Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053657/tk2118sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053657/tk2118Isup2.hkl |
CCDC reference: 634066
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.084
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT115_ALERT_5_B ADDSYM Detects Noncrystallographic Inversion ... 100 PerFi PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. H2B .. 2.04 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT128_ALERT_4_C Non-standard setting of Space group Pna21 .... Pbn21
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.50 From the CIF: _reflns_number_total 1594 Count of symmetry unique reflns 1649 Completeness (_total/calc) 96.66% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H16N2O2 | F(000) = 520 |
Mr = 244.29 | Dx = 1.273 Mg m−3 |
Orthorhombic, Pbn21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ab | Cell parameters from 97 reflections |
a = 7.0644 (6) Å | θ = 14–40° |
b = 7.5770 (7) Å | µ = 0.09 mm−1 |
c = 23.8053 (10) Å | T = 100 K |
V = 1274.23 (17) Å3 | Prism, colourless |
Z = 4 | 0.33 × 0.30 × 0.28 mm |
Bruker–Nonius KappaCCD diffractometer | 1594 independent reflections |
Radiation source: fine-focus sealed tube | 1530 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 9 pixels mm-1 | θmax = 28.5°, θmin = 3.4° |
ω scans | h = −9→9 |
Absorption correction: gaussian integration (Coppens, 1970) | k = −10→10 |
Tmin = 0.972, Tmax = 0.976 | l = −31→31 |
13155 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2427P] where P = (Fo2 + 2Fc2)/3 |
1594 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.26 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
Experimental. IR (cm-1): 3445 (aromatic NH2), 3059 (aromatic C—H), 2884 (aliphatic C—H), 1275 (C—N), 1504 (aromatic C═C). 1H NMR: d 4.0 (s, CH2—O),4.1–3.4 (s, Ar—NH2), 7.2–6.5 (s, aromatic protons). |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.55414 (16) | 0.12426 (15) | 0.49391 (5) | 0.0128 (3) | |
O2 | 0.56105 (16) | 0.40525 (15) | 0.57785 (5) | 0.0135 (3) | |
N1 | 0.2784 (2) | 0.6233 (2) | 0.59909 (7) | 0.0198 (4) | |
N2 | 0.3172 (2) | −0.1449 (2) | 0.48493 (6) | 0.0165 (4) | |
C1 | 0.5343 (2) | 0.0573 (2) | 0.44011 (8) | 0.0122 (4) | |
C2 | 0.6339 (3) | 0.1177 (2) | 0.39343 (8) | 0.0155 (4) | |
C3 | 0.6015 (3) | 0.0389 (2) | 0.34126 (8) | 0.0189 (5) | |
C4 | 0.4726 (3) | −0.0977 (3) | 0.33620 (8) | 0.0206 (5) | |
C5 | 0.3732 (3) | −0.1583 (2) | 0.38334 (8) | 0.0185 (5) | |
C6 | 0.4030 (2) | −0.0818 (2) | 0.43586 (8) | 0.0140 (4) | |
C7 | 0.7055 (2) | 0.2471 (2) | 0.50274 (7) | 0.0133 (4) | |
C8 | 0.7142 (2) | 0.2879 (2) | 0.56454 (7) | 0.0135 (4) | |
C9 | 0.5447 (2) | 0.4543 (2) | 0.63346 (7) | 0.0126 (4) | |
C10 | 0.6617 (3) | 0.3960 (2) | 0.67652 (7) | 0.0161 (4) | |
C11 | 0.6310 (3) | 0.4574 (2) | 0.73137 (7) | 0.0201 (5) | |
C12 | 0.4849 (3) | 0.5735 (3) | 0.74229 (8) | 0.0226 (5) | |
C13 | 0.3672 (3) | 0.6319 (2) | 0.69887 (8) | 0.0202 (5) | |
C14 | 0.3954 (2) | 0.5737 (2) | 0.64386 (8) | 0.0152 (4) | |
H1A | 0.18400 | 0.69260 | 0.60490 | 0.0240* | |
H1B | 0.30080 | 0.58440 | 0.56580 | 0.0240* | |
H2 | 0.72080 | 0.20920 | 0.39690 | 0.0190* | |
H2A | 0.24250 | −0.23440 | 0.48340 | 0.0200* | |
H2B | 0.33910 | −0.09410 | 0.51660 | 0.0200* | |
H3 | 0.66690 | 0.07840 | 0.30980 | 0.0230* | |
H4 | 0.45190 | −0.14960 | 0.30130 | 0.0250* | |
H5 | 0.28680 | −0.25020 | 0.37960 | 0.0220* | |
H7A | 0.68280 | 0.35430 | 0.48150 | 0.0160* | |
H7B | 0.82440 | 0.19630 | 0.49030 | 0.0160* | |
H8A | 0.70290 | 0.18000 | 0.58620 | 0.0160* | |
H8B | 0.83420 | 0.34300 | 0.57370 | 0.0160* | |
H10 | 0.75930 | 0.31700 | 0.66910 | 0.0190* | |
H11 | 0.70930 | 0.41990 | 0.76040 | 0.0240* | |
H12 | 0.46460 | 0.61320 | 0.77880 | 0.0270* | |
H13 | 0.26930 | 0.71010 | 0.70670 | 0.0240* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0127 (5) | 0.0123 (5) | 0.0134 (5) | −0.0049 (4) | 0.0023 (4) | −0.0026 (4) |
O2 | 0.0134 (5) | 0.0118 (5) | 0.0152 (6) | 0.0031 (4) | −0.0009 (4) | −0.0019 (4) |
N1 | 0.0167 (7) | 0.0189 (7) | 0.0237 (7) | 0.0073 (5) | −0.0011 (6) | −0.0007 (6) |
N2 | 0.0142 (6) | 0.0153 (6) | 0.0200 (7) | −0.0052 (5) | 0.0008 (5) | −0.0004 (5) |
C1 | 0.0125 (7) | 0.0109 (6) | 0.0131 (7) | 0.0036 (6) | −0.0003 (6) | −0.0009 (6) |
C2 | 0.0143 (8) | 0.0136 (7) | 0.0186 (8) | 0.0011 (6) | 0.0029 (6) | 0.0013 (6) |
C3 | 0.0227 (8) | 0.0181 (8) | 0.0159 (8) | 0.0062 (7) | 0.0032 (7) | 0.0029 (6) |
C4 | 0.0255 (9) | 0.0201 (8) | 0.0163 (8) | 0.0057 (7) | −0.0058 (7) | −0.0037 (6) |
C5 | 0.0185 (9) | 0.0157 (8) | 0.0212 (9) | 0.0002 (6) | −0.0064 (6) | −0.0022 (7) |
C6 | 0.0122 (7) | 0.0127 (7) | 0.0170 (8) | 0.0027 (6) | −0.0023 (6) | 0.0001 (6) |
C7 | 0.0118 (7) | 0.0107 (6) | 0.0174 (7) | −0.0024 (5) | 0.0011 (6) | −0.0020 (6) |
C8 | 0.0118 (7) | 0.0102 (7) | 0.0185 (7) | 0.0023 (6) | −0.0008 (6) | −0.0018 (6) |
C9 | 0.0128 (7) | 0.0088 (7) | 0.0161 (8) | −0.0033 (6) | −0.0005 (6) | −0.0012 (6) |
C10 | 0.0174 (8) | 0.0129 (7) | 0.0179 (8) | −0.0015 (6) | −0.0025 (7) | −0.0003 (6) |
C11 | 0.0274 (9) | 0.0179 (8) | 0.0149 (8) | −0.0050 (7) | −0.0035 (7) | 0.0018 (6) |
C12 | 0.0326 (10) | 0.0205 (9) | 0.0148 (8) | −0.0060 (8) | 0.0043 (7) | −0.0032 (7) |
C13 | 0.0225 (10) | 0.0158 (8) | 0.0224 (9) | −0.0002 (7) | 0.0072 (7) | −0.0027 (7) |
C14 | 0.0140 (7) | 0.0116 (7) | 0.0201 (8) | −0.0008 (6) | 0.0011 (7) | 0.0004 (6) |
O1—C1 | 1.385 (2) | C9—C14 | 1.412 (2) |
O1—C7 | 1.4331 (19) | C10—C11 | 1.403 (2) |
O2—C8 | 1.4358 (19) | C11—C12 | 1.381 (3) |
O2—C9 | 1.380 (2) | C12—C13 | 1.398 (3) |
N1—C14 | 1.400 (2) | C13—C14 | 1.396 (3) |
N2—C6 | 1.400 (2) | C2—H2 | 0.9300 |
N1—H1B | 0.8600 | C3—H3 | 0.9300 |
N1—H1A | 0.8600 | C4—H4 | 0.9300 |
N2—H2B | 0.8600 | C5—H5 | 0.9300 |
N2—H2A | 0.8600 | C7—H7A | 0.9700 |
C1—C6 | 1.408 (2) | C7—H7B | 0.9700 |
C1—C2 | 1.393 (3) | C8—H8A | 0.9700 |
C2—C3 | 1.397 (3) | C8—H8B | 0.9700 |
C3—C4 | 1.384 (3) | C10—H10 | 0.9300 |
C4—C5 | 1.401 (3) | C11—H11 | 0.9300 |
C5—C6 | 1.394 (3) | C12—H12 | 0.9300 |
C7—C8 | 1.505 (2) | C13—H13 | 0.9300 |
C9—C10 | 1.389 (2) | ||
O1···O2 | 2.9203 (17) | C14···H1Aiv | 3.0800 |
O1···N2 | 2.6470 (19) | H1A···H13 | 2.5000 |
O1···N2i | 3.1602 (19) | H1A···O2i | 2.4500 |
O1···C7ii | 3.3308 (19) | H1A···C8i | 3.0600 |
O2···N1 | 2.6405 (19) | H1A···C9i | 2.6500 |
O2···C8iii | 3.3208 (19) | H1A···C14i | 3.0800 |
O2···O1 | 2.9203 (17) | H1B···O2 | 2.3000 |
O2···N1iv | 3.2512 (19) | H1B···N2v | 2.8200 |
O1···H7Aii | 2.7800 | H1B···H2Av | 2.4300 |
O1···H2B | 2.3100 | H1B···N2i | 2.7200 |
O1···H2Ai | 2.3700 | H1B···H2Bi | 2.0400 |
O2···H1B | 2.3000 | H2···C7 | 2.5400 |
O2···H1Aiv | 2.4500 | H2···H7A | 2.3100 |
O2···H8Aiii | 2.6700 | H2···H7B | 2.3400 |
N1···O2 | 2.6405 (19) | H2···C3iii | 3.0900 |
N1···N2v | 3.247 (2) | H2···C4iii | 2.9900 |
N1···O2i | 3.2512 (19) | H2···C5iii | 3.0600 |
N2···O1 | 2.6470 (19) | H2A···H1Bvi | 2.4300 |
N2···O1iv | 3.1602 (19) | H2A···H5 | 2.4900 |
N2···N1vi | 3.247 (2) | H2A···O1iv | 2.3700 |
N1···H2Bi | 2.6900 | H2A···C1iv | 2.7200 |
N1···H2Bv | 2.9400 | H2A···C6iv | 3.0400 |
N2···H1Bvi | 2.8200 | H2B···O1 | 2.3100 |
N2···H1Biv | 2.7200 | H2B···N1vi | 2.9400 |
N2···H7Bii | 2.8100 | H2B···N1iv | 2.6900 |
C1···C7ii | 3.336 (2) | H2B···H1Biv | 2.0400 |
C6···C7ii | 3.445 (2) | H3···C12xi | 2.9900 |
C7···C6iii | 3.445 (2) | H4···C11xii | 2.9200 |
C7···C1iii | 3.336 (2) | H4···H11xii | 2.5400 |
C7···O1iii | 3.3308 (19) | H5···H2A | 2.4900 |
C8···C9ii | 3.462 (2) | H5···C1iv | 3.0600 |
C8···O2ii | 3.3208 (19) | H7A···C2 | 2.7800 |
C9···C8iii | 3.462 (2) | H7A···H2 | 2.3100 |
C1···H7Aii | 2.7100 | H7A···O1iii | 2.7800 |
C1···H5i | 3.0600 | H7A···C1iii | 2.7100 |
C1···H2Ai | 2.7200 | H7B···C2 | 2.7400 |
C2···H7B | 2.7400 | H7B···H2 | 2.3400 |
C2···H7A | 2.7800 | H7B···N2iii | 2.8100 |
C3···H2ii | 3.0900 | H7B···C6iii | 2.8700 |
C3···H12vii | 3.0600 | H8A···C10 | 2.7200 |
C4···H11viii | 2.9200 | H8A···H10 | 2.2700 |
C4···H2ii | 2.9900 | H8A···O2ii | 2.6700 |
C5···H2ii | 3.0600 | H8A···C8ii | 3.0700 |
C6···H2Ai | 3.0400 | H8A···C9ii | 2.7100 |
C6···H7Bii | 2.8700 | H8A···H8Bii | 2.5800 |
C7···H2 | 2.5400 | H8B···C10 | 2.7600 |
C8···H10 | 2.5200 | H8B···H10 | 2.3400 |
C8···H1Aiv | 3.0600 | H8B···H8Aiii | 2.5800 |
C8···H8Aiii | 3.0700 | H10···C8 | 2.5200 |
C9···H1Aiv | 2.6500 | H10···H8A | 2.2700 |
C9···H8Aiii | 2.7100 | H10···H8B | 2.3400 |
C10···H8A | 2.7200 | H10···C13ii | 3.0700 |
C10···H8B | 2.7600 | H11···H4ix | 2.5400 |
C11···H4ix | 2.9200 | H11···C4xiii | 2.9200 |
C12···H3x | 2.9900 | H12···C3xiv | 3.0600 |
