Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402447X/nc6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680402447X/nc6003Isup2.hkl |
CCDC reference: 255871
Key indicators
- Single-crystal X-ray study
- T = 105 K
- R factor = 0.033
- wR factor = 0.092
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level B CRYSS02_ALERT_3_B The value of _exptl_crystal_size_mid is > 0.8 Mid crystal size given = 0.950 CRYSS02_ALERT_3_B The value of _exptl_crystal_size_max is > 1.0 Maximum crystal size given = 1.050
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 0 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C9H8NO3·C4H6N3O·H2O | F(000) = 648 |
Mr = 308.30 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6264 reflections |
a = 11.4821 (2) Å | θ = 1.9–28.3° |
b = 7.2107 (1) Å | µ = 0.11 mm−1 |
c = 18.2817 (3) Å | T = 105 K |
β = 106.692 (1)° | Block, colourless |
V = 1449.83 (4) Å3 | 1.05 × 0.95 × 0.22 mm |
Z = 4 |
Siemens SMART CCD diffractometer | 3603 independent reflections |
Radiation source: fine-focus sealed tube | 3354 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.3 pixels mm-1 | θmax = 28.3°, θmin = 1.9° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −15→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→9 |
Tmin = 0.816, Tmax = 0.976 | l = −19→24 |
13211 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0477P)2 + 0.4875P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.012 |
3603 reflections | Δρmax = 0.37 e Å−3 |
230 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0199 (18) |
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. Data were collected by measuring five sets of exposures; two with the detector set at 2θ = 29° and three with 2θ = 55°, crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL reflections. |
x | y | z | Uiso*/Ueq | ||
O8A | 0.45862 (7) | 1.21529 (10) | 0.39978 (5) | 0.02693 (18) | |
N1A | 0.56816 (7) | 1.03457 (11) | 0.34117 (5) | 0.02109 (18) | |
H1A | 0.6058 (13) | 1.133 (2) | 0.3308 (8) | 0.025* | |
N3A | 0.44267 (7) | 0.90339 (10) | 0.40698 (5) | 0.01778 (17) | |
H3A | 0.3876 (12) | 0.9213 (18) | 0.4338 (7) | 0.021* | |
N7A | 0.42465 (8) | 0.58902 (12) | 0.41828 (5) | 0.02420 (19) | |
H71A | 0.3705 (13) | 0.610 (2) | 0.4463 (8) | 0.029* | |
H72A | 0.4465 (13) | 0.476 (2) | 0.4100 (8) | 0.029* | |
C2A | 0.48918 (8) | 1.06172 (13) | 0.38369 (5) | 0.01927 (19) | |
C4A | 0.47444 (8) | 0.72824 (12) | 0.39255 (5) | 0.01852 (18) | |
