Bis(propane-1,3-diaminium) benzene-1,2,4,5-tetra­carboxyl­ate dihydrate

The title salt, (PnH₂)₂(Btc)·2H₂O or 2C₃H₁₂N₂²⁺·C₁₀H₂O₈⁴⁻·2H₂O, has been prepared from propane-1,3-diamine (Pn) and benzene-1,2,4,5-tetra­carboxylic acid (BtcH₄). A wide range of noncovalent inter­actions, consisting of ion pairing and hydrogen bonding with D...A distances ranging from 2.7075 (15) to 2.9726 (15) Å, connect the various components into a supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.068
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H12 N2

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           30.00
           From the CIF: _reflns_number_total               2912
           Count of symmetry unique reflns         2935
           Completeness (_total/calc)             99.22%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(propane-1,3-diaminium) benzene-1,2,4,5-tetracarboxylate dihydrate

Crystal data

2C3H12N2^2+·C10H2O8^4^−·2H2O	F(000) = 468
Mr = 438.44	Dx = 1.490 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7787 reflections
a = 6.9869 (3) Å	θ = 2.7–34.8°
b = 18.3967 (8) Å	µ = 0.12 mm^−1
c = 8.2995 (4) Å	T = 100 K
β = 113.617 (1)°	Prism, colourless
V = 977.43 (8) Å^3	0.5 × 0.4 × 0.3 mm
Z = 2

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 30.0°, θmin = 2.2°
φ and ω scans	h = −9→9
10346 measured reflections	k = −25→25
2912 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: difference Fourier map
wR(F^2) = 0.068	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.1032P] where P = (Fo^2 + 2Fc^2)/3
2912 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.39 e Å^−3
1 restraint	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.40517 (15)	0.10119 (6)	0.14831 (13)	0.01387 (19)
O2	−0.22221 (16)	0.08956 (6)	0.43809 (12)	0.01510 (19)
O3	0.10266 (15)	0.01130 (5)	0.32543 (12)	0.01085 (17)
O4	0.30996 (16)	0.05365 (6)	0.58972 (12)	0.01384 (19)
O5	0.58886 (15)	0.30122 (6)	0.42084 (13)	0.01346 (19)
O6	0.41102 (16)	0.32217 (6)	0.13316 (12)	0.01394 (19)
O7	−0.12977 (16)	0.35582 (5)	−0.04316 (13)	0.0151 (2)
O8	0.07224 (14)	0.40236 (5)	0.21825 (12)	0.01124 (18)
C1	−0.11969 (19)	0.23006 (7)	0.19794 (16)	0.0086 (2)
H1A	−0.2602	0.2462	0.1417	0.010*
