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The search for new tuberculostatics is important considering the occurrence of drug-resistant strains of Mycobacterium tuberculosis. Three polymorphs of N′-(1,3-dithiolan-2-ylidene)-4-nitrobenzohydrazide (a potentially tuberculostatic agent), C10H9N3O3S2, denoted (I1), (I2) and (I3), and the monohydrate of this compound, C10H9N3O3S2·H2O, (I4), have been characterized by single-crystal X-ray diffraction. The conformations of the molecules in all these structures are very similar. Structures (I1), (I2) and (I3) provide an example of packing polymorphism resulting from different intermolecular interactions.
Supporting information
CCDC references: 1571916; 1571915; 1571914; 1571913
Data collection: APEX2 (Bruker, 2002) for I2, I3, I4. Cell refinement: SAINT-Plus (Bruker, 2003) for I2, I3, I4. Data reduction: SAINT-Plus (Bruker, 2003) for I2, I3, I4. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for I2, I3, I4. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015) for I1; SHELXL97 (Sheldrick, 2008) for I2, I3, I4. Molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006) for I2, I3, I4. Software used to prepare material for publication: PLATON (Spek, 2009) for I2, I3, I4.
Crystal data top
C10H9N3O3S2 | F(000) = 584 |
Mr = 283.32 | Dx = 1.670 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 15.0609 (2) Å | Cell parameters from 9917 reflections |
b = 5.0408 (1) Å | θ = 3.2–70.6° |
c = 16.0954 (2) Å | µ = 4.36 mm−1 |
β = 112.72° | T = 100 K |
V = 1127.14 (3) Å3 | Needle, colourless |
Z = 4 | 0.56 × 0.05 × 0.04 mm |
Data collection top
Bruker SMART APEXII CCD diffractometer | 2105 reflections with I > 2σ(I) |
ω scan | Rint = 0.023 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | θmax = 70.6°, θmin = 3.2° |
Tmin = 0.749, Tmax = 1.000 | h = −18→17 |
12799 measured reflections | k = −6→6 |
2142 independent reflections | l = −19→19 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0324P)2 + 0.8787P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2142 reflections | Δρmax = 0.36 e Å−3 |
166 parameters | Δρmin = −0.25 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 | |
C1 | 0.23701 (9) | 0.9478 (3) | 0.45401 (8) | 0.0108 (3) | |
C4 | 0.46277 (9) | 0.7061 (3) | 0.58175 (8) | 0.0104 (3) | |
C11 | 0.09051 (9) | 1.2146 (3) | 0.46177 (9) | 0.0144 (3) | |
H11A | 0.070839 | 1.093472 | 0.498313 | 0.017* | |
H11B | 0.062270 | 1.386985 | 0.462615 | 0.017* | |
C21 | 0.05734 (9) | 1.1120 (3) | 0.36573 (9) | 0.0142 (3) | |
H21A | 0.064639 | 1.248702 | 0.326415 | 0.017* | |
H21B | −0.009904 | 1.060827 | 0.343872 | 0.017* | |
C41 | 0.55798 (9) | 0.8016 (3) | 0.64870 (8) | 0.0103 (3) | |
C42 | 0.63923 (9) | 0.6575 (3) | 0.65369 (8) | 0.0123 (3) | |
H42 | 0.632583 | 0.512557 | 0.616009 | 0.015* | |
C43 | 0.72944 (9) | 0.7302 (3) | 0.71459 (9) | 0.0126 (3) | |
H43 | 0.783968 | 0.636233 | 0.718265 | 0.015* | |
C44 | 0.73666 (9) | 0.9464 (3) | 0.77000 (8) | 0.0114 (3) | |
C45 | 0.65751 (9) | 1.0907 (3) | 0.76768 (8) | 0.0128 (3) | |
H45 | 0.664583 | 1.232831 | 0.806564 | 0.015* | |
C46 | 0.56734 (9) | 1.0177 (3) | 0.70581 (8) | 0.0122 (3) | |
H46 | 0.513110 | 1.112714 | 0.702388 | 0.015* | |
N2 | 0.31362 (8) | 0.8127 (2) | 0.47039 (7) | 0.0123 (2) | |
N3 | 0.39653 (7) | 0.8970 (2) | 0.54177 (7) | 0.0115 (2) | |
H3 | 0.4115 (11) | 1.060 (4) | 0.5492 (11) | 0.014* | |
