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The asymmetric unit of the title compound, C
12H
13N
3O
2·H
2O, comprises two crystallographically independent organic molecules and two water molecules. There is an O—H
N hydrogen bond between each water molecule and the 2-substituted pyridyl ring of an organic molecule. The water molecules are further engaged in disordered O—H
O hydrogen bonds with each other, leading to the formation of a one-dimensional zigzag chain running parallel to the
b axis.
Supporting information
CCDC reference: 640294
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.061
- wR factor = 0.176
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.10 Ratio
| Author Response: The two crystallographically independent terminal
resulted in ellipsoids with large tensors. In order to avoid such an error,
statistical structural disorder for these terminal moieties was attempted
but it did not lead to sensible refinement of the overall structure.
|
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.58 Ratio
| Author Response: Please see our response to _vrf_PLAT220_I since the H-atoms
have been refined with a riding model and Uiso fixed at 1.2 or 1.5 times
Ueq(C) of the parent carbon atom.
|
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 0.950
Test value = 0.800
| Author Response: Please see our response to _vrf_DIFMX02_I.
|
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
| Author Response: Even though crystal data was collected up to 0.73 \%A resolution,
the crystal (the largest available) still diffracted quite weakly at
high angle. Increasing the exposure time per frame allowed a
significantly better signal-to-noise ratio but after approximately 24
hours, the collected data showed significant evidence of radiation
damage. Therefore, applying a cut-off at 0.83 \%A resolution results
in a good number of reflection observed at the 2s level and a
good merging R value.
Collection of higher-angle data is likely only to be possible
using a synchrotron or a rotating-anode source. Given the quality of
the present crystal solution, efforts in this direction are not
warranted.
|
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.95 e/A
| Author Response: Please see our response to _vrf_DIFMX02_I.
|
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.27 Ratio
| Author Response: The two crystallographically independent terminal
resulted in ellipsoids with large tensors. In order to avoid such an error,
statistical structural disorder for these terminal moieties was attempted
but it did not lead to sensible refinement of the overall structure.
|
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.73 Ratio
| Author Response: Please see our response to _vrf_PLAT220_I since the H-atoms
have been refined with a riding model and Uiso fixed at 1.2 or 1.5 times
Ueq(C) of the parent carbon atom.
|
Alert level C
DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75
_refine_diff_density_min given = -0.765
Test value = -0.600
| Author Response: Please see our response to _vrf_DIFMX02_I.
|
DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75
The relevant atom site should be identified.
| Author Response: Please see our response to _vrf_DIFMX02_I.
|
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
| Author Response: The two crystallographically independent terminal
in particular that associated with the C23 and C24 carbon atoms.
Indeed, the highest peak in the last difference Fourier map synthesis
was located at 0.76 A from C23, and the deepest hole at 0.35 A from
H23A (H-atom bound to C23).
|
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.35
From the CIF: _diffrn_reflns_theta_full 25.35
From the CIF: _reflns_number_total 4387
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 4628
Completeness (_total/calc) 94.79%
| Author Response: Please see our response to _vrf_PLAT029_I.
|
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
| Author Response: Please see our response to _vrf_PLAT029_I.
|
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.76 e/A
| Author Response: Please see our response to _vrf_DIFMX02_I.
|
PLAT213_ALERT_2_C Atom C23 has ADP max/min Ratio ............. 3.60 prola
| Author Response: Please see our response to _vrf_PLAT220_I.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23
| Author Response: Please see our response to _vrf_PLAT220_I.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
| Author Response: Please see our response to _vrf_PLAT220_I.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O4
| Author Response: Please see our response to _vrf_PLAT220_I.
|
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.07
2 ALERT level A = In general: serious problem
5 ALERT level B = Potentially serious problem
11 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
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Bruker 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL.
