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In the hydrated title salt, [C22H48N4]Cl4·4H2O, the cation lies about an inversion centre. The macrocyclic ring adopts an exodentate (3,4,3,4)-D conformation. In the crystal, O—H...Cl, N—H...Cl and N—H...O hydrogen bonds connect the chloride anions, tetra­protonated cations and water mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001006/wm5597sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001006/wm5597Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001006/wm5597Isup3.cml
Supplementary material

CCDC reference: 2059324

Key indicators

  • Single-crystal synchrotron study
  • T = 220 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.105
  • Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 26 Report
Alert level G ABSMU01_ALERT_1_G Calculation of _exptl_absorpt_correction_mu not performed for this radiation type. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 6 Note PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 4 Report PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum Found in CIF ...... Please Check PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT092_ALERT_4_G Check: Wavelength Given is not Cu,Ga,Mo,Ag,In Ka 0.61000 Ang. PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 Report PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records 2 Report PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note Cl PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 3 Note Cl PLAT793_ALERT_4_G Model has Chirality at C3 (Centro SPGR) S Verify PLAT793_ALERT_4_G Model has Chirality at C8 (Centro SPGR) S Verify PLAT793_ALERT_4_G Model has Chirality at C9 (Centro SPGR) S Verify PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 6 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 35 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 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 17 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 10 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: PAL BL2D-SMDC (Shin et al., 2016); cell refinement: HKL3000sm (Otwinowski et al., 2003); data reduction: HKL3000sm (Otwinowski et al., 2003); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

3,14-Diethyl-2,6,13,17-tetraazoniatricyclo[16.4.0.07,12]docosane tetrachloride tetrahydrate top
Crystal data top
C22H48N44+·4Cl·4H2OF(000) = 632
Mr = 582.50Dx = 1.323 Mg m3
Monoclinic, P21/nSynchrotron radiation, λ = 0.610 Å
a = 7.6550 (15) ÅCell parameters from 50732 reflections
b = 23.533 (5) Åθ = 0.4–33.7°
c = 8.3130 (17) ŵ = 0.28 mm1
β = 102.45 (3)°T = 220 K
V = 1462.3 (5) Å3Block, colorless
Z = 20.08 × 0.07 × 0.04 mm
Data collection top
Rayonix MX225HS CCD area detector
diffractometer
3517 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnetRint = 0.038
ω scanθmax = 25.0°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements)
(HKL3000sm Scalepack; Otwinowski et al., 2003)
h = 1010
Tmin = 0.868, Tmax = 1.000k = 3232
14961 measured reflectionsl = 1111
4016 independent reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2081P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
4016 reflectionsΔρmax = 0.41 e Å3
167 parametersΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
Cl10.71371 (4)0.51779 (2)1.23367 (4)0.02947 (10)
Cl20.80805 (4)0.29797 (2)1.26093 (4)0.03510 (10)
O10.82713 (14)0.41203 (4)1.06447 (12)0.0341 (2)
H1O10.822 (2)0.3768 (4)1.1119 (19)0.041*
H2O10.792 (2)0.4405 (5)1.1271 (18)0.041*
O20.21622 (14)0.29355 (5)0.47672 (14)0.0405 (2)
H1O20.1034 (16)0.2916 (8)0.4106 (19)0.049*
H2O20.233 (2)0.2681 (6)0.5609 (16)0.049*
N10.68792 (13)0.46398 (4)0.76471 (12)0.0234 (2)
H1A0.5765350.4737330.7730540.028*
H1B0.7289000.4384970.8446680.028*
N20.49393 (13)0.36101 (4)0.42080 (12)0.0239 (2)
H2A0.4093390.3344080.4202410.029*
H2B0.5889740.3433950.3957240.029*
C10.74209 (15)0.56567 (5)0.68089 (15)0.0247 (2)
H1C0.7130360.5514030.5674930.030*
H1D0.8405690.5928810.6893200.030*
C20.80442 (16)0.51617 (5)0.79715 (16)0.0255 (2)
H2C0.9261510.5057820.7889040.031*
H2D0.8094750.5288370.9103660.031*
C30.67631 (15)0.43519 (5)0.60043 (14)0.0232 (2)
H30.6226100.4620090.5117580.028*
C40.86023 (16)0.41738 (5)0.57551 (15)0.0270 (2)
H4A0.8481640.4012940.4649270.032*
H4B0.9374350.4509400.5834760.032*
C50.94712 (16)0.37373 (6)0.70283 (17)0.0307 (3)
H5A0.9687650.3908410.8128220.037*
H5B1.0628410.3623170.6807860.037*
C60.82840 (18)0.32133 (6)0.69882 (17)0.0325 (3)
H6A0.8812230.2962190.7904890.039*
H6B0.8250260.3005290.5960630.039*
C70.63628 (17)0.33618 (5)0.71111 (16)0.0288 (3)
H7A0.5621680.3019860.6871450.035*
H7B0.6369100.3475510.8246450.035*
C80.55016 (15)0.38374 (5)0.59487 (14)0.0237 (2)
H80.4414390.3966780.6305830.028*
C90.42198 (15)0.40325 (5)0.28341 (14)0.0240 (2)
H90.5162850.4319900.2828030.029*
C100.38798 (17)0.37228 (5)0.11758 (15)0.0285 (2)
H10A0.3610970.4008480.0299360.034*
H10B0.4990990.3532890.1076740.034*
C110.2386 (2)0.32840 (6)0.08671 (18)0.0371 (3)
H11A0.2598080.3006030.1749460.056*
H11B0.2358810.3094710.0174590.056*
H11C0.1249520.3471330.0829580.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02435 (15)0.02771 (17)0.04097 (18)0.00112 (10)0.01724 (12)0.00061 (11)
Cl20.03364 (17)0.03180 (18)0.04254 (19)0.00500 (12)0.01410 (14)0.00293 (12)
O10.0398 (5)0.0299 (5)0.0361 (5)0.0030 (4)0.0156 (4)0.0005 (4)
O20.0314 (5)0.0430 (6)0.0482 (6)0.0074 (4)0.0111 (4)0.0115 (5)
N10.0220 (4)0.0202 (5)0.0305 (5)0.0007 (3)0.0112 (4)0.0001 (4)
N20.0223 (4)0.0193 (4)0.0322 (5)0.0009 (3)0.0107 (4)0.0002 (4)
C10.0242 (5)0.0191 (5)0.0339 (6)0.0003 (4)0.0134 (4)0.0003 (4)
C20.0227 (5)0.0204 (5)0.0343 (6)0.0008 (4)0.0083 (4)0.0021 (4)
C30.0229 (5)0.0199 (5)0.0290 (5)0.0017 (4)0.0106 (4)0.0011 (4)
C40.0250 (5)0.0241 (5)0.0361 (6)0.0028 (4)0.0161 (5)0.0031 (5)
C50.0240 (5)0.0294 (6)0.0410 (6)0.0034 (5)0.0123 (5)0.0023 (5)
C60.0343 (6)0.0239 (6)0.0400 (7)0.0035 (5)0.0097 (5)0.0025 (5)
C70.0299 (6)0.0224 (6)0.0352 (6)0.0038 (4)0.0096 (5)0.0036 (5)
C80.0224 (5)0.0210 (5)0.0304 (5)0.0019 (4)0.0114 (4)0.0011 (4)
C90.0229 (5)0.0203 (5)0.0312 (5)0.0006 (4)0.0114 (4)0.0017 (4)
C100.0292 (6)0.0284 (6)0.0310 (6)0.0044 (5)0.0133 (5)0.0006 (5)
C110.0415 (7)0.0312 (7)0.0381 (7)0.0035 (6)0.0077 (6)0.0063 (6)
Geometric parameters (Å, º) top
O1—H1O10.924 (9)C4—C51.5213 (18)
O1—H2O10.922 (9)C4—H4A0.9800
O2—H1O20.919 (9)C4—H4B0.9800
O2—H2O20.910 (9)C5—C61.5279 (19)
N1—C21.5076 (15)C5—H5A0.9800
N1—C31.5099 (15)C5—H5B0.9800
N1—H1A0.9000C6—C71.5364 (18)
N1—H1B0.9000C6—H6A0.9800
N2—C81.5155 (16)C6—H6B0.9800
N2—C91.5247 (15)C7—C81.5318 (17)
N2—H2A0.9000C7—H7A0.9800
N2—H2B0.9000C7—H7B0.9800
C1—C21.5231 (17)C8—H80.9900
C1—C9i1.5366 (16)C9—C101.5312 (17)
C1—H1C0.9800C9—H90.9900
C1—H1D0.9800C10—C111.5208 (19)
C2—H2C0.9800C10—H10A0.9800
C2—H2D0.9800C10—H10B0.9800
C3—C41.5253 (16)C11—H11A0.9700
C3—C81.5431 (16)C11—H11B0.9700
C3—H30.9900C11—H11C0.9700
H1O1—O1—H2O1111.5 (13)C6—C5—H5A109.4
H1O2—O2—H2O2112.6 (15)C4—C5—H5B109.4
C2—N1—C3116.40 (9)C6—C5—H5B109.4
C2—N1—H1A108.2H5A—C5—H5B108.0
C3—N1—H1A108.2C5—C6—C7112.85 (11)
C2—N1—H1B108.2C5—C6—H6A109.0
C3—N1—H1B108.2C7—C6—H6A109.0
H1A—N1—H1B107.3C5—C6—H6B109.0
C8—N2—C9117.87 (9)C7—C6—H6B109.0
C8—N2—H2A107.8H6A—C6—H6B107.8
C9—N2—H2A107.8C8—C7—C6114.35 (10)
C8—N2—H2B107.8C8—C7—H7A108.7
C9—N2—H2B107.8C6—C7—H7A108.7
H2A—N2—H2B107.2C8—C7—H7B108.7
C2—C1—C9i113.50 (10)C6—C7—H7B108.7
C2—C1—H1C108.9H7A—C7—H7B107.6
C9i—C1—H1C108.9N2—C8—C7109.85 (10)
C2—C1—H1D108.9N2—C8—C3110.65 (9)
C9i—C1—H1D108.9C7—C8—C3111.90 (10)
H1C—C1—H1D107.7N2—C8—H8108.1
N1—C2—C1114.66 (10)C7—C8—H8108.1
N1—C2—H2C108.6C3—C8—H8108.1
C1—C2—H2C108.6N2—C9—C10109.14 (9)
N1—C2—H2D108.6N2—C9—C1i110.12 (9)
C1—C2—H2D108.6C10—C9—C1i114.39 (10)
H2C—C2—H2D107.6N2—C9—H9107.6
N1—C3—C4111.72 (10)C10—C9—H9107.6
N1—C3—C8107.08 (9)C1i—C9—H9107.6
C4—C3—C8111.74 (10)C11—C10—C9116.80 (10)
N1—C3—H3108.7C11—C10—H10A108.1
C4—C3—H3108.7C9—C10—H10A108.1
C8—C3—H3108.7C11—C10—H10B108.1
C5—C4—C3111.65 (10)C9—C10—H10B108.1
C5—C4—H4A109.3H10A—C10—H10B107.3
C3—C4—H4A109.3C10—C11—H11A109.5
C5—C4—H4B109.3C10—C11—H11B109.5
C3—C4—H4B109.3H11A—C11—H11B109.5
H4A—C4—H4B108.0C10—C11—H11C109.5
C4—C5—C6111.17 (11)H11A—C11—H11C109.5
C4—C5—H5A109.4H11B—C11—H11C109.5
C3—N1—C2—C163.32 (13)C6—C7—C8—N276.17 (13)
C9i—C1—C2—N174.65 (13)C6—C7—C8—C347.14 (14)
C2—N1—C3—C457.74 (13)N1—C3—C8—N2165.93 (9)
C2—N1—C3—C8179.62 (9)C4—C3—C8—N271.44 (12)
N1—C3—C4—C562.83 (13)N1—C3—C8—C771.22 (12)
C8—C3—C4—C557.11 (13)C4—C3—C8—C751.41 (13)
C3—C4—C5—C657.11 (13)C8—N2—C9—C10175.45 (9)
C4—C5—C6—C752.02 (14)C8—N2—C9—C1i58.20 (12)
C5—C6—C7—C847.89 (15)N2—C9—C10—C1167.17 (13)
C9—N2—C8—C7174.08 (9)C1i—C9—C10—C1156.69 (15)
C9—N2—C8—C350.04 (12)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···Cl20.92 (1)2.25 (1)3.1616 (11)172 (1)
O1—H2O1···Cl10.92 (1)2.17 (1)3.0746 (11)169 (1)
O2—H1O2···Cl2ii0.92 (1)2.34 (1)3.2518 (15)172 (2)
O2—H2O2···Cl2iii0.91 (1)2.26 (1)3.1622 (12)173 (2)
N1—H1A···Cl1iv0.902.223.1072 (12)169
N1—H1B···O10.901.922.7740 (15)157
N2—H2A···O20.901.912.7716 (14)161
N2—H2B···Cl2v0.902.453.3357 (12)167
Symmetry codes: (ii) x1, y, z1; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+2; (v) x, y, z1.
 

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