Piperazinediium 3-nitro­phthalate dihydrate

Guo, M.-L.

doi:10.1107/S1600536804014692

Piperazinediium 3-nitrophthalate dihydrate

The title salt, C₄H₁₂N₂²⁺·C₈H₃NO₆^2-·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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014692/lh6232sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014692/lh6232Isup2.hkl Contains datablock I

CCDC reference: 245327

checkCIF report

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

Computing details top

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
M_r = 333.30	D_x = 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	R_int = 0.062
φ and ω scans	θ_max = 26.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→18
T_min = 0.954, T_max = 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(F_o²) + (0.0991P)² + 0.5343P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.004
3053 reflections	Δρ_max = 0.48 e Å⁻³
415 parameters	Δρ_min = −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	U_iso*/U_eq
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···O11^iv	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.

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Piperazinediium 3-nitro­phthalate dihydrate

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Piperazinediium 3-nitrophthalate dihydrate