In the crystal structure of the title compound, C10H10N3+·NO3−·H2O, (I), the asymmetric unit contains two crystallographically independent but similar subunits. The protonated C10H10N3+ cation adopts the normal trans–trans configuration and approximately planar geometry. Multiple hydrogen-bonding interactions expand the structure, resulting in a two-dimensional layered architecture, which is further stabilized by aromatic π–π stacking interactions between the protonated cations.
Supporting information
CCDC reference: 236105
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.068
- wR factor = 0.182
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors .... N8
| Author Response: The atom N8 belongs to a nitrate anion. The larger
than normal displacement ellipsoids for the O atoms (O4, O5 and
O6) suggest that this anion may be partially disordered (a similar
situation may also occur for the nitrate anion containing N7).
In the present refinement a disorder model of the nitrate anion
was not used. It should also be noted that the highest density peak,
of 0.73e/\%A^3^ in the final difference Fourier is approximately
1.36 \%A from N8.
|
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C15 .. 8.61 su
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N7
| Author Response: The atom N8 belongs to a nitrate anion. The larger
than normal displacement ellipsoids for the O atoms (O4, O5 and
O6) suggest that this anion may be partially disordered (a similar
situation may also occur for the nitrate anion containing N7).
In the present refinement a disorder model of the nitrate anion
was not used. It should also be noted that the highest density peak,
of 0.73e/\%A^3^ in the final difference Fourier is approximately
1.36 \%A from N8.
|
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.732
Test value = 0.600
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.73 e/A 3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C15 .. 2.95 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 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
6 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
1 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.
(2-Pyridinio-2'-pyridyl)amine nitrate hydrate
top
Crystal data top
C10H12N4O4 | Z = 4 |
Mr = 252.24 | F(000) = 528 |
Triclinic, P1 | Dx = 1.433 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.795 (2) Å | Cell parameters from 845 reflections |
