Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605094X/sj2181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680605094X/sj2181Isup2.hkl |
CCDC reference: 634003
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.108
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O1 .. 2.73 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O1 .. 2.88 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O2 .. O3 .. 2.88 Ang. PLAT756_ALERT_4_C H...A Calc 2.59000, Rep 2.59(2) ...... Senseless su H7B -N4 1.555 2.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun is supervisor of Shea-Lin Ng whereas Muhammad I. Saleh is supervisor of Adassalam Abdelhafiz Tameem, Abdulssalam Salhin, Bahruddin Saad and Ismail Ab. Rahman in this collaborative publication. School of Chemical Sciences, Universiti Sains Malaysia is involved in the extraction and synthesis of the title compound and X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia is involved in the structure determination. All parties are involved in writing up the manuscript. |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C7H6N4O4 | Z = 2 |
Mr = 210.16 | F(000) = 216 |
Triclinic, P1 | Dx = 1.650 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.2482 (1) Å | Cell parameters from 4353 reflections |
b = 9.7774 (2) Å | θ = 2.1–30.0° |
c = 10.3407 (2) Å | µ = 0.14 mm−1 |
α = 86.825 (1)° | T = 100 K |
β = 83.966 (1)° | Block, yellow |
γ = 82.413 (1)° | 0.35 × 0.18 × 0.10 mm |
V = 423.02 (2) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 2447 independent reflections |
Radiation source: fine-focus sealed tube | 2027 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.953, Tmax = 0.987 | l = −14→14 |
14315 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.0932P] where P = (Fo2 + 2Fc2)/3 |
2447 reflections | (Δ/σ)max < 0.001 |
140 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Experimental. The data were collected with the Oxford Cryosystem Cobra low-temperature attachment. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2054 (2) | 0.09156 (8) | 0.51817 (8) | 0.0221 (2) | |
O2 | 0.5236 (2) | 0.21176 (8) | 0.60011 (8) | 0.02262 (19) | |
O3 | 0.9924 (2) | 0.56900 (9) | 0.35352 (9) | 0.0281 (2) | |
O4 | 0.9353 (3) | 0.60095 (9) | 0.14773 (9) | 0.0340 (2) | |
N1 | 0.3974 (2) | 0.17820 (9) | 0.50762 (9) | 0.0169 (2) | |
N2 | 0.8936 (2) | 0.53759 (10) | 0.25321 (10) | 0.0224 (2) | |
N3 | 0.2312 (2) | 0.07638 (10) | 0.26471 (9) | 0.0182 (2) | |
N4 | 0.1731 (2) | 0.02809 (10) | 0.14755 (9) | 0.0218 (2) | |
C1 | 0.4744 (2) | 0.24062 (11) | 0.37983 (10) | 0.0163 (2) | |
C2 | 0.6420 (3) | 0.35429 (11) | 0.37625 (10) | 0.0175 (2) | |
H2A | 0.6997 | 0.3861 | 0.4524 | 0.021* | |
C3 | 0.7204 (3) | 0.41842 (11) | 0.25779 (11) | 0.0190 (2) | |
C4 | 0.6414 (3) | 0.37050 (12) | 0.14196 (11) | 0.0207 (2) | |
H4A | 0.6977 | 0.4152 | 0.0628 | 0.025* | |
C5 | 0.4813 (3) | 0.25779 (11) | 0.14539 (10) | 0.0195 (2) | |
H5A | 0.4318 | 0.2260 | 0.0678 | 0.023* | |
C6 | 0.3884 (3) | 0.18780 (11) | 0.26494 (10) | 0.0173 (2) | |
C7 | 0.0496 (3) | −0.08426 (12) | 0.15642 (11) | 0.0235 (2) | |
H7A | 0.0029 | −0.1312 | 0.2396 | 0.028* | |
H7B | 0.0082 | −0.1207 | 0.0760 | 0.028* | |
H3A | 0.177 (4) | 0.0327 (16) | 0.3350 (16) | 0.029 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0249 (4) | 0.0242 (4) | 0.0185 (4) | −0.0108 (3) | −0.0005 (3) | 0.0018 (3) |
O2 | 0.0276 (4) | 0.0248 (4) | 0.0174 (4) | −0.0073 (3) | −0.0069 (3) | 0.0009 (3) |
O3 | 0.0297 (5) | 0.0231 (4) | 0.0338 (5) | −0.0091 (4) | −0.0071 (4) | 0.0001 (3) |
O4 | 0.0497 (6) | 0.0245 (5) | 0.0278 (5) | −0.0149 (4) | 0.0062 (4) | 0.0047 (3) |
N1 | 0.0179 (4) | 0.0168 (4) | 0.0160 (4) | −0.0025 (3) | −0.0018 (3) | 0.0005 (3) |
N2 | 0.0229 (5) | 0.0168 (4) | 0.0265 (5) | −0.0035 (4) | 0.0023 (4) | 0.0009 (4) |
N3 | 0.0230 (5) | 0.0195 (4) | 0.0130 (4) | −0.0060 (4) | −0.0024 (3) | 0.0017 (3) |
N4 | 0.0281 (5) | 0.0230 (5) | 0.0156 (4) | −0.0060 (4) | −0.0050 (4) | −0.0002 (3) |
C1 | 0.0157 (5) | 0.0174 (5) | 0.0151 (5) | −0.0016 (4) | −0.0003 (4) | 0.0027 (4) |
C2 | 0.0165 (5) | 0.0169 (5) | 0.0187 (5) | −0.0012 (4) | −0.0018 (4) | −0.0003 (4) |
C3 | 0.0176 (5) | 0.0162 (5) | 0.0228 (5) | −0.0029 (4) | −0.0006 (4) | 0.0020 (4) |
C4 | 0.0215 (5) | 0.0209 (5) | 0.0183 (5) | −0.0019 (4) | 0.0003 (4) | 0.0048 (4) |
C5 | 0.0224 (5) | 0.0211 (5) | 0.0148 (5) | −0.0033 (4) | −0.0012 (4) | 0.0021 (4) |
C6 | 0.0166 (5) | 0.0178 (5) | 0.0169 (5) | −0.0009 (4) | −0.0013 (4) | 0.0012 (4) |
C7 | 0.0311 (6) | 0.0242 (6) | 0.0167 (5) | −0.0079 (5) | −0.0035 (4) | −0.0006 (4) |
O1—N1 | 1.2445 (12) | C1—C6 | 1.4215 (14) |
O2—N1 | 1.2243 (11) | C2—C3 | 1.3744 (15) |
O3—N2 | 1.2277 (13) | C2—H2A | 0.9300 |
O4—N2 | 1.2322 (13) | C3—C4 | 1.3983 (16) |
N1—C1 | 1.4484 (13) | C4—C5 | 1.3664 (16) |
N2—C3 | 1.4541 (14) | C4—H4A | 0.9300 |
N3—C6 | 1.3510 (14) | C5—C6 | 1.4239 (15) |
N3—N4 | 1.3816 (12) | C5—H5A | 0.9300 |
N3—H3A | 0.849 (17) | C7—H7A | 0.9663 |
N4—C7 | 1.2734 (15) | C7—H7B | 0.9639 |
C1—C2 | 1.3938 (15) | ||
O2—N1—O1 | 122.79 (9) | C2—C3—C4 | 121.52 (10) |
O2—N1—C1 | 119.17 (9) | C2—C3—N2 | 119.00 (10) |
O1—N1—C1 | 118.04 (9) | C4—C3—N2 | 119.48 (10) |
O3—N2—O4 | 123.60 (10) | C5—C4—C3 | 119.81 (10) |
O3—N2—C3 | 118.66 (9) | C5—C4—H4A | 120.1 |
O4—N2—C3 | 117.74 (10) | C3—C4—H4A | 120.1 |
C6—N3—N4 | 119.44 (9) | C4—C5—C6 | 121.57 (10) |
C6—N3—H3A | 121.2 (10) | C4—C5—H5A | 119.2 |
N4—N3—H3A | 119.3 (10) | C6—C5—H5A | 119.2 |
C7—N4—N3 | 114.93 (9) | N3—C6—C1 | 123.60 (10) |
C2—C1—C6 | 122.07 (9) | N3—C6—C5 | 120.00 (10) |
C2—C1—N1 | 115.93 (9) | C1—C6—C5 | 116.39 (10) |
C6—C1—N1 | 122.00 (9) | N4—C7—H7A | 121.5 |
C3—C2—C1 | 118.62 (10) | N4—C7—H7B | 116.7 |
C3—C2—H2A | 120.7 | H7A—C7—H7B | 121.8 |
C1—C2—H2A | 120.7 | ||
C6—N3—N4—C7 | 173.97 (10) | O4—N2—C3—C4 | 7.45 (16) |
O2—N1—C1—C2 | −11.77 (14) | C2—C3—C4—C5 | 0.30 (17) |
O1—N1—C1—C2 | 168.58 (9) | N2—C3—C4—C5 | 179.39 (10) |
O2—N1—C1—C6 | 167.30 (9) | C3—C4—C5—C6 | 0.71 (17) |
O1—N1—C1—C6 | −12.34 (15) | N4—N3—C6—C1 | −176.50 (10) |
C6—C1—C2—C3 | 1.28 (16) | N4—N3—C6—C5 | 2.52 (16) |
N1—C1—C2—C3 | −179.65 (9) | C2—C1—C6—N3 | 178.73 (10) |
C1—C2—C3—C4 | −1.27 (17) | N1—C1—C6—N3 | −0.28 (16) |
C1—C2—C3—N2 | 179.63 (9) | C2—C1—C6—C5 | −0.32 (16) |
O3—N2—C3—C2 | 7.16 (15) | N1—C1—C6—C5 | −179.33 (9) |
O4—N2—C3—C2 | −173.44 (10) | C4—C5—C6—N3 | −179.77 (10) |
O3—N2—C3—C4 | −171.95 (10) | C4—C5—C6—C1 | −0.69 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1 | 0.849 (17) | 2.03 (2) | 2.623 (1) | 126 (1) |
C5—H5A···N4 | 0.93 | 2.41 | 2.743 (2) | 101 |
N3—H3A···O1i | 0.849 (17) | 2.49 (2) | 3.271 (1) | 153 (2) |
C2—H2A···O3ii | 0.93 | 2.59 | 3.498 (1) | 164 |
C4—H4A···O4iii | 0.93 | 2.54 | 3.346 (2) | 145 |
C7—H7A···O1i | 0.97 | 2.60 | 3.425 (1) | 143 |
C7—H7B···N4iv | 0.96 | 2.59 (2) | 3.373 (2) | 138 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+1, −z; (iv) −x, −y, −z. |
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