N4 | 0.83275 (7) | 1.0254 (2) | 0.83377 (7) | 0.0139 (2) | |
O5 | 0.44738 (6) | 0.46871 (18) | 0.56594 (6) | 0.0139 (2) | |
O41 | 0.90200 (6) | 0.8870 (2) | 0.83924 (6) | 0.0193 (2) | |
O42 | 0.83989 (7) | 1.2271 (2) | 0.87863 (7) | 0.0224 (2) | |
S1 | 0.22099 (2) | 1.23996 (6) | 0.50580 (2) | 0.01251 (10) | |
S2 | 0.13160 (2) | 0.82734 (6) | 0.36729 (2) | 0.01382 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0105 (6) | 0.0108 (6) | 0.0115 (6) | −0.0020 (5) | 0.0046 (5) | 0.0000 (5) |
C4 | 0.0096 (6) | 0.0126 (6) | 0.0109 (6) | 0.0000 (5) | 0.0059 (5) | 0.0008 (5) |
C11 | 0.0078 (6) | 0.0173 (6) | 0.0181 (7) | 0.0016 (5) | 0.0050 (5) | 0.0012 (5) |
C21 | 0.0092 (6) | 0.0142 (6) | 0.0173 (6) | 0.0015 (5) | 0.0029 (5) | 0.0018 (5) |
C41 | 0.0101 (6) | 0.0110 (6) | 0.0101 (6) | −0.0009 (5) | 0.0044 (5) | 0.0024 (5) |
C42 | 0.0132 (6) | 0.0117 (6) | 0.0124 (6) | 0.0001 (5) | 0.0056 (5) | −0.0010 (5) |
C43 | 0.0102 (6) | 0.0140 (6) | 0.0147 (6) | 0.0023 (5) | 0.0060 (5) | 0.0015 (5) |
C44 | 0.0096 (6) | 0.0140 (6) | 0.0097 (6) | −0.0022 (5) | 0.0026 (5) | 0.0019 (5) |
C45 | 0.0153 (6) | 0.0118 (6) | 0.0119 (6) | −0.0005 (5) | 0.0058 (5) | −0.0014 (5) |
C46 | 0.0111 (6) | 0.0125 (6) | 0.0141 (6) | 0.0021 (5) | 0.0061 (5) | 0.0013 (5) |
N2 | 0.0090 (5) | 0.0119 (5) | 0.0139 (5) | −0.0012 (4) | 0.0021 (4) | −0.0011 (4) |
N3 | 0.0086 (5) | 0.0094 (5) | 0.0143 (5) | −0.0014 (4) | 0.0019 (4) | −0.0015 (4) |
N4 | 0.0115 (5) | 0.0170 (6) | 0.0123 (5) | −0.0017 (5) | 0.0036 (4) | 0.0009 (4) |
O5 | 0.0119 (4) | 0.0101 (4) | 0.0177 (4) | −0.0006 (4) | 0.0035 (4) | −0.0002 (4) |
O41 | 0.0098 (4) | 0.0234 (5) | 0.0216 (5) | 0.0021 (4) | 0.0026 (4) | −0.0008 (4) |
O42 | 0.0173 (5) | 0.0229 (5) | 0.0233 (5) | −0.0047 (4) | 0.0038 (4) | −0.0106 (4) |
S1 | 0.00895 (16) | 0.01277 (17) | 0.01515 (17) | 0.00000 (11) | 0.00393 (12) | −0.00342 (11) |
S2 | 0.00943 (16) | 0.01248 (17) | 0.01553 (17) | −0.00012 (11) | 0.00038 (12) | −0.00253 (11) |
Geometric parameters (Å, º) top
C1—N2 | 1.2766 (17) | C41—C42 | 1.3984 (18) |
C1—S1 | 1.7542 (13) | C42—C43 | 1.3829 (18) |
C1—S2 | 1.7680 (12) | C42—H42 | 0.9300 |
C4—O5 | 1.2269 (16) | C43—C44 | 1.3855 (19) |
C4—N3 | 1.3562 (17) | C43—H43 | 0.9300 |
C4—C41 | 1.5018 (17) | C44—C45 | 1.3846 (18) |
C11—C21 | 1.5198 (18) | C44—N4 | 1.4694 (16) |
C11—S1 | 1.8179 (13) | C45—C46 | 1.3881 (18) |
C11—H11A | 0.9700 | C45—H45 | 0.9300 |
C11—H11B | 0.9700 | C46—H46 | 0.9300 |
C21—S2 | 1.8136 (13) | N2—N3 | 1.3970 (15) |
C21—H21A | 0.9700 | N3—H3 | 0.850 (18) |
C21—H21B | 0.9700 | N4—O42 | 1.2277 (15) |
C41—C46 | 1.3968 (18) | N4—O41 | 1.2292 (15) |
| | | |
N2—C1—S1 | 128.98 (10) | C41—C42—H42 | 120.0 |
N2—C1—S2 | 116.37 (10) | C42—C43—C44 | 118.43 (12) |
S1—C1—S2 | 114.65 (7) | C42—C43—H43 | 120.8 |
O5—C4—N3 | 123.24 (12) | C44—C43—H43 | 120.8 |
O5—C4—C41 | 120.86 (11) | C45—C44—C43 | 122.89 (12) |
N3—C4—C41 | 115.89 (11) | C45—C44—N4 | 118.81 (11) |
C21—C11—S1 | 107.56 (9) | C43—C44—N4 | 118.30 (11) |
C21—C11—H11A | 110.2 | C44—C45—C46 | 118.27 (12) |
S1—C11—H11A | 110.2 | C44—C45—H45 | 120.9 |
C21—C11—H11B | 110.2 | C46—C45—H45 | 120.9 |
S1—C11—H11B | 110.2 | C45—C46—C41 | 120.07 (12) |
H11A—C11—H11B | 108.5 | C45—C46—H46 | 120.0 |
C11—C21—S2 | 107.24 (9) | C41—C46—H46 | 120.0 |
C11—C21—H21A | 110.3 | C1—N2—N3 | 117.19 (11) |
S2—C21—H21A | 110.3 | C4—N3—N2 | 115.76 (11) |
C11—C21—H21B | 110.3 | C4—N3—H3 | 120.9 (11) |
S2—C21—H21B | 110.3 | N2—N3—H3 | 121.0 (11) |
H21A—C21—H21B | 108.5 | O42—N4—O41 | 123.28 (11) |
C46—C41—C42 | 120.23 (11) | O42—N4—C44 | 118.31 (11) |
C46—C41—C4 | 123.22 (11) | O41—N4—C44 | 118.41 (11) |
C42—C41—C4 | 116.52 (11) | C1—S1—C11 | 94.70 (6) |
C43—C42—C41 | 120.09 (12) | C1—S2—C21 | 95.75 (6) |
C43—C42—H42 | 120.0 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O5i | 0.850 (18) | 2.118 (18) | 2.9687 (15) | 179.2 (18) |
Symmetry code: (i) x, y+1, z. |
Crystal data top
C10H9N3O3S2 | Z = 2 |
Mr = 283.32 | F(000) = 292 |
Triclinic, P1 | Dx = 1.662 Mg m−3 |
a = 5.0506 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.0441 (3) Å | Cell parameters from 6181 reflections |
c = 14.1954 (5) Å | θ = 5.6–70.6° |
α = 96.877 (1)° | µ = 4.34 mm−1 |
β = 95.134 (2)° | T = 100 K |
γ = 96.306 (1)° | Plate, colourless |
V = 566.02 (4) Å3 | 0.93 × 0.08 × 0.03 mm |
Data collection top
Bruker SMART APEXII CCD diffractometer | 2013 reflections with I > 2σ(I) |
ω scan | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | θmax = 70.6°, θmin = 3.2° |
Tmin = 0.570, Tmax = 0.753 | h = −6→6 |
6795 measured reflections | k = −9→9 |
2044 independent reflections | l = −17→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0378P)2 + 0.3785P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max = 0.001 |
S = 1.09 | Δρmax = 0.35 e Å−3 |
2044 reflections | Δρmin = −0.34 e Å−3 |
167 parameters | Extinction correction: SHELXL-2016/6 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0109 (9) |
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 | |
C1 | 0.9519 (3) | 0.83114 (17) | 0.23898 (10) | 0.0104 (3) | |
C4 | 1.2380 (3) | 0.79658 (17) | 0.46338 (10) | 0.0110 (3) | |
C11 | 0.6246 (3) | 0.67488 (18) | 0.09203 (10) | 0.0141 (3) | |
H11A | 0.724453 | 0.584755 | 0.068911 | 0.017* | |
H11B | 0.439253 | 0.646726 | 0.065250 | 0.017* | |
C21 | 0.7408 (3) | 0.84032 (18) | 0.06236 (10) | 0.0128 (3) | |
H21A | 0.619648 | 0.924802 | 0.072605 | 0.015* | |
H21B | 0.768383 | 0.825242 | −0.004732 | 0.015* | |
C41 | 1.1675 (3) | 0.76173 (17) | 0.56009 (10) | 0.0105 (3) | |
C42 | 1.3559 (3) | 0.82985 (18) | 0.63692 (10) | 0.0122 (3) | |
H42 | 1.510037 | 0.896660 | 0.626419 | 0.015* | |
C43 | 1.3146 (3) | 0.79855 (18) | 0.72838 (10) | 0.0127 (3) | |
H43 | 1.438497 | 0.844206 | 0.779928 | 0.015* | |
C44 | 1.0841 (3) | 0.69744 (17) | 0.74134 (10) | 0.0111 (3) | |
C45 | 0.8932 (3) | 0.62754 (17) | 0.66716 (10) | 0.0121 (3) | |
H45 | 0.741234 | 0.559278 | 0.678181 | 0.015* | |
C46 | 0.9349 (3) | 0.66220 (17) | 0.57555 (10) | 0.0115 (3) | |
H46 | 0.807768 | 0.619030 | 0.524546 | 0.014* | |
N2 | 1.1079 (2) | 0.87801 (15) | 0.31583 (8) | 0.0119 (3) | |
N3 | 1.0335 (2) | 0.81433 (15) | 0.39825 (8) | 0.0111 (3) | |
H3 | 0.881 (4) | 0.815 (2) | 0.4118 (13) | 0.013* | |
N4 | 1.0417 (3) | 0.66466 (15) | 0.83894 (9) | 0.0138 (3) | |
O5 | 1.4725 (2) | 0.80828 (14) | 0.44588 (7) | 0.0160 (2) | |
O41 | 1.2166 (2) | 0.72301 (13) | 0.90382 (7) | 0.0177 (2) | |
O42 | 0.8325 (2) | 0.58172 (15) | 0.85171 (8) | 0.0234 (3) | |
S1 | 0.64609 (7) | 0.69932 (4) | 0.22165 (2) | 0.01259 (13) | |
S2 | 1.05729 (7) | 0.90621 (4) | 0.13483 (2) | 0.01304 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0115 (7) | 0.0106 (6) | 0.0100 (6) | 0.0036 (5) | 0.0023 (5) | 0.0015 (5) |
C4 | 0.0125 (7) | 0.0098 (6) | 0.0101 (7) | 0.0019 (5) | 0.0002 (5) | −0.0004 (5) |
C11 | 0.0188 (7) | 0.0145 (7) | 0.0078 (6) | 0.0019 (6) | −0.0026 (6) | 0.0002 (5) |
C21 | 0.0138 (7) | 0.0158 (7) | 0.0086 (6) | 0.0031 (6) | −0.0009 (6) | 0.0015 (5) |
C41 | 0.0126 (7) | 0.0101 (6) | 0.0097 (6) | 0.0055 (5) | 0.0011 (5) | 0.0015 (5) |
C42 | 0.0117 (7) | 0.0120 (7) | 0.0129 (7) | 0.0014 (5) | 0.0008 (6) | 0.0016 (5) |
C43 | 0.0142 (7) | 0.0125 (7) | 0.0104 (7) | 0.0023 (5) | −0.0020 (6) | −0.0006 (5) |
C44 | 0.0165 (7) | 0.0101 (6) | 0.0081 (6) | 0.0052 (5) | 0.0025 (6) | 0.0019 (5) |
C45 | 0.0127 (7) | 0.0110 (7) | 0.0130 (7) | 0.0020 (5) | 0.0023 (6) | 0.0022 (5) |
C46 | 0.0125 (7) | 0.0116 (6) | 0.0100 (7) | 0.0030 (5) | −0.0012 (5) | −0.0003 (5) |
N2 | 0.0123 (6) | 0.0152 (6) | 0.0087 (6) | 0.0018 (5) | 0.0010 (5) | 0.0030 (4) |
N3 | 0.0098 (6) | 0.0160 (6) | 0.0081 (6) | 0.0018 (5) | 0.0019 (5) | 0.0027 (4) |
N4 | 0.0195 (6) | 0.0118 (6) | 0.0107 (6) | 0.0035 (5) | 0.0018 (5) | 0.0018 (5) |
O5 | 0.0114 (5) | 0.0259 (6) | 0.0122 (5) | 0.0050 (4) | 0.0020 (4) | 0.0050 (4) |
O41 | 0.0232 (6) | 0.0196 (5) | 0.0092 (5) | 0.0024 (4) | −0.0031 (4) | 0.0017 (4) |
O42 | 0.0257 (6) | 0.0284 (6) | 0.0147 (5) | −0.0085 (5) | 0.0055 (5) | 0.0048 (4) |
S1 | 0.0136 (2) | 0.0149 (2) | 0.00805 (19) | −0.00273 (14) | −0.00096 (14) | 0.00199 (13) |
S2 | 0.0120 (2) | 0.0187 (2) | 0.00858 (19) | 0.00005 (14) | 0.00076 (14) | 0.00433 (13) |
Geometric parameters (Å, º) top
C1—N2 | 1.2788 (19) | C41—C42 | 1.397 (2) |
C1—S1 | 1.7552 (14) | C42—C43 | 1.381 (2) |
C1—S2 | 1.7657 (14) | C42—H42 | 0.9300 |
C4—O5 | 1.2279 (18) | C43—C44 | 1.385 (2) |
C4—N3 | 1.3546 (18) | C43—H43 | 0.9300 |
C4—C41 | 1.4991 (19) | C44—C45 | 1.383 (2) |
C11—C21 | 1.517 (2) | C44—N4 | 1.4706 (18) |
C11—S1 | 1.8190 (14) | C45—C46 | 1.391 (2) |
C11—H11A | 0.9700 | C45—H45 | 0.9300 |
C11—H11B | 0.9700 | C46—H46 | 0.9300 |
C21—S2 | 1.8121 (14) | N2—N3 | 1.3975 (17) |
C21—H21A | 0.9700 | N3—H3 | 0.81 (2) |
C21—H21B | 0.9700 | N4—O42 | 1.2259 (17) |
C41—C46 | 1.397 (2) | N4—O41 | 1.2283 (16) |
| | | |
N2—C1—S1 | 128.98 (11) | C41—C42—H42 | 119.8 |
N2—C1—S2 | 116.29 (11) | C42—C43—C44 | 118.29 (13) |
S1—C1—S2 | 114.73 (8) | C42—C43—H43 | 120.9 |
O5—C4—N3 | 122.70 (13) | C44—C43—H43 | 120.9 |
O5—C4—C41 | 120.21 (12) | C45—C44—C43 | 123.04 (13) |
N3—C4—C41 | 117.10 (12) | C45—C44—N4 | 119.01 (13) |
C21—C11—S1 | 108.04 (9) | C43—C44—N4 | 117.95 (12) |
C21—C11—H11A | 110.1 | C44—C45—C46 | 118.14 (13) |
S1—C11—H11A | 110.1 | C44—C45—H45 | 120.9 |
C21—C11—H11B | 110.1 | C46—C45—H45 | 120.9 |
S1—C11—H11B | 110.1 | C45—C46—C41 | 120.09 (13) |
H11A—C11—H11B | 108.4 | C45—C46—H46 | 120.0 |
C11—C21—S2 | 107.18 (9) | C41—C46—H46 | 120.0 |
C11—C21—H21A | 110.3 | C1—N2—N3 | 117.14 (12) |
S2—C21—H21A | 110.3 | C4—N3—N2 | 115.61 (12) |
C11—C21—H21B | 110.3 | C4—N3—H3 | 122.1 (13) |
S2—C21—H21B | 110.3 | N2—N3—H3 | 120.0 (13) |
H21A—C21—H21B | 108.5 | O42—N4—O41 | 123.18 (12) |
C46—C41—C42 | 120.04 (13) | O42—N4—C44 | 118.42 (12) |
C46—C41—C4 | 123.86 (12) | O41—N4—C44 | 118.40 (12) |
C42—C41—C4 | 116.06 (13) | C1—S1—C11 | 95.16 (7) |
C43—C42—C41 | 120.38 (14) | C1—S2—C21 | 95.48 (7) |
C43—C42—H42 | 119.8 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O5i | 0.81 (2) | 2.16 (2) | 2.9676 (16) | 178.2 (18) |
Symmetry code: (i) x−1, y, z. |
Crystal data top
C10H9N3O3S2 | F(000) = 584 |