b = 9.734 (3) Å | θ = 2.3–25.0° |
c = 17.164 (5) Å | µ = 0.11 mm−1 |
α = 95.982 (6)° | T = 293 K |
β = 102.332 (6)° | Block, colorless |
γ = 110.480 (5)° | 0.30 × 0.20 × 0.20 mm |
V = 1168.9 (6) Å3 | |
Data collection top
BRUKER SMART 1000 diffractometer | 2266 reflections with I > 2σ(I) |
ω scans | Rint = 0.018 |
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1998)] | θmax = 25.0° |
Tmin = 0.967, Tmax = 0.978 | h = −9→6 |
4852 measured reflections | k = −10→11 |
4088 independent reflections | l = −20→19 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.068 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.642P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.182 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.73 e Å−3 |
4088 reflections | Δρmin = −0.45 e Å−3 |
328 parameters | |
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. Full-MATRIX |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.4234 (5) | 0.7232 (4) | 0.1797 (2) | 0.1012 (12) | |
O2 | 0.5142 (4) | 0.9570 (3) | 0.1957 (2) | 0.0934 (11) | |
O3 | 0.6887 (5) | 0.8491 (5) | 0.1603 (2) | 0.1119 (13) | |
O4 | 0.3006 (7) | 0.3156 (5) | 0.3487 (3) | 0.166 (2) | |
O5 | 0.3951 (4) | 0.1399 (4) | 0.3268 (2) | 0.0846 (9) | |
O6 | 0.1037 (5) | 0.1059 (4) | 0.2904 (3) | 0.1204 (15) | |
N1 | 0.8552 (4) | 0.6273 (3) | 1.05874 (17) | 0.0490 (8) | |
H1 | 0.9256 | 0.7017 | 1.0979 | 0.059* | |
N2 | 0.6526 (4) | 0.5560 (3) | 0.92712 (17) | 0.0497 (8) | |
H2 | 0.6351 | 0.4644 | 0.9294 | 0.060* | |
N3 | 0.7338 (4) | 0.3693 (3) | 1.01641 (18) | 0.0544 (8) | |
N4 | 0.7763 (4) | 0.4024 (3) | 0.43517 (16) | 0.0455 (7) | |
H4 | 0.7938 | 0.3435 | 0.3995 | 0.055* | |
N5 | 0.7179 (4) | 0.4306 (4) | 0.56278 (18) | 0.0577 (8) | |
H5 | 0.7310 | 0.5215 | 0.5605 | 0.069* | |
N6 | 0.7849 (4) | 0.6410 (3) | 0.4740 (2) | 0.0609 (9) | |
N7 | 0.5448 (5) | 0.8439 (4) | 0.17742 (18) | 0.0565 (8) | |
N8 | 0.2665 (6) | 0.1826 (4) | 0.3265 (2) | 0.0663 (9) | |
C1 | 0.7652 (5) | 0.6628 (4) | 0.9918 (2) | 0.0428 (8) | |
C2 | 0.7893 (5) | 0.8104 (4) | 0.9876 (2) | 0.0512 (9) | |
H2A | 0.8662 | 0.8868 | 1.0318 | 0.061* | |
C3 | 0.7012 (6) | 0.8424 (5) | 0.9193 (3) | 0.0635 (11) | |
H3A | 0.7172 | 0.9410 | 0.9169 | 0.076* | |
C4 | 0.5864 (6) | 0.7290 (5) | 0.8525 (3) | 0.0658 (11) | |
H4A | 0.5262 | 0.7508 | 0.8053 | 0.079* | |
C5 | 0.5646 (6) | 0.5876 (5) | 0.8578 (2) | 0.0610 (11) | |
H5A | 0.4889 | 0.5105 | 0.8137 | 0.073* | |
C6 | 0.8503 (5) | 0.4890 (4) | 1.0734 (2) | 0.0438 (8) | |
C7 | 0.9653 (5) | 0.4803 (5) | 1.1449 (2) | 0.0588 (10) | |
H7A | 1.0476 | 0.5660 | 1.1827 | 0.071* | |
C8 | 0.9537 (6) | 0.3406 (5) | 1.1580 (3) | 0.0653 (11) | |
H8A | 1.0286 | 0.3308 | 1.2054 | 0.078* | |
C9 | 0.8313 (7) | 0.2156 (5) | 1.1010 (3) | 0.0695 (12) | |
H9A | 0.8204 | 0.1204 | 1.1093 | 0.083* | |
C10 | 0.7263 (6) | 0.2354 (4) | 1.0316 (3) | 0.0647 (11) | |
H10A | 0.6447 | 0.1510 | 0.9927 | 0.078* | |
C11 | 0.7365 (4) | 0.3464 (4) | 0.5016 (2) | 0.0439 (9) | |
C12 | 0.7182 (5) | 0.1998 (4) | 0.5069 (2) | 0.0578 (10) | |
H12A | 0.7308 | 0.1399 | 0.4644 | 0.069* | |
C13 | 0.6827 (6) | 0.1452 (5) | 0.5727 (3) | 0.0723 (13) | |
H13A | 0.6725 | 0.0480 | 0.5760 | 0.087* | |
C14 | 0.6615 (6) | 0.2315 (6) | 0.6348 (3) | 0.0772 (14) | |
H14A | 0.6360 | 0.1927 | 0.6802 | 0.093* | |
C15 | 0.6771 (6) | 0.3730 (6) | 0.6308 (2) | 0.0752 (14) | |
H15A | 0.6610 | 0.4314 | 0.6729 | 0.090* | |
C16 | 0.7924 (5) | 0.5405 (4) | 0.4173 (2) | 0.0463 (9) | |
C17 | 0.8179 (5) | 0.5694 (5) | 0.3418 (2) | 0.0619 (11) | |
H17A | 0.8222 | 0.4971 | 0.3032 | 0.074* | |
C18 | 0.8365 (6) | 0.7099 (6) | 0.3267 (3) | 0.0807 (15) | |
H18A | 0.8536 | 0.7342 | 0.2772 | 0.097* | |
C19 | 0.8296 (6) | 0.8139 (6) | 0.3857 (4) | 0.0909 (17) | |
H19A | 0.8426 | 0.9091 | 0.3766 | 0.109* | |
C20 | 0.8036 (6) | 0.7754 (5) | 0.4567 (4) | 0.0812 (14) | |
H20A | 0.7983 | 0.8462 | 0.4959 | 0.097* | |
O1W | 0.1092 (4) | 0.8689 (3) | 0.17904 (16) | 0.0676 (8) | |
H1WA | 0.0799 | 0.9230 | 0.2159 | 0.101* | |
H1WB | 0.2305 | 0.8834 | 0.1833 | 0.101* | |
O2W | 0.8092 (4) | 0.1897 (3) | 0.32182 (17) | 0.0761 (9) | |
H2WA | 0.9166 | 0.1859 | 0.3126 | 0.114* | |
H2WB | 0.6988 | 0.1329 | 0.2849 | 0.114* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.107 (3) | 0.063 (2) | 0.111 (3) | 0.006 (2) | 0.039 (2) | −0.0044 (18) |
O2 | 0.079 (2) | 0.057 (2) | 0.135 (3) | 0.0331 (17) | 0.011 (2) | −0.0049 (18) |
O3 | 0.100 (3) | 0.164 (4) | 0.131 (3) | 0.085 (3) | 0.072 (2) | 0.067 (3) |
O4 | 0.176 (5) | 0.113 (4) | 0.195 (5) | 0.062 (3) | 0.049 (4) | −0.047 (3) |
O5 | 0.072 (2) | 0.087 (2) | 0.099 (2) | 0.0426 (19) | 0.0114 (18) | 0.0162 (18) |
O6 | 0.060 (2) | 0.100 (3) | 0.180 (4) | 0.027 (2) | 0.021 (2) | −0.025 (3) |
N1 | 0.0561 (19) | 0.0378 (17) | 0.0493 (18) | 0.0166 (14) | 0.0102 (15) | 0.0059 (13) |
N2 | 0.0535 (19) | 0.0460 (18) | 0.0503 (18) | 0.0209 (15) | 0.0129 (15) | 0.0087 (15) |
N3 | 0.065 (2) | 0.0389 (18) | 0.061 (2) | 0.0212 (15) | 0.0193 (17) | 0.0092 (15) |
N4 | 0.0487 (18) | 0.0434 (17) | 0.0411 (16) | 0.0152 (14) | 0.0104 (14) | 0.0063 (13) |
N5 | 0.0495 (19) | 0.065 (2) | 0.055 (2) | 0.0215 (16) | 0.0112 (16) | 0.0057 (17) |
N6 | 0.054 (2) | 0.0414 (19) | 0.087 (2) | 0.0207 (15) | 0.0142 (18) | 0.0104 (17) |
N7 | 0.062 (2) | 0.059 (2) | 0.0506 (19) | 0.0256 (19) | 0.0146 (17) | 0.0092 (16) |
N8 | 0.075 (3) | 0.052 (2) | 0.073 (2) | 0.028 (2) | 0.023 (2) | −0.0054 (18) |
C1 | 0.043 (2) | 0.045 (2) | 0.043 (2) | 0.0168 (16) | 0.0153 (17) | 0.0095 (17) |
C2 | 0.057 (2) | 0.042 (2) | 0.058 (2) | 0.0181 (18) | 0.0195 (19) | 0.0135 (18) |
C3 | 0.076 (3) | 0.056 (3) | 0.078 (3) | 0.035 (2) | 0.033 (2) | 0.031 (2) |
C4 | 0.079 (3) | 0.079 (3) | 0.061 (3) | 0.046 (3) | 0.026 (2) | 0.034 (2) |
C5 | 0.060 (3) | 0.077 (3) | 0.045 (2) | 0.030 (2) | 0.0075 (19) | 0.007 (2) |
C6 | 0.044 (2) | 0.043 (2) | 0.052 (2) | 0.0190 (17) | 0.0203 (18) | 0.0160 (17) |
C7 | 0.054 (2) | 0.063 (3) | 0.063 (3) | 0.023 (2) | 0.016 (2) | 0.021 (2) |
C8 | 0.070 (3) | 0.078 (3) | 0.070 (3) | 0.041 (3) | 0.030 (2) | 0.041 (3) |
C9 | 0.087 (3) | 0.057 (3) | 0.096 (3) | 0.043 (3) | 0.050 (3) | 0.038 (3) |
C10 | 0.086 (3) | 0.042 (2) | 0.076 (3) | 0.028 (2) | 0.033 (3) | 0.015 (2) |
C11 | 0.0327 (19) | 0.051 (2) | 0.040 (2) | 0.0119 (16) | 0.0020 (16) | 0.0050 (17) |
C12 | 0.052 (2) | 0.051 (2) | 0.062 (3) | 0.0135 (18) | 0.009 (2) | 0.0157 (19) |
C13 | 0.061 (3) | 0.073 (3) | 0.078 (3) | 0.018 (2) | 0.014 (2) | 0.029 (3) |
C14 | 0.058 (3) | 0.097 (4) | 0.075 (3) | 0.022 (3) | 0.014 (2) | 0.044 (3) |
C15 | 0.050 (3) | 0.125 (4) | 0.047 (3) | 0.034 (3) | 0.013 (2) | 0.002 (3) |
C16 | 0.035 (2) | 0.046 (2) | 0.054 (2) | 0.0144 (16) | 0.0045 (17) | 0.0132 (18) |
C17 | 0.051 (2) | 0.063 (3) | 0.064 (3) | 0.013 (2) | 0.007 (2) | 0.024 (2) |
C18 | 0.050 (3) | 0.092 (4) | 0.092 (4) | 0.014 (3) | 0.007 (2) | 0.051 (3) |
C19 | 0.059 (3) | 0.056 (3) | 0.155 (5) | 0.020 (2) | 0.014 (3) | 0.046 (4) |
C20 | 0.067 (3) | 0.056 (3) | 0.121 (4) | 0.028 (2) | 0.020 (3) | 0.015 (3) |
O1W | 0.0533 (16) | 0.0633 (18) | 0.0747 (18) | 0.0179 (13) | 0.0089 (14) | −0.0028 (14) |
O2W | 0.0599 (18) | 0.082 (2) | 0.0789 (19) | 0.0285 (15) | 0.0166 (15) | −0.0142 (16) |
Geometric parameters (Å, º) top
O1—N7 | 1.235 (4) | C5—H5A | 0.9300 |
O2—N7 | 1.229 (4) | C6—C7 | 1.386 (5) |
O3—N7 | 1.205 (4) | C7—C8 | 1.376 (5) |
O4—N8 | 1.227 (5) | C7—H7A | 0.9300 |
O5—N8 | 1.212 (4) | C8—C9 | 1.374 (6) |
O6—N8 | 1.207 (4) | C8—H8A | 0.9300 |
N1—C1 | 1.357 (4) | C9—C10 | 1.366 (6) |
N1—C6 | 1.384 (4) | C9—H9A | 0.9300 |
N1—H1 | 0.8600 | C10—H10A | 0.9300 |
N2—C1 | 1.337 (4) | C11—C12 | 1.398 (5) |
N2—C5 | 1.363 (4) | C12—C13 | 1.337 (5) |
N2—H2 | 0.8600 | C12—H12A | 0.9300 |
N3—C6 | 1.335 (4) | C13—C14 | 1.363 (6) |
N3—C10 | 1.339 (5) | C13—H13A | 0.9300 |
N4—C11 | 1.362 (4) | C14—C15 | 1.350 (6) |
N4—C16 | 1.380 (4) | C14—H14A | 0.9300 |
N4—H4 | 0.8600 | C15—H15A | 0.9300 |
N5—C11 | 1.328 (4) | C16—C17 | 1.394 (5) |
N5—C15 | 1.396 (5) | C17—C18 | 1.382 (6) |
N5—H5 | 0.8600 | C17—H17A | 0.9300 |
N6—C16 | 1.331 (5) | C18—C19 | 1.379 (7) |
N6—C20 | 1.337 (5) | C18—H18A | 0.9300 |
C1—C2 | 1.393 (5) | C19—C20 | 1.347 (7) |
C2—C3 | 1.351 (5) | C19—H19A | 0.9300 |
C2—H2A | 0.9300 | C20—H20A | 0.9300 |
C3—C4 | 1.393 (6) | O1W—H1WA | 0.8977 |
C3—H3A | 0.9300 | O1W—H1WB | 0.8916 |
C4—C5 | 1.342 (5) | O2W—H2WA | 0.8964 |
C4—H4A | 0.9300 | O2W—H2WB | 0.8992 |
| | | |
C1—N1—C6 | 129.6 (3) | C9—C8—C7 | 120.0 (4) |
C1—N1—H1 | 115.2 | C9—C8—H8A | 120.0 |
C6—N1—H1 | 115.2 | C7—C8—H8A | 120.0 |
C1—N2—C5 | 122.1 (3) | C10—C9—C8 | 118.0 (4) |
C1—N2—H2 | 119.0 | C10—C9—H9A | 121.0 |
C5—N2—H2 | 119.0 | C8—C9—H9A | 121.0 |
C6—N3—C10 | 117.1 (3) | N3—C10—C9 | 123.9 (4) |
C11—N4—C16 | 128.9 (3) | N3—C10—H10A | 118.1 |
C11—N4—H4 | 115.5 | C9—C10—H10A | 118.1 |
C16—N4—H4 | 115.5 | N5—C11—N4 | 120.7 (3) |
C11—N5—C15 | 120.6 (4) | N5—C11—C12 | 119.1 (3) |
C11—N5—H5 | 119.7 | N4—C11—C12 | 120.2 (3) |
C15—N5—H5 | 119.7 | C13—C12—C11 | 120.5 (4) |
C16—N6—C20 | 117.5 (4) | C13—C12—H12A | 119.7 |
O3—N7—O2 | 122.3 (4) | C11—C12—H12A | 119.7 |
O3—N7—O1 | 120.7 (4) | C12—C13—C14 | 120.2 (5) |
O2—N7—O1 | 117.0 (4) | C12—C13—H13A | 119.9 |
O6—N8—O5 | 122.3 (4) | C14—C13—H13A | 119.9 |
O6—N8—O4 | 115.8 (4) | C15—C14—C13 | 120.4 (4) |
O5—N8—O4 | 120.3 (4) | C15—C14—H14A | 119.8 |
N2—C1—N1 | 120.3 (3) | C13—C14—H14A | 119.8 |
N2—C1—C2 | 118.2 (3) | C14—C15—N5 | 119.3 (4) |
N1—C1—C2 | 121.5 (3) | C14—C15—H15A | 120.3 |
C3—C2—C1 | 120.0 (4) | N5—C15—H15A | 120.3 |
C3—C2—H2A | 120.0 | N6—C16—N4 | 117.8 (3) |
C1—C2—H2A | 120.0 | N6—C16—C17 | 123.1 (4) |
C2—C3—C4 | 120.5 (4) | N4—C16—C17 | 119.0 (3) |
C2—C3—H3A | 119.7 | C18—C17—C16 | 117.3 (4) |
C4—C3—H3A | 119.7 | C18—C17—H17A | 121.4 |
C5—C4—C3 | 118.5 (4) | C16—C17—H17A | 121.4 |
C5—C4—H4A | 120.7 | C19—C18—C17 | 119.5 (5) |
C3—C4—H4A | 120.7 | C19—C18—H18A | 120.3 |
C4—C5—N2 | 120.6 (4) | C17—C18—H18A | 120.3 |
C4—C5—H5A | 119.7 | C20—C19—C18 | 119.0 (5) |
N2—C5—H5A | 119.7 | C20—C19—H19A | 120.5 |
N3—C6—N1 | 117.3 (3) | C18—C19—H19A | 120.5 |
N3—C6—C7 | 123.1 (3) | N6—C20—C19 | 123.7 (5) |
N1—C6—C7 | 119.6 (3) | N6—C20—H20A | 118.2 |
C8—C7—C6 | 117.8 (4) | C19—C20—H20A | 118.2 |
C8—C7—H7A | 121.1 | H1WA—O1W—H1WB | 119.6 |
C6—C7—H7A | 121.1 | H2WA—O2W—H2WB | 117.8 |
| | | |
C5—N2—C1—N1 | −177.8 (3) | C15—N5—C11—N4 | −180.0 (3) |
C5—N2—C1—C2 | 1.1 (5) | C15—N5—C11—C12 | −1.2 (5) |
C6—N1—C1—N2 | −0.3 (5) | C16—N4—C11—N5 | −4.0 (5) |
C6—N1—C1—C2 | −179.2 (3) | C16—N4—C11—C12 | 177.3 (3) |
N2—C1—C2—C3 | −0.5 (5) | N5—C11—C12—C13 | −0.1 (5) |
N1—C1—C2—C3 | 178.5 (3) | N4—C11—C12—C13 | 178.7 (3) |
C1—C2—C3—C4 | −0.3 (6) | C11—C12—C13—C14 | 0.9 (6) |
C2—C3—C4—C5 | 0.4 (6) | C12—C13—C14—C15 | −0.4 (7) |
C3—C4—C5—N2 | 0.2 (6) | C13—C14—C15—N5 | −0.8 (6) |
C1—N2—C5—C4 | −1.0 (5) | C11—N5—C15—C14 | 1.6 (5) |
C10—N3—C6—N1 | −178.5 (3) | C20—N6—C16—N4 | 179.0 (3) |
C10—N3—C6—C7 | 2.0 (5) | C20—N6—C16—C17 | −0.2 (5) |
C1—N1—C6—N3 | −4.0 (5) | C11—N4—C16—N6 | 6.4 (5) |
C1—N1—C6—C7 | 175.5 (3) | C11—N4—C16—C17 | −174.4 (3) |
N3—C6—C7—C8 | −1.8 (5) | N6—C16—C17—C18 | 0.2 (5) |
N1—C6—C7—C8 | 178.8 (3) | N4—C16—C17—C18 | −179.0 (3) |
C6—C7—C8—C9 | 0.2 (6) | C16—C17—C18—C19 | 0.1 (6) |
C7—C8—C9—C10 | 1.0 (6) | C17—C18—C19—C20 | −0.4 (7) |
C6—N3—C10—C9 | −0.7 (6) | C16—N6—C20—C19 | −0.1 (6) |
C8—C9—C10—N3 | −0.8 (6) | C18—C19—C20—N6 | 0.4 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1wi | 0.86 | 1.92 | 2.775 (5) | 173 |
N2—H2···N3 | 0.86 | 1.99 | 2.650 (5) | 132 |
N2—H2···O1ii | 0.86 | 2.32 | 2.910 (4) | 126 |
N4—H4···O2w | 0.86 | 1.95 | 2.808 (4) | 173 |
N5—H5···N6 | 0.86 | 2.00 | 2.651 (5) | 131 |
N5—H5···O4ii | 0.86 | 2.22 | 2.827 (5) | 127 |
O1w—H1wa···O6iii | 0.90 | 2.01 | 2.857 (4) | 157 |
O1w—H1wb···O2 | 0.89 | 2.03 | 2.908 (5) | 169 |
O2w—H2wa···O6iv | 0.90 | 1.96 | 2.823 (4) | 161 |
O2w—H2wb···O2v | 0.90 | 2.03 | 2.883 (4) | 157 |
Symmetry codes: (i) x+1, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x+1, y, z; (v) x, y−1, z. |