C2	−0.07765 (18)	0.16244 (7)	0.28105 (15)	0.0078 (2)
C3	0.13020 (18)	0.13896 (7)	0.36272 (15)	0.0081 (2)
C4	0.29284 (19)	0.18337 (7)	0.36406 (16)	0.0085 (2)
H4A	0.4334	0.1675	0.4220	0.010*
C5	0.24993 (18)	0.25101 (7)	0.28055 (15)	0.0078 (2)
C6	0.04190 (19)	0.27452 (7)	0.19615 (15)	0.0078 (2)
C7	−0.24864 (19)	0.11439 (7)	0.29165 (16)	0.0090 (2)
C8	0.18251 (19)	0.06292 (7)	0.43431 (16)	0.0088 (2)
C9	0.42988 (18)	0.29563 (7)	0.27721 (16)	0.0088 (2)
C10	−0.00862 (19)	0.34974 (7)	0.11534 (17)	0.0091 (2)
N1	1.57084 (16)	0.47009 (6)	0.77952 (14)	0.0110 (2)
H1NA	1.6686	0.4810	0.7384	0.013*
H1NB	1.5100	0.5100	0.8004	0.013*
H1NC	1.6432	0.4420	0.8730	0.013*
N2	0.93424 (16)	0.38537 (6)	0.49159 (14)	0.01003 (19)
H2NA	0.9063	0.4278	0.5315	0.012*
H2NB	0.8136	0.3604	0.4434	0.012*
H2NC	0.9652	0.3969	0.3994	0.012*
C11	1.28022 (19)	0.38875 (7)	0.74731 (16)	0.0104 (2)
H11A	1.2264	0.4271	0.8019	0.013*
H11B	1.3781	0.3582	0.8432	0.013*
C12	1.3998 (2)	0.42471 (7)	0.65116 (16)	0.0108 (2)
H12A	1.4598	0.3872	0.5995	0.013*
H12B	1.3046	0.4556	0.5547	0.013*
C13	1.09837 (19)	0.34181 (7)	0.63121 (16)	0.0111 (2)
H13A	1.1507	0.3036	0.5752	0.013*
H13B	1.0357	0.3175	0.7049	0.013*
N3	1.35003 (17)	0.16265 (6)	0.83077 (15)	0.0120 (2)
H3NA	1.3925	0.2045	0.7996	0.014*
H3NB	1.3471	0.1317	0.7458	0.014*
H3NC	1.4468	0.1482	0.9353	0.014*
N4	0.83810 (17)	0.01779 (6)	0.94997 (14)	0.01014 (19)
H4NA	0.7046	0.0087	0.9323	0.012*
H4NB	0.8762	−0.0191	0.8981	0.012*
H4NC	0.9234	0.0195	1.0649	0.012*
C14	1.0874 (2)	0.09565 (7)	0.89472 (18)	0.0118 (2)
H14A	1.1298	0.0545	0.8395	0.014*
H14B	1.1731	0.0937	1.0228	0.014*
C15	1.1324 (2)	0.16650 (7)	0.82213 (17)	0.0120 (2)
H15A	1.0316	0.1733	0.6989	0.014*
H15B	1.1189	0.2081	0.8927	0.014*
C16	0.85895 (19)	0.08663 (7)	0.86286 (16)	0.0106 (2)
H16A	0.8119	0.1285	0.9126	0.013*
H16B	0.7718	0.0843	0.7351	0.013*
O1W	0.43506 (15)	−0.04266 (5)	0.86545 (12)	0.01299 (19)
H1WA	0.4692	−0.0864	0.8571	0.016*
H1WB	0.3940	−0.0271	0.7605	0.016*
O2W	0.61356 (16)	0.25166 (6)	0.74503 (13)	0.01586 (19)
H2WA	0.7021	0.2813	0.8136	0.019*
H2WB	0.6053	0.2615	0.6424	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0107 (4)	0.0150 (5)	0.0126 (4)	−0.0041 (3)	0.0011 (3)	0.0027 (4)
O2	0.0168 (4)	0.0179 (5)	0.0114 (4)	−0.0053 (4)	0.0064 (3)	0.0013 (4)
O3	0.0135 (4)	0.0073 (4)	0.0120 (4)	−0.0008 (3)	0.0054 (3)	−0.0011 (3)
O4	0.0157 (4)	0.0107 (4)	0.0114 (4)	0.0014 (3)	0.0014 (3)	0.0023 (3)
O5	0.0112 (4)	0.0163 (5)	0.0115 (4)	−0.0052 (3)	0.0031 (3)	0.0000 (3)
O6	0.0143 (4)	0.0158 (5)	0.0119 (4)	−0.0034 (3)	0.0056 (3)	0.0027 (3)
O7	0.0177 (5)	0.0113 (4)	0.0106 (4)	−0.0010 (3)	−0.0001 (4)	0.0017 (3)
O8	0.0152 (4)	0.0079 (4)	0.0115 (4)	−0.0019 (3)	0.0062 (3)	−0.0003 (3)
C1	0.0084 (5)	0.0090 (5)	0.0081 (5)	−0.0001 (4)	0.0029 (4)	−0.0001 (4)
C2	0.0082 (5)	0.0078 (5)	0.0074 (5)	−0.0012 (4)	0.0030 (4)	−0.0009 (4)
C3	0.0094 (5)	0.0067 (5)	0.0075 (5)	−0.0006 (4)	0.0028 (4)	−0.0004 (4)
C4	0.0084 (5)	0.0075 (5)	0.0089 (5)	−0.0001 (4)	0.0029 (4)	0.0001 (4)
C5	0.0092 (5)	0.0069 (5)	0.0079 (4)	−0.0020 (4)	0.0041 (4)	−0.0007 (4)
C6	0.0103 (5)	0.0061 (5)	0.0065 (4)	−0.0003 (4)	0.0029 (4)	−0.0004 (4)
C7	0.0091 (5)	0.0071 (5)	0.0119 (5)	−0.0005 (4)	0.0053 (4)	−0.0004 (4)
C8	0.0085 (5)	0.0085 (5)	0.0107 (5)	0.0007 (4)	0.0053 (4)	0.0013 (4)
C9	0.0085 (5)	0.0068 (5)	0.0122 (5)	−0.0006 (4)	0.0052 (4)	−0.0005 (4)
C10	0.0097 (5)	0.0071 (5)	0.0114 (5)	−0.0004 (4)	0.0052 (4)	0.0011 (4)
N1	0.0095 (4)	0.0113 (5)	0.0115 (5)	0.0000 (4)	0.0035 (4)	0.0008 (4)
N2	0.0094 (4)	0.0094 (5)	0.0105 (4)	−0.0009 (3)	0.0032 (4)	−0.0005 (4)
C11	0.0105 (5)	0.0114 (5)	0.0093 (5)	−0.0009 (4)	0.0039 (4)	−0.0011 (4)
C12	0.0120 (5)	0.0104 (5)	0.0095 (5)	−0.0008 (4)	0.0040 (4)	−0.0011 (4)
C13	0.0115 (5)	0.0091 (5)	0.0110 (5)	−0.0001 (4)	0.0027 (4)	0.0012 (4)
N3	0.0123 (5)	0.0124 (5)	0.0106 (4)	−0.0028 (4)	0.0037 (4)	0.0011 (4)
N4	0.0116 (4)	0.0088 (5)	0.0109 (4)	0.0002 (4)	0.0055 (4)	0.0000 (4)
C14	0.0108 (5)	0.0102 (5)	0.0156 (5)	0.0003 (4)	0.0065 (4)	0.0024 (4)
C15	0.0119 (5)	0.0106 (5)	0.0138 (5)	−0.0001 (4)	0.0054 (4)	0.0016 (4)
C16	0.0113 (5)	0.0096 (5)	0.0113 (5)	0.0003 (4)	0.0049 (4)	0.0014 (4)
O1W	0.0155 (4)	0.0108 (4)	0.0116 (4)	0.0023 (3)	0.0043 (3)	0.0008 (3)
O2W	0.0193 (4)	0.0156 (5)	0.0124 (4)	−0.0064 (4)	0.0060 (4)	−0.0004 (4)

Geometric parameters (Å, º)

O1—C7	1.2759 (15)	C11—C12	1.5189 (18)
O2—C7	1.2411 (16)	C11—C13	1.5191 (17)
O3—C8	1.2750 (15)	C11—H11A	0.9900
O4—C8	1.2512 (15)	C11—H11B	0.9900
O5—C9	1.2666 (15)	C12—H12A	0.9900
O6—C9	1.2486 (15)	C12—H12B	0.9900
O7—C10	1.2520 (15)	C13—H13A	0.9900
O8—C10	1.2646 (15)	C13—H13B	0.9900
C1—C2	1.3954 (17)	N3—C15	1.4953 (17)
C1—C6	1.3990 (17)	N3—H3NA	0.9000
C1—H1A	0.9500	N3—H3NB	0.9001
C2—C3	1.4023 (16)	N3—H3NC	0.9000
C2—C7	1.5167 (17)	N4—C16	1.4939 (16)
C3—C4	1.3961 (17)	N4—H4NA	0.9000
C3—C8	1.5065 (17)	N4—H4NB	0.9000
C4—C5	1.3971 (17)	N4—H4NC	0.9000
C4—H4A	0.9500	C14—C16	1.5186 (17)
C5—C6	1.4052 (16)	C14—C15	1.5208 (18)
C5—C9	1.5110 (16)	C14—H14A	0.9900
C6—C10	1.5164 (17)	C14—H14B	0.9900
N1—C12	1.4965 (17)	C15—H15A	0.9900
N1—H1NA	0.9000	C15—H15B	0.9900
N1—H1NB	0.9001	C16—H16A	0.9900
N1—H1NC	0.9000	C16—H16B	0.9900
N2—C13	1.4951 (16)	O1W—H1WA	0.8500
N2—H2NA	0.9000	O1W—H1WB	0.8500
N2—H2NB	0.9000	O2W—H2WA	0.8501
N2—H2NC	0.9000	O2W—H2WB	0.8500
C2—C1—C6	121.03 (11)	C13—C11—H11B	108.7
C2—C1—H1A	119.5	H11A—C11—H11B	107.6
C6—C1—H1A	119.5	N1—C12—C11	108.62 (10)
C1—C2—C3	119.06 (11)	N1—C12—H12A	110.0
C1—C2—C7	122.24 (11)	C11—C12—H12A	110.0
C3—C2—C7	118.67 (11)	N1—C12—H12B	110.0
C4—C3—C2	120.37 (11)	C11—C12—H12B	110.0
C4—C3—C8	118.18 (10)	H12A—C12—H12B	108.3
C2—C3—C8	121.15 (11)	N2—C13—C11	111.95 (10)
C3—C4—C5	120.34 (11)	N2—C13—H13A	109.2
C3—C4—H4A	119.8	C11—C13—H13A	109.2
C5—C4—H4A	119.8	N2—C13—H13B	109.2
C4—C5—C6	119.67 (11)	C11—C13—H13B	109.2
C4—C5—C9	118.56 (11)	H13A—C13—H13B	107.9
C6—C5—C9	121.72 (11)	C15—N3—H3NA	113.1
C1—C6—C5	119.52 (11)	C15—N3—H3NB	106.8
C1—C6—C10	119.49 (11)	H3NA—N3—H3NB	102.8
C5—C6—C10	120.82 (11)	C15—N3—H3NC	114.6
O2—C7—O1	125.36 (12)	H3NA—N3—H3NC	108.8
O2—C7—C2	117.37 (11)	H3NB—N3—H3NC	110.0
O1—C7—C2	117.24 (11)	C16—N4—H4NA	111.9
O4—C8—O3	123.90 (12)	C16—N4—H4NB	107.7
O4—C8—C3	119.54 (11)	H4NA—N4—H4NB	105.6
O3—C8—C3	116.36 (10)	C16—N4—H4NC	109.4
O6—C9—O5	125.85 (12)	H4NA—N4—H4NC	112.5
O6—C9—C5	117.43 (11)	H4NB—N4—H4NC	109.6
O5—C9—C5	116.70 (11)	C16—C14—C15	113.22 (10)
O7—C10—O8	124.91 (12)	C16—C14—H14A	108.9
O7—C10—C6	119.07 (11)	C15—C14—H14A	108.9
O8—C10—C6	115.98 (10)	C16—C14—H14B	108.9
C12—N1—H1NA	111.4	C15—C14—H14B	108.9
C12—N1—H1NB	106.8	H14A—C14—H14B	107.7
H1NA—N1—H1NB	112.3	N3—C15—C14	107.94 (10)
C12—N1—H1NC	107.8	N3—C15—H15A	110.1
H1NA—N1—H1NC	101.8	C14—C15—H15A	110.1
H1NB—N1—H1NC	116.6	N3—C15—H15B	110.1
C13—N2—H2NA	113.1	C14—C15—H15B	110.1
C13—N2—H2NB	111.2	H15A—C15—H15B	108.4
H2NA—N2—H2NB	107.7	N4—C16—C14	107.92 (10)
C13—N2—H2NC	114.5	N4—C16—H16A	110.1
H2NA—N2—H2NC	105.6	C14—C16—H16A	110.1
H2NB—N2—H2NC	104.1	N4—C16—H16B	110.1
C12—C11—C13	114.25 (10)	C14—C16—H16B	110.1
C12—C11—H11A	108.7	H16A—C16—H16B	108.4
C13—C11—H11A	108.7	H1WA—O1W—H1WB	103.0
C12—C11—H11B	108.7	H2WA—O2W—H2WB	105.9
C6—C1—C2—C3	−0.41 (17)	C1—C2—C7—O1	51.56 (16)
C6—C1—C2—C7	177.45 (11)	C3—C2—C7—O1	−130.58 (13)
C1—C2—C3—C4	1.40 (17)	C4—C3—C8—O4	58.37 (16)
C7—C2—C3—C4	−176.53 (11)	C2—C3—C8—O4	−127.84 (13)
C1—C2—C3—C8	−172.26 (11)	C4—C3—C8—O3	−116.76 (12)
C7—C2—C3—C8	9.81 (17)	C2—C3—C8—O3	57.03 (16)
C2—C3—C4—C5	−1.46 (18)	C4—C5—C9—O6	132.08 (13)
C8—C3—C4—C5	172.38 (11)	C6—C5—C9—O6	−45.29 (17)
C3—C4—C5—C6	0.51 (18)	C4—C5—C9—O5	−46.27 (16)
C3—C4—C5—C9	−176.91 (11)	C6—C5—C9—O5	136.36 (12)
C2—C1—C6—C5	−0.52 (17)	C1—C6—C10—O7	−59.63 (16)
C2—C1—C6—C10	−175.87 (11)	C5—C6—C10—O7	125.07 (13)
C4—C5—C6—C1	0.47 (17)	C1—C6—C10—O8	118.12 (13)
C9—C5—C6—C1	177.81 (11)	C5—C6—C10—O8	−57.17 (16)
C4—C5—C6—C10	175.76 (11)	C13—C11—C12—N1	178.94 (10)
C9—C5—C6—C10	−6.90 (17)	C12—C11—C13—N2	−63.19 (14)
C1—C2—C7—O2	−130.35 (13)	C16—C14—C15—N3	−169.42 (10)
C3—C2—C7—O2	47.52 (16)	C15—C14—C16—N4	−176.37 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O3^i	0.90	1.96	2.8512 (16)	173
N1—H1NB···O1^ii	0.90	1.94	2.8409 (16)	174
N1—H1NC···O7^iii	0.90	2.15	2.9145 (15)	142
N1—H1NC···O1W^iv	0.90	2.46	2.9726 (15)	117
N2—H2NA···O3^ii	0.90	1.96	2.8379 (15)	166
N2—H2NB···O5	0.90	1.86	2.7257 (16)	161
N2—H2NC···O8^v	0.90	1.93	2.8154 (15)	167
N3—H3NA···O2W^v	0.90	1.98	2.7618 (17)	145
N3—H3NB···O4^v	0.90	1.88	2.7664 (15)	167
N3—H3NC···O1^iii	0.90	1.86	2.7455 (15)	165
N4—H4NA···O1W	0.90	1.98	2.8418 (17)	161
N4—H4NB···O8^vi	0.90	1.85	2.7481 (15)	174
N4—H4NC···O3^vii	0.90	2.02	2.9200 (14)	173
O1W—H1WA···O6^vi	0.85	1.87	2.7075 (15)	170
O1W—H1WB···O4	0.85	1.97	2.7454 (14)	151
O2W—H2WA···O7^vii	0.85	1.89	2.7299 (15)	173
O2W—H2WB···O5	0.85	1.94	2.7800 (15)	170

Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) x+2, y, z+1; (iv) −x+2, y+1/2, −z+2; (v) x+1, y, z; (vi) −x+1, y−1/2, −z+1; (vii) x+1, y, z+1.