Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600198X/cv6637sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680600198X/cv6637Isup2.hkl |
CCDC reference: 298422
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.163
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 0.897 Test value = 0.800 PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.15 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.90 e/A 3
Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. plate CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H20 N2 O5
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C18H20N2O5 | Z = 2 |
Mr = 344.36 | F(000) = 364 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
a = 8.1399 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4654 (11) Å | Cell parameters from 1756 reflections |
c = 13.3901 (17) Å | θ = 2.5–25.4° |
α = 103.201 (2)° | µ = 0.10 mm−1 |
β = 101.383 (2)° | T = 293 K |
γ = 92.577 (2)° | Plate, dark brown |
V = 876.70 (19) Å3 | 0.42 × 0.31 × 0.09 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 3379 independent reflections |
Radiation source: fine-focus sealed tube | 2691 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→8 |
Tmin = 0.961, Tmax = 0.991 | l = −16→16 |
5013 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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0837P)2 + 0.2739P] where P = (Fo2 + 2Fc2)/3 |
3379 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.90 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 | −0.6360 (2) | 0.1370 (2) | 0.08171 (13) | 0.0656 (5) | |
O2 | 0.12213 (19) | 0.34993 (17) | 0.35285 (13) | 0.0544 (4) | |
O3 | 0.12707 (17) | 0.75264 (16) | 0.49969 (11) | 0.0467 (4) | |
O4 | 0.22825 (19) | 1.16182 (16) | 0.63531 (13) | 0.0553 (4) | |
O5 | −0.3430 (2) | 1.3551 (2) | 0.90252 (13) | 0.0661 (5) | |
N1 | −0.0842 (2) | 0.52288 (19) | 0.35599 (13) | 0.0443 (4) | |
H1A | −0.1037 | 0.6201 | 0.3844 | 0.053* | |
N2 | 0.0279 (2) | 0.9742 (2) | 0.64732 (14) | 0.0481 (4) | |
H2A | −0.0071 | 0.8723 | 0.6264 | 0.058* | |
C1 | −0.8019 (3) | 0.1820 (4) | 0.0832 (2) | 0.0786 (8) | |
H1B | −0.8810 | 0.1054 | 0.0293 | 0.118* | |
H1C | −0.8101 | 0.2890 | 0.0709 | 0.118* | |
H1D | −0.8266 | 0.1820 | 0.1504 | 0.118* | |
C2 | −0.5060 (3) | 0.2332 (3) | 0.15378 (16) | 0.0493 (5) | |
C3 | −0.3464 (3) | 0.1988 (3) | 0.14093 (18) | 0.0576 (6) | |
H3A | −0.3333 | 0.1124 | 0.0869 | 0.069* | |
C4 | −0.2064 (3) | 0.2904 (3) | 0.20690 (17) | 0.0532 (6) | |
H4A | −0.0995 | 0.2662 | 0.1971 | 0.064* | |
C5 | −0.2244 (3) | 0.4194 (2) | 0.28829 (15) | 0.0415 (5) | |
C6 | −0.3837 (3) | 0.4515 (3) | 0.30119 (16) | 0.0486 (5) | |
H6A | −0.3970 | 0.5370 | 0.3557 | 0.058* | |
C7 | −0.5252 (3) | 0.3595 (3) | 0.23492 (17) | 0.0509 (5) | |
H7A | −0.6321 | 0.3828 | 0.2451 | 0.061* | |
C8 | 0.0740 (2) | 0.4855 (2) | 0.38015 (15) | 0.0403 (5) | |
C9 | 0.2025 (3) | 0.6236 (2) | 0.44305 (16) | 0.0442 (5) | |
H9A | 0.2850 | 0.5837 | 0.4919 | 0.053* | |
H9B | 0.2607 | 0.6644 | 0.3961 | 0.053* | |
C10 | 0.2453 (3) | 0.8876 (2) | 0.55327 (17) | 0.0464 (5) | |
H10A | 0.2940 | 0.9294 | 0.5028 | 0.056* | |
H10B | 0.3355 | 0.8527 | 0.6001 | 0.056* | |
C11 | 0.1639 (2) | 1.0208 (2) | 0.61572 (16) | 0.0426 (5) | |
C12 | −0.0657 (3) | 1.0743 (2) | 0.71168 (16) | 0.0449 (5) | |
C13 | 0.0063 (3) | 1.2156 (3) | 0.78677 (17) | 0.0535 (6) | |
H13A | 0.1198 | 1.2491 | 0.7957 | 0.064* | |
C14 | −0.0906 (3) | 1.3057 (3) | 0.84783 (18) | 0.0568 (6) | |
H14A | −0.0419 | 1.4006 | 0.8972 | 0.068* | |
C15 | −0.2597 (3) | 1.2574 (3) | 0.83693 (17) | 0.0500 (5) | |
C16 | −0.3308 (3) | 1.1174 (3) | 0.76306 (18) | 0.0542 (6) | |
H16A | −0.4440 | 1.0833 | 0.7547 | 0.065* | |
C17 | −0.2334 (3) | 1.0269 (3) | 0.70097 (18) | 0.0532 (6) | |
H17A | −0.2826 | 0.9326 | 0.6512 | 0.064* | |
C18 | −0.5179 (3) | 1.3073 (4) | 0.8914 (2) | 0.0732 (8) | |
H18A | −0.5634 | 1.3842 | 0.9409 | 0.110* | |
H18B | −0.5307 | 1.2010 | 0.9043 | 0.110* | |
H18C | −0.5770 | 1.3048 | 0.8214 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0533 (10) | 0.0686 (11) | 0.0613 (10) | −0.0135 (8) | 0.0041 (8) | −0.0009 (8) |
O2 | 0.0523 (9) | 0.0337 (8) | 0.0732 (10) | 0.0061 (6) | 0.0154 (8) | 0.0026 (7) |
O3 | 0.0444 (8) | 0.0342 (7) | 0.0532 (8) | −0.0001 (6) | 0.0077 (6) | −0.0032 (6) |
O4 | 0.0533 (9) | 0.0338 (8) | 0.0728 (10) | −0.0022 (7) | 0.0125 (8) | 0.0030 (7) |
O5 | 0.0616 (11) | 0.0681 (11) | 0.0618 (10) | 0.0058 (9) | 0.0185 (8) | −0.0021 (8) |
N1 | 0.0480 (10) | 0.0289 (8) | 0.0510 (10) | 0.0027 (7) | 0.0091 (8) | 0.0014 (7) |
N2 | 0.0525 (10) | 0.0298 (9) | 0.0579 (11) | 0.0008 (7) | 0.0106 (8) | 0.0039 (8) |
C1 | 0.0484 (14) | 0.095 (2) | 0.0802 (18) | −0.0083 (14) | −0.0018 (13) | 0.0118 (16) |
C2 | 0.0493 (12) | 0.0481 (12) | 0.0464 (11) | −0.0079 (10) | 0.0052 (9) | 0.0097 (10) |
C3 | 0.0555 (14) | 0.0530 (13) | 0.0533 (13) | −0.0007 (11) | 0.0123 (11) | −0.0089 (10) |
C4 | 0.0460 (12) | 0.0504 (13) | 0.0558 (13) | 0.0018 (10) | 0.0132 (10) | −0.0036 (10) |
C5 | 0.0447 (11) | 0.0342 (10) | 0.0445 (10) | 0.0014 (8) | 0.0096 (9) | 0.0078 (8) |
C6 | 0.0507 (12) | 0.0449 (12) | 0.0472 (12) | 0.0065 (10) | 0.0115 (10) | 0.0037 (9) |
C7 | 0.0432 (12) | 0.0558 (13) | 0.0520 (12) | 0.0024 (10) | 0.0119 (10) | 0.0085 (10) |
C8 | 0.0444 (11) | 0.0315 (10) | 0.0446 (10) | 0.0016 (8) | 0.0135 (9) | 0.0052 (8) |
C9 | 0.0445 (11) | 0.0356 (10) | 0.0502 (11) | 0.0028 (9) | 0.0101 (9) | 0.0060 (9) |
C10 | 0.0445 (11) | 0.0356 (11) | 0.0530 (12) | 0.0001 (9) | 0.0055 (9) | 0.0035 (9) |
C11 | 0.0412 (11) | 0.0336 (10) | 0.0460 (11) | 0.0006 (8) | −0.0010 (8) | 0.0048 (8) |
C12 | 0.0488 (12) | 0.0366 (10) | 0.0479 (11) | 0.0037 (9) | 0.0068 (9) | 0.0104 (9) |
C13 | 0.0470 (12) | 0.0523 (13) | 0.0525 (13) | −0.0012 (10) | 0.0043 (10) | 0.0019 (10) |
C14 | 0.0562 (14) | 0.0512 (13) | 0.0504 (12) | −0.0011 (11) | 0.0042 (10) | −0.0057 (10) |
C15 | 0.0547 (13) | 0.0492 (12) | 0.0457 (11) | 0.0087 (10) | 0.0106 (10) | 0.0102 (10) |
C16 | 0.0473 (12) | 0.0530 (13) | 0.0592 (13) | −0.0022 (10) | 0.0103 (10) | 0.0100 (11) |
C17 | 0.0528 (13) | 0.0428 (12) | 0.0587 (13) | −0.0031 (10) | 0.0095 (11) | 0.0049 (10) |
C18 | 0.0642 (16) | 0.0807 (19) | 0.0736 (17) | 0.0053 (14) | 0.0274 (14) | 0.0057 (14) |
O1—C2 | 1.369 (2) | C5—C6 | 1.373 (3) |
O1—C1 | 1.422 (3) | C6—C7 | 1.385 (3) |
O2—C8 | 1.228 (2) | C6—H6A | 0.9300 |
O3—C10 | 1.414 (2) | C7—H7A | 0.9300 |
O3—C9 | 1.418 (2) | C8—C9 | 1.505 (3) |
O4—C11 | 1.231 (2) | C9—H9A | 0.9700 |
O5—C15 | 1.367 (3) | C9—H9B | 0.9700 |
O5—C18 | 1.432 (3) | C10—C11 | 1.505 (3) |
N1—C8 | 1.335 (3) | C10—H10A | 0.9700 |
N1—C5 | 1.425 (2) | C10—H10B | 0.9700 |
N1—H1A | 0.8600 | C12—C17 | 1.376 (3) |
N2—C11 | 1.335 (3) | C12—C13 | 1.393 (3) |
N2—C12 | 1.423 (3) | C13—C14 | 1.377 (3) |
N2—H2A | 0.8600 | C13—H13A | 0.9300 |
C1—H1B | 0.9600 | C14—C15 | 1.388 (3) |
C1—H1C | 0.9600 | C14—H14A | 0.9300 |
C1—H1D | 0.9600 | C15—C16 | 1.377 (3) |
C2—C7 | 1.378 (3) | C16—C17 | 1.389 (3) |
C2—C3 | 1.379 (3) | C16—H16A | 0.9300 |
C3—C4 | 1.375 (3) | C17—H17A | 0.9300 |
C3—H3A | 0.9300 | C18—H18A | 0.9600 |
C4—C5 | 1.391 (3) | C18—H18B | 0.9600 |
C4—H4A | 0.9300 | C18—H18C | 0.9600 |
C2—O1—C1 | 117.6 (2) | C8—C9—H9A | 109.3 |
C10—O3—C9 | 111.98 (15) | O3—C9—H9B | 109.3 |
C15—O5—C18 | 116.59 (19) | C8—C9—H9B | 109.3 |
C8—N1—C5 | 127.12 (16) | H9A—C9—H9B | 107.9 |
C8—N1—H1A | 116.4 | O3—C10—C11 | 111.11 (16) |
C5—N1—H1A | 116.4 | O3—C10—H10A | 109.4 |
C11—N2—C12 | 127.27 (17) | C11—C10—H10A | 109.4 |
C11—N2—H2A | 116.4 | O3—C10—H10B | 109.4 |
C12—N2—H2A | 116.4 | C11—C10—H10B | 109.4 |
O1—C1—H1B | 109.5 | H10A—C10—H10B | 108.0 |
O1—C1—H1C | 109.5 | O4—C11—N2 | 125.28 (19) |
H1B—C1—H1C | 109.5 | O4—C11—C10 | 118.35 (19) |
O1—C1—H1D | 109.5 | N2—C11—C10 | 116.36 (17) |
H1B—C1—H1D | 109.5 | C17—C12—C13 | 118.7 (2) |
H1C—C1—H1D | 109.5 | C17—C12—N2 | 118.45 (19) |
O1—C2—C7 | 124.7 (2) | C13—C12—N2 | 122.81 (19) |
O1—C2—C3 | 115.8 (2) | C14—C13—C12 | 120.0 (2) |
C7—C2—C3 | 119.5 (2) | C14—C13—H13A | 120.0 |
C4—C3—C2 | 120.9 (2) | C12—C13—H13A | 120.0 |
C4—C3—H3A | 119.6 | C13—C14—C15 | 121.1 (2) |
C2—C3—H3A | 119.6 | C13—C14—H14A | 119.4 |
C3—C4—C5 | 120.1 (2) | C15—C14—H14A | 119.4 |
C3—C4—H4A | 120.0 | O5—C15—C16 | 125.0 (2) |
C5—C4—H4A | 120.0 | O5—C15—C14 | 116.1 (2) |
C6—C5—C4 | 118.59 (19) | C16—C15—C14 | 118.9 (2) |
C6—C5—N1 | 118.90 (18) | C15—C16—C17 | 120.0 (2) |
C4—C5—N1 | 122.47 (19) | C15—C16—H16A | 120.0 |
C5—C6—C7 | 121.5 (2) | C17—C16—H16A | 120.0 |
C5—C6—H6A | 119.2 | C12—C17—C16 | 121.3 (2) |
C7—C6—H6A | 119.2 | C12—C17—H17A | 119.4 |
C2—C7—C6 | 119.4 (2) | C16—C17—H17A | 119.4 |
C2—C7—H7A | 120.3 | O5—C18—H18A | 109.5 |
C6—C7—H7A | 120.3 | O5—C18—H18B | 109.5 |
O2—C8—N1 | 125.32 (18) | H18A—C18—H18B | 109.5 |
O2—C8—C9 | 118.35 (18) | O5—C18—H18C | 109.5 |
N1—C8—C9 | 116.30 (16) | H18A—C18—H18C | 109.5 |
O3—C9—C8 | 111.66 (16) | H18B—C18—H18C | 109.5 |
O3—C9—H9A | 109.3 | ||
C1—O1—C2—C7 | 7.6 (3) | C9—O3—C10—C11 | −178.11 (17) |
C1—O1—C2—C3 | −171.6 (2) | C12—N2—C11—O4 | −2.3 (3) |
O1—C2—C3—C4 | 178.1 (2) | C12—N2—C11—C10 | 176.27 (18) |
C7—C2—C3—C4 | −1.1 (4) | O3—C10—C11—O4 | −154.66 (18) |
C2—C3—C4—C5 | 0.3 (4) | O3—C10—C11—N2 | 26.7 (3) |
C3—C4—C5—C6 | 0.4 (3) | C11—N2—C12—C17 | 152.9 (2) |
C3—C4—C5—N1 | −177.1 (2) | C11—N2—C12—C13 | −28.9 (3) |
C8—N1—C5—C6 | 156.0 (2) | C17—C12—C13—C14 | −0.6 (3) |
C8—N1—C5—C4 | −26.5 (3) | N2—C12—C13—C14 | −178.9 (2) |
C4—C5—C6—C7 | −0.4 (3) | C12—C13—C14—C15 | 0.7 (4) |
N1—C5—C6—C7 | 177.15 (19) | C18—O5—C15—C16 | −0.9 (3) |
O1—C2—C7—C6 | −178.1 (2) | C18—O5—C15—C14 | 179.4 (2) |
C3—C2—C7—C6 | 1.0 (3) | C13—C14—C15—O5 | 179.2 (2) |
C5—C6—C7—C2 | −0.3 (3) | C13—C14—C15—C16 | −0.5 (4) |
C5—N1—C8—O2 | −5.3 (3) | O5—C15—C16—C17 | −179.6 (2) |
C5—N1—C8—C9 | 172.64 (18) | C14—C15—C16—C17 | 0.0 (3) |
C10—O3—C9—C8 | −175.95 (16) | C13—C12—C17—C16 | 0.2 (3) |
O2—C8—C9—O3 | −158.94 (18) | N2—C12—C17—C16 | 178.6 (2) |
N1—C8—C9—O3 | 23.0 (2) | C15—C16—C17—C12 | 0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.86 | 2.19 | 2.951 (2) | 147 |
N2—H2A···O2ii | 0.86 | 2.16 | 2.952 (2) | 152 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
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