544 (12) | 0.0422 (10) | −0.0057 (10) | 0.0204 (9) | 0.0108 (9) |
F3 | 0.0522 (11) | 0.0475 (11) | 0.0749 (13) | 0.0078 (9) | 0.0280 (9) | 0.0042 (9) |
C1 | 0.0346 (18) | 0.046 (2) | 0.0368 (17) | −0.0039 (15) | 0.0097 (14) | 0.0006 (14) |
N1 | 0.0471 (16) | 0.0453 (15) | 0.0422 (14) | −0.0032 (13) | 0.0132 (12) | 0.0035 (12) |
C2 | 0.045 (2) | 0.053 (2) | 0.055 (2) | −0.0097 (17) | 0.0124 (16) | 0.0094 (17) |
C3 | 0.042 (2) | 0.081 (3) | 0.072 (3) | −0.012 (2) | 0.0180 (18) | 0.017 (2) |
C4 | 0.039 (2) | 0.082 (3) | 0.054 (2) | 0.011 (2) | 0.0173 (16) | 0.009 (2) |
N2 | 0.056 (3) | 0.122 (4) | 0.097 (3) | 0.022 (3) | 0.032 (2) | 0.028 (3) |
O1 | 0.058 (2) | 0.154 (4) | 0.284 (6) | 0.012 (2) | 0.075 (3) | 0.051 (4) |
O2 | 0.100 (3) | 0.147 (4) | 0.146 (3) | 0.039 (3) | 0.061 (2) | −0.020 (3) |
C5 | 0.060 (2) | 0.057 (2) | 0.077 (3) | 0.003 (2) | 0.028 (2) | −0.003 (2) |
C6 | 0.047 (2) | 0.050 (2) | 0.064 (2) | −0.0071 (18) | 0.0225 (17) | −0.0045 (17) |
C7 | 0.078 (3) | 0.057 (3) | 0.141 (4) | −0.013 (2) | 0.040 (3) | 0.024 (3) |
O1W | 0.155 (3) | 0.0443 (16) | 0.076 (2) | 0.0150 (17) | 0.064 (2) | 0.0115 (14) |
Geometric parameters (Å, º) top
Si1—F2i | 1.6577 (16) | C3—C4 | 1.365 (5) |
Si1—F2 | 1.6577 (16) | C3—H3 | 0.9300 |
Si1—F3i | 1.6789 (17) | C4—C5 | 1.359 (5) |
Si1—F3 | 1.6790 (17) | C4—N2 | 1.480 (5) |
Si1—F1 | 1.6868 (16) | N2—O1 | 1.193 (5) |
Si1—F1i | 1.6868 (16) | N2—O2 | 1.217 (5) |
C1—C6 | 1.372 (4) | C5—C6 | 1.371 (4) |
C1—C2 | 1.378 (4) | C5—H5 | 0.9300 |
C1—N1 | 1.470 (3) | C6—H6 | 0.9300 |
N1—H1A | 0.8900 | C7—H7A | 0.9600 |
N1—H1B | 0.8900 | C7—H7B | 0.9600 |
N1—H1C | 0.8900 | C7—H7C | 0.9600 |
C2—C3 | 1.389 (5) | O1W—H1W | 0.819 (19) |
C2—C7 | 1.499 (5) | O1W—H2W | 0.818 (19) |
| | | |
F2i—Si1—F2 | 180.0 | C1—C2—C7 | 122.6 (3) |
F2i—Si1—F3i | 89.78 (9) | C3—C2—C7 | 121.3 (3) |
F2—Si1—F3i | 90.22 (9) | C4—C3—C2 | 120.6 (3) |
F2i—Si1—F3 | 90.22 (9) | C4—C3—H3 | 119.7 |
F2—Si1—F3 | 89.78 (9) | C2—C3—H3 | 119.7 |
F3i—Si1—F3 | 180.0 | C5—C4—C3 | 122.7 (3) |
F2i—Si1—F1 | 89.81 (8) | C5—C4—N2 | 118.7 (4) |
F2—Si1—F1 | 90.19 (8) | C3—C4—N2 | 118.6 (4) |
F3i—Si1—F1 | 89.73 (9) | O1—N2—O2 | 123.8 (4) |
F3—Si1—F1 | 90.27 (9) | O1—N2—C4 | 118.7 (5) |
F2i—Si1—F1i | 90.19 (8) | O2—N2—C4 | 117.4 (4) |
F2—Si1—F1i | 89.81 (8) | C4—C5—C6 | 117.7 (3) |
F3i—Si1—F1i | 90.27 (9) | C4—C5—H5 | 121.1 |
F3—Si1—F1i | 89.73 (9) | C6—C5—H5 | 121.1 |
F1—Si1—F1i | 180.0 | C5—C6—C1 | 120.0 (3) |
C6—C1—C2 | 122.9 (3) | C5—C6—H6 | 120.0 |
C6—C1—N1 | 117.3 (3) | C1—C6—H6 | 120.0 |
C2—C1—N1 | 119.7 (3) | C2—C7—H7A | 109.5 |
C1—N1—H1A | 109.5 | C2—C7—H7B | 109.5 |
C1—N1—H1B | 109.5 | H7A—C7—H7B | 109.5 |
H1A—N1—H1B | 109.5 | C2—C7—H7C | 109.5 |
C1—N1—H1C | 109.5 | H7A—C7—H7C | 109.5 |
H1A—N1—H1C | 109.5 | H7B—C7—H7C | 109.5 |
H1B—N1—H1C | 109.5 | H1W—O1W—H2W | 111 (5) |
C1—C2—C3 | 116.0 (3) | | |
| | | |
C6—C1—C2—C3 | −1.4 (5) | C3—C4—N2—O1 | 19.7 (6) |
N1—C1—C2—C3 | −178.4 (3) | C5—C4—N2—O2 | 16.4 (6) |
C6—C1—C2—C7 | 177.1 (4) | C3—C4—N2—O2 | −162.5 (4) |
N1—C1—C2—C7 | 0.1 (5) | C3—C4—C5—C6 | 0.0 (5) |
C1—C2—C3—C4 | 1.7 (5) | N2—C4—C5—C6 | −178.9 (3) |
C7—C2—C3—C4 | −176.8 (4) | C4—C5—C6—C1 | 0.4 (5) |
C2—C3—C4—C5 | −1.0 (6) | C2—C1—C6—C5 | 0.4 (5) |
C2—C3—C4—N2 | 177.8 (3) | N1—C1—C6—C5 | 177.5 (3) |
C5—C4—N2—O1 | −161.4 (4) | | |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···F1ii | 0.89 | 2.02 | 2.787 (3) | 144 |
N1—H1A···F2iii | 0.89 | 2.24 | 3.040 (3) | 149 |
N1—H1B···O1W | 0.89 | 1.86 | 2.719 (4) | 162 |
N1—H1C···F1 | 0.89 | 1.88 | 2.761 (3) | 172 |
C3—H3···O2iv | 0.93 | 2.57 | 3.412 (5) | 151 |
C6—H6···F1 | 0.93 | 2.53 | 3.227 (4) | 132 |
C6—H6···F3 | 0.93 | 2.44 | 3.361 (4) | 170 |
O1W—H1W···F3v | 0.819 (19) | 2.03 (2) | 2.837 (3) | 168 (5) |
O1W—H2W···F3vi | 0.818 (19) | 2.04 (2) | 2.859 (3) | 174 (5) |
Symmetry codes: (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, y+1, z; (vi) x, −y+1/2, z+1/2. |