Ethyl [3-(2-pyridyl)pyrazol-1-yl]acetate monohydrate
top
Crystal data top
C12H13N3O2·H2O | F(000) = 1056 |
Mr = 249.27 | Dx = 1.315 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9034 reflections |
a = 22.332 (2) Å | θ = 2.9–30.1° |
b = 4.7356 (5) Å | µ = 0.10 mm−1 |
c = 24.651 (3) Å | T = 100 K |
β = 104.929 (6)° | Needle, colourless |
V = 2519.0 (5) Å3 | 0.40 × 0.16 × 0.08 mm |
Z = 8 | |
Data collection top
Bruker X8 APEXII diffractometer | 4387 independent reflections |
Radiation source: fine-focus sealed tube | 3182 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω and φ scans | θmax = 25.4°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −26→26 |
Tmin = 0.927, Tmax = 0.985 | k = −5→5 |
27588 measured reflections | l = −28→27 |
Refinement top
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0711P)2 + 4.6214P] where P = (Fo2 + 2Fc2)/3 |
4387 reflections | (Δ/σ)max = 0.003 |
345 parameters | Δρmax = 0.95 e Å−3 |
13 restraints | Δρmin = −0.77 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.14974 (10) | −0.1946 (5) | 0.09385 (10) | 0.0260 (6) | |
N2 | 0.14440 (9) | 0.2986 (5) | 0.20435 (9) | 0.0202 (5) | |
N3 | 0.09557 (10) | 0.4700 (5) | 0.20315 (9) | 0.0216 (5) | |
O1 | 0.05648 (9) | 0.2543 (4) | 0.29203 (8) | 0.0305 (5) | |
O2 | 0.10854 (8) | 0.5945 (4) | 0.34809 (8) | 0.0261 (5) | |
C1 | 0.18800 (13) | −0.3854 (7) | 0.08040 (13) | 0.0323 (7) | |
H1 | 0.1741 | −0.4824 | 0.0457 | 0.039* | |
C2 | 0.24594 (13) | −0.4496 (6) | 0.11357 (13) | 0.0304 (7) | |
H2 | 0.2713 | −0.5860 | 0.1020 | 0.037* | |
C3 | 0.26606 (12) | −0.3103 (6) | 0.16403 (12) | 0.0256 (7) | |
H3 | 0.3057 | −0.3498 | 0.1882 | 0.031* | |
C4 | 0.22787 (11) | −0.1124 (6) | 0.17904 (11) | 0.0217 (6) | |
H4 | 0.2410 | −0.0135 | 0.2136 | 0.026* | |
C5 | 0.17003 (11) | −0.0597 (6) | 0.14304 (11) | 0.0192 (6) | |
C6 | 0.12735 (11) | 0.1496 (6) | 0.15679 (11) | 0.0198 (6) | |
C7 | 0.06734 (12) | 0.2240 (6) | 0.12577 (12) | 0.0267 (6) | |
H7 | 0.0447 | 0.1492 | 0.0907 | 0.032* | |
C8 | 0.04862 (12) | 0.4279 (6) | 0.15721 (12) | 0.0272 (7) | |
H8 | 0.0097 | 0.5220 | 0.1483 | 0.033* | |
C9 | 0.09717 (12) | 0.6474 (6) | 0.25111 (11) | 0.0226 (6) | |
H9A | 0.0656 | 0.7982 | 0.2404 | 0.027* | |
H9B | 0.1384 | 0.7379 | 0.2638 | 0.027* | |
C10 | 0.08445 (11) | 0.4738 (6) | 0.29833 (11) | 0.0221 (6) | |
C11 | 0.09967 (14) | 0.4351 (7) | 0.39598 (12) | 0.0317 (7) | |
