Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003393/ci6338sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003393/ci6338Isup2.hkl |
CCDC reference: 236093
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.142
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.680 1.000 Tmin' and Tmax expected: 0.964 0.982 RR' = 0.693 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.69
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT230_ALERT_2_C Hirshfeld Test Diff for O1A - N2A = 5.69 su PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.14 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C11H12N2O2 | Z = 4 |
Mr = 204.23 | F(000) = 432 |
Triclinic, P1 | Dx = 1.300 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.229 (2) Å | Cell parameters from 1705 reflections |
b = 11.828 (3) Å | θ = 2.8–27.4° |
c = 12.088 (3) Å | µ = 0.09 mm−1 |
α = 67.403 (4)° | T = 100 K |
β = 86.940 (4)° | Block, light yellow |
γ = 74.256 (4)° | 0.40 × 0.25 × 0.20 mm |
V = 1043.8 (5) Å3 |
Bruker CCD area-detector diffractometer | 3980 independent reflections |
Radiation source: fine-focus sealed tube | 2616 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −8→10 |
Tmin = 0.68, Tmax = 1.00 | k = −14→14 |
7051 measured reflections | l = −14→14 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0899P)2] where P = (Fo2 + 2Fc2)/3 |
3980 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 20 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. |
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 | ||
O1A | 0.7952 (2) | 0.53774 (17) | 0.20466 (14) | 0.0299 (4) | |
O2A | 0.9550 (2) | 0.44383 (16) | 0.36947 (15) | 0.0293 (4) | |
N1A | 0.5920 (2) | 0.60278 (17) | 0.66399 (16) | 0.0204 (5) | |
H1AA | 0.6751 | 0.5601 | 0.7195 | 0.025* | |
N2A | 0.8216 (3) | 0.51688 (19) | 0.31127 (18) | 0.0232 (5) | |
C2A | 0.4358 (3) | 0.6727 (2) | 0.6803 (2) | 0.0202 (5) | |
C3A | 0.3401 (3) | 0.7278 (2) | 0.5730 (2) | 0.0214 (5) | |
H3AA | 0.2281 | 0.7820 | 0.5590 | 0.026* | |
C4A | 0.4395 (3) | 0.6887 (2) | 0.48718 (19) | 0.0193 (5) | |
C5A | 0.4113 (3) | 0.7095 (2) | 0.3666 (2) | 0.0218 (5) | |
H5AA | 0.3056 | 0.7608 | 0.3251 | 0.026* | |
C6A | 0.5387 (3) | 0.6547 (2) | 0.3089 (2) | 0.0218 (5) | |
H6AA | 0.5226 | 0.6690 | 0.2268 | 0.026* | |
C7A | 0.6922 (3) | 0.5775 (2) | 0.3732 (2) | 0.0205 (5) | |
C8A | 0.7267 (3) | 0.5524 (2) | 0.4919 (2) | 0.0204 (5) | |
H8AA | 0.8319 | 0.4992 | 0.5330 | 0.024* | |
C9A | 0.5978 (3) | 0.6100 (2) | 0.54776 (19) | 0.0185 (5) | |
C10A | 0.3895 (3) | 0.6800 (2) | 0.7988 (2) | 0.0230 (5) | |
H10A | 0.3885 | 0.5941 | 0.8566 | 0.028* | |
H10B | 0.2734 | 0.7364 | 0.7901 | 0.028* | |
C11A | 0.5075 (3) | 0.7291 (2) | 0.8505 (2) | 0.0257 (6) | |
H11A | 0.5139 | 0.8130 | 0.7912 | 0.031* | |
H11B | 0.6224 | 0.6699 | 0.8646 | 0.031* | |
