Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314622002012/hb4400sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314622002012/hb4400Isup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314622002012/hb4400Isup3.cml |
CCDC reference: 2153454
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.095
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O3 ..O3 . 2.74 Ang. 1-x,1-y,1-z = 5_666 Check
Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 10 Report
Alert level G PLAT432_ALERT_2_G Short Inter X...Y Contact C4 ..C6 . 3.20 Ang. 3/2-x,1/2-y,1-z = 7_656 Check PLAT432_ALERT_2_G Short Inter X...Y Contact C6 ..C6 . 3.16 Ang. 1-x,y,1/2-z = 2_655 Check PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 17 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).
C8H8N2O4 | F(000) = 816 |
Mr = 196.16 | Dx = 1.569 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.6643 (3) Å | Cell parameters from 5235 reflections |
b = 18.5534 (5) Å | θ = 4.8–69.3° |
c = 9.3072 (2) Å | µ = 1.10 mm−1 |
β = 95.5075 (14)° | T = 90 K |
V = 1661.13 (8) Å3 | Lath, yellow |
Z = 8 | 0.21 × 0.07 × 0.02 mm |
Bruker Kappa APEXII DUO CCD diffractometer | 1543 independent reflections |
Radiation source: IµS microfocus | 1486 reflections with I > 2σ(I) |
QUAZAR multilayer optics monochromator | Rint = 0.028 |
φ and ω scans | θmax = 69.3°, θmin = 4.8° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −11→7 |
Tmin = 0.872, Tmax = 0.978 | k = −22→20 |
6856 measured reflections | l = −11→10 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0487P)2 + 1.5639P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
1543 reflections | Δρmax = 0.29 e Å−3 |
134 parameters | Δρmin = −0.23 e Å−3 |
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. All H atoms were located in difference maps and those on C were thereafter treated as riding in geometrically idealized positions with C—H distances 0.95 Å for phenyl and 0.98 Å for methyl. The coordinates of the N—H and O—H hydrogen atoms were refined. Uiso(H) values were assigned as 1.2Ueq for the attached atom (1.5 for OH and methyl). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.49965 (11) | 0.11112 (5) | 0.49610 (11) | 0.0180 (2) | |
H1O | 0.435 (2) | 0.1126 (10) | 0.551 (2) | 0.027* | |
O2 | 0.36347 (11) | 0.35035 (5) | 0.64809 (11) | 0.0240 (3) | |
O3 | 0.47807 (11) | 0.43019 (5) | 0.53985 (12) | 0.0239 (3) | |
O4 | 0.79942 (10) | 0.37109 (5) | 0.17917 (10) | 0.0208 (3) | |
N1 | 0.44852 (12) | 0.36642 (6) | 0.56392 (12) | 0.0163 (3) | |
N2 | 0.65588 (12) | 0.39184 (6) | 0.35604 (12) | 0.0149 (3) | |
H2N | 0.6134 (17) | 0.4246 (10) | 0.4050 (18) | 0.018* | |
C1 | 0.53400 (14) | 0.18008 (7) | 0.46502 (14) | 0.0143 (3) | |
C2 | 0.47727 (13) | 0.23927 (7) | 0.52723 (13) | 0.0146 (3) | |
H2 | 0.4113 | 0.2327 | 0.5955 | 0.018* | |
C3 | 0.51647 (13) | 0.30877 (7) | 0.49012 (13) | 0.0138 (3) | |
C4 | 0.61410 (13) | 0.32179 (7) | 0.39015 (13) | 0.0137 (3) | |
C5 | 0.66952 (13) | 0.26010 (7) | 0.32904 (13) | 0.0140 (3) | |
H5 | 0.7356 | 0.2659 | 0.2606 | 0.017* | |
C6 | 0.63082 (13) | 0.19119 (7) | 0.36548 (13) | 0.0143 (3) | |
H6 | 0.6708 | 0.1509 | 0.3220 | 0.017* | |
C7 | 0.74622 (13) | 0.41291 (7) | 0.25993 (14) | 0.0152 (3) | |
C8 | 0.77664 (15) | 0.49227 (7) | 0.26014 (16) | 0.0211 (3) | |
H8A | 0.8474 | 0.5036 | 0.3395 | 0.032* | |
