Three 4-(4-fluoro­phen­yl)piperazin-1-ium salts containing organic anions: supra­molecular assembly in one, two and three dimensions

Harish Chinthal, C.; Yathirajan, H.S.; Archana, S.D.; Foro, S.; Glidewell, C.

doi:10.1107/S2056989020006398

Three 4-(4-fluorophenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

C. Harish Chinthal, H. S. Yathirajan, S. D. Archana, S. Foro and C. Glidewell

Three salts containing the 4-(4-fluorophenyl)piperazin-1-ium cation have been prepared and structurally characterized.

Keywords: piperazines; piperazinium salts; crystal structure; molecular conformation; hydrogen bonding; supramolecular assembly.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020006398/wm5557sup1.cif Contains datablocks global, I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006398/wm5557Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006398/wm5557IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020006398/wm5557IIIsup4.hkl Contains datablock III
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020006398/wm5557Isup5.cml Supplementary material

CCDC references: 2003726; 2003725; 2003724

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.041
wR factor = 0.108
Data-to-parameter ratio = 14.4

Structure: II

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.033
wR factor = 0.089
Data-to-parameter ratio = 14.3

Structure: III

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.045
wR factor = 0.085
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        N33 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.400 Check

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        341 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O31      ..C32              3.01 Ang.
                                                1-x,1-y,2-z  =      3_667 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        272 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00482 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.425 Check
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         59 %

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT791_ALERT_4_G Model has Chirality at C32         (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C33         (Sohnke SpGr)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        152 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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 top

For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).

4-(4-Fluorophenyl)piperazin-1-ium 2-hydroxy-3,5-dinitrobenzoate (I) top

Crystal data top

C₁₀H₁₄FN₂⁺·C₇H₃N₂O₇⁻	F(000) = 848
M_r = 408.35	D_x = 1.504 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.6829 (6) Å	Cell parameters from 3905 reflections
b = 13.1701 (6) Å	θ = 2.6–27.8°
c = 13.5563 (7) Å	µ = 0.13 mm⁻¹
β = 108.970 (5)°	T = 293 K
V = 1803.71 (17) Å³	Block, yellow
Z = 4	0.50 × 0.44 × 0.34 mm

Data collection top

Oxford Diffraction Xcalibur with Sapphire CCD diffractometer	3905 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ω scans	θ_max = 27.8°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→8
T_min = 0.874, T_max = 0.958	k = −17→12
7194 measured reflections	l = −11→17