H11A | 0.1185 | 0.2454 | 0.3969 | 0.038* | |
H11B | 0.0549 | 0.4116 | 0.3930 | 0.038* | |
C12 | 0.1295 (2) | 0.5929 (11) | 0.44772 (15) | 0.0821 (17) | |
H12A | 0.1744 | 0.5990 | 0.4522 | 0.123* | |
H12B | 0.1208 | 0.4984 | 0.4802 | 0.123* | |
H12C | 0.1131 | 0.7858 | 0.4450 | 0.123* | |
N4 | 0.13995 (10) | 0.7214 (5) | 0.59836 (10) | 0.0244 (5) | |
N5 | 0.14357 (9) | 0.2208 (5) | 0.70981 (9) | 0.0199 (5) | |
N6 | 0.09557 (10) | 0.0492 (4) | 0.71125 (9) | 0.0205 (5) | |
O3 | 0.05836 (10) | 0.2304 (5) | 0.80469 (10) | 0.0387 (6) | |
O4 | 0.11124 (10) | −0.1265 (6) | 0.85499 (9) | 0.0473 (7) | |
C13 | 0.17597 (13) | 0.9154 (6) | 0.58258 (12) | 0.0277 (7) | |
H13 | 0.1590 | 1.0183 | 0.5491 | 0.033* | |
C14 | 0.23591 (13) | 0.9747 (6) | 0.61188 (12) | 0.0266 (6) | |
H14 | 0.2599 | 1.1112 | 0.5986 | 0.032* | |
C15 | 0.26003 (12) | 0.8294 (6) | 0.66121 (12) | 0.0246 (6) | |
H15 | 0.3011 | 0.8659 | 0.6828 | 0.030* | |
C16 | 0.22401 (11) | 0.6307 (6) | 0.67883 (12) | 0.0218 (6) | |
H16 | 0.2399 | 0.5289 | 0.7127 | 0.026* | |
C17 | 0.16401 (11) | 0.5816 (5) | 0.64625 (11) | 0.0191 (6) | |
C18 | 0.12330 (11) | 0.3721 (5) | 0.66278 (11) | 0.0187 (6) | |
C19 | 0.06234 (12) | 0.2962 (6) | 0.63481 (12) | 0.0261 (6) | |
H19 | 0.0377 | 0.3711 | 0.6006 | 0.031* | |
C20 | 0.04619 (12) | 0.0914 (6) | 0.66742 (12) | 0.0254 (6) | |
H20 | 0.0074 | −0.0032 | 0.6605 | 0.031* | |
C21 | 0.10115 (13) | −0.1367 (6) | 0.75851 (11) | 0.0242 (6) | |
H21A | 0.1437 | −0.2143 | 0.7698 | 0.029* | |
H21B | 0.0720 | −0.2967 | 0.7474 | 0.029* | |
C22 | 0.08733 (12) | 0.0156 (6) | 0.80798 (13) | 0.0274 (7) | |
C23 | 0.09520 (17) | −0.0295 (14) | 0.90468 (15) | 0.103 (2) | |
H23A | 0.0731 | −0.1814 | 0.9192 | 0.123* | |
H23B | 0.0670 | 0.1346 | 0.8952 | 0.123* | |
C24 | 0.1508 (2) | 0.0518 (15) | 0.94815 (18) | 0.114 (3) | |
H24A | 0.1852 | −0.0729 | 0.9463 | 0.171* | |
H24B | 0.1425 | 0.0352 | 0.9852 | 0.171* | |
H24C | 0.1617 | 0.2475 | 0.9420 | 0.171* | |
O1W | 0.03239 (11) | 0.7511 (5) | 0.01011 (10) | 0.0507 (7) | |
H1A | 0.0699 (9) | 0.761 (7) | 0.0427 (8) | 0.076* | |
H1B | −0.0006 (11) | 0.626 (8) | 0.0178 (15) | 0.076* | 0.50 |
H1C | 0.0162 (15) | 0.942 (3) | −0.0035 (17) | 0.076* | 0.50 |
O2W | 0.01234 (11) | 0.7517 (5) | 0.52880 (10) | 0.0514 (7) | |
H2A | 0.0571 (4) | 0.768 (7) | 0.5492 (13) | 0.077* | |
H2B | −0.0065 (15) | 0.939 (3) | 0.515 (2) | 0.077* | 0.50 |
H2C | 0.0049 (16) | 0.607 (8) | 0.4983 (15) | 0.077* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0221 (12) | 0.0280 (13) | 0.0276 (14) | 0.0040 (10) | 0.0061 (11) | −0.0044 (10) |
N2 | 0.0159 (11) | 0.0224 (12) | 0.0233 (13) | 0.0005 (9) | 0.0070 (10) | −0.0008 (9) |
N3 | 0.0173 (11) | 0.0238 (12) | 0.0242 (13) | 0.0013 (9) | 0.0061 (10) | −0.0037 (10) |
O1 | 0.0319 (11) | 0.0267 (11) | 0.0377 (12) | −0.0087 (9) | 0.0177 (10) | −0.0071 (9) |
O2 | 0.0273 (10) | 0.0307 (11) | 0.0223 (11) | −0.0062 (8) | 0.0098 (9) | −0.0017 (8) |
C1 | 0.0287 (16) | 0.0364 (18) | 0.0320 (18) | 0.0053 (13) | 0.0081 (14) | −0.0095 (14) |
C2 | 0.0247 (15) | 0.0297 (17) | 0.0405 (18) | 0.0066 (12) | 0.0149 (14) | −0.0038 (13) |
C3 | 0.0148 (13) | 0.0277 (16) | 0.0348 (17) | 0.0015 (11) | 0.0072 (12) | 0.0056 (12) |
C4 | 0.0183 (13) | 0.0232 (14) | 0.0235 (15) | −0.0016 (11) | 0.0050 (12) | −0.0008 (11) |
C5 | 0.0154 (13) | 0.0229 (14) | 0.0206 (14) | 0.0000 (10) | 0.0069 (11) | 0.0005 (11) |
C6 | 0.0174 (13) | 0.0220 (14) | 0.0199 (14) | −0.0002 (10) | 0.0049 (11) | −0.0006 (11) |
C7 | 0.0194 (14) | 0.0346 (17) | 0.0242 (15) | 0.0053 (12) | 0.0021 (12) | −0.0057 (12) |
C8 | 0.0188 (14) | 0.0319 (16) | 0.0298 (16) | 0.0072 (11) | 0.0043 (13) | −0.0030 (13) |
C9 | 0.0244 (14) | 0.0194 (14) | 0.0261 (15) | −0.0017 (11) | 0.0104 (12) | −0.0040 (11) |
C10 | 0.0163 (13) | 0.0242 (15) | 0.0285 (16) | 0.0014 (11) | 0.0107 (12) | −0.0041 (12) |
C11 | 0.0327 (16) | 0.0353 (18) | 0.0312 (17) | −0.0044 (13) | 0.0158 (14) | 0.0024 (13) |
C12 | 0.124 (4) | 0.094 (4) | 0.028 (2) | −0.069 (3) | 0.020 (2) | −0.006 (2) |
N4 | 0.0244 (12) | 0.0214 (12) | 0.0264 (13) | −0.0028 (9) | 0.0049 (10) | −0.0017 (10) |
N5 | 0.0166 (11) | 0.0182 (11) | 0.0266 (13) | −0.0004 (9) | 0.0087 (10) | −0.0016 (9) |
N6 | 0.0186 (11) | 0.0170 (12) | 0.0272 (13) | 0.0004 (9) | 0.0080 (10) | −0.0007 (9) |
O3 | 0.0345 (12) | 0.0357 (13) | 0.0519 (14) | 0.0062 (10) | 0.0221 (11) | −0.0107 (11) |
O4 | 0.0374 (13) | 0.0805 (19) | 0.0242 (12) | 0.0218 (12) | 0.0086 (10) | −0.0043 (12) |
C13 | 0.0355 (16) | 0.0238 (15) | 0.0236 (15) | −0.0034 (12) | 0.0071 (13) | −0.0008 (12) |
C14 | 0.0289 (15) | 0.0217 (15) | 0.0333 (17) | −0.0066 (11) | 0.0156 (13) | −0.0043 (12) |
C15 | 0.0182 (13) | 0.0219 (15) | 0.0343 (17) | −0.0017 (11) | 0.0079 (12) | −0.0070 (12) |
C16 | 0.0171 (13) | 0.0216 (14) | 0.0263 (16) | 0.0028 (10) | 0.0046 (12) | −0.0031 (11) |
C17 | 0.0192 (13) | 0.0166 (13) | 0.0224 (15) | 0.0010 (10) | 0.0071 (12) | −0.0050 (11) |
C18 | 0.0168 (13) | 0.0158 (13) | 0.0240 (15) | 0.0014 (10) | 0.0063 (11) | −0.0030 (11) |
C19 | 0.0197 (14) | 0.0254 (15) | 0.0308 (16) | −0.0021 (11) | 0.0025 (12) | 0.0016 (12) |
C20 | 0.0159 (13) | 0.0259 (15) | 0.0326 (17) | −0.0031 (11) | 0.0029 (13) | −0.0012 (12) |
C21 | 0.0259 (14) | 0.0193 (14) | 0.0299 (16) | 0.0003 (11) | 0.0116 (13) | −0.0001 (11) |
C22 | 0.0194 (14) | 0.0311 (17) | 0.0342 (17) | −0.0028 (12) | 0.0116 (13) | −0.0065 (13) |
C23 | 0.071 (3) | 0.207 (7) | 0.029 (2) | 0.065 (4) | 0.010 (2) | −0.026 (3) |
C24 | 0.104 (4) | 0.189 (7) | 0.069 (3) | −0.085 (4) | 0.058 (3) | −0.075 (4) |
O1W | 0.0407 (13) | 0.0485 (15) | 0.0482 (15) | 0.0002 (11) | −0.0149 (12) | −0.0008 (12) |
O2W | 0.0410 (14) | 0.0463 (15) | 0.0530 (16) | −0.0080 (11) | −0.0132 (12) | 0.0070 (12) |
Geometric parameters (Å, º) top
N1—C5 | 1.342 (3) | N5—N6 | 1.353 (3) |
N1—C1 | 1.343 (3) | N6—C20 | 1.345 (3) |
N2—C6 | 1.337 (3) | N6—C21 | 1.440 (3) |
N2—N3 | 1.354 (3) | O3—C22 | 1.197 (3) |
N3—C8 | 1.345 (4) | O4—C22 | 1.327 (4) |
N3—C9 | 1.443 (3) | O4—C23 | 1.437 (4) |
O1—C10 | 1.202 (3) | C13—C14 | 1.376 (4) |
O2—C10 | 1.334 (3) | C13—H13 | 0.950 |
O2—C11 | 1.457 (3) | C14—C15 | 1.380 (4) |
C1—C2 | 1.375 (4) | C14—H14 | 0.950 |
C1—H1 | 0.950 | C15—C16 | 1.379 (4) |
C2—C3 | 1.377 (4) | C15—H15 | 0.950 |
C2—H2 | 0.950 | C16—C17 | 1.393 (4) |
C3—C4 | 1.380 (4) | C16—H16 | 0.950 |
C3—H3 | 0.950 | C17—C18 | 1.472 (4) |
C4—C5 | 1.388 (4) | C18—C19 | 1.405 (4) |
C4—H4 | 0.950 | C19—C20 | 1.366 (4) |
C5—C6 | 1.474 (3) | C19—H19 | 0.950 |
C6—C7 | 1.406 (4) | C20—H20 | 0.950 |
C7—C8 | 1.369 (4) | C21—C22 | 1.515 (4) |
C7—H7 | 0.950 | C21—H21A | 0.990 |
C8—H8 | 0.950 | C21—H21B | 0.990 |
C9—C10 | 1.511 (4) | C23—C24 | 1.467 (6) |
C9—H9A | 0.990 | C23—H23A | 0.990 |
C9—H9B | 0.990 | C23—H23B | 0.990 |
C11—C12 | 1.481 (5) | C24—H24A | 0.980 |
C11—H11A | 0.990 | C24—H24B | 0.980 |
C11—H11B | 0.990 | C24—H24C | 0.980 |
C12—H12A | 0.980 | O1W—H1A | 1.00 (1) |
C12—H12B | 0.980 | O1W—H1B | 1.00 (1) |
C12—H12C | 0.980 | O1W—H1C | 1.00 (1) |
N4—C17 | 1.339 (3) | O2W—H2A | 1.00 (1) |
N4—C13 | 1.343 (3) | O2W—H2B | 1.00 (1) |
N5—C18 | 1.339 (3) | O2W—H2C | 1.00 (1) |
| | | |
C5—N1—C1 | 117.1 (2) | C20—N6—C21 | 128.5 (2) |
C6—N2—N3 | 104.6 (2) | N5—N6—C21 | 119.0 (2) |
C8—N3—N2 | 112.2 (2) | C22—O4—C23 | 116.7 (3) |
C8—N3—C9 | 128.7 (2) | N4—C13—C14 | 124.2 (3) |
N2—N3—C9 | 118.8 (2) | N4—C13—H13 | 117.9 |
C10—O2—C11 | 114.6 (2) | C14—C13—H13 | 117.9 |
N1—C1—C2 | 124.3 (3) | C13—C14—C15 | 117.8 (3) |
N1—C1—H1 | 117.9 | C13—C14—H14 | 121.1 |
C2—C1—H1 | 117.9 | C15—C14—H14 | 121.1 |
C1—C2—C3 | 118.0 (3) | C16—C15—C14 | 119.4 (3) |
C1—C2—H2 | 121.0 | C16—C15—H15 | 120.3 |
C3—C2—H2 | 121.0 | C14—C15—H15 | 120.3 |
C2—C3—C4 | 119.2 (3) | C15—C16—C17 | 119.0 (3) |
C2—C3—H3 | 120.4 | C15—C16—H16 | 120.5 |
C4—C3—H3 | 120.4 | C17—C16—H16 | 120.5 |
C3—C4—C5 | 119.2 (3) | N4—C17—C16 | 122.2 (2) |
C3—C4—H4 | 120.4 | N4—C17—C18 | 116.2 (2) |
C5—C4—H4 | 120.4 | C16—C17—C18 | 121.6 (2) |
N1—C5—C4 | 122.3 (2) | N5—C18—C19 | 110.9 (2) |
N1—C5—C6 | 116.1 (2) | N5—C18—C17 | 120.3 (2) |
C4—C5—C6 | 121.6 (2) | C19—C18—C17 | 128.8 (2) |
N2—C6—C7 | 111.2 (2) | C20—C19—C18 | 105.2 (2) |
N2—C6—C5 | 120.1 (2) | C20—C19—H19 | 127.4 |
C7—C6—C5 | 128.7 (2) | C18—C19—H19 | 127.4 |
C8—C7—C6 | 104.8 (2) | N6—C20—C19 | 107.0 (2) |
C8—C7—H7 | 127.6 | N6—C20—H20 | 126.5 |
C6—C7—H7 | 127.6 | C19—C20—H20 | 126.5 |
N3—C8—C7 | 107.2 (2) | N6—C21—C22 | 111.5 (2) |
N3—C8—H8 | 126.4 | N6—C21—H21A | 109.3 |
C7—C8—H8 | 126.4 | C22—C21—H21A | 109.3 |
N3—C9—C10 | 110.2 (2) | N6—C21—H21B | 109.3 |
N3—C9—H9A | 109.6 | C22—C21—H21B | 109.3 |
C10—C9—H9A | 109.6 | H21A—C21—H21B | 108.0 |
N3—C9—H9B | 109.6 | O3—C22—O4 | 125.4 (3) |
C10—C9—H9B | 109.6 | O3—C22—C21 | 124.6 (3) |
H9A—C9—H9B | 108.1 | O4—C22—C21 | 110.0 (2) |
O1—C10—O2 | 124.2 (3) | O4—C23—C24 | 110.9 (3) |
O1—C10—C9 | 124.4 (3) | O4—C23—H23A | 109.5 |
O2—C10—C9 | 111.3 (2) | C24—C23—H23A | 109.5 |
O2—C11—C12 | 108.1 (3) | O4—C23—H23B | 109.5 |
O2—C11—H11A | 110.1 | C24—C23—H23B | 109.5 |
C12—C11—H11A | 110.1 | H23A—C23—H23B | 108.0 |
O2—C11—H11B | 110.1 | C23—C24—H24A | 109.5 |
C12—C11—H11B | 110.1 | C23—C24—H24B | 109.5 |
H11A—C11—H11B | 108.4 | H24A—C24—H24B | 109.5 |
C11—C12—H12A | 109.5 | C23—C24—H24C | 109.5 |
C11—C12—H12B | 109.5 | H24A—C24—H24C | 109.5 |
H12A—C12—H12B | 109.5 | H24B—C24—H24C | 109.5 |
C11—C12—H12C | 109.5 | H1A—O1W—H1B | 112.39 (17) |
H12A—C12—H12C | 109.5 | H1A—O1W—H1C | 112.40 (17) |
H12B—C12—H12C | 109.5 | H1B—O1W—H1C | 112.39 (17) |
C17—N4—C13 | 117.3 (2) | H2A—O2W—H2B | 112.39 (17) |
C18—N5—N6 | 104.5 (2) | H2A—O2W—H2C | 112.38 (17) |
C20—N6—N5 | 112.4 (2) | H2B—O2W—H2C | 112.38 (17) |
| | | |
C6—N2—N3—C8 | 1.3 (3) | C18—N5—N6—C20 | −0.9 (3) |
C6—N2—N3—C9 | 175.6 (2) | C18—N5—N6—C21 | −177.5 (2) |
C5—N1—C1—C2 | 0.0 (4) | C17—N4—C13—C14 | 1.2 (4) |
N1—C1—C2—C3 | 0.3 (5) | N4—C13—C14—C15 | −1.4 (4) |
C1—C2—C3—C4 | −0.4 (4) | C13—C14—C15—C16 | 0.7 (4) |
C2—C3—C4—C5 | 0.3 (4) | C14—C15—C16—C17 | 0.0 (4) |
C1—N1—C5—C4 | −0.1 (4) | C13—N4—C17—C16 | −0.4 (4) |
C1—N1—C5—C6 | 179.7 (2) | C13—N4—C17—C18 | 179.5 (2) |
C3—C4—C5—N1 | 0.0 (4) | C15—C16—C17—N4 | −0.2 (4) |
C3—C4—C5—C6 | −179.8 (2) | C15—C16—C17—C18 | 179.9 (2) |
N3—N2—C6—C7 | −0.8 (3) | N6—N5—C18—C19 | 0.3 (3) |
N3—N2—C6—C5 | 179.1 (2) | N6—N5—C18—C17 | −178.8 (2) |
N1—C5—C6—N2 | −178.4 (2) | N4—C17—C18—N5 | 179.5 (2) |
C4—C5—C6—N2 | 1.4 (4) | C16—C17—C18—N5 | −0.6 (4) |
N1—C5—C6—C7 | 1.4 (4) | N4—C17—C18—C19 | 0.6 (4) |
C4—C5—C6—C7 | −178.7 (3) | C16—C17—C18—C19 | −179.6 (3) |
N2—C6—C7—C8 | 0.0 (3) | N5—C18—C19—C20 | 0.4 (3) |
C5—C6—C7—C8 | −179.9 (3) | C17—C18—C19—C20 | 179.4 (3) |
N2—N3—C8—C7 | −1.3 (3) | N5—N6—C20—C19 | 1.2 (3) |
C9—N3—C8—C7 | −174.9 (3) | C21—N6—C20—C19 | 177.3 (2) |
C6—C7—C8—N3 | 0.8 (3) | C18—C19—C20—N6 | −0.9 (3) |
C8—N3—C9—C10 | 97.2 (3) | C20—N6—C21—C22 | −94.1 (3) |
N2—N3—C9—C10 | −76.0 (3) | N5—N6—C21—C22 | 81.8 (3) |
C11—O2—C10—O1 | 1.3 (4) | C23—O4—C22—O3 | 7.0 (5) |
C11—O2—C10—C9 | −178.4 (2) | C23—O4—C22—C21 | −172.1 (3) |
N3—C9—C10—O1 | −24.1 (4) | N6—C21—C22—O3 | 20.7 (4) |
N3—C9—C10—O2 | 155.5 (2) | N6—C21—C22—O4 | −160.2 (2) |
C10—O2—C11—C12 | 179.2 (3) | C22—O4—C23—C24 | −120.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···N1i | 1.00 (1) | 1.91 (2) | 2.900 (3) | 168 (3) |
O1W—H1B···O1Wii | 1.00 (1) | 1.98 (3) | 2.762 (5) | 133 (4) |
O1W—H1C···O1Wiii | 1.00 (1) | 1.80 (2) | 2.743 (5) | 157 (4) |
O2W—H2A···N4 | 1.00 (1) | 1.95 (2) | 2.926 (3) | 166 (3) |
O2W—H2B···O2Wiv | 1.00 (1) | 1.81 (3) | 2.729 (5) | 152 (4) |
O2W—H2C···O2Wv | 1.00 (1) | 1.83 (2) | 2.757 (5) | 153 (5) |
C8—H8···O3v | 0.95 | 2.44 | 3.219 (3) | 140 |
C9—H9A···O1i | 0.99 | 2.54 | 3.252 (3) | 129 |
C19—H19···O2W | 0.95 | 2.49 | 3.351 (4) | 151 |
C20—H20···O1vi | 0.95 | 2.38 | 3.181 (3) | 141 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) −x, −y+2, −z+1; (v) −x, −y+1, −z+1; (vi) −x, −y, −z+1. |
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