C13···H10iii | 3.0700 | H13···H1A | 2.5000 |
C1—O1—C7 | 116.69 (12) | N1—C14—C9 | 118.66 (16) |
C8—O2—C9 | 116.21 (12) | N1—C14—C13 | 123.02 (15) |
C14—N1—H1A | 120.00 | C1—C2—H2 | 121.00 |
C14—N1—H1B | 120.00 | C3—C2—H2 | 120.00 |
H1A—N1—H1B | 120.00 | C2—C3—H3 | 120.00 |
C6—N2—H2A | 120.00 | C4—C3—H3 | 120.00 |
C6—N2—H2B | 120.00 | C3—C4—H4 | 120.00 |
H2A—N2—H2B | 120.00 | C5—C4—H4 | 120.00 |
C2—C1—C6 | 121.44 (17) | C4—C5—H5 | 120.00 |
O1—C1—C2 | 124.51 (14) | C6—C5—H5 | 120.00 |
O1—C1—C6 | 114.05 (15) | O1—C7—H7A | 110.00 |
C1—C2—C3 | 119.09 (16) | O1—C7—H7B | 110.00 |
C2—C3—C4 | 120.33 (18) | C8—C7—H7A | 110.00 |
C3—C4—C5 | 120.34 (18) | C8—C7—H7B | 110.00 |
C4—C5—C6 | 120.42 (17) | H7A—C7—H7B | 108.00 |
N2—C6—C5 | 122.74 (14) | O2—C8—H8A | 110.00 |
C1—C6—C5 | 118.38 (16) | O2—C8—H8B | 110.00 |
N2—C6—C1 | 118.75 (16) | C7—C8—H8A | 110.00 |
O1—C7—C8 | 107.90 (12) | C7—C8—H8B | 110.00 |
O2—C8—C7 | 108.19 (12) | H8A—C8—H8B | 108.00 |
C10—C9—C14 | 121.27 (16) | C9—C10—H10 | 120.00 |
O2—C9—C14 | 113.80 (14) | C11—C10—H10 | 120.00 |
O2—C9—C10 | 124.93 (14) | C10—C11—H11 | 120.00 |
C9—C10—C11 | 119.30 (17) | C12—C11—H11 | 120.00 |
C10—C11—C12 | 120.13 (17) | C11—C12—H12 | 120.00 |
C11—C12—C13 | 120.46 (17) | C13—C12—H12 | 120.00 |
C12—C13—C14 | 120.57 (17) | C12—C13—H13 | 120.00 |
C9—C14—C13 | 118.27 (16) | C14—C13—H13 | 120.00 |
C7—O1—C1—C2 | −8.7 (2) | C4—C5—C6—N2 | −175.58 (17) |
C7—O1—C1—C6 | 170.81 (12) | C4—C5—C6—C1 | 0.2 (3) |
C1—O1—C7—C8 | −174.15 (12) | O1—C7—C8—O2 | −75.68 (14) |
C8—O2—C9—C14 | 178.22 (12) | O2—C9—C10—C11 | 179.40 (15) |
C9—O2—C8—C7 | 178.74 (12) | C14—C9—C10—C11 | −0.2 (3) |
C8—O2—C9—C10 | −1.4 (2) | O2—C9—C14—N1 | 2.5 (2) |
O1—C1—C6—N2 | −4.0 (2) | O2—C9—C14—C13 | −179.83 (14) |
C2—C1—C6—C5 | −0.4 (2) | C10—C9—C14—N1 | −177.96 (15) |
O1—C1—C6—C5 | −179.91 (14) | C10—C9—C14—C13 | −0.2 (2) |
C6—C1—C2—C3 | 0.4 (3) | C9—C10—C11—C12 | 0.5 (3) |
O1—C1—C2—C3 | 179.88 (15) | C10—C11—C12—C13 | −0.5 (3) |
C2—C1—C6—N2 | 175.55 (15) | C11—C12—C13—C14 | 0.1 (3) |
C1—C2—C3—C4 | −0.2 (3) | C12—C13—C14—N1 | 177.90 (17) |
C2—C3—C4—C5 | 0.0 (3) | C12—C13—C14—C9 | 0.3 (3) |
C3—C4—C5—C6 | 0.0 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+3/2, y−1/2, z; (iii) −x+3/2, y+1/2, z; (iv) −x+1/2, y−1/2, z; (v) x, y+1, z; (vi) x, y−1, z; (vii) −x+1, −y+1, z−1/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) −x+1, −y, z+1/2; (x) x−1/2, −y+1/2, z+1/2; (xi) x+1/2, −y+1/2, z−1/2; (xii) −x+1, −y, z−1/2; (xiii) x+1/2, −y+1/2, z+1/2; (xiv) −x+1, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.45 | 3.2512 (19) | 155 |
N1—H1B···O2 | 0.86 | 2.30 | 2.6405 (19) | 104 |
N2—H2A···O1iv | 0.86 | 2.37 | 3.1602 (19) | 154 |
N2—H2B···O1 | 0.86 | 2.31 | 2.6470 (19) | 104 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (iv) −x+1/2, y−1/2, z. |
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