C12A | 0.4493 (3) | 0.7423 (3) | 0.9680 (2) | 0.0328 (6) | |
H12A | 0.5290 | 0.7740 | 0.9976 | 0.049* | |
H12B | 0.4450 | 0.6591 | 1.0277 | 0.049* | |
H12C | 0.3365 | 0.8023 | 0.9543 | 0.049* | |
O1B | 1.0916 (2) | 0.67913 (17) | 1.20003 (15) | 0.0374 (5) | |
O2B | 1.1694 (2) | 0.53805 (16) | 1.12174 (15) | 0.0288 (4) | |
N1B | 0.8769 (2) | 0.77012 (18) | 0.70143 (16) | 0.0204 (5) | |
H1BA | 0.9219 | 0.7021 | 0.6853 | 0.024* | |
N2B | 1.0889 (3) | 0.6451 (2) | 1.11582 (17) | 0.0243 (5) | |
C2B | 0.7741 (3) | 0.8825 (2) | 0.6231 (2) | 0.0213 (5) | |
C3B | 0.7285 (3) | 0.9665 (2) | 0.6784 (2) | 0.0239 (6) | |
H3BA | 0.6577 | 1.0510 | 0.6441 | 0.029* | |
C4B | 0.8061 (3) | 0.9048 (2) | 0.7970 (2) | 0.0225 (5) | |
C5B | 0.8084 (3) | 0.9404 (2) | 0.8949 (2) | 0.0282 (6) | |
H5BA | 0.7470 | 1.0232 | 0.8892 | 0.034* | |
C6B | 0.9000 (3) | 0.8548 (2) | 0.9991 (2) | 0.0279 (6) | |
H6BA | 0.9028 | 0.8783 | 1.0656 | 0.033* | |
C7B | 0.9894 (3) | 0.7325 (2) | 1.0066 (2) | 0.0222 (5) | |
C8B | 0.9894 (3) | 0.6920 (2) | 0.9134 (2) | 0.0212 (5) | |
H8BA | 1.0485 | 0.6082 | 0.9209 | 0.025* | |
C9B | 0.8986 (3) | 0.7802 (2) | 0.80899 (19) | 0.0181 (5) | |
C10B | 0.7279 (3) | 0.9004 (2) | 0.4985 (2) | 0.0250 (6) | |
H10C | 0.6479 | 0.9856 | 0.4592 | 0.030* | |
H10D | 0.6689 | 0.8363 | 0.5028 | 0.030* | |
C11B | 0.8803 (3) | 0.8883 (3) | 0.4209 (2) | 0.0324 (6) | |
H11C | 0.9433 | 0.9492 | 0.4196 | 0.039* | |
H11D | 0.9573 | 0.8014 | 0.4570 | 0.039* | |
C12B | 0.8263 (4) | 0.9146 (3) | 0.2925 (2) | 0.0402 (7) | |
H12D | 0.9265 | 0.9062 | 0.2457 | 0.060* | |
H12E | 0.7516 | 1.0012 | 0.2560 | 0.060* | |
H12F | 0.7659 | 0.8534 | 0.2934 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0259 (10) | 0.0474 (11) | 0.0251 (10) | −0.0164 (9) | 0.0068 (8) | −0.0194 (8) |
O2A | 0.0183 (10) | 0.0378 (10) | 0.0366 (10) | −0.0064 (8) | 0.0016 (8) | −0.0201 (8) |
N1A | 0.0122 (10) | 0.0262 (11) | 0.0224 (10) | −0.0051 (9) | −0.0018 (8) | −0.0086 (8) |
N2A | 0.0129 (11) | 0.0294 (11) | 0.0316 (12) | −0.0101 (9) | 0.0041 (9) | −0.0135 (9) |
C2A | 0.0115 (12) | 0.0248 (12) | 0.0266 (12) | −0.0084 (10) | 0.0012 (9) | −0.0101 (10) |
C3A | 0.0119 (12) | 0.0261 (13) | 0.0278 (13) | −0.0064 (10) | −0.0014 (10) | −0.0110 (11) |
C4A | 0.0160 (12) | 0.0204 (12) | 0.0223 (12) | −0.0082 (10) | −0.0012 (9) | −0.0067 (10) |
C5A | 0.0172 (13) | 0.0233 (12) | 0.0244 (12) | −0.0064 (10) | −0.0030 (10) | −0.0074 (10) |
C6A | 0.0224 (14) | 0.0254 (13) | 0.0195 (12) | −0.0111 (11) | −0.0009 (10) | −0.0075 (10) |
C7A | 0.0188 (13) | 0.0226 (12) | 0.0243 (12) | −0.0091 (10) | 0.0046 (10) | −0.0115 (10) |
C8A | 0.0144 (12) | 0.0249 (12) | 0.0246 (12) | −0.0089 (10) | 0.0007 (9) | −0.0100 (10) |
C9A | 0.0137 (12) | 0.0218 (12) | 0.0229 (12) | −0.0095 (10) | −0.0017 (9) | −0.0082 (10) |
C10A | 0.0142 (12) | 0.0335 (14) | 0.0271 (13) | −0.0113 (11) | 0.0037 (10) | −0.0149 (11) |
C11A | 0.0166 (13) | 0.0386 (15) | 0.0283 (13) | −0.0128 (11) | 0.0031 (10) | −0.0164 (11) |
C12A | 0.0277 (15) | 0.0489 (17) | 0.0300 (14) | −0.0184 (13) | 0.0045 (11) | −0.0189 (13) |
O1B | 0.0387 (12) | 0.0468 (12) | 0.0291 (10) | −0.0088 (10) | −0.0047 (8) | −0.0182 (9) |
O2B | 0.0175 (9) | 0.0340 (10) | 0.0320 (10) | −0.0038 (8) | −0.0044 (7) | −0.0110 (8) |
N1B | 0.0132 (10) | 0.0269 (11) | 0.0241 (10) | −0.0074 (8) | 0.0022 (8) | −0.0119 (9) |
N2B | 0.0141 (11) | 0.0356 (12) | 0.0260 (11) | −0.0108 (9) | 0.0012 (8) | −0.0121 (10) |
C2B | 0.0145 (12) | 0.0254 (12) | 0.0219 (12) | −0.0096 (10) | 0.0008 (9) | −0.0041 (10) |
C3B | 0.0191 (13) | 0.0233 (12) | 0.0260 (13) | −0.0060 (10) | −0.0016 (10) | −0.0055 (10) |
C4B | 0.0184 (13) | 0.0256 (12) | 0.0237 (12) | −0.0081 (10) | 0.0014 (10) | −0.0081 (10) |
C5B | 0.0281 (15) | 0.0284 (13) | 0.0299 (14) | −0.0060 (11) | 0.0013 (11) | −0.0141 (11) |
C6B | 0.0311 (15) | 0.0314 (14) | 0.0239 (13) | −0.0090 (12) | 0.0004 (11) | −0.0131 (11) |
C7B | 0.0149 (12) | 0.0286 (13) | 0.0205 (12) | −0.0072 (10) | −0.0010 (9) | −0.0057 (10) |
C8B | 0.0118 (12) | 0.0255 (13) | 0.0267 (13) | −0.0076 (10) | 0.0039 (10) | −0.0093 (10) |
C9B | 0.0106 (12) | 0.0262 (12) | 0.0195 (11) | −0.0096 (10) | 0.0033 (9) | −0.0081 (10) |
C10B | 0.0181 (13) | 0.0323 (14) | 0.0247 (13) | −0.0107 (11) | 0.0014 (10) | −0.0086 (11) |
C11B | 0.0191 (14) | 0.0540 (18) | 0.0288 (14) | −0.0114 (13) | 0.0029 (11) | −0.0204 (13) |
C12B | 0.0390 (18) | 0.0568 (19) | 0.0261 (14) | −0.0099 (15) | 0.0023 (12) | −0.0196 (13) |
O1A—N2A | 1.235 (2) | O1B—N2B | 1.233 (2) |
O2A—N2A | 1.244 (3) | O2B—N2B | 1.236 (2) |
N1A—C9A | 1.374 (3) | N1B—C2B | 1.374 (3) |
N1A—C2A | 1.377 (3) | N1B—C9B | 1.376 (3) |
N1A—H1AA | 0.88 | N1B—H1BA | 0.88 |
N2A—C7A | 1.457 (3) | N2B—C7B | 1.446 (3) |
C2A—C3A | 1.381 (3) | C2B—C3B | 1.362 (3) |
C2A—C10A | 1.491 (3) | C2B—C10B | 1.493 (3) |
C3A—C4A | 1.425 (3) | C3B—C4B | 1.427 (3) |
C3A—H3AA | 0.95 | C3B—H3BA | 0.95 |
C4A—C5A | 1.403 (3) | C4B—C5B | 1.402 (3) |
C4A—C9A | 1.421 (3) | C4B—C9B | 1.418 (3) |
C5A—C6A | 1.381 (3) | C5B—C6B | 1.373 (4) |
C5A—H5AA | 0.95 | C5B—H5BA | 0.95 |
C6A—C7A | 1.403 (3) | C6B—C7B | 1.405 (3) |
C6A—H6AA | 0.95 | C6B—H6BA | 0.95 |
C7A—C8A | 1.378 (3) | C7B—C8B | 1.382 (3) |
C8A—C9A | 1.389 (3) | C8B—C9B | 1.381 (3) |
C8A—H8AA | 0.95 | C8B—H8BA | 0.95 |
C10A—C11A | 1.523 (3) | C10B—C11B | 1.535 (3) |
C10A—H10A | 0.99 | C10B—H10C | 0.99 |
C10A—H10B | 0.99 | C10B—H10D | 0.99 |
C11A—C12A | 1.526 (3) | C11B—C12B | 1.527 (4) |
C11A—H11A | 0.99 | C11B—H11C | 0.99 |
C11A—H11B | 0.99 | C11B—H11D | 0.99 |
C12A—H12A | 0.98 | C12B—H12D | 0.98 |
C12A—H12B | 0.98 | C12B—H12E | 0.98 |
C12A—H12C | 0.98 | C12B—H12F | 0.98 |
C9A—N1A—C2A | 109.5 (2) | C2B—N1B—C9B | 109.59 (19) |
C9A—N1A—H1AA | 125.3 | C2B—N1B—H1BA | 125.2 |
C2A—N1A—H1AA | 125.3 | C9B—N1B—H1BA | 125.2 |
O1A—N2A—O2A | 122.39 (19) | O1B—N2B—O2B | 121.9 (2) |
O1A—N2A—C7A | 119.6 (2) | O1B—N2B—C7B | 119.4 (2) |
O2A—N2A—C7A | 118.0 (2) | O2B—N2B—C7B | 118.66 (19) |
N1A—C2A—C3A | 108.7 (2) | C3B—C2B—N1B | 109.0 (2) |
N1A—C2A—C10A | 122.0 (2) | C3B—C2B—C10B | 129.1 (2) |
C3A—C2A—C10A | 129.4 (2) | N1B—C2B—C10B | 121.9 (2) |
C2A—C3A—C4A | 107.8 (2) | C2B—C3B—C4B | 107.8 (2) |
C2A—C3A—H3AA | 126.1 | C2B—C3B—H3BA | 126.1 |
C4A—C3A—H3AA | 126.1 | C4B—C3B—H3BA | 126.1 |
C5A—C4A—C9A | 119.2 (2) | C5B—C4B—C9B | 118.7 (2) |
C5A—C4A—C3A | 134.5 (2) | C5B—C4B—C3B | 134.9 (2) |
C9A—C4A—C3A | 106.3 (2) | C9B—C4B—C3B | 106.5 (2) |
C6A—C5A—C4A | 119.4 (2) | C6B—C5B—C4B | 119.6 (2) |
C6A—C5A—H5AA | 120.3 | C6B—C5B—H5BA | 120.2 |
C4A—C5A—H5AA | 120.3 | C4B—C5B—H5BA | 120.2 |
C5A—C6A—C7A | 119.0 (2) | C5B—C6B—C7B | 119.6 (2) |
C5A—C6A—H6AA | 120.5 | C5B—C6B—H6BA | 120.2 |
C7A—C6A—H6AA | 120.5 | C7B—C6B—H6BA | 120.2 |
C8A—C7A—C6A | 124.3 (2) | C8B—C7B—C6B | 123.1 (2) |
C8A—C7A—N2A | 117.9 (2) | C8B—C7B—N2B | 118.2 (2) |
C6A—C7A—N2A | 117.7 (2) | C6B—C7B—N2B | 118.7 (2) |
C7A—C8A—C9A | 115.7 (2) | C9B—C8B—C7B | 116.3 (2) |
C7A—C8A—H8AA | 122.1 | C9B—C8B—H8BA | 121.9 |
C9A—C8A—H8AA | 122.1 | C7B—C8B—H8BA | 121.9 |
N1A—C9A—C8A | 129.8 (2) | N1B—C9B—C8B | 130.1 (2) |
N1A—C9A—C4A | 107.78 (19) | N1B—C9B—C4B | 107.1 (2) |
C8A—C9A—C4A | 122.4 (2) | C8B—C9B—C4B | 122.8 (2) |
C2A—C10A—C11A | 114.47 (19) | C2B—C10B—C11B | 113.6 (2) |
C2A—C10A—H10A | 108.6 | C2B—C10B—H10C | 108.9 |
C11A—C10A—H10A | 108.6 | C11B—C10B—H10C | 108.9 |
C2A—C10A—H10B | 108.6 | C2B—C10B—H10D | 108.9 |
C11A—C10A—H10B | 108.6 | C11B—C10B—H10D | 108.9 |
H10A—C10A—H10B | 107.6 | H10C—C10B—H10D | 107.7 |
C10A—C11A—C12A | 112.6 (2) | C12B—C11B—C10B | 111.7 (2) |
C10A—C11A—H11A | 109.1 | C12B—C11B—H11C | 109.3 |
C12A—C11A—H11A | 109.1 | C10B—C11B—H11C | 109.3 |
C10A—C11A—H11B | 109.1 | C12B—C11B—H11D | 109.3 |
C12A—C11A—H11B | 109.1 | C10B—C11B—H11D | 109.3 |
H11A—C11A—H11B | 107.8 | H11C—C11B—H11D | 107.9 |
C11A—C12A—H12A | 109.5 | C11B—C12B—H12D | 109.5 |
C11A—C12A—H12B | 109.5 | C11B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
C11A—C12A—H12C | 109.5 | C11B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O2Bi | 0.88 | 2.10 | 2.965 (3) | 167 |
N1B—H1BA···O2Aii | 0.88 | 2.07 | 2.948 (3) | 173 |
C8A—H8AA···O2Aii | 0.95 | 2.53 | 3.203 (3) | 128 |
C11A—H11B···O2Bi | 0.99 | 2.54 | 3.448 (3) | 153 |
C10B—H10D···Cg1 | 0.99 | 2.78 | 3.726 (3) | 161 |
C11A—H11A···Cg2 | 0.99 | 2.72 | 3.346 (3) | 121 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+1, −z+1. |
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