C5A | 0.55994 (9) | 0.70653 (13) | 0.34968 (6) | 0.0219 (2) | |
H5A | 0.5841 (12) | 0.5851 (19) | 0.3396 (8) | 0.026* | |
C6A | 0.60371 (9) | 0.86145 (14) | 0.32578 (6) | 0.0228 (2) | |
H6A | 0.6609 | 0.8500 | 0.2974 | 0.027* | |
O1B | 0.26393 (7) | 0.64887 (10) | 0.50238 (5) | 0.02592 (17) | |
O2B | 0.27520 (6) | 0.95479 (9) | 0.48376 (4) | 0.02223 (16) | |
O3B | 0.29065 (6) | 0.67759 (10) | 0.68514 (4) | 0.02376 (17) | |
N1B | 0.10942 (7) | 0.69880 (12) | 0.59320 (5) | 0.02063 (18) | |
H1B | 0.0391 (13) | 0.6689 (19) | 0.5804 (8) | 0.025* | |
C1B | 0.23597 (8) | 0.81349 (13) | 0.51056 (5) | 0.01905 (19) | |
C2B | 0.14518 (8) | 0.85632 (13) | 0.55571 (6) | 0.02079 (19) | |
H21B | 0.0726 (12) | 0.9012 (19) | 0.5193 (8) | 0.025* | |
H22B | 0.1778 (12) | 0.9540 (19) | 0.5921 (8) | 0.025* | |
C3B | 0.18638 (8) | 0.61736 (13) | 0.65378 (5) | 0.01910 (18) | |
C4B | 0.14347 (8) | 0.44383 (13) | 0.68277 (5) | 0.01820 (18) | |
C5B | 0.05472 (9) | 0.32875 (14) | 0.63609 (5) | 0.02133 (19) | |
H5B | 0.0161 | 0.3631 | 0.5847 | 0.026* | |
C6B | 0.02306 (10) | 0.16374 (15) | 0.66513 (6) | 0.0253 (2) | |
H6B | −0.0374 | 0.0857 | 0.6335 | 0.030* | |
C7B | 0.07965 (10) | 0.11288 (15) | 0.74038 (6) | 0.0269 (2) | |
H7B | 0.0593 | −0.0012 | 0.7596 | 0.032* | |
C8B | 0.16595 (9) | 0.22883 (16) | 0.78747 (6) | 0.0277 (2) | |
H8B | 0.2031 | 0.1955 | 0.8392 | 0.033* | |
C9B | 0.19784 (9) | 0.39373 (15) | 0.75871 (6) | 0.0235 (2) | |
H9B | 0.2570 | 0.4727 | 0.7909 | 0.028* | |
O1C | 0.14587 (7) | 0.30238 (11) | 0.47806 (4) | 0.02487 (17) | |
H11C | 0.1884 (15) | 0.402 (2) | 0.4913 (9) | 0.037* | |
H12C | 0.1942 (15) | 0.207 (2) | 0.4834 (9) | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O8A | 0.0242 (4) | 0.0127 (3) | 0.0433 (4) | 0.0008 (3) | 0.0087 (3) | −0.0022 (3) |
N1A | 0.0191 (4) | 0.0168 (4) | 0.0266 (4) | −0.0021 (3) | 0.0054 (3) | 0.0005 (3) |
N3A | 0.0164 (3) | 0.0126 (3) | 0.0235 (4) | 0.0009 (3) | 0.0045 (3) | −0.0016 (3) |
N7A | 0.0304 (4) | 0.0122 (4) | 0.0321 (4) | 0.0012 (3) | 0.0122 (4) | −0.0007 (3) |
C2A | 0.0150 (4) | 0.0147 (4) | 0.0248 (4) | −0.0003 (3) | 0.0006 (3) | −0.0008 (3) |
C4A | 0.0181 (4) | 0.0140 (4) | 0.0209 (4) | 0.0015 (3) | 0.0015 (3) | −0.0017 (3) |
C5A | 0.0220 (4) | 0.0172 (4) | 0.0261 (5) | 0.0027 (3) | 0.0061 (4) | −0.0039 (3) |
C6A | 0.0200 (4) | 0.0233 (5) | 0.0252 (5) | 0.0006 (4) | 0.0063 (3) | −0.0034 (4) |
O1B | 0.0267 (4) | 0.0164 (3) | 0.0381 (4) | −0.0003 (3) | 0.0147 (3) | −0.0009 (3) |
O2B | 0.0223 (3) | 0.0169 (3) | 0.0288 (4) | 0.0001 (2) | 0.0094 (3) | 0.0018 (3) |
O3B | 0.0168 (3) | 0.0220 (3) | 0.0306 (4) | −0.0029 (3) | 0.0038 (3) | 0.0011 (3) |
N1B | 0.0136 (4) | 0.0209 (4) | 0.0274 (4) | −0.0007 (3) | 0.0059 (3) | 0.0026 (3) |
C1B | 0.0151 (4) | 0.0179 (4) | 0.0226 (4) | 0.0000 (3) | 0.0029 (3) | 0.0003 (3) |
C2B | 0.0171 (4) | 0.0176 (4) | 0.0276 (5) | 0.0025 (3) | 0.0064 (3) | 0.0029 (4) |
C3B | 0.0164 (4) | 0.0183 (4) | 0.0237 (4) | 0.0009 (3) | 0.0077 (3) | −0.0013 (3) |
C4B | 0.0157 (4) | 0.0197 (4) | 0.0207 (4) | 0.0007 (3) | 0.0076 (3) | −0.0005 (3) |
C5B | 0.0230 (4) | 0.0233 (5) | 0.0189 (4) | −0.0031 (4) | 0.0081 (3) | −0.0013 (3) |
C6B | 0.0271 (5) | 0.0247 (5) | 0.0266 (5) | −0.0070 (4) | 0.0118 (4) | −0.0023 (4) |
C7B | 0.0264 (5) | 0.0278 (5) | 0.0312 (5) | −0.0007 (4) | 0.0157 (4) | 0.0072 (4) |
C8B | 0.0233 (5) | 0.0367 (6) | 0.0238 (5) | 0.0025 (4) | 0.0078 (4) | 0.0085 (4) |
C9B | 0.0174 (4) | 0.0291 (5) | 0.0229 (5) | −0.0001 (4) | 0.0039 (3) | 0.0003 (4) |
O1C | 0.0186 (3) | 0.0204 (3) | 0.0337 (4) | −0.0010 (3) | 0.0044 (3) | −0.0017 (3) |
O8A—C2A | 1.2228 (12) | N1B—H1B | 0.802 (15) |
N1A—C6A | 1.3675 (13) | C1B—C2B | 1.5355 (13) |
N1A—C2A | 1.3675 (13) | C2B—H21B | 0.961 (14) |
N1A—H1A | 0.880 (15) | C2B—H22B | 0.968 (14) |
N3A—C4A | 1.3613 (11) | C3B—C4B | 1.4965 (13) |
N3A—C2A | 1.3786 (12) | C4B—C9B | 1.3963 (13) |
N3A—H3A | 0.913 (14) | C4B—C5B | 1.3985 (13) |
N7A—C4A | 1.3077 (13) | C5B—C6B | 1.3931 (14) |
N7A—H71A | 0.925 (15) | C5B—H5B | 0.9500 |
N7A—H72A | 0.880 (16) | C6B—C7B | 1.3913 (15) |
C4A—C5A | 1.4299 (13) | C6B—H6B | 0.9500 |
C5A—C6A | 1.3482 (14) | C7B—C8B | 1.3900 (16) |
C5A—H5A | 0.953 (14) | C7B—H7B | 0.9500 |
C6A—H6A | 0.9500 | C8B—C9B | 1.3910 (15) |
O1B—C1B | 1.2497 (12) | C8B—H8B | 0.9500 |
O2B—C1B | 1.2681 (12) | C9B—H9B | 0.9500 |
O3B—C3B | 1.2476 (12) | O1C—H11C | 0.860 (17) |
N1B—C3B | 1.3379 (12) | O1C—H12C | 0.874 (17) |
N1B—C2B | 1.4457 (12) | ||
C6A—N1A—C2A | 122.24 (8) | N1B—C2B—H21B | 106.5 (8) |
C6A—N1A—H1A | 119.9 (9) | C1B—C2B—H21B | 106.5 (8) |
C2A—N1A—H1A | 116.9 (9) | N1B—C2B—H22B | 110.6 (8) |
C4A—N3A—C2A | 124.01 (8) | C1B—C2B—H22B | 109.2 (8) |
C4A—N3A—H3A | 120.0 (8) | H21B—C2B—H22B | 108.6 (11) |
C2A—N3A—H3A | 116.0 (8) | O3B—C3B—N1B | 123.10 (9) |
C4A—N7A—H71A | 120.4 (9) | O3B—C3B—C4B | 119.89 (8) |
C4A—N7A—H72A | 118.3 (9) | N1B—C3B—C4B | 116.99 (8) |
H71A—N7A—H72A | 121.2 (13) | C9B—C4B—C5B | 119.51 (9) |
O8A—C2A—N1A | 123.32 (9) | C9B—C4B—C3B | 118.03 (8) |
O8A—C2A—N3A | 120.81 (9) | C5B—C4B—C3B | 122.43 (8) |
N1A—C2A—N3A | 115.85 (8) | C6B—C5B—C4B | 119.89 (9) |
N7A—C4A—N3A | 118.25 (9) | C6B—C5B—H5B | 120.1 |
N7A—C4A—C5A | 123.57 (9) | C4B—C5B—H5B | 120.1 |
N3A—C4A—C5A | 118.17 (8) | C7B—C6B—C5B | 120.20 (9) |
C6A—C5A—C4A | 117.74 (9) | C7B—C6B—H6B | 119.9 |
C6A—C5A—H5A | 122.8 (8) | C5B—C6B—H6B | 119.9 |
C4A—C5A—H5A | 119.4 (8) | C8B—C7B—C6B | 120.08 (10) |
C5A—C6A—N1A | 121.91 (9) | C8B—C7B—H7B | 120.0 |
C5A—C6A—H6A | 119.0 | C6B—C7B—H7B | 120.0 |
N1A—C6A—H6A | 119.0 | C7B—C8B—C9B | 119.88 (9) |
C3B—N1B—C2B | 121.82 (8) | C7B—C8B—H8B | 120.1 |
C3B—N1B—H1B | 119.6 (10) | C9B—C8B—H8B | 120.1 |
C2B—N1B—H1B | 118.1 (10) | C8B—C9B—C4B | 120.39 (9) |
O1B—C1B—O2B | 125.80 (9) | C8B—C9B—H9B | 119.8 |
O1B—C1B—C2B | 119.52 (8) | C4B—C9B—H9B | 119.8 |
O2B—C1B—C2B | 114.67 (8) | H11C—O1C—H12C | 109.6 (15) |
N1B—C2B—C1B | 115.21 (8) | ||
O1B—C1B—C2B—N1B | 6.87 (13) | C4A—C5A—C6A—N1A | −0.30 (14) |
O2B—C1B—C2B—N1B | −173.87 (8) | C2A—N1A—C6A—C5A | 2.10 (15) |
C1B—C2B—N1B—C3B | 70.48 (12) | C2B—N1B—C3B—O3B | 4.80 (15) |
C2B—N1B—C3B—C4B | −173.84 (8) | O3B—C3B—C4B—C9B | 24.38 (13) |
N1B—C3B—C4B—C5B | 25.23 (13) | O3B—C3B—C4B—C5B | −153.46 (9) |
N1B—C3B—C4B—C9B | −156.93 (9) | C9B—C4B—C5B—C6B | −1.29 (14) |
C6A—N1A—C2A—O8A | 178.05 (9) | C3B—C4B—C5B—C6B | 176.52 (9) |
C6A—N1A—C2A—N3A | −3.12 (13) | C4B—C5B—C6B—C7B | −0.14 (15) |
C4A—N3A—C2A—O8A | −178.56 (9) | C5B—C6B—C7B—C8B | 1.58 (16) |
C4A—N3A—C2A—N1A | 2.58 (13) | C6B—C7B—C8B—C9B | −1.57 (16) |
C2A—N3A—C4A—N7A | 179.42 (9) | C7B—C8B—C9B—C4B | 0.13 (15) |
C2A—N3A—C4A—C5A | −0.94 (13) | C5B—C4B—C9B—C8B | 1.30 (14) |
N7A—C4A—C5A—C6A | 179.35 (9) | C3B—C4B—C9B—C8B | −176.61 (9) |
N3A—C4A—C5A—C6A | −0.27 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3Bi | 0.880 (15) | 1.887 (15) | 2.7595 (11) | 170.8 (13) |
N3A—H3A···O2B | 0.913 (14) | 1.799 (14) | 2.7121 (11) | 178.1 (12) |
N7A—H71A···O1B | 0.925 (15) | 1.829 (15) | 2.7543 (12) | 179.3 (14) |
N7A—H72A···O8Aii | 0.880 (16) | 1.897 (16) | 2.7576 (11) | 165.6 (14) |
C5A—H5A···O3Biii | 0.953 (14) | 2.496 (14) | 3.4128 (12) | 161.3 (11) |
N1B—H1B···O1Civ | 0.803 (15) | 2.096 (15) | 2.8453 (11) | 155.4 (13) |
O1C—H11C···O1B | 0.861 (17) | 1.968 (17) | 2.8163 (10) | 168.5 (15) |
O1C—H12C···O2Bii | 0.874 (17) | 2.039 (17) | 2.8998 (10) | 168.1 (15) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1. |
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