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0493P)² + 0.4487P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3905 reflections	Δρ_max = 0.29 e Å⁻³
271 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.23326 (15)	0.37624 (11)	0.56770 (10)	0.0410 (3)
H11	0.2339 (18)	0.3081 (15)	0.5648 (13)	0.049*
H12	0.1870 (18)	0.3961 (14)	0.6103 (14)	0.049*
C2	0.16795 (18)	0.41660 (13)	0.46103 (12)	0.0458 (4)
H2A	0.0754	0.3969	0.4369	0.055*
H2B	0.2098	0.3883	0.4135	0.055*
C3	0.17888 (16)	0.53003 (12)	0.46196 (13)	0.0446 (4)
H3A	0.1373	0.5561	0.3920	0.054*
H3B	0.1328	0.5583	0.5066	0.054*
N4	0.31711 (13)	0.56110 (10)	0.49976 (10)	0.0386 (3)
C5	0.38008 (18)	0.52566 (14)	0.60598 (13)	0.0507 (4)
H5A	0.3366	0.5558	0.6515	0.061*
H5B	0.4721	0.5466	0.6302	0.061*
C6	0.37196 (18)	0.41196 (14)	0.61064 (15)	0.0527 (4)
H6A	0.4238	0.3820	0.5712	0.063*
H6B	0.4093	0.3898	0.6825	0.063*
C21	0.34479 (15)	0.66117 (12)	0.47504 (12)	0.0369 (3)
C22	0.29655 (18)	0.69322 (13)	0.37175 (13)	0.0481 (4)
H22	0.2418	0.6502	0.3218	0.058*
C23	0.3279 (2)	0.78703 (14)	0.34172 (15)	0.0545 (5)
H23	0.2948	0.8074	0.2724	0.065*
C24	0.40826 (18)	0.84938 (13)	0.41541 (16)	0.0505 (4)
F24	0.44076 (13)	0.94182 (8)	0.38489 (10)	0.0748 (4)
C25	0.45600 (18)	0.82219 (13)	0.51707 (16)	0.0533 (5)
H25	0.5101	0.8664	0.5660	0.064*
C26	0.42392 (17)	0.72812 (13)	0.54787 (13)	0.0464 (4)
H26	0.4557	0.7097	0.6179	0.056*
C37	0.15341 (16)	0.07140 (13)	0.28960 (12)	0.0422 (4)
O31	0.11601 (13)	0.02065 (10)	0.21079 (8)	0.0549 (3)
O32	0.19930 (15)	0.16315 (11)	0.28736 (10)	0.0644 (4)
H32	0.224 (3)	0.1886 (19)	0.358 (2)	0.097*
C31	0.15560 (14)	0.03293 (11)	0.39367 (11)	0.0336 (3)
C32	0.21010 (14)	0.09577 (11)	0.48464 (11)	0.0328 (3)
O33	0.24279 (12)	0.18739 (8)	0.47606 (8)	0.0461 (3)
C33	0.22155 (15)	0.04718 (11)	0.58166 (11)	0.0346 (3)
C34	0.17610 (15)	−0.04917 (12)	0.58678 (12)	0.0384 (4)
H34	0.1844	−0.0782	0.6511	0.046*
C35	0.11827 (15)	−0.10288 (12)	0.49668 (12)	0.0379 (3)
C36	0.10914 (14)	−0.06281 (12)	0.39986 (12)	0.0365 (3)
H36	0.0717	−0.1008	0.3396	0.044*
N33	0.28212 (14)	0.09929 (11)	0.68062 (10)	0.0456 (3)
O34	0.33859 (15)	0.17925 (10)	0.68299 (10)	0.0654 (4)
O35	0.2769 (2)	0.05901 (14)	0.75965 (10)	0.0944 (6)
N35	0.06646 (15)	−0.20338 (11)	0.50384 (13)	0.0497 (4)
O36	0.09063 (16)	−0.24215 (11)	0.58996 (12)	0.0768 (5)
O37	−0.00086 (15)	−0.24444 (10)	0.42356 (12)	0.0668 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0566 (9)	0.0317 (7)	0.0400 (7)	−0.0031 (6)	0.0228 (6)	−0.0008 (6)
C2	0.0570 (10)	0.0409 (9)	0.0380 (8)	−0.0130 (8)	0.0132 (7)	−0.0001 (7)
C3	0.0416 (9)	0.0372 (9)	0.0506 (9)	−0.0068 (7)	0.0088 (7)	0.0042 (7)
N4	0.0405 (7)	0.0348 (7)	0.0378 (7)	−0.0064 (6)	0.0091 (5)	0.0011 (5)
C5	0.0513 (10)	0.0503 (10)	0.0426 (9)	−0.0115 (8)	0.0044 (8)	0.0038 (8)
C6	0.0504 (10)	0.0503 (11)	0.0544 (10)	0.0019 (8)	0.0131 (8)	0.0131 (9)
C21	0.0373 (8)	0.0338 (8)	0.0422 (8)	−0.0041 (6)	0.0166 (6)	−0.0040 (6)
C22	0.0613 (11)	0.0398 (9)	0.0434 (9)	−0.0120 (8)	0.0171 (8)	−0.0032 (7)
C23	0.0682 (12)	0.0464 (10)	0.0528 (10)	−0.0056 (9)	0.0251 (9)	0.0068 (8)
C24	0.0522 (10)	0.0331 (9)	0.0740 (13)	−0.0064 (8)	0.0313 (9)	0.0020 (8)
F24	0.0864 (9)	0.0408 (6)	0.1059 (10)	−0.0168 (6)	0.0432 (7)	0.0086 (6)
C25	0.0485 (10)	0.0404 (10)	0.0705 (12)	−0.0149 (8)	0.0187 (9)	−0.0135 (9)
C26	0.0464 (9)	0.0439 (10)	0.0466 (9)	−0.0088 (8)	0.0121 (7)	−0.0059 (7)
C37	0.0451 (9)	0.0506 (10)	0.0317 (8)	0.0017 (8)	0.0138 (7)	0.0028 (7)
O31	0.0654 (8)	0.0674 (8)	0.0314 (6)	−0.0048 (7)	0.0151 (5)	−0.0039 (6)
O32	0.1018 (11)	0.0559 (8)	0.0392 (7)	−0.0167 (8)	0.0279 (7)	0.0062 (6)
C31	0.0340 (7)	0.0384 (8)	0.0304 (7)	0.0037 (6)	0.0132 (6)	0.0013 (6)
C32	0.0346 (7)	0.0330 (8)	0.0337 (7)	0.0025 (6)	0.0152 (6)	0.0016 (6)
O33	0.0662 (8)	0.0337 (6)	0.0416 (6)	−0.0063 (5)	0.0219 (5)	0.0001 (5)
C33	0.0364 (8)	0.0376 (8)	0.0312 (7)	0.0025 (6)	0.0126 (6)	−0.0002 (6)
C34	0.0393 (8)	0.0419 (9)	0.0370 (8)	0.0051 (7)	0.0165 (7)	0.0095 (7)
C35	0.0362 (8)	0.0323 (8)	0.0476 (9)	0.0007 (6)	0.0169 (7)	0.0039 (7)
C36	0.0341 (8)	0.0374 (8)	0.0387 (8)	0.0005 (6)	0.0130 (6)	−0.0037 (6)
N33	0.0534 (8)	0.0503 (9)	0.0327 (7)	0.0013 (7)	0.0133 (6)	0.0002 (6)
O34	0.0900 (11)	0.0529 (8)	0.0464 (7)	−0.0153 (7)	0.0128 (7)	−0.0104 (6)
O35	0.1494 (17)	0.0992 (13)	0.0325 (7)	−0.0423 (11)	0.0265 (8)	0.0008 (7)
N35	0.0475 (8)	0.0385 (8)	0.0662 (10)	−0.0035 (6)	0.0228 (7)	0.0050 (7)
O36	0.0962 (11)	0.0551 (9)	0.0759 (10)	−0.0183 (8)	0.0235 (8)	0.0238 (8)
O37	0.0731 (9)	0.0487 (8)	0.0777 (10)	−0.0215 (7)	0.0232 (8)	−0.0112 (7)

Geometric parameters (Å, º) top

N1—C6	1.481 (2)	C24—F24	1.3664 (19)
N1—C2	1.485 (2)	C25—C26	1.386 (2)
N1—H11	0.898 (19)	C25—H25	0.9300
N1—H12	0.912 (19)	C26—H26	0.9300
C2—C3	1.498 (2)	C37—O31	1.2125 (19)
C2—H2A	0.9700	C37—O32	1.308 (2)
C2—H2B	0.9700	C37—C31	1.492 (2)
C3—N4	1.456 (2)	O32—H32	0.97 (3)
C3—H3A	0.9700	C31—C36	1.368 (2)
C3—H3B	0.9700	C31—C32	1.441 (2)
N4—C21	1.4147 (19)	C32—O33	1.2719 (18)
N4—C5	1.454 (2)	C32—C33	1.4318 (19)
C5—C6	1.502 (2)	C33—C34	1.368 (2)
C5—H5A	0.9700	C33—N33	1.4578 (19)
C5—H5B	0.9700	C34—C35	1.372 (2)
C6—H6A	0.9700	C34—H34	0.9300
C6—H6B	0.9700	C35—C36	1.388 (2)
C21—C26	1.387 (2)	C35—N35	1.450 (2)
C21—C22	1.391 (2)	C36—H36	0.9300
C22—C23	1.376 (2)	N33—O34	1.2089 (19)
C22—H22	0.9300	N33—O35	1.2129 (18)
C23—C24	1.361 (3)	N35—O37	1.2187 (19)
C23—H23	0.9300	N35—O36	1.2224 (19)
C24—C25	1.353 (3)

C6—N1—C2	111.24 (13)	C24—C23—H23	120.6
C6—N1—H11	108.3 (12)	C22—C23—H23	120.6
C2—N1—H11	108.8 (11)	C25—C24—C23	121.80 (16)
C6—N1—H12	109.8 (11)	C25—C24—F24	119.70 (17)
C2—N1—H12	109.5 (11)	C23—C24—F24	118.50 (17)
H11—N1—H12	109.1 (16)	C24—C25—C26	119.69 (16)
N1—C2—C3	109.76 (13)	C24—C25—H25	120.2
N1—C2—H2A	109.7	C26—C25—H25	120.2
C3—C2—H2A	109.7	C25—C26—C21	120.47 (16)
N1—C2—H2B	109.7	C25—C26—H26	119.8
C3—C2—H2B	109.7	C21—C26—H26	119.8
H2A—C2—H2B	108.2	O31—C37—O32	120.48 (15)
N4—C3—C2	110.53 (14)	O31—C37—C31	123.05 (16)
N4—C3—H3A	109.5	O32—C37—C31	116.42 (14)
C2—C3—H3A	109.5	C37—O32—H32	106.3 (15)
N4—C3—H3B	109.5	C36—C31—C32	122.05 (13)
C2—C3—H3B	109.5	C36—C31—C37	118.46 (13)
H3A—C3—H3B	108.1	C32—C31—C37	119.46 (13)
C21—N4—C5	117.95 (13)	O33—C32—C33	124.33 (13)
C21—N4—C3	116.41 (13)	O33—C32—C31	120.87 (13)
C5—N4—C3	110.38 (13)	C33—C32—C31	114.80 (13)
N4—C5—C6	110.31 (14)	C34—C33—C32	122.36 (13)
N4—C5—H5A	109.6	C34—C33—N33	116.65 (13)
C6—C5—H5A	109.6	C32—C33—N33	120.98 (13)
N4—C5—H5B	109.6	C33—C34—C35	119.82 (14)
C6—C5—H5B	109.6	C33—C34—H34	120.1
H5A—C5—H5B	108.1	C35—C34—H34	120.1
N1—C6—C5	111.34 (15)	C34—C35—C36	121.23 (14)
N1—C6—H6A	109.4	C34—C35—N35	118.82 (14)
C5—C6—H6A	109.4	C36—C35—N35	119.95 (14)
N1—C6—H6B	109.4	C31—C36—C35	119.54 (14)
C5—C6—H6B	109.4	C31—C36—H36	120.2
H6A—C6—H6B	108.0	C35—C36—H36	120.2
C26—C21—C22	117.66 (15)	O34—N33—O35	121.56 (15)
C26—C21—N4	123.34 (14)	O34—N33—C33	120.20 (13)
C22—C21—N4	118.92 (14)	O35—N33—C33	118.22 (15)
C23—C22—C21	121.61 (16)	O37—N35—O36	123.20 (15)
C23—C22—H22	119.2	O37—N35—C35	118.20 (15)
C21—C22—H22	119.2	O36—N35—C35	118.59 (15)
C24—C23—C22	118.74 (17)

C6—N1—C2—C3	−54.64 (19)	O32—C37—C31—C32	−1.7 (2)
N1—C2—C3—N4	58.34 (18)	C36—C31—C32—O33	−174.27 (14)
C2—C3—N4—C21	160.93 (13)	C37—C31—C32—O33	7.8 (2)
C2—C3—N4—C5	−61.10 (18)	C36—C31—C32—C33	4.9 (2)
C21—N4—C5—C6	−163.70 (14)	C37—C31—C32—C33	−173.01 (13)
C3—N4—C5—C6	59.05 (19)	O33—C32—C33—C34	175.03 (14)
C2—N1—C6—C5	53.7 (2)	C31—C32—C33—C34	−4.1 (2)
N4—C5—C6—N1	−55.5 (2)	O33—C32—C33—N33	−4.5 (2)
C5—N4—C21—C26	−2.9 (2)	C31—C32—C33—N33	176.36 (13)
C3—N4—C21—C26	131.79 (17)	C32—C33—C34—C35	0.6 (2)
C5—N4—C21—C22	173.56 (16)	N33—C33—C34—C35	−179.81 (14)
C3—N4—C21—C22	−51.7 (2)	C33—C34—C35—C36	2.4 (2)
C26—C21—C22—C23	1.3 (3)	C33—C34—C35—N35	−177.75 (14)
N4—C21—C22—C23	−175.35 (16)	C32—C31—C36—C35	−2.2 (2)
C21—C22—C23—C24	0.1 (3)	C37—C31—C36—C35	175.71 (14)
C22—C23—C24—C25	−1.1 (3)	C34—C35—C36—C31	−1.6 (2)
C22—C23—C24—F24	178.99 (16)	N35—C35—C36—C31	178.55 (14)
C23—C24—C25—C26	0.6 (3)	C34—C33—N33—O34	171.04 (15)
F24—C24—C25—C26	−179.47 (16)	C32—C33—N33—O34	−9.4 (2)
C24—C25—C26—C21	0.9 (3)	C34—C33—N33—O35	−7.2 (2)
C22—C21—C26—C25	−1.8 (2)	C32—C33—N33—O35	172.40 (16)
N4—C21—C26—C25	174.71 (15)	C34—C35—N35—O37	169.81 (15)
O31—C37—C31—C36	−2.3 (2)	C36—C35—N35—O37	−10.4 (2)
O32—C37—C31—C36	−179.71 (15)	C34—C35—N35—O36	−9.1 (2)
O31—C37—C31—C32	175.74 (15)	C36—C35—N35—O36	170.72 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O33	0.90 (2)	2.014 (19)	2.7968 (18)	144.8 (15)
N1—H11···O34	0.90 (2)	2.352 (19)	3.049 (2)	134.4 (14)
N1—H12···O31ⁱ	0.912 (19)	2.075 (19)	2.959 (2)	163.0 (17)
N1—H12···O32ⁱ	0.912 (19)	2.487 (18)	3.1576 (19)	130.7 (15)
O32—H32···O33	0.97 (3)	1.55 (3)	2.4676 (17)	157 (3)
C2—H2B···O35ⁱⁱ	0.97	2.51	3.313 (2)	140

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

4-(4-Fluorophenyl)piperazin-1-ium hydrogen oxalate (II) top

Crystal data top

C₁₀H₁₄FN₂⁺·C₂HO₄⁻	F(000) = 568
M_r = 270.26	D_x = 1.483 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.0606 (6) Å	Cell parameters from 2596 reflections
b = 5.7820 (2) Å	θ = 3.3–27.8°
c = 12.5815 (5) Å	µ = 0.12 mm⁻¹
β = 102.761 (4)°	T = 293 K
V = 1210.44 (8) Å³	Block, colourless
Z = 4	0.34 × 0.34 × 0.28 mm

Data collection top

Oxford Diffraction Xcalibur with Sapphire CCD diffractometer	2596 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.009
ω scans	θ_max = 27.8°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→22
T_min = 0.877, T_max = 0.966	k = −7→5
4450 measured reflections	l = −16→9

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0443P)² + 0.346P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.32 e Å⁻³
2596 reflections	Δρ_min = −0.14 e Å⁻³
182 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0084 (12)
Primary atom site location: difference Fourier map

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.34076 (6)	0.76074 (19)	0.62909 (9)	0.0310 (2)
H11	0.3629 (9)	0.731 (3)	0.7011 (13)	0.037*
H12	0.3813 (9)	0.831 (3)	0.6035 (12)	0.037*
C2	0.27227 (7)	0.9240 (2)	0.62039 (10)	0.0316 (3)
H2A	0.2911	1.0681	0.6566	0.038*
H2B	0.2324	0.8584	0.6559	0.038*
C3	0.23469 (8)	0.9699 (2)	0.50098 (10)	0.0324 (3)
H3A	0.1896	1.0749	0.4950	0.039*
H3B	0.2739	1.0411	0.4660	0.039*
N4	0.20732 (6)	0.75101 (17)	0.44718 (8)	0.0268 (2)
C5	0.27693 (7)	0.5982 (2)	0.45117 (10)	0.0319 (3)
H5A	0.3154	0.6735	0.4163	0.038*
H5B	0.2595	0.4561	0.4120	0.038*
C6	0.31618 (8)	0.5431 (2)	0.56812 (11)	0.0347 (3)
H6A	0.2788	0.4590	0.6017	0.042*
H6B	0.3629	0.4461	0.5705	0.042*
C21	0.15689 (7)	0.7661 (2)	0.34045 (9)	0.0276 (3)
C22	0.10736 (8)	0.5776 (2)	0.30382 (11)	0.0364 (3)
H22	0.1070	0.4520	0.3499	0.044*
C23	0.05858 (8)	0.5743 (3)	0.19977 (12)	0.0424 (3)
H23	0.0262	0.4472	0.1753	0.051*
C24	0.05932 (8)	0.7625 (3)	0.13391 (11)	0.0418 (3)
F24	0.01133 (7)	0.75923 (18)	0.03205 (7)	0.0688 (3)
C25	0.10587 (9)	0.9541 (3)	0.16709 (11)	0.0418 (3)
H25	0.1044	1.0806	0.1210	0.050*
C26	0.15542 (8)	0.9549 (2)	0.27143 (10)	0.0344 (3)
H26	0.1877	1.0826	0.2950	0.041*
C31	0.47968 (7)	0.58033 (19)	0.86963 (9)	0.0239 (2)
C32	0.43856 (7)	0.3385 (2)	0.84980 (9)	0.0258 (2)
O31	0.55249 (5)	0.58853 (15)	0.91087 (7)	0.0319 (2)
O32	0.43316 (5)	0.74960 (14)	0.84049 (7)	0.0315 (2)
O33	0.36759 (5)	0.31730 (17)	0.81152 (8)	0.0417 (2)
O34	0.48994 (5)	0.16802 (15)	0.87815 (7)	0.0320 (2)
H34	0.4648 (10)	0.029 (3)	0.8663 (13)	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0245 (5)	0.0331 (6)	0.0310 (5)	−0.0043 (4)	−0.0037 (4)	0.0048 (4)
C2	0.0321 (6)	0.0295 (6)	0.0305 (6)	−0.0019 (5)	0.0008 (5)	−0.0036 (5)
C3	0.0355 (6)	0.0246 (6)	0.0324 (6)	0.0032 (5)	−0.0025 (5)	−0.0014 (5)
N4	0.0250 (5)	0.0250 (5)	0.0273 (5)	0.0024 (4)	−0.0007 (4)	−0.0001 (4)
C5	0.0302 (6)	0.0289 (6)	0.0345 (6)	0.0046 (5)	0.0025 (5)	−0.0019 (5)
C6	0.0301 (6)	0.0278 (6)	0.0411 (7)	0.0033 (5)	−0.0032 (5)	0.0027 (5)
C21	0.0245 (5)	0.0300 (6)	0.0265 (6)	0.0042 (5)	0.0019 (4)	−0.0010 (5)
C22	0.0349 (7)	0.0339 (7)	0.0363 (7)	−0.0028 (5)	−0.0008 (5)	0.0016 (5)
C23	0.0370 (7)	0.0411 (8)	0.0424 (7)	−0.0024 (6)	−0.0058 (6)	−0.0082 (6)
C24	0.0402 (7)	0.0471 (8)	0.0303 (6)	0.0124 (6)	−0.0093 (5)	−0.0052 (6)
F24	0.0811 (7)	0.0650 (6)	0.0406 (5)	0.0116 (5)	−0.0291 (5)	−0.0051 (5)
C25	0.0503 (8)	0.0382 (7)	0.0326 (7)	0.0108 (6)	−0.0001 (6)	0.0061 (6)
C26	0.0363 (6)	0.0300 (6)	0.0338 (6)	0.0018 (5)	0.0011 (5)	0.0003 (5)
C31	0.0273 (5)	0.0224 (5)	0.0215 (5)	0.0006 (4)	0.0042 (4)	−0.0009 (4)
C32	0.0269 (6)	0.0248 (6)	0.0241 (5)	−0.0004 (4)	0.0026 (4)	−0.0004 (4)
O31	0.0246 (4)	0.0274 (4)	0.0405 (5)	−0.0014 (3)	0.0006 (3)	−0.0036 (4)
O32	0.0324 (5)	0.0224 (4)	0.0360 (5)	0.0037 (3)	−0.0002 (4)	0.0008 (3)
O33	0.0272 (5)	0.0349 (5)	0.0560 (6)	−0.0030 (4)	−0.0057 (4)	−0.0029 (4)
O34	0.0292 (4)	0.0200 (4)	0.0442 (5)	−0.0003 (3)	0.0026 (4)	0.0000 (4)

Geometric parameters (Å, º) top

N1—C6	1.4854 (16)	C21—C26	1.3917 (18)
N1—C2	1.4872 (16)	C21—C22	1.3935 (17)
N1—H11	0.918 (16)	C22—C23	1.3875 (18)
N1—H12	0.920 (16)	C22—H22	0.9300
C2—C3	1.5208 (16)	C23—C24	1.370 (2)
C2—H2A	0.9700	C23—H23	0.9300
C2—H2B	0.9700	C24—F24	1.3600 (15)
C3—N4	1.4622 (15)	C24—C25	1.373 (2)
C3—H3A	0.9700	C25—C26	1.3956 (17)
C3—H3B	0.9700	C25—H25	0.9300
N4—C21	1.4284 (14)	C26—H26	0.9300
N4—C5	1.4723 (15)	C31—O31	1.2368 (13)
C5—C6	1.5098 (17)	C31—O32	1.2625 (13)
C5—H5A	0.9700	C31—C32	1.5597 (16)
C5—H5B	0.9700	C32—O33	1.2064 (14)
C6—H6A	0.9700	C32—O34	1.3148 (14)
C6—H6B	0.9700	O34—H34	0.908 (18)

C6—N1—C2	111.85 (9)	C5—C6—H6A	109.7
C6—N1—H11	110.9 (9)	N1—C6—H6B	109.7
C2—N1—H11	109.8 (9)	C5—C6—H6B	109.7
C6—N1—H12	110.0 (9)	H6A—C6—H6B	108.2
C2—N1—H12	109.5 (9)	C26—C21—C22	118.75 (11)
H11—N1—H12	104.5 (13)	C26—C21—N4	123.95 (11)
N1—C2—C3	109.65 (10)	C22—C21—N4	117.30 (11)
N1—C2—H2A	109.7	C23—C22—C21	121.10 (13)
C3—C2—H2A	109.7	C23—C22—H22	119.4
N1—C2—H2B	109.7	C21—C22—H22	119.4
C3—C2—H2B	109.7	C24—C23—C22	118.41 (13)
H2A—C2—H2B	108.2	C24—C23—H23	120.8
N4—C3—C2	109.16 (10)	C22—C23—H23	120.8
N4—C3—H3A	109.8	F24—C24—C23	118.36 (13)
C2—C3—H3A	109.8	F24—C24—C25	119.02 (13)
N4—C3—H3B	109.8	C23—C24—C25	122.63 (12)
C2—C3—H3B	109.8	C24—C25—C26	118.56 (13)
H3A—C3—H3B	108.3	C24—C25—H25	120.7
C21—N4—C3	116.55 (9)	C26—C25—H25	120.7
C21—N4—C5	112.49 (9)	C21—C26—C25	120.53 (12)
C3—N4—C5	109.32 (9)	C21—C26—H26	119.7
N4—C5—C6	109.92 (10)	C25—C26—H26	119.7
N4—C5—H5A	109.7	O31—C31—O32	126.93 (11)
C6—C5—H5A	109.7	O31—C31—C32	118.43 (10)
N4—C5—H5B	109.7	O32—C31—C32	114.64 (9)
C6—C5—H5B	109.7	O33—C32—O34	125.62 (11)
H5A—C5—H5B	108.2	O33—C32—C31	122.08 (10)
N1—C6—C5	109.77 (10)	O34—C32—C31	112.29 (9)
N1—C6—H6A	109.7	C32—O34—H34	110.9 (10)

C6—N1—C2—C3	−55.37 (14)	N4—C21—C22—C23	−177.69 (12)
N1—C2—C3—N4	58.86 (13)	C21—C22—C23—C24	−0.9 (2)
C2—C3—N4—C21	168.31 (10)	C22—C23—C24—F24	−179.84 (13)
C2—C3—N4—C5	−62.77 (13)	C22—C23—C24—C25	−0.5 (2)
C21—N4—C5—C6	−166.31 (10)	F24—C24—C25—C26	−179.45 (13)
C3—N4—C5—C6	62.56 (13)	C23—C24—C25—C26	1.2 (2)
C2—N1—C6—C5	54.78 (14)	C22—C21—C26—C25	−0.68 (19)
N4—C5—C6—N1	−57.70 (14)	N4—C21—C26—C25	178.36 (12)
C3—N4—C21—C26	23.67 (17)	C24—C25—C26—C21	−0.6 (2)
C5—N4—C21—C26	−103.72 (14)	O31—C31—C32—O33	178.81 (11)
C3—N4—C21—C22	−157.27 (11)	O32—C31—C32—O33	−1.35 (16)
C5—N4—C21—C22	75.34 (14)	O31—C31—C32—O34	−1.92 (14)
C26—C21—C22—C23	1.42 (19)	O32—C31—C32—O34	177.92 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O32	0.918 (16)	1.896 (16)	2.7769 (14)	160.2 (15)
N1—H12···O31ⁱ	0.920 (16)	1.902 (17)	2.7507 (14)	152.6 (15)
N1—H12···O34ⁱ	0.920 (16)	2.354 (16)	2.9588 (14)	123.1 (13)
O34—H34···O32ⁱⁱ	0.908 (17)	1.712 (17)	2.6102 (12)	170.0 (17)
C2—H2A···O33ⁱⁱⁱ	0.97	2.54	3.4454 (15)	155
C5—H5A···O32^iv	0.97	2.45	3.3849 (15)	163
C6—H6B···O31^v	0.97	2.50	3.4259 (15)	159
C2—H2B···Cg1^vi	0.97	2.65	3.6124 (14)	170
C23—H23···Cg1^vii	0.93	2.94	3.5865 (16)	128

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, −y+3/2, z−1/2; (v) −x+1, y−1/2, −z+3/2; (vi) x, −y+3/2, z+1/2; (vii) −x, y−1/2, −z+1/2.

4-(4-Fluorophenyl)piperazin-1-ium hydrogen (2R,3R)-tartrate monohydrate (III) top

Crystal data top

C₁₀H₁₄FN₂⁺·C₄H₅O₆⁻·H₂O	D_x = 1.414 Mg m⁻³
M_r = 348.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3036 reflections
a = 7.0961 (4) Å	θ = 2.7–27.8°
b = 7.4967 (4) Å	µ = 0.12 mm⁻¹
c = 30.757 (2) Å	T = 293 K
V = 1636.19 (17) Å³	Needle, yellow
Z = 4	0.40 × 0.22 × 0.10 mm
F(000) = 736

Data collection top

Oxford Diffraction Xcalibur with Sapphire CCD diffractometer	3036 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2347 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.8°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→7
T_min = 0.904, T_max = 0.988	k = −7→9
4553 measured reflections	l = −39→20

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0206P)² + 0.5183P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
3036 reflections	Δρ_max = 0.18 e Å⁻³
238 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 683 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.6296 (4)	0.2270 (5)	0.60097 (11)	0.0454 (8)
H11	0.688 (5)	0.200 (5)	0.5771 (12)	0.054*
H12	0.623 (5)	0.349 (5)	0.5995 (12)	0.054*
C2	0.7310 (4)	0.1802 (5)	0.64079 (12)	0.0464 (9)
H2A	0.8493	0.2450	0.6418	0.056*
H2B	0.7597	0.0537	0.6405	0.056*
C3	0.6174 (5)	0.2235 (5)	0.68063 (11)	0.0424 (9)
H3A	0.6852	0.1847	0.7063	0.051*
H3B	0.5998	0.3516	0.6826	0.051*
N4	0.4346 (3)	0.1361 (4)	0.67912 (8)	0.0359 (7)
C5	0.3323 (5)	0.1901 (5)	0.64017 (11)	0.0464 (9)
H5A	0.3106	0.3178	0.6410	0.056*
H5B	0.2107	0.1311	0.6396	0.056*
C6	0.4402 (5)	0.1435 (6)	0.59966 (11)	0.0521 (10)
H6A	0.4530	0.0150	0.5974	0.063*
H6B	0.3720	0.1855	0.5743	0.063*
C21	0.3285 (5)	0.1373 (4)	0.71803 (10)	0.0350 (7)
C22	0.3867 (5)	0.2237 (5)	0.75550 (11)	0.0439 (9)
H22	0.4981	0.2890	0.7551	0.053*
C23	0.2824 (6)	0.2149 (5)	0.79359 (12)	0.0554 (11)
H23	0.3243	0.2707	0.8188	0.066*
C24	0.1175 (6)	0.1230 (5)	0.79317 (12)	0.0541 (10)
F24	0.0137 (4)	0.1146 (4)	0.83031 (7)	0.0923 (9)
C25	0.0551 (5)	0.0358 (6)	0.75739 (12)	0.0547 (11)
H25	−0.0575	−0.0276	0.7582	0.066*
C26	0.1605 (5)	0.0422 (5)	0.71956 (12)	0.0456 (9)
H26	0.1185	−0.0178	0.6949	0.055*
C31	0.9787 (4)	0.8324 (4)	0.56468 (10)	0.0317 (7)
C32	1.0513 (4)	0.6417 (4)	0.56228 (10)	0.0269 (7)
H32A	1.0143	0.5796	0.5890	0.032*
C33	0.9627 (4)	0.5450 (4)	0.52373 (9)	0.0270 (7)
H33A	0.8260	0.5415	0.5281	0.032*
C34	1.0350 (4)	0.3543 (4)	0.52206 (10)	0.0285 (7)
O31	0.8084 (3)	0.8554 (3)	0.57208 (8)	0.0416 (6)
O32	1.0978 (3)	0.9520 (3)	0.55833 (9)	0.0510 (7)
O33	1.2503 (3)	0.6346 (3)	0.55866 (8)	0.0381 (6)
H33	1.279 (5)	0.722 (5)	0.5451 (12)	0.057*
O34	0.9995 (3)	0.6363 (3)	0.48486 (7)	0.0397 (6)
H34	1.101 (6)	0.610 (5)	0.4746 (12)	0.060*
O35	1.1228 (3)	0.2964 (3)	0.49167 (8)	0.0453 (6)
O36	0.9946 (3)	0.2667 (3)	0.55754 (7)	0.0341 (5)
H36	1.040 (5)	0.148 (5)	0.5570 (11)	0.051*
O41	0.5786 (4)	0.5889 (4)	0.60508 (10)	0.0566 (8)
H41	0.659 (7)	0.681 (6)	0.5942 (14)	0.085*
H42	0.477 (7)	0.607 (6)	0.5968 (15)	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0359 (17)	0.061 (2)	0.0389 (18)	−0.0067 (17)	0.0065 (15)	−0.0021 (18)
C2	0.0323 (18)	0.058 (2)	0.049 (2)	−0.0006 (17)	0.0024 (18)	0.004 (2)
C3	0.0353 (19)	0.054 (2)	0.038 (2)	−0.0045 (17)	−0.0052 (17)	−0.0010 (19)
N4	0.0317 (14)	0.0420 (16)	0.0339 (15)	−0.0036 (14)	0.0002 (13)	−0.0030 (14)
C5	0.0322 (17)	0.070 (3)	0.037 (2)	−0.0069 (18)	−0.0011 (17)	−0.004 (2)
C6	0.0374 (19)	0.080 (3)	0.039 (2)	−0.017 (2)	0.0033 (17)	−0.010 (2)
C21	0.0416 (17)	0.0331 (17)	0.0304 (18)	0.0017 (17)	0.0000 (16)	−0.0018 (16)
C22	0.050 (2)	0.041 (2)	0.040 (2)	−0.0004 (18)	−0.0025 (19)	−0.0011 (18)
C23	0.078 (3)	0.056 (2)	0.032 (2)	0.007 (2)	−0.004 (2)	−0.005 (2)
C24	0.069 (3)	0.061 (3)	0.032 (2)	0.010 (2)	0.013 (2)	0.010 (2)
F24	0.101 (2)	0.131 (3)	0.0449 (14)	0.0048 (19)	0.0275 (15)	0.0101 (16)
C25	0.048 (2)	0.066 (3)	0.050 (2)	−0.005 (2)	0.010 (2)	0.010 (2)
C26	0.045 (2)	0.053 (2)	0.040 (2)	−0.0076 (19)	0.0030 (18)	−0.0018 (19)
C31	0.0327 (17)	0.0241 (15)	0.0382 (19)	0.0000 (14)	−0.0036 (15)	0.0015 (14)
C32	0.0241 (14)	0.0230 (14)	0.0337 (18)	−0.0003 (13)	−0.0011 (13)	0.0030 (15)
C33	0.0237 (14)	0.0263 (14)	0.0311 (17)	0.0013 (14)	0.0003 (14)	0.0038 (15)
C34	0.0276 (14)	0.0281 (15)	0.0298 (17)	−0.0001 (15)	−0.0028 (14)	−0.0002 (16)
O31	0.0319 (12)	0.0327 (12)	0.0604 (16)	0.0040 (11)	0.0029 (11)	0.0000 (13)
O32	0.0352 (12)	0.0217 (10)	0.096 (2)	−0.0011 (11)	0.0024 (14)	0.0034 (14)
O33	0.0244 (11)	0.0261 (11)	0.0639 (17)	−0.0006 (10)	−0.0059 (11)	0.0078 (13)
O34	0.0400 (13)	0.0421 (13)	0.0371 (14)	0.0082 (12)	0.0024 (11)	0.0137 (12)
O35	0.0533 (15)	0.0436 (14)	0.0391 (14)	0.0126 (13)	0.0113 (13)	−0.0048 (12)
O36	0.0399 (13)	0.0205 (10)	0.0419 (13)	0.0022 (10)	0.0052 (11)	0.0037 (11)
O41	0.0408 (16)	0.0624 (18)	0.0666 (19)	−0.0045 (14)	−0.0111 (14)	0.0216 (15)

Geometric parameters (Å, º) top

N1—C2	1.463 (4)	C23—H23	0.9300
N1—C6	1.483 (4)	C24—C25	1.355 (5)
N1—H11	0.87 (4)	C24—F24	1.361 (4)
N1—H12	0.92 (4)	C25—C26	1.384 (5)
C2—C3	1.503 (5)	C25—H25	0.9300
C2—H2A	0.9700	C26—H26	0.9300
C2—H2B	0.9700	C31—O31	1.241 (4)
C3—N4	1.454 (4)	C31—O32	1.248 (4)
C3—H3A	0.9700	C31—C32	1.522 (4)
C3—H3B	0.9700	C32—O33	1.418 (3)
N4—C21	1.414 (4)	C32—C33	1.525 (4)
N4—C5	1.458 (4)	C32—H32A	0.9800
C5—C6	1.503 (5)	C33—O34	1.402 (3)
C5—H5A	0.9700	C33—C34	1.519 (4)
C5—H5B	0.9700	C33—H33A	0.9800
C6—H6A	0.9700	C34—O35	1.204 (4)
C6—H6B	0.9700	C34—O36	1.306 (4)
C21—C22	1.385 (4)	O33—H33	0.80 (4)
C21—C26	1.390 (5)	O34—H34	0.81 (4)
C22—C23	1.387 (5)	O36—H36	0.95 (4)
C22—H22	0.9300	O41—H41	0.95 (5)
C23—C24	1.358 (6)	O41—H42	0.78 (5)