H8B | 0.6914 | 0.5192 | 0.2729 | 0.032* | |
H8C | 0.8109 | 0.5058 | 0.1681 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0214 (5) | 0.0120 (5) | 0.0220 (5) | −0.0007 (4) | 0.0096 (4) | 0.0002 (4) |
O2 | 0.0279 (6) | 0.0189 (5) | 0.0287 (6) | 0.0003 (4) | 0.0202 (4) | 0.0005 (4) |
O3 | 0.0298 (6) | 0.0121 (5) | 0.0327 (6) | −0.0014 (4) | 0.0180 (5) | −0.0002 (4) |
O4 | 0.0256 (5) | 0.0158 (5) | 0.0234 (5) | 0.0000 (4) | 0.0141 (4) | −0.0013 (4) |
N1 | 0.0175 (6) | 0.0143 (6) | 0.0182 (6) | 0.0003 (4) | 0.0073 (4) | −0.0003 (4) |
N2 | 0.0148 (6) | 0.0129 (5) | 0.0179 (6) | 0.0009 (4) | 0.0061 (4) | −0.0006 (4) |
C1 | 0.0142 (6) | 0.0132 (6) | 0.0155 (6) | −0.0010 (5) | 0.0005 (5) | 0.0010 (5) |
C2 | 0.0143 (6) | 0.0159 (7) | 0.0143 (6) | −0.0002 (5) | 0.0041 (5) | 0.0001 (5) |
C3 | 0.0140 (6) | 0.0141 (7) | 0.0136 (6) | 0.0017 (5) | 0.0026 (5) | −0.0019 (5) |
C4 | 0.0124 (6) | 0.0153 (6) | 0.0133 (6) | −0.0002 (5) | 0.0004 (5) | 0.0004 (5) |
C5 | 0.0122 (6) | 0.0165 (7) | 0.0138 (6) | 0.0003 (5) | 0.0031 (5) | −0.0003 (5) |
C6 | 0.0134 (6) | 0.0152 (6) | 0.0145 (6) | 0.0016 (5) | 0.0025 (5) | −0.0013 (5) |
C7 | 0.0142 (6) | 0.0143 (6) | 0.0173 (6) | 0.0006 (5) | 0.0028 (5) | 0.0010 (5) |
C8 | 0.0245 (7) | 0.0142 (7) | 0.0266 (7) | −0.0006 (5) | 0.0125 (6) | −0.0002 (5) |
O1—C1 | 1.3599 (16) | C2—C3 | 1.3966 (18) |
O1—H1O | 0.84 (2) | C2—H2 | 0.9500 |
O2—N1 | 1.2255 (15) | C3—C4 | 1.4081 (18) |
O3—N1 | 1.2424 (15) | C4—C5 | 1.4067 (18) |
O4—C7 | 1.2270 (17) | C5—C6 | 1.3835 (18) |
N1—C3 | 1.4608 (17) | C5—H5 | 0.9500 |
N2—C7 | 1.3657 (18) | C6—H6 | 0.9500 |
N2—C4 | 1.4063 (17) | C7—C8 | 1.5014 (18) |
N2—H2N | 0.883 (19) | C8—H8A | 0.9800 |
C1—C2 | 1.3795 (18) | C8—H8B | 0.9800 |
C1—C6 | 1.3938 (19) | C8—H8C | 0.9800 |
C1—O1—H1O | 108.0 (12) | N2—C4—C3 | 122.20 (12) |
O2—N1—O3 | 121.80 (11) | C5—C4—C3 | 115.65 (12) |
O2—N1—C3 | 118.79 (11) | C6—C5—C4 | 122.03 (12) |
O3—N1—C3 | 119.41 (11) | C6—C5—H5 | 119.0 |
C7—N2—C4 | 128.89 (12) | C4—C5—H5 | 119.0 |
C7—N2—H2N | 119.9 (11) | C5—C6—C1 | 120.94 (12) |
C4—N2—H2N | 111.2 (11) | C5—C6—H6 | 119.5 |
O1—C1—C2 | 123.01 (12) | C1—C6—H6 | 119.5 |
O1—C1—C6 | 118.27 (12) | O4—C7—N2 | 123.52 (12) |
C2—C1—C6 | 118.72 (12) | O4—C7—C8 | 121.83 (12) |
C1—C2—C3 | 120.20 (12) | N2—C7—C8 | 114.66 (11) |
C1—C2—H2 | 119.9 | C7—C8—H8A | 109.5 |
C3—C2—H2 | 119.9 | C7—C8—H8B | 109.5 |
C2—C3—C4 | 122.46 (12) | H8A—C8—H8B | 109.5 |
C2—C3—N1 | 114.51 (11) | C7—C8—H8C | 109.5 |
C4—C3—N1 | 123.02 (12) | H8A—C8—H8C | 109.5 |
N2—C4—C5 | 122.14 (12) | H8B—C8—H8C | 109.5 |
O1—C1—C2—C3 | −179.68 (11) | N1—C3—C4—N2 | 1.39 (19) |
C6—C1—C2—C3 | 0.19 (19) | C2—C3—C4—C5 | 0.31 (18) |
C1—C2—C3—C4 | −0.29 (19) | N1—C3—C4—C5 | 180.00 (11) |
C1—C2—C3—N1 | 180.00 (11) | N2—C4—C5—C6 | 178.36 (11) |
O2—N1—C3—C2 | −1.17 (17) | C3—C4—C5—C6 | −0.25 (18) |
O3—N1—C3—C2 | 178.91 (11) | C4—C5—C6—C1 | 0.18 (19) |
O2—N1—C3—C4 | 179.12 (12) | O1—C1—C6—C5 | 179.74 (11) |
O3—N1—C3—C4 | −0.79 (19) | C2—C1—C6—C5 | −0.13 (19) |
C7—N2—C4—C5 | 3.1 (2) | C4—N2—C7—O4 | 5.1 (2) |
C7—N2—C4—C3 | −178.38 (12) | C4—N2—C7—C8 | −174.86 (12) |
C2—C3—C4—N2 | −178.30 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4i | 0.84 (2) | 1.88 (2) | 2.7183 (14) | 172.0 (18) |
N2—H2N···O3 | 0.883 (19) | 1.901 (17) | 2.6363 (15) | 139.6 (15) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |