The title salt, C4H12N22+·C8H3NO62-·2H2O, crystallizes in the orthorhombic space group Pna21. All O atoms of the 3-nitrophthalate anion are involved in hydrogen bonding with the piperazine dication and the water molecules of crystallization.
Supporting information
CCDC reference: 245327
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.056
- wR factor = 0.161
- Data-to-parameter ratio = 7.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.36
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C8 ... 1.53 Ang.
Alert level G
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 26.35
From the CIF: _reflns_number_total 3053
Count of symmetry unique reflns 3065
Completeness (_total/calc) 99.61%
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
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Piperazinediium 3-nitrophthalate dihydrate
top
Crystal data top
C4H12N22+·C8H3NO62−·2H2O | F(000) = 1408 |
Mr = 333.30 | Dx = 1.510 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 993 reflections |
a = 18.436 (8) Å | θ = 2.4–26.0° |
b = 6.551 (3) Å | µ = 0.13 mm−1 |
c = 24.274 (10) Å | T = 293 K |
V = 2932 (2) Å3 | Prism, colorless |
Z = 8 | 0.20 × 0.16 × 0.14 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3053 independent reflections |
Radiation source: fine-focus sealed tube | 2278 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→18 |
Tmin = 0.954, Tmax = 0.982 | k = −6→8 |
15732 measured reflections | l = −30→27 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0991P)2 + 0.5343P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.004 |
3053 reflections | Δρmax = 0.48 e Å−3 |
415 parameters | Δρmin = −0.25 e Å−3 |
7 restraints | Absolute structure: Flack & Bernardinelli (1999) |
Primary atom site location: structure-invariant direct methods | |
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 | |
O1 | 0.5468 (3) | 0.8171 (12) | 0.9237 (3) | 0.085 (2) | |
O2 | 0.5427 (3) | 0.6877 (10) | 0.8432 (3) | 0.0667 (15) | |
O3 | 0.4509 (2) | 0.9262 (6) | 0.76768 (19) | 0.0368 (10) | |
O4 | 0.4329 (2) | 0.5935 (6) | 0.75621 (17) | 0.0361 (10) | |
O5 | 0.2870 (2) | 0.8229 (8) | 0.75487 (18) | 0.0465 (10) | |
O6 | 0.2058 (2) | 0.6583 (7) | 0.80453 (19) | 0.0488 (11) | |
O7 | 0.2994 (3) | 0.6751 (11) | 0.4216 (3) | 0.0776 (17) | |
O8 | 0.2957 (3) | 0.8078 (10) | 0.5010 (2) | 0.0628 (14) | |
O9 | 0.2047 (2) | 0.5657 (6) | 0.57669 (17) | 0.0340 (10) | |
O10 | 0.1880 (2) | 0.9007 (7) | 0.58925 (18) | 0.0380 (11) | |
O11 | 0.0430 (2) | 0.6885 (7) | 0.59398 (16) | 0.0343 (8) | |
O12 | −0.0397 (2) | 0.8455 (7) | 0.54261 (19) | 0.0483 (11) | |
N1 | 0.5131 (4) | 0.7509 (7) | 0.8844 (3) | 0.0371 (16) | |
N2 | 0.2658 (3) | 0.7427 (7) | 0.4603 (3) | 0.0350 (15) | |
N3 | 0.0953 (2) | 0.4652 (6) | 0.7583 (2) | 0.0301 (10) | |
H3A | 0.0532 | 0.5350 | 0.7577 | 0.036* | |
H3B | 0.1300 | 0.5491 | 0.7713 | 0.036* | |
N4 | 0.1725 (2) | 0.0959 (7) | 0.7373 (2) | 0.0341 (11) | |
H4A | 0.2129 | 0.0188 | 0.7370 | 0.041* | |
H4B | 0.1357 | 0.0197 | 0.7243 | 0.041* | |
N5 | 0.3483 (2) | 0.4514 (7) | 0.58521 (18) | 0.0275 (9) | |
H5A | 0.3828 | 0.5395 | 0.5740 | 0.033* | |
H5B | 0.3054 | 0.5168 | 0.5847 | 0.033* | |
N6 | 0.4272 (2) | 0.0828 (7) | 0.60588 (18) | 0.0288 (9) | |
H6A | 0.3908 | 0.0004 | 0.6166 | 0.035* | |
H6B | 0.4687 | 0.0104 | 0.6070 | 0.035* | |
C1 | 0.4337 (4) | 0.7504 (6) | 0.8868 (3) | 0.0223 (14) | |
C2 | 0.4042 (4) | 0.7500 (8) | 0.9390 (4) | 0.038 (2) | |
H2 | 0.4339 | 0.7570 | 0.9700 | 0.046* | |
C3 | 0.3289 (4) | 0.7390 (8) | 0.9445 (3) | 0.0345 (18) | |
H3 | 0.3073 | 0.7378 | 0.9791 | 0.041* | |
C4 | 0.2867 (4) | 0.7298 (8) | 0.8967 (3) | 0.0283 (15) | |
H4 | 0.2366 | 0.7199 | 0.9000 | 0.034* | |
C5 | 0.3171 (3) | 0.7348 (7) | 0.8448 (3) | 0.0228 (14) | |
C6 | 0.2667 (3) | 0.7360 (8) | 0.7964 (3) | 0.0253 (14) | |
C7 | 0.3923 (4) | 0.7456 (6) | 0.8390 (3) | 0.0199 (14) | |
C8 | 0.4286 (3) | 0.7551 (7) | 0.7824 (3) | 0.0215 (14) | |
C9 | 0.1868 (4) | 0.7432 (8) | 0.4567 (3) | 0.0289 (16) | |
C10 | 0.1549 (4) | 0.7440 (7) | 0.4051 (3) | 0.0261 (16) | |
H10 | 0.1836 | 0.7379 | 0.3736 | 0.031* | |
C11 | 0.0829 (4) | 0.7534 (7) | 0.4006 (3) | 0.0288 (17) | |
H11 | 0.0617 | 0.7516 | 0.3658 | 0.035* | |
C12 | 0.0396 (4) | 0.7659 (7) | 0.4464 (3) | 0.0300 (15) | |
H12 | −0.0105 | 0.7758 | 0.4427 | 0.036* | |
C13 | 0.0712 (3) | 0.7635 (7) | 0.4989 (3) | 0.0221 (14) | |
C14 | 0.0213 (4) | 0.7695 (8) | 0.5490 (3) | 0.0291 (15) | |
C15 | 0.1463 (3) | 0.7506 (6) | 0.5058 (3) | 0.0223 (14) | |
C16 | 0.1815 (3) | 0.7385 (8) | 0.5624 (3) | 0.0278 (17) | |
C17 | 0.0878 (3) | 0.2863 (9) | 0.7963 (4) | 0.0368 (15) | |
H17A | 0.0466 | 0.2037 | 0.7852 | 0.044* | |
H17B | 0.0793 | 0.3339 | 0.8336 | 0.044* | |
C18 | 0.1564 (3) | 0.1593 (9) | 0.7944 (2) | 0.0344 (12) | |
H18A | 0.1966 | 0.2384 | 0.8088 | 0.041* | |
H18B | 0.1505 | 0.0394 | 0.8174 | 0.041* | |
C19 | 0.1829 (4) | 0.2736 (9) | 0.7017 (3) | 0.0332 (16) | |
H19A | 0.1942 | 0.2290 | 0.6645 | 0.040* | |
H19B | 0.2232 | 0.3547 | 0.7151 | 0.040* | |
C20 | 0.1143 (3) | 0.4019 (9) | 0.7012 (2) | 0.0340 (12) | |
H20A | 0.1217 | 0.5220 | 0.6785 | 0.041* | |
H20B | 0.0748 | 0.3235 | 0.6854 | 0.041* | |
C21 | 0.3644 (3) | 0.3820 (8) | 0.6420 (2) | 0.0309 (11) | |
H21A | 0.3243 | 0.3001 | 0.6554 | 0.037* | |
H21B | 0.3692 | 0.4999 | 0.6659 | 0.037* | |
C22 | 0.4326 (3) | 0.2590 (8) | 0.6443 (3) | 0.0284 (15) | |
H22A | 0.4736 | 0.3437 | 0.6342 | 0.034* | |
H22B | 0.4403 | 0.2099 | 0.6816 | 0.034* | |
C23 | 0.4137 (3) | 0.1540 (9) | 0.5483 (2) | 0.0327 (12) | |
H23A | 0.4539 | 0.2375 | 0.5359 | 0.039* | |
H23B | 0.4095 | 0.0375 | 0.5239 | 0.039* | |
C24 | 0.3459 (4) | 0.2742 (9) | 0.5472 (3) | 0.0324 (15) | |
H24A | 0.3056 | 0.1866 | 0.5573 | 0.039* | |
H24B | 0.3374 | 0.3226 | 0.5100 | 0.039* | |
O13 | 0.0572 (2) | 0.8851 (6) | 0.69548 (19) | 0.0427 (10) | |
H13A | 0.0152 | 0.8951 | 0.7097 | 0.064* | |
H13B | 0.0545 | 0.8454 | 0.6622 | 0.064* | |
O14 | 0.3141 (2) | 0.8637 (6) | 0.64553 (18) | 0.0466 (11) | |
H14A | 0.3080 | 0.8269 | 0.6788 | 0.070* | |
H14B | 0.2737 | 0.8833 | 0.6296 | 0.070* | |
O15 | 0.3355 (3) | 0.2569 (6) | 0.7680 (3) | 0.0432 (14) | |
H15A | 0.3674 | 0.3498 | 0.7724 | 0.065* | |
H15B | 0.3510 | 0.1631 | 0.7456 | 0.065* | |
O16 | 0.0907 (3) | 0.2376 (6) | 0.5767 (3) | 0.0418 (14) | |
H16A | 0.1170 | 0.3437 | 0.5741 | 0.063* | |
H16B | 0.1168 | 0.1307 | 0.5755 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.038 (3) | 0.156 (6) | 0.061 (4) | −0.005 (4) | −0.020 (3) | −0.046 (4) |
O2 | 0.031 (3) | 0.109 (4) | 0.061 (3) | 0.016 (3) | −0.001 (2) | −0.029 (4) |
O3 | 0.030 (2) | 0.033 (2) | 0.048 (3) | −0.0008 (17) | 0.014 (2) | 0.009 (2) |
O4 | 0.042 (2) | 0.034 (2) | 0.033 (2) | −0.0066 (17) | 0.0090 (18) | −0.009 (2) |
O5 | 0.037 (2) | 0.073 (3) | 0.029 (2) | 0.010 (2) | −0.0062 (18) | 0.010 (3) |
O6 | 0.031 (2) | 0.063 (3) | 0.053 (3) | −0.012 (2) | −0.0101 (19) | −0.008 (2) |
O7 | 0.049 (3) | 0.126 (5) | 0.058 (3) | 0.011 (4) | 0.019 (3) | −0.020 (4) |
O8 | 0.029 (2) | 0.114 (4) | 0.045 (3) | −0.016 (3) | 0.003 (2) | −0.010 (4) |
O9 | 0.031 (2) | 0.030 (2) | 0.041 (2) | 0.0064 (16) | −0.0076 (18) | 0.0074 (19) |
O10 | 0.041 (2) | 0.033 (2) | 0.040 (2) | 0.0038 (18) | −0.0126 (19) | −0.012 (2) |
O11 | 0.030 (2) | 0.050 (2) | 0.0236 (19) | −0.0054 (19) | 0.0044 (16) | 0.004 (2) |
O12 | 0.025 (2) | 0.060 (3) | 0.060 (3) | 0.014 (2) | 0.0080 (19) | −0.005 (2) |
N1 | 0.031 (3) | 0.034 (3) | 0.046 (4) | 0.0021 (19) | −0.013 (3) | −0.003 (2) |
N2 | 0.027 (3) | 0.053 (4) | 0.025 (3) | 0.002 (2) | 0.008 (3) | −0.0037 (19) |
N3 | 0.0204 (19) | 0.029 (2) | 0.041 (2) | 0.0011 (17) | −0.0036 (18) | −0.004 (2) |
N4 | 0.028 (2) | 0.030 (2) | 0.044 (3) | 0.0098 (19) | −0.0031 (19) | −0.007 (2) |
N5 | 0.024 (2) | 0.030 (2) | 0.029 (2) | 0.0039 (17) | −0.0035 (17) | 0.0043 (19) |
N6 | 0.027 (2) | 0.031 (2) | 0.028 (2) | 0.0067 (18) | 0.0017 (17) | −0.0003 (19) |
C1 | 0.025 (3) | 0.011 (3) | 0.030 (4) | 0.0012 (16) | 0.001 (3) | −0.0042 (17) |
C2 | 0.048 (5) | 0.027 (4) | 0.040 (4) | 0.001 (2) | −0.003 (4) | 0.002 (2) |
C3 | 0.036 (4) | 0.040 (4) | 0.028 (4) | −0.002 (2) | 0.009 (3) | −0.002 (2) |
C4 | 0.023 (3) | 0.035 (3) | 0.027 (3) | 0.000 (2) | 0.009 (3) | −0.003 (2) |
C5 | 0.027 (3) | 0.018 (3) | 0.023 (3) | −0.0036 (18) | −0.001 (3) | −0.005 (2) |
C6 | 0.022 (3) | 0.031 (3) | 0.023 (3) | 0.0033 (19) | −0.011 (3) | −0.006 (2) |
C7 | 0.023 (3) | 0.017 (3) | 0.020 (3) | 0.0003 (16) | 0.001 (3) | 0.0005 (17) |
C8 | 0.022 (3) | 0.023 (3) | 0.019 (3) | −0.0022 (17) | 0.002 (3) | −0.0016 (19) |
C9 | 0.027 (4) | 0.033 (4) | 0.027 (3) | 0.000 (2) | 0.009 (3) | −0.002 (2) |
C10 | 0.040 (4) | 0.030 (4) | 0.009 (3) | −0.0001 (19) | 0.011 (3) | −0.0039 (18) |
C11 | 0.049 (4) | 0.021 (3) | 0.017 (3) | −0.004 (2) | −0.008 (3) | 0.0003 (18) |
C12 | 0.032 (4) | 0.021 (3) | 0.038 (4) | −0.002 (2) | −0.006 (3) | 0.003 (2) |
C13 | 0.023 (3) | 0.021 (3) | 0.023 (3) | −0.0007 (17) | 0.001 (3) | 0.0031 (19) |
C14 | 0.022 (3) | 0.027 (3) | 0.038 (4) | −0.003 (2) | −0.005 (3) | −0.005 (2) |
C15 | 0.022 (3) | 0.016 (3) | 0.029 (3) | −0.0018 (16) | 0.000 (3) | −0.0004 (18) |
C16 | 0.013 (3) | 0.038 (4) | 0.033 (4) | −0.0003 (19) | 0.006 (3) | −0.001 (2) |
C17 | 0.025 (3) | 0.036 (3) | 0.049 (4) | 0.002 (2) | 0.010 (3) | −0.004 (3) |
C18 | 0.033 (3) | 0.037 (3) | 0.033 (3) | 0.004 (2) | 0.002 (2) | 0.006 (3) |
C19 | 0.022 (3) | 0.036 (3) | 0.042 (4) | 0.003 (2) | 0.005 (3) | 0.000 (3) |
C20 | 0.034 (3) | 0.043 (3) | 0.026 (3) | 0.006 (2) | −0.004 (2) | 0.001 (2) |
C21 | 0.028 (3) | 0.036 (3) | 0.028 (3) | 0.005 (2) | 0.002 (2) | −0.003 (2) |
C22 | 0.023 (3) | 0.047 (4) | 0.016 (3) | 0.002 (2) | −0.001 (3) | −0.003 (2) |
C23 | 0.034 (3) | 0.042 (3) | 0.022 (2) | 0.007 (2) | 0.000 (2) | −0.008 (2) |
C24 | 0.033 (3) | 0.041 (3) | 0.024 (3) | −0.003 (2) | −0.005 (3) | 0.001 (3) |
O13 | 0.038 (2) | 0.050 (2) | 0.040 (2) | −0.0024 (18) | 0.0054 (18) | −0.0099 (19) |
O14 | 0.043 (2) | 0.065 (3) | 0.032 (2) | −0.015 (2) | 0.0007 (18) | 0.003 (2) |
O15 | 0.042 (3) | 0.043 (3) | 0.045 (3) | −0.0042 (17) | −0.003 (3) | −0.0003 (18) |
O16 | 0.034 (3) | 0.043 (3) | 0.049 (3) | −0.0022 (16) | 0.003 (3) | −0.0047 (18) |
Geometric parameters (Å, º) top
O1—N1 | 1.218 (9) | C7—C8 | 1.530 (9) |
O2—N1 | 1.212 (9) | C9—C10 | 1.385 (11) |
O3—C8 | 1.246 (6) | C9—C15 | 1.408 (10) |
O4—C8 | 1.237 (6) | C10—C11 | 1.332 (9) |
O5—C6 | 1.216 (9) | C10—H10 | 0.9300 |
O6—C6 | 1.248 (7) | C11—C12 | 1.372 (11) |
O7—N2 | 1.209 (8) | C11—H11 | 0.9300 |
O8—N2 | 1.209 (8) | C12—C13 | 1.400 (11) |
O9—C16 | 1.258 (7) | C12—H12 | 0.9300 |
O10—C16 | 1.252 (7) | C13—C15 | 1.398 (9) |
O11—C14 | 1.278 (9) | C13—C14 | 1.526 (10) |
O12—C14 | 1.240 (7) | C15—C16 | 1.521 (10) |
N1—C1 | 1.466 (9) | C17—C18 | 1.515 (8) |
N2—C9 | 1.459 (10) | C17—H17A | 0.9700 |
N3—C20 | 1.490 (7) | C17—H17B | 0.9700 |
N3—C17 | 1.497 (9) | C18—H18A | 0.9700 |
N3—H3A | 0.9000 | C18—H18B | 0.9700 |
N3—H3B | 0.9000 | C19—C20 | 1.518 (8) |
N4—C19 | 1.463 (9) | C19—H19A | 0.9700 |
N4—C18 | 1.477 (7) | C19—H19B | 0.9700 |
N4—H4A | 0.9000 | C20—H20A | 0.9700 |
N4—H4B | 0.9000 | C20—H20B | 0.9700 |
N5—C21 | 1.480 (7) | C21—C22 | 1.494 (8) |
N5—C24 | 1.485 (8) | C21—H21A | 0.9700 |
N5—H5A | 0.9000 | C21—H21B | 0.9700 |
N5—H5B | 0.9000 | C22—H22A | 0.9700 |
N6—C22 | 1.487 (8) | C22—H22B | 0.9700 |
N6—C23 | 1.494 (7) | C23—C24 | 1.478 (8) |
N6—H6A | 0.9000 | C23—H23A | 0.9700 |
N6—H6B | 0.9000 | C23—H23B | 0.9700 |
C1—C2 | 1.380 (11) | C24—H24A | 0.9700 |
C1—C7 | 1.388 (10) | C24—H24B | 0.9700 |
C2—C3 | 1.397 (10) | O13—H13A | 0.8501 |
C2—H2 | 0.9300 | O13—H13B | 0.8507 |
C3—C4 | 1.398 (11) | O14—H14A | 0.8500 |
C3—H3 | 0.9300 | O14—H14B | 0.8500 |
C4—C5 | 1.379 (10) | O15—H15A | 0.8524 |
C4—H4 | 0.9300 | O15—H15B | 0.8682 |
C5—C7 | 1.395 (9) | O16—H16A | 0.8505 |
C5—C6 | 1.500 (9) | O16—H16B | 0.8505 |
| | | |
O2—N1—O1 | 122.5 (7) | C13—C12—H12 | 120.2 |
O2—N1—C1 | 118.8 (6) | C15—C13—C12 | 121.5 (7) |
O1—N1—C1 | 118.7 (7) | C15—C13—C14 | 120.2 (6) |
O7—N2—O8 | 122.1 (7) | C12—C13—C14 | 118.3 (6) |
O7—N2—C9 | 117.7 (7) | O12—C14—O11 | 123.9 (7) |
O8—N2—C9 | 120.2 (6) | O12—C14—C13 | 117.2 (6) |
C20—N3—C17 | 112.1 (5) | O11—C14—C13 | 118.8 (5) |
C20—N3—H3A | 109.2 | C13—C15—C9 | 115.2 (7) |
C17—N3—H3A | 109.2 | C13—C15—C16 | 122.3 (6) |
C20—N3—H3B | 109.2 | C9—C15—C16 | 122.5 (6) |
C17—N3—H3B | 109.2 | O10—C16—O9 | 126.0 (7) |
H3A—N3—H3B | 107.9 | O10—C16—C15 | 117.8 (5) |
C19—N4—C18 | 111.0 (5) | O9—C16—C15 | 116.1 (5) |
C19—N4—H4A | 109.4 | N3—C17—C18 | 109.5 (5) |
C18—N4—H4A | 109.4 | N3—C17—H17A | 109.8 |
C19—N4—H4B | 109.4 | C18—C17—H17A | 109.8 |
C18—N4—H4B | 109.4 | N3—C17—H17B | 109.8 |
H4A—N4—H4B | 108.0 | C18—C17—H17B | 109.8 |
C21—N5—C24 | 110.2 (4) | H17A—C17—H17B | 108.2 |
C21—N5—H5A | 109.6 | N4—C18—C17 | 110.5 (5) |
C24—N5—H5A | 109.6 | N4—C18—H18A | 109.5 |
C21—N5—H5B | 109.6 | C17—C18—H18A | 109.5 |
C24—N5—H5B | 109.6 | N4—C18—H18B | 109.5 |
H5A—N5—H5B | 108.1 | C17—C18—H18B | 109.5 |
C22—N6—C23 | 110.8 (4) | H18A—C18—H18B | 108.1 |
C22—N6—H6A | 109.5 | N4—C19—C20 | 109.6 (5) |
C23—N6—H6A | 109.5 | N4—C19—H19A | 109.7 |
C22—N6—H6B | 109.5 | C20—C19—H19A | 109.7 |
C23—N6—H6B | 109.5 | N4—C19—H19B | 109.7 |
H6A—N6—H6B | 108.1 | C20—C19—H19B | 109.7 |
C2—C1—C7 | 123.5 (7) | H19A—C19—H19B | 108.2 |
C2—C1—N1 | 115.5 (7) | N3—C20—C19 | 110.1 (5) |
C7—C1—N1 | 121.0 (7) | N3—C20—H20A | 109.6 |
C1—C2—C3 | 118.6 (8) | C19—C20—H20A | 109.6 |
C1—C2—H2 | 120.7 | N3—C20—H20B | 109.6 |
C3—C2—H2 | 120.7 | C19—C20—H20B | 109.6 |
C2—C3—C4 | 118.4 (8) | H20A—C20—H20B | 108.2 |
C2—C3—H3 | 120.8 | N5—C21—C22 | 111.7 (5) |
C4—C3—H3 | 120.8 | N5—C21—H21A | 109.3 |
C5—C4—C3 | 122.1 (6) | C22—C21—H21A | 109.3 |
C5—C4—H4 | 118.9 | N5—C21—H21B | 109.3 |
C3—C4—H4 | 118.9 | C22—C21—H21B | 109.3 |
C4—C5—C7 | 119.8 (7) | H21A—C21—H21B | 107.9 |
C4—C5—C6 | 117.7 (6) | N6—C22—C21 | 109.8 (5) |
C7—C5—C6 | 122.5 (6) | N6—C22—H22A | 109.7 |
O5—C6—O6 | 126.9 (6) | C21—C22—H22A | 109.7 |
O5—C6—C5 | 117.4 (5) | N6—C22—H22B | 109.7 |
O6—C6—C5 | 115.5 (6) | C21—C22—H22B | 109.7 |
C1—C7—C5 | 117.5 (6) | H22A—C22—H22B | 108.2 |
C1—C7—C8 | 120.6 (6) | C24—C23—N6 | 109.0 (5) |
C5—C7—C8 | 121.9 (6) | C24—C23—H23A | 109.9 |
O4—C8—O3 | 126.9 (6) | N6—C23—H23A | 109.9 |
O4—C8—C7 | 117.0 (4) | C24—C23—H23B | 109.9 |
O3—C8—C7 | 116.0 (4) | N6—C23—H23B | 109.9 |
C10—C9—C15 | 122.8 (7) | H23A—C23—H23B | 108.3 |
C10—C9—N2 | 118.6 (6) | C23—C24—N5 | 112.3 (5) |
C15—C9—N2 | 118.6 (7) | C23—C24—H24A | 109.1 |
C11—C10—C9 | 119.8 (6) | N5—C24—H24A | 109.1 |
C11—C10—H10 | 120.1 | C23—C24—H24B | 109.1 |
C9—C10—H10 | 120.1 | N5—C24—H24B | 109.1 |
C10—C11—C12 | 121.1 (7) | H24A—C24—H24B | 107.9 |
C10—C11—H11 | 119.5 | H13A—O13—H13B | 110.8 |
C12—C11—H11 | 119.5 | H14A—O14—H14B | 111.1 |
C11—C12—C13 | 119.7 (7) | H15A—O15—H15B | 110.9 |
C11—C12—H12 | 120.2 | H16A—O16—H16B | 110.3 |
| | | |
O2—N1—C1—C2 | 156.9 (6) | C9—C10—C11—C12 | 1.1 (8) |
O1—N1—C1—C2 | −23.9 (8) | C10—C11—C12—C13 | −1.6 (7) |
O2—N1—C1—C7 | −21.6 (8) | C11—C12—C13—C15 | 0.6 (7) |
O1—N1—C1—C7 | 157.6 (6) | C11—C12—C13—C14 | −177.7 (4) |
C7—C1—C2—C3 | 1.7 (7) | C15—C13—C14—O12 | 157.2 (5) |
N1—C1—C2—C3 | −176.8 (4) | C12—C13—C14—O12 | −24.5 (7) |
C1—C2—C3—C4 | −0.3 (8) | C15—C13—C14—O11 | −26.0 (7) |
C2—C3—C4—C5 | −1.1 (8) | C12—C13—C14—O11 | 152.3 (5) |
C3—C4—C5—C7 | 1.2 (8) | C12—C13—C15—C9 | 0.8 (7) |
C3—C4—C5—C6 | −176.6 (5) | C14—C13—C15—C9 | 179.1 (4) |
C4—C5—C6—O5 | 149.7 (6) | C12—C13—C15—C16 | −177.3 (4) |
C7—C5—C6—O5 | −28.0 (7) | C14—C13—C15—C16 | 1.0 (7) |
C4—C5—C6—O6 | −25.6 (7) | C10—C9—C15—C13 | −1.4 (7) |
C7—C5—C6—O6 | 156.6 (5) | N2—C9—C15—C13 | 176.2 (4) |
C2—C1—C7—C5 | −1.6 (7) | C10—C9—C15—C16 | 176.7 (5) |
N1—C1—C7—C5 | 176.8 (4) | N2—C9—C15—C16 | −5.7 (7) |
C2—C1—C7—C8 | 177.5 (4) | C13—C15—C16—O10 | −79.0 (7) |
N1—C1—C7—C8 | −4.1 (6) | C9—C15—C16—O10 | 103.0 (6) |
C4—C5—C7—C1 | 0.1 (7) | C13—C15—C16—O9 | 104.4 (6) |
C6—C5—C7—C1 | 177.8 (4) | C9—C15—C16—O9 | −73.6 (7) |
C4—C5—C7—C8 | −179.0 (5) | C20—N3—C17—C18 | 54.8 (7) |
C6—C5—C7—C8 | −1.2 (7) | C19—N4—C18—C17 | 60.2 (6) |
C1—C7—C8—O4 | 103.8 (6) | N3—C17—C18—N4 | −56.0 (7) |
C5—C7—C8—O4 | −77.1 (7) | C18—N4—C19—C20 | −60.3 (7) |
C1—C7—C8—O3 | −76.2 (6) | C17—N3—C20—C19 | −55.7 (6) |
C5—C7—C8—O3 | 102.9 (6) | N4—C19—C20—N3 | 57.5 (7) |
O7—N2—C9—C10 | −24.5 (8) | C24—N5—C21—C22 | 55.0 (6) |
O8—N2—C9—C10 | 155.7 (6) | C23—N6—C22—C21 | 58.1 (6) |
O7—N2—C9—C15 | 157.8 (6) | N5—C21—C22—N6 | −56.4 (6) |
O8—N2—C9—C15 | −22.0 (8) | C22—N6—C23—C24 | −58.6 (6) |
C15—C9—C10—C11 | 0.5 (8) | N6—C23—C24—N5 | 57.8 (7) |
N2—C9—C10—C11 | −177.1 (5) | C21—N5—C24—C23 | −56.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.90 | 1.92 | 2.765 (6) | 156 |
N3—H3B···O6 | 0.90 | 1.77 | 2.648 (6) | 166 |
N4—H4A···O5ii | 0.90 | 1.92 | 2.799 (6) | 164 |
N4—H4B···O13ii | 0.90 | 1.83 | 2.730 (6) | 175 |
N5—H5A···O12iii | 0.90 | 1.79 | 2.664 (6) | 165 |
N5—H5B···O9 | 0.90 | 1.89 | 2.760 (6) | 161 |
N6—H6B···O11iv | 0.90 | 1.92 | 2.793 (6) | 164 |
N6—H6A···O14ii | 0.90 | 1.81 | 2.708 (6) | 172 |
O13—H13A···O4i | 0.85 | 1.89 | 2.729 (6) | 167 |
O13—H13B···O11 | 0.85 | 1.96 | 2.792 (6) | 166 |
O14—H14A···O5 | 0.85 | 1.89 | 2.714 (6) | 164 |
O14—H14B···O10 | 0.85 | 1.86 | 2.707 (6) | 173 |
O15—H15A···O4 | 0.85 | 2.04 | 2.858 (6) | 161 |
O15—H15B···O3ii | 0.87 | 2.47 | 3.036 (6) | 124 |
O15—H15B···O5ii | 0.87 | 2.53 | 2.997 (7) | 115 |
O16—H16A···O9 | 0.85 | 2.18 | 3.007 (6) | 166 |
O16—H16B···O10ii | 0.85 | 2.03 | 2.861 (6) | 167 |
Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x, y−1, z; (iii) x+1/2, −y+3/2, z; (iv) x+1/2, −y+1/2, z. |