Mr = 283.32 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 7.8582 (6) Å | Cell parameters from 9309 reflections |
b = 6.1279 (4) Å | θ = 5.7–72.4° |
c = 24.4164 (17) Å | µ = 4.22 mm−1 |
β = 98.211 (2)° | T = 100 K |
V = 1163.70 (14) Å3 | Plate, colourless |
Z = 4 | 0.38 × 0.37 × 0.08 mm |
Data collection top
Bruker SMART APEXII CCD diffractometer | 2293 reflections with I > 2σ(I) |
ω scan | Rint = 0.042 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | θmax = 72.4°, θmin = 3.7° |
Tmin = 0.293, Tmax = 0.662 | h = −9→9 |
2300 measured reflections | k = 0→7 |
2300 independent reflections | l = 0→30 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0629P)2 + 0.6885P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.001 |
2300 reflections | Δρmax = 0.44 e Å−3 |
167 parameters | Δρmin = −0.60 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.27403 (19) | 0.8154 (2) | 0.29175 (6) | 0.0114 (3) | |
C4 | 0.02621 (19) | 0.7084 (2) | 0.17039 (6) | 0.0118 (3) | |
C11 | 0.5133 (2) | 1.1018 (3) | 0.33254 (6) | 0.0159 (3) | |
H11A | 0.609234 | 1.185490 | 0.322728 | 0.019* | |
H11B | 0.466033 | 1.178855 | 0.361640 | 0.019* | |
C21 | 0.5734 (2) | 0.8762 (3) | 0.35244 (6) | 0.0158 (3) | |
H21A | 0.637750 | 0.885177 | 0.389360 | 0.019* | |
H21B | 0.647693 | 0.814785 | 0.327921 | 0.019* | |
C41 | −0.05310 (19) | 0.8397 (3) | 0.12140 (6) | 0.0116 (3) | |
C42 | −0.1740 (2) | 0.7365 (3) | 0.08220 (7) | 0.0140 (3) | |
H42 | −0.207739 | 0.593879 | 0.088059 | 0.017* | |
C43 | −0.2436 (2) | 0.8467 (3) | 0.03462 (6) | 0.0159 (3) | |
H43 | −0.325709 | 0.780995 | 0.008592 | 0.019* | |
C44 | −0.1877 (2) | 1.0573 (3) | 0.02693 (6) | 0.0153 (3) | |
C45 | −0.0662 (2) | 1.1628 (3) | 0.06433 (6) | 0.0148 (3) | |
H45 | −0.029988 | 1.303490 | 0.057564 | 0.018* | |
C46 | 0.00035 (19) | 1.0516 (2) | 0.11251 (6) | 0.0130 (3) | |
H46 | 0.080608 | 1.119300 | 0.138757 | 0.016* | |
N2 | 0.14883 (17) | 0.7093 (2) | 0.26448 (5) | 0.0126 (3) | |
N3 | 0.07176 (17) | 0.8271 (2) | 0.21740 (5) | 0.0121 (3) | |
H3 | 0.016 (3) | 0.937 (4) | 0.2235 (8) | 0.015* | |
N4 | −0.26201 (19) | 1.1754 (3) | −0.02341 (6) | 0.0204 (3) | |
O5 | 0.05660 (14) | 0.51366 (18) | 0.16611 (5) | 0.0159 (3) | |
O41 | −0.35840 (18) | 1.0753 (2) | −0.05869 (5) | 0.0294 (3) | |
O42 | −0.2243 (2) | 1.3682 (2) | −0.02764 (6) | 0.0372 (4) | |
S1 | 0.34971 (5) | 1.06971 (6) | 0.27249 (2) | 0.01503 (15) | |
S2 | 0.38495 (5) | 0.70489 (6) | 0.35298 (2) | 0.01385 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0143 (7) | 0.0106 (7) | 0.0097 (7) | 0.0021 (5) | 0.0033 (5) | 0.0013 (5) |
C4 | 0.0098 (6) | 0.0124 (8) | 0.0131 (7) | −0.0009 (5) | 0.0014 (5) | 0.0001 (5) |
C11 | 0.0147 (7) | 0.0170 (8) | 0.0150 (8) | −0.0036 (6) | −0.0005 (6) | −0.0009 (6) |
C21 | 0.0136 (7) | 0.0187 (8) | 0.0142 (7) | −0.0007 (6) | −0.0010 (5) | −0.0009 (6) |
C41 | 0.0116 (7) | 0.0118 (7) | 0.0114 (7) | 0.0022 (6) | 0.0016 (5) | −0.0023 (6) |
C42 | 0.0139 (7) | 0.0132 (7) | 0.0145 (8) | −0.0003 (6) | 0.0010 (6) | −0.0033 (6) |
C43 | 0.0139 (7) | 0.0200 (8) | 0.0133 (7) | 0.0014 (6) | −0.0003 (6) | −0.0054 (6) |
C44 | 0.0182 (8) | 0.0184 (8) | 0.0095 (7) | 0.0065 (6) | 0.0027 (6) | 0.0002 (6) |
C45 | 0.0183 (7) | 0.0129 (7) | 0.0137 (7) | 0.0024 (6) | 0.0039 (6) | −0.0008 (6) |
C46 | 0.0127 (7) | 0.0136 (7) | 0.0125 (7) | 0.0008 (5) | 0.0007 (5) | −0.0026 (5) |
N2 | 0.0150 (6) | 0.0109 (6) | 0.0112 (6) | 0.0013 (5) | −0.0009 (5) | 0.0016 (4) |
N3 | 0.0141 (6) | 0.0092 (6) | 0.0117 (6) | 0.0027 (5) | −0.0025 (5) | 0.0003 (5) |
N4 | 0.0245 (7) | 0.0242 (8) | 0.0118 (7) | 0.0085 (6) | 0.0006 (6) | 0.0001 (5) |
O5 | 0.0188 (5) | 0.0100 (5) | 0.0183 (5) | 0.0016 (4) | 0.0012 (4) | −0.0016 (4) |
O41 | 0.0295 (7) | 0.0378 (8) | 0.0174 (6) | 0.0012 (6) | −0.0091 (5) | 0.0013 (5) |
O42 | 0.0618 (10) | 0.0229 (7) | 0.0226 (7) | 0.0040 (7) | −0.0088 (6) | 0.0070 (5) |
S1 | 0.0165 (2) | 0.0136 (2) | 0.0141 (2) | −0.00375 (13) | −0.00081 (15) | 0.00427 (12) |
S2 | 0.0150 (2) | 0.0144 (2) | 0.0112 (2) | −0.00060 (13) | −0.00138 (15) | 0.00337 (12) |
Geometric parameters (Å, º) top
C1—N2 | 1.283 (2) | C41—C42 | 1.400 (2) |
C1—S2 | 1.7553 (15) | C42—C43 | 1.387 (2) |
C1—S1 | 1.7560 (15) | C42—H42 | 0.9300 |
C4—O5 | 1.2247 (19) | C43—C44 | 1.385 (2) |
C4—N3 | 1.363 (2) | C43—H43 | 0.9300 |
C4—C41 | 1.501 (2) | C44—C45 | 1.384 (2) |
C11—C21 | 1.518 (2) | C44—N4 | 1.473 (2) |
C11—S1 | 1.8172 (16) | C45—C46 | 1.395 (2) |
C11—H11A | 0.9700 | C45—H45 | 0.9300 |
C11—H11B | 0.9700 | C46—H46 | 0.9300 |
C21—S2 | 1.8170 (16) | N2—N3 | 1.4179 (17) |
C21—H21A | 0.9700 | N3—H3 | 0.83 (2) |
C21—H21B | 0.9700 | N4—O42 | 1.226 (2) |
C41—C46 | 1.392 (2) | N4—O41 | 1.227 (2) |
| | | |
N2—C1—S2 | 119.82 (12) | C41—C42—H42 | 120.0 |
N2—C1—S1 | 125.06 (12) | C44—C43—C42 | 118.20 (14) |
S2—C1—S1 | 115.12 (9) | C44—C43—H43 | 120.9 |
O5—C4—N3 | 124.13 (14) | C42—C43—H43 | 120.9 |
O5—C4—C41 | 121.19 (14) | C45—C44—C43 | 123.26 (15) |
N3—C4—C41 | 114.50 (13) | C45—C44—N4 | 118.37 (14) |
C21—C11—S1 | 108.17 (11) | C43—C44—N4 | 118.36 (14) |
C21—C11—H11A | 110.1 | C44—C45—C46 | 117.95 (14) |
S1—C11—H11A | 110.1 | C44—C45—H45 | 121.0 |
C21—C11—H11B | 110.1 | C46—C45—H45 | 121.0 |
S1—C11—H11B | 110.1 | C41—C46—C45 | 120.15 (14) |
H11A—C11—H11B | 108.4 | C41—C46—H46 | 119.9 |
C11—C21—S2 | 108.16 (10) | C45—C46—H46 | 119.9 |
C11—C21—H21A | 110.1 | C1—N2—N3 | 111.72 (12) |
S2—C21—H21A | 110.1 | C4—N3—N2 | 116.21 (12) |
C11—C21—H21B | 110.1 | C4—N3—H3 | 120.3 (14) |
S2—C21—H21B | 110.1 | N2—N3—H3 | 116.3 (14) |
H21A—C21—H21B | 108.4 | O42—N4—O41 | 123.72 (14) |
C46—C41—C42 | 120.37 (14) | O42—N4—C44 | 118.15 (14) |
C46—C41—C4 | 121.60 (13) | O41—N4—C44 | 118.13 (14) |
C42—C41—C4 | 117.84 (14) | C1—S1—C11 | 96.17 (7) |
C43—C42—C41 | 120.05 (15) | C1—S2—C21 | 94.42 (7) |
C43—C42—H42 | 120.0 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N2i | 0.83 (2) | 2.16 (2) | 2.9843 (19) | 175 (2) |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
Crystal data top
C10H9N3O3S2·H2O | F(000) = 624 |
Mr = 301.34 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 7.3654 (3) Å | Cell parameters from 9981 reflections |
b = 6.4550 (2) Å | θ = 3.4–72.5° |
c = 25.8911 (9) Å | µ = 4.09 mm−1 |
β = 90.808 (1)° | T = 100 K |
V = 1230.84 (8) Å3 | Plate, colourless |
Z = 4 | 0.60 × 0.46 × 0.03 mm |
Data collection top
Bruker SMART APEXII CCD diffractometer | 2406 reflections with I > 2σ(I) |
ω scan | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | θmax = 72.5°, θmin = 3.4° |
Tmin = 0.507, Tmax = 0.754 | h = −9→9 |
13701 measured reflections | k = −7→6 |
2423 independent reflections | l = −31→32 |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.032P)2 + 0.9597P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
2423 reflections | Δρmax = 0.53 e Å−3 |
181 parameters | Δρmin = −0.26 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 | |
C1 | 0.49542 (16) | 0.7865 (2) | 0.72028 (5) | 0.0116 (2) | |
N2 | 0.47914 (15) | 0.72085 (17) | 0.67374 (4) | 0.0141 (2) | |
N3 | 0.56255 (15) | 0.84599 (18) | 0.63652 (4) | 0.0129 (2) | |
H3 | 0.546 (2) | 0.977 (3) | 0.6387 (7) | 0.015* | |
C4 | 0.60402 (17) | 0.7527 (2) | 0.59136 (5) | 0.0127 (3) | |
O5 | 0.58811 (15) | 0.56561 (15) | 0.58418 (4) | 0.0215 (2) | |
C41 | 0.67658 (16) | 0.8897 (2) | 0.54942 (5) | 0.0111 (2) | |
C42 | 0.68418 (17) | 0.8029 (2) | 0.50001 (5) | 0.0127 (3) | |
H42 | 0.644557 | 0.667756 | 0.494600 | 0.015* | |
C43 | 0.75040 (17) | 0.9172 (2) | 0.45911 (5) | 0.0132 (3) | |
H43 | 0.755957 | 0.860402 | 0.426153 | 0.016* | |
C44 | 0.80809 (16) | 1.1178 (2) | 0.46848 (5) | 0.0118 (3) | |
C45 | 0.80235 (17) | 1.2094 (2) | 0.51684 (5) | 0.0130 (3) | |
H45 | 0.841577 | 1.344905 | 0.521914 | 0.016* | |
C46 | 0.73622 (17) | 1.0925 (2) | 0.55751 (5) | 0.0127 (3) | |
H46 | 0.731640 | 1.149894 | 0.590416 | 0.015* | |
N4 | 0.88001 (15) | 1.23893 (18) | 0.42488 (4) | 0.0149 (2) | |
O41 | 0.90489 (15) | 1.14833 (16) | 0.38404 (4) | 0.0242 (2) | |
O42 | 0.91342 (15) | 1.42324 (16) | 0.43183 (4) | 0.0242 (2) | |
S1 | 0.62612 (4) | 0.99731 (5) | 0.74193 (2) | 0.01691 (10) | |
S2 | 0.38078 (4) | 0.65196 (5) | 0.76904 (2) | 0.01598 (10) | |
C11 | 0.5457 (2) | 0.9915 (2) | 0.80762 (6) | 0.0244 (3) | |
H11A | 0.637506 | 1.047898 | 0.830887 | 0.029* | |
H11B | 0.436793 | 1.075001 | 0.810446 | 0.029* | |
C21 | 0.5053 (2) | 0.7706 (3) | 0.82192 (5) | 0.0234 (3) | |
H21A | 0.433759 | 0.766511 | 0.853070 | 0.028* | |
H21B | 0.617641 | 0.695948 | 0.828371 | 0.028* | |
O1W | 0.45304 (15) | 0.26144 (15) | 0.64596 (4) | 0.0213 (2) | |
H2W | 0.444 (3) | 0.298 (3) | 0.6759 (4) | 0.032* | |
H1W | 0.487 (3) | 0.366 (2) | 0.6314 (6) | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0120 (6) | 0.0117 (6) | 0.0111 (6) | 0.0001 (5) | 0.0018 (5) | 0.0009 (5) |
N2 | 0.0192 (6) | 0.0120 (5) | 0.0110 (5) | −0.0019 (4) | 0.0035 (4) | 0.0012 (4) |
N3 | 0.0200 (6) | 0.0086 (5) | 0.0102 (5) | −0.0014 (4) | 0.0031 (4) | 0.0010 (4) |
C4 | 0.0142 (6) | 0.0126 (6) | 0.0115 (6) | 0.0011 (5) | 0.0013 (5) | 0.0006 (5) |
O5 | 0.0384 (6) | 0.0109 (5) | 0.0155 (5) | −0.0013 (4) | 0.0108 (4) | −0.0007 (4) |
C41 | 0.0105 (5) | 0.0120 (6) | 0.0109 (6) | 0.0019 (5) | 0.0007 (4) | 0.0012 (5) |
C42 | 0.0144 (6) | 0.0106 (6) | 0.0130 (6) | 0.0006 (5) | 0.0008 (5) | −0.0008 (5) |
C43 | 0.0150 (6) | 0.0138 (6) | 0.0107 (6) | 0.0018 (5) | 0.0011 (5) | −0.0016 (5) |
C44 | 0.0103 (6) | 0.0138 (6) | 0.0114 (6) | 0.0009 (5) | 0.0015 (4) | 0.0034 (5) |
C45 | 0.0129 (6) | 0.0116 (6) | 0.0144 (6) | −0.0009 (5) | 0.0001 (5) | 0.0001 (5) |
C46 | 0.0138 (6) | 0.0142 (6) | 0.0101 (6) | 0.0001 (5) | 0.0000 (5) | −0.0016 (5) |
N4 | 0.0154 (5) | 0.0162 (6) | 0.0130 (5) | −0.0005 (4) | 0.0014 (4) | 0.0031 (4) |
O41 | 0.0376 (6) | 0.0224 (6) | 0.0127 (5) | −0.0028 (4) | 0.0082 (4) | 0.0008 (4) |
O42 | 0.0352 (6) | 0.0164 (5) | 0.0211 (5) | −0.0079 (4) | 0.0047 (4) | 0.0031 (4) |
S1 | 0.01991 (18) | 0.01910 (19) | 0.01174 (17) | −0.00822 (12) | 0.00094 (12) | −0.00152 (12) |
S2 | 0.01892 (18) | 0.01772 (19) | 0.01142 (17) | −0.00419 (12) | 0.00424 (12) | 0.00176 (12) |
C11 | 0.0313 (8) | 0.0307 (9) | 0.0111 (7) | −0.0074 (6) | 0.0022 (6) | −0.0067 (6) |
C21 | 0.0252 (7) | 0.0337 (8) | 0.0112 (7) | −0.0021 (6) | 0.0014 (5) | 0.0007 (6) |
O1W | 0.0377 (6) | 0.0112 (5) | 0.0153 (5) | −0.0013 (4) | 0.0088 (4) | 0.0007 (4) |
Geometric parameters (Å, º) top
C1—N2 | 1.2814 (17) | C44—N4 | 1.4775 (16) |
C1—S1 | 1.7543 (13) | C45—C46 | 1.3891 (18) |
C1—S2 | 1.7582 (13) | C45—H45 | 0.9300 |
N2—N3 | 1.4054 (15) | C46—H46 | 0.9300 |
N3—C4 | 1.3540 (17) | N4—O41 | 1.2243 (15) |
N3—H3 | 0.858 (18) | N4—O42 | 1.2277 (16) |
C4—O5 | 1.2270 (17) | S1—C11 | 1.8092 (15) |
C4—C41 | 1.5047 (17) | S2—C21 | 1.8075 (15) |
C41—C46 | 1.3954 (19) | C11—C21 | 1.504 (2) |
C41—C42 | 1.3984 (18) | C11—H11A | 0.9700 |
C42—C43 | 1.3849 (18) | C11—H11B | 0.9700 |
C42—H42 | 0.9300 | C21—H21A | 0.9700 |
C43—C44 | 1.3836 (19) | C21—H21B | 0.9700 |
C43—H43 | 0.9300 | O1W—H2W | 0.814 (9) |
C44—C45 | 1.3858 (18) | O1W—H1W | 0.814 (9) |
| | | |
N2—C1—S1 | 126.92 (10) | C44—C45—H45 | 121.0 |
N2—C1—S2 | 118.19 (10) | C46—C45—H45 | 121.0 |
S1—C1—S2 | 114.87 (7) | C45—C46—C41 | 120.57 (12) |
C1—N2—N3 | 114.75 (11) | C45—C46—H46 | 119.7 |
C4—N3—N2 | 116.26 (11) | C41—C46—H46 | 119.7 |
C4—N3—H3 | 122.0 (12) | O41—N4—O42 | 123.88 (12) |
N2—N3—H3 | 117.3 (11) | O41—N4—C44 | 117.82 (11) |
O5—C4—N3 | 123.12 (12) | O42—N4—C44 | 118.29 (11) |
O5—C4—C41 | 120.23 (11) | C1—S1—C11 | 95.68 (7) |
N3—C4—C41 | 116.63 (11) | C1—S2—C21 | 95.21 (7) |
C46—C41—C42 | 119.78 (12) | C21—C11—S1 | 108.63 (10) |
C46—C41—C4 | 123.88 (11) | C21—C11—H11A | 110.0 |
C42—C41—C4 | 116.33 (11) | S1—C11—H11A | 110.0 |
C43—C42—C41 | 120.34 (12) | C21—C11—H11B | 110.0 |
C43—C42—H42 | 119.8 | S1—C11—H11B | 110.0 |
C41—C42—H42 | 119.8 | H11A—C11—H11B | 108.3 |
C44—C43—C42 | 118.36 (12) | C11—C21—S2 | 108.38 (10) |
C44—C43—H43 | 120.8 | C11—C21—H21A | 110.0 |
C42—C43—H43 | 120.8 | S2—C21—H21A | 110.0 |
C43—C44—C45 | 122.99 (12) | C11—C21—H21B | 110.0 |
C43—C44—N4 | 118.28 (11) | S2—C21—H21B | 110.0 |
C45—C44—N4 | 118.72 (12) | H21A—C21—H21B | 108.4 |
C44—C45—C46 | 117.96 (12) | H2W—O1W—H1W | 103.4 (16) |
| | | |
S1—C1—N2—N3 | −6.44 (17) | N4—C44—C45—C46 | −179.30 (11) |
S2—C1—N2—N3 | 175.08 (9) | C44—C45—C46—C41 | −0.42 (19) |
C1—N2—N3—C4 | 157.92 (12) | C42—C41—C46—C45 | 0.30 (19) |
N2—N3—C4—O5 | −7.15 (19) | C4—C41—C46—C45 | 179.70 (11) |
N2—N3—C4—C41 | 174.25 (10) | C43—C44—N4—O41 | −8.38 (17) |
O5—C4—C41—C46 | −165.43 (13) | C45—C44—N4—O41 | 171.26 (12) |
N3—C4—C41—C46 | 13.21 (18) | C43—C44—N4—O42 | 172.52 (12) |
O5—C4—C41—C42 | 13.98 (18) | C45—C44—N4—O42 | −7.85 (18) |
N3—C4—C41—C42 | −167.38 (11) | N2—C1—S1—C11 | 173.37 (13) |
C46—C41—C42—C43 | −0.05 (19) | S2—C1—S1—C11 | −8.11 (9) |
C4—C41—C42—C43 | −179.49 (11) | N2—C1—S2—C21 | 165.37 (11) |
C41—C42—C43—C44 | −0.06 (19) | S1—C1—S2—C21 | −13.28 (9) |
C42—C43—C44—C45 | −0.08 (19) | C1—S1—C11—C21 | 32.19 (12) |
C42—C43—C44—N4 | 179.54 (11) | S1—C11—C21—S2 | −45.10 (13) |
C43—C44—C45—C46 | 0.32 (19) | C1—S2—C21—C11 | 35.18 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O5 | 0.81 (1) | 1.93 (1) | 2.7291 (14) | 166 (2) |
O1W—H1W···N2 | 0.81 (1) | 2.54 (2) | 3.0569 (15) | 123 (2) |
N3—H3···O1Wi | 0.858 (18) | 1.968 (19) | 2.8120 (15) | 167.6 (16) |
Symmetry code: (i) x, y+1, z. |
Torsion angles top | C1—N2—N3—C4 | O5—C4—C41—C42 |
I1 | 153.60 (13) | 34.5 (2) |
I2 | 150.23 (13) | 33.1 (2) |
I3 | 139.33 (15) | 35.0 (2) |
I4 | 157.69 (12) | 13.96 (19) |
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