C2—N1—C6	111.5 (3)	C21—C22—H22	119.3
C2—N1—H11	115 (2)	C23—C22—H22	119.3
C6—N1—H11	108 (3)	C24—C23—C22	118.4 (4)
C2—N1—H12	108 (2)	C24—C23—H23	120.8
C6—N1—H12	112 (3)	C22—C23—H23	120.8
H11—N1—H12	102 (3)	C25—C24—C23	122.3 (4)
N1—C2—C3	111.5 (3)	C25—C24—F24	118.9 (4)
N1—C2—H2A	109.3	C23—C24—F24	118.8 (4)
C3—C2—H2A	109.3	C24—C25—C26	119.3 (4)
N1—C2—H2B	109.3	C24—C25—H25	120.3
C3—C2—H2B	109.3	C26—C25—H25	120.3
H2A—C2—H2B	108.0	C25—C26—C21	120.6 (3)
N4—C3—C2	110.8 (3)	C25—C26—H26	119.7
N4—C3—H3A	109.5	C21—C26—H26	119.7
C2—C3—H3A	109.5	O31—C31—O32	126.0 (3)
N4—C3—H3B	109.5	O31—C31—C32	118.0 (3)
C2—C3—H3B	109.5	O32—C31—C32	116.0 (3)
H3A—C3—H3B	108.1	O33—C32—C31	112.1 (2)
C21—N4—C3	116.4 (3)	O33—C32—C33	109.4 (2)
C21—N4—C5	115.4 (3)	C31—C32—C33	110.2 (2)
C3—N4—C5	110.2 (3)	O33—C32—H32A	108.4
N4—C5—C6	111.3 (3)	C31—C32—H32A	108.4
N4—C5—H5A	109.4	C33—C32—H32A	108.4
C6—C5—H5A	109.4	O34—C33—C34	111.6 (2)
N4—C5—H5B	109.4	O34—C33—C32	110.7 (2)
C6—C5—H5B	109.4	C34—C33—C32	109.5 (2)
H5A—C5—H5B	108.0	O34—C33—H33A	108.3
N1—C6—C5	109.9 (3)	C34—C33—H33A	108.3
N1—C6—H6A	109.7	C32—C33—H33A	108.3
C5—C6—H6A	109.7	O35—C34—O36	125.5 (3)
N1—C6—H6B	109.7	O35—C34—C33	122.7 (3)
C5—C6—H6B	109.7	O36—C34—C33	111.8 (3)
H6A—C6—H6B	108.2	C32—O33—H33	105 (3)
C22—C21—C26	117.9 (3)	C33—O34—H34	112 (3)
C22—C21—N4	123.3 (3)	C34—O36—H36	113 (2)
C26—C21—N4	118.8 (3)	H41—O41—H42	108 (4)
C21—C22—C23	121.4 (4)

C6—N1—C2—C3	−54.1 (4)	C23—C24—C25—C26	−1.0 (6)
N1—C2—C3—N4	55.9 (4)	F24—C24—C25—C26	−179.4 (3)
C2—C3—N4—C21	168.2 (3)	C24—C25—C26—C21	−0.2 (6)
C2—C3—N4—C5	−57.9 (4)	C22—C21—C26—C25	0.4 (5)
C21—N4—C5—C6	−166.5 (3)	N4—C21—C26—C25	178.2 (3)
C3—N4—C5—C6	59.1 (4)	O31—C31—C32—O33	−173.2 (3)
C2—N1—C6—C5	54.1 (4)	O32—C31—C32—O33	7.7 (4)
N4—C5—C6—N1	−56.8 (4)	O31—C31—C32—C33	64.7 (4)
C3—N4—C21—C22	3.3 (5)	O32—C31—C32—C33	−114.4 (3)
C5—N4—C21—C22	−128.2 (3)	O33—C32—C33—O34	−66.5 (3)
C3—N4—C21—C26	−174.3 (3)	C31—C32—C33—O34	57.2 (3)
C5—N4—C21—C26	54.1 (4)	O33—C32—C33—C34	56.9 (3)
C26—C21—C22—C23	0.6 (5)	C31—C32—C33—C34	−179.4 (2)
N4—C21—C22—C23	−177.1 (3)	O34—C33—C34—O35	4.2 (4)
C21—C22—C23—C24	−1.7 (6)	C32—C33—C34—O35	−118.7 (3)
C22—C23—C24—C25	2.0 (6)	O34—C33—C34—O36	−177.5 (2)
C22—C23—C24—F24	−179.6 (3)	C32—C33—C34—O36	59.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 represents the centroid of the ring (C21–C26).

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O36	0.87 (4)	2.31 (4)	2.929 (4)	128 (3)
N1—H11···O35ⁱ	0.87 (4)	2.17 (4)	2.855 (4)	136 (3)
N1—H12···O41	0.92 (4)	1.83 (4)	2.740 (5)	169 (3)
O33—H33···O32	0.80 (4)	2.19 (4)	2.614 (3)	113 (3)
O33—H33···O34ⁱⁱ	0.80 (4)	2.10 (4)	2.805 (3)	146 (3)
O34—H34···O35	0.81 (4)	2.41 (4)	2.702 (3)	102 (3)
O34—H34···O31ⁱⁱ	0.81 (4)	2.07 (4)	2.806 (3)	151 (4)
O36—H36···O32ⁱⁱⁱ	0.95 (4)	1.53 (4)	2.470 (3)	175 (3)
O41—H41···O31	0.96 (5)	1.82 (5)	2.771 (4)	178 (5)
O41—H42···O33^iv	0.78 (5)	2.00 (5)	2.754 (4)	163 (5)
C25—H25···Cg1^v	0.93	2.86	3.649 (5)	144

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x, y−1/2, −z+3/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Three 4-(4-fluoro­phen­yl)piperazin-1-ium salts containing organic anions: supra­molecular assembly in one, two and three dimensions

Supporting information

Key indicators

checkCIF/PLATON results

Three 4-(4-fluorophenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions