Crystal structures of two formamidinium hexa­fluorido­phosphate salts, one with batch-dependent disorder

Neary, M.C.; Corfield, P.W.R.; Parkin, S.R.; Saba, S.

doi:10.1107/S2056989023010848

Crystal structures of two formamidinium hexafluoridophosphate salts, one with batch-dependent disorder

M. C. Neary, P. W. R. Corfield, S. R. Parkin and S. Saba

The crystal structures of two nitrogen heterocycle hexafluoridophosphate salts with terminal animinium groups are described. Unexpectedly, there is cation disorder in crystals of the morpholinoformamidinium compound obtained from ethanol recrystallization, which is not found in the original crystals.

Keywords: crystal structure; formamidinium ion; nitrogen heterocycles; hexafluoridophosphate; hydrogen bonding; disorder.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023010848/wm5706sup1.cif Contains datablocks 1, 1recryst, 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010848/wm57061sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010848/wm57061recrystsup3.hkl Contains datablock 1recryst
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010848/wm57062sup4.hkl Contains datablock 2
	Tagged Image Format File (TIF) image https://doi.org/10.1107/S2056989023010848/wm5706sup5.tif Infrared Spectra of the Two Compounds

CCDC references: 2320366; 2320365; 2320364

checkCIF report

Key indicators

Structure: 1

Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R factor = 0.025
wR factor = 0.071
Data-to-parameter ratio = 11.9

Structure: 1recryst

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.032
wR factor = 0.088
Data-to-parameter ratio = 20.1

Structure: 2

Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.007 Å
R factor = 0.049
wR factor = 0.135
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.975 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
                0  2  0,   0  4  0,   0 12  0,  10  3  2,   0  0  8,   0  0 10,

Alert level G
PLAT168_ALERT_4_G The CIF-Embedded .res File Contains EXYZ Records          3 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          4 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       6.09 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       0.91 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A      ..F4A      .       2.62 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 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
  11 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 1recryst



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.500
           From the CIF: _refine_ls_abs_structure_Flack_su   20.000
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         P1 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
                0  2  0,   0  4  0,   0  6  0,   0  8  0,   2  2  1,   0  0  2,
                2  0  2,   0  2  2,   2  0  3,   0  0  4,
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note
                0  8  0,   2  2  1,   0  2  2,   2  0  3,   0  0  4,

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         24 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
              H8C3  H8C4
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.997 Report
PLAT168_ALERT_4_G The CIF-Embedded .res File Contains EXYZ Records          3 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          3 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          2 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  2  )       100% Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  5  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  6  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )      12.14 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       6.86 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  5  )       6.13 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  6  )       0.87 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact F4       ..F5B      .       2.81 Ang.
                                                    1+x,y,z  =      1_655 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A2     ..F3       .       2.63 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         39 Note
              H2A1    H2A2    H3A1    H3A2    H5A1    H5A2    H6A1    H6A2
              H8A1    H8A2    H2B1    H2B2    H3B1    H3B2    H5B1    H5B2
              H6B1    H6B2    H8B1    H8B2    N1B'    C2B'    H2C3    H2C4
              C3B'    H3C3    H3C4    O4B'    C5B'    H5C3    H5C4    C6B'
              H6C3    H6C4    C7B'    H7B'    N8B'    H8C3    H8C4
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          4 Note
              F6 P
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        154 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  1  0,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 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
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  26 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  16 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.490
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
              Calc: F6 P, C5 H11 N2
              Rep.: C5 H11 N2 +, F6 P -
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.37 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00733 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         26 Report
                4  0  0,   6  0  0,   8  0  0,   7  1  0,   2  2  0,   8  2  0,
                0  8  0,   5  1  1,   7  1  1,  -8  0  2,  -2  0  2,   0  0  2,
                4  0  2,   6  0  2,  -1  1  2,   5  1  2,   7  1  2,  -2  2  2,
                5  1  3,  -4 10  3,   5  1  6,  -2  2  7,  -2  0  8,   3  1  8,
               -8  0 10,  -4  0 14,

Alert level G
PLAT111_ALERT_2_G ADDSYM Detects New (Pseudo) Centre of Symmetry .         92 %Fit
PLAT113_ALERT_2_G ADDSYM Suggests Possible Pseudo/New  Space Group       C2/c Check
              Check Model Parameter Symmmetry for Reflection Data Support
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of         P1 Check
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of         P2 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Morpholinoformamidinium hexafluorophosphate (1) top

Crystal data top

C₅H₁₁N₂O⁺·PF₆⁻	D_x = 1.788 Mg m⁻³
M_r = 260.13	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9781 reflections
a = 10.4638 (3) Å	θ = 4.2–74.6°
b = 13.4495 (4) Å	µ = 3.30 mm⁻¹
c = 13.7340 (4) Å	T = 130 K
V = 1932.83 (10) Å³	Block, colorless
Z = 8	0.29 × 0.09 × 0.06 mm
F(000) = 1056

Data collection top

Bruker D8 with PHOTON III area detector diffractometer	1923 reflections with I > 2σ(I)
Radiation source: microfocus	R_int = 0.034
φ and ω shutterless scans	θ_max = 74.6°, θ_min = 6.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −13→12
T_min = 0.570, T_max = 0.754	k = −16→16
36889 measured reflections	l = −17→15
1969 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.025	w = 1/[σ²(F_o²) + (0.0373P)² + 0.517P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.071	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.29 e Å⁻³
1969 reflections	Δρ_min = −0.28 e Å⁻³
165 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00052 (10)

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	Occ. (<1)
N1	0.17230 (9)	0.55859 (6)	0.73256 (6)	0.01938 (19)
C2	0.20187 (10)	0.51175 (7)	0.82640 (7)	0.0203 (2)
H2A	0.152903	0.449208	0.833665	0.030*
H2B	0.178416	0.556828	0.880516	0.030*
C3	0.34450 (10)	0.49023 (8)	0.82874 (8)	0.0220 (2)
H3A	0.392565	0.553533	0.825341	0.033*
H3B	0.366643	0.456964	0.890787	0.033*
O4	0.38048 (9)	0.42787 (6)	0.74877 (5)	0.02532 (19)
C5	0.34896 (11)	0.47236 (9)	0.65681 (8)	0.0279 (3)
H5A	0.373554	0.426656	0.603505	0.042*
H5B	0.398048	0.534754	0.648785	0.042*
C6	0.20684 (12)	0.49485 (8)	0.64996 (8)	0.0266 (2)
H6A	0.157068	0.432289	0.652136	0.040*
H6B	0.187731	0.529177	0.587877	0.040*
C7	0.14903 (9)	0.65374 (8)	0.71986 (8)	0.0198 (2)
H7	0.1387 (12)	0.6771 (10)	0.6554 (10)	0.023 (3)*
N8	0.13576 (10)	0.71972 (7)	0.78845 (7)	0.0252 (2)
H8A	0.1442 (14)	0.7058 (12)	0.8468 (13)	0.035 (3)*
H8B	0.1207 (16)	0.7800 (13)	0.7735 (12)	0.035 (3)*
P1A	0.39982 (2)	0.74360 (2)	0.49827 (2)	0.01852 (12)	0.870 (8)
F1A	0.36762 (8)	0.75062 (5)	0.61181 (5)	0.03015 (19)	0.870 (8)
F2A	0.43172 (8)	0.73592 (6)	0.38461 (5)	0.0350 (2)	0.870 (8)
F3A	0.2971 (3)	0.82864 (17)	0.47542 (12)	0.0382 (4)	0.870 (8)
F4A	0.2907 (2)	0.66066 (17)	0.48512 (12)	0.0372 (4)	0.870 (8)
F5A	0.5015 (2)	0.65703 (19)	0.52252 (9)	0.0372 (5)	0.870 (8)
F6A	0.5081 (2)	0.82470 (19)	0.51297 (13)	0.0418 (5)	0.870 (8)
P1B	0.39982 (2)	0.74360 (2)	0.49827 (2)	0.01852 (12)	0.130 (8)
F1B	0.36762 (8)	0.75062 (5)	0.61181 (5)	0.03015 (19)	0.130 (8)
F2B	0.43172 (8)	0.73592 (6)	0.38461 (5)	0.0350 (2)	0.130 (8)
F3B	0.2743 (11)	0.8078 (9)	0.4866 (8)	0.028 (2)*	0.130 (8)
F4B	0.3249 (11)	0.6487 (8)	0.4898 (7)	0.024 (2)*	0.130 (8)
F5B	0.5314 (7)	0.6899 (8)	0.5077 (6)	0.0209 (18)*	0.130 (8)
F6B	0.4809 (8)	0.8509 (7)	0.4946 (6)	0.0246 (19)*	0.130 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0225 (4)	0.0178 (4)	0.0179 (4)	−0.0003 (3)	−0.0010 (3)	−0.0006 (3)
C2	0.0246 (5)	0.0177 (4)	0.0187 (4)	−0.0004 (4)	0.0013 (4)	0.0030 (4)
C3	0.0247 (5)	0.0201 (5)	0.0213 (5)	0.0014 (4)	−0.0003 (4)	0.0000 (4)
O4	0.0317 (4)	0.0189 (4)	0.0254 (4)	0.0059 (3)	0.0032 (3)	0.0006 (3)
C5	0.0371 (6)	0.0250 (5)	0.0215 (5)	0.0069 (4)	0.0064 (4)	0.0000 (4)
C6	0.0367 (6)	0.0230 (5)	0.0200 (5)	0.0016 (4)	−0.0026 (4)	−0.0051 (4)
C7	0.0169 (5)	0.0214 (5)	0.0212 (5)	0.0003 (4)	−0.0001 (4)	0.0030 (4)
N8	0.0330 (5)	0.0180 (5)	0.0246 (5)	0.0048 (4)	0.0020 (4)	0.0018 (4)
P1A	0.01731 (18)	0.02057 (17)	0.01767 (17)	−0.00065 (9)	0.00018 (9)	−0.00186 (8)
F1A	0.0365 (4)	0.0350 (4)	0.0190 (3)	0.0065 (3)	0.0023 (3)	−0.0025 (2)
F2A	0.0409 (4)	0.0441 (4)	0.0202 (3)	−0.0083 (3)	0.0070 (3)	−0.0029 (3)
F3A	0.0463 (9)	0.0355 (8)	0.0329 (6)	0.0184 (7)	−0.0065 (6)	0.0044 (6)
F4A	0.0325 (8)	0.0400 (7)	0.0392 (6)	−0.0187 (7)	0.0066 (6)	−0.0102 (5)
F5A	0.0391 (7)	0.0389 (9)	0.0336 (5)	0.0200 (7)	0.0017 (5)	−0.0011 (5)
F6A	0.0385 (7)	0.0446 (9)	0.0423 (6)	−0.0229 (7)	0.0000 (6)	−0.0070 (6)
P1B	0.01731 (18)	0.02057 (17)	0.01767 (17)	−0.00065 (9)	0.00018 (9)	−0.00186 (8)
F1B	0.0365 (4)	0.0350 (4)	0.0190 (3)	0.0065 (3)	0.0023 (3)	−0.0025 (2)
F2B	0.0409 (4)	0.0441 (4)	0.0202 (3)	−0.0083 (3)	0.0070 (3)	−0.0029 (3)

Geometric parameters (Å, º) top

N1—C7	1.3142 (13)	C7—H7	0.946 (14)
N1—C2	1.4675 (12)	N8—H8A	0.827 (18)
N1—C6	1.4672 (13)	N8—H8B	0.850 (18)
C2—C3	1.5206 (14)	P1A—F6A	1.5856 (10)
C2—H2A	0.9900	P1A—F3A	1.6003 (14)
C2—H2B	0.9900	P1A—F4A	1.6063 (14)
C3—O4	1.4322 (12)	P1A—F5A	1.6120 (11)
C3—H3A	0.9900	P1A—F1A	1.5982 (7)
C3—H3B	0.9900	P1A—F2A	1.5997 (7)
O4—C5	1.4360 (13)	P1B—F4B	1.502 (12)
C5—C6	1.5204 (16)	P1B—F3B	1.581 (13)
C5—H5A	0.9900	P1B—F5B	1.560 (6)
C5—H5B	0.9900	P1B—F1B	1.5982 (7)
C6—H6A	0.9900	P1B—F2B	1.5997 (7)
C6—H6B	0.9900	P1B—F6B	1.674 (8)
C7—N8	1.3016 (15)

C7—N1—C2	125.00 (9)	C7—N8—H8B	119.6 (11)
C7—N1—C6	120.79 (9)	H8A—N8—H8B	118.0 (15)
C2—N1—C6	112.10 (8)	F6A—P1A—F3A	90.75 (9)
N1—C2—C3	107.89 (8)	F6A—P1A—F4A	179.05 (8)
N1—C2—H2A	110.1	F3A—P1A—F4A	89.83 (10)
C3—C2—H2A	110.1	F6A—P1A—F5A	89.94 (9)
N1—C2—H2B	110.1	F3A—P1A—F5A	179.02 (8)
C3—C2—H2B	110.1	F4A—P1A—F5A	89.47 (8)
H2A—C2—H2B	108.4	F6A—P1A—F1A	89.19 (6)
O4—C3—C2	110.69 (8)	F3A—P1A—F1A	90.44 (7)
O4—C3—H3A	109.5	F4A—P1A—F1A	90.05 (6)
C2—C3—H3A	109.5	F5A—P1A—F1A	88.87 (6)
O4—C3—H3B	109.5	F6A—P1A—F2A	91.12 (6)
C2—C3—H3B	109.5	F3A—P1A—F2A	89.70 (7)
H3A—C3—H3B	108.1	F4A—P1A—F2A	89.64 (6)
C5—O4—C3	111.72 (8)	F5A—P1A—F2A	90.99 (6)
O4—C5—C6	111.22 (9)	F1A—P1A—F2A	179.66 (4)
O4—C5—H5A	109.4	F4B—P1B—F3B	91.3 (5)
C6—C5—H5A	109.4	F4B—P1B—F5B	94.2 (4)
O4—C5—H5B	109.4	F3B—P1B—F5B	174.3 (4)
C6—C5—H5B	109.4	F4B—P1B—F1B	90.9 (4)
H5A—C5—H5B	108.0	F3B—P1B—F1B	83.8 (4)
C5—C6—N1	108.02 (9)	F5B—P1B—F1B	97.6 (3)
C5—C6—H6A	110.1	F4B—P1B—F2B	88.8 (4)
N1—C6—H6A	110.1	F3B—P1B—F2B	96.3 (4)
C5—C6—H6B	110.1	F5B—P1B—F2B	82.4 (3)
N1—C6—H6B	110.1	F1B—P1B—F2B	179.66 (4)
H6A—C6—H6B	108.4	F4B—P1B—F6B	173.7 (5)
N1—C7—N8	125.98 (10)	F3B—P1B—F6B	87.0 (4)
N1—C7—H7	118.0 (8)	F5B—P1B—F6B	87.4 (4)
N8—C7—H7	116.0 (8)	F1B—P1B—F6B	94.9 (3)
C7—N8—H8A	122.4 (11)	F2B—P1B—F6B	85.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F4Aⁱ	0.99	2.62	3.183 (2)	116
C2—H2A···F4Bⁱ	0.99	2.53	3.126 (11)	119
C2—H2B···F3Aⁱⁱ	0.99	2.37	3.1290 (19)	133
C7—H7···F2Aⁱⁱⁱ	0.946 (14)	2.522 (13)	3.0711 (12)	117.1 (9)
N8—H8A···F3Aⁱⁱ	0.827 (18)	2.428 (17)	3.141 (2)	144.9 (13)
N8—H8A···F5A^iv	0.827 (18)	2.425 (16)	3.0699 (16)	135.4 (13)
N8—H8A···F3Bⁱⁱ	0.827 (18)	2.36 (2)	3.105 (12)	150.1 (14)
N8—H8A···F5B^iv	0.827 (18)	2.331 (18)	3.031 (6)	142.8 (13)
N8—H8B···O4^v	0.850 (18)	2.018 (18)	2.8572 (13)	168.8 (16)

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

Morpholinoformamidinium hexafluorophosphate (1recryst) top

Crystal data top

C₅H₁₁N₂O⁺·PF₆⁻	D_x = 1.797 Mg m⁻³
M_r = 260.13	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 9865 reflections
a = 10.4504 (14) Å	θ = 3.4–33.2°
b = 13.7170 (16) Å	µ = 0.36 mm⁻¹
c = 13.4157 (14) Å	T = 100 K
V = 1923.1 (4) Å³	Block, colourless
Z = 8	0.24 × 0.23 × 0.14 mm
F(000) = 1056

Data collection top

Bruker D8 Venture dual source diffractometer	7300 independent reflections
Radiation source: microsource	5163 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.040
φ and ω scans	θ_max = 33.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −16→16
T_min = 0.856, T_max = 0.971	k = −21→20
42268 measured reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.039P)² + 0.260P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.088	(Δ/σ)_max = 0.016
S = 1.02	Δρ_max = 0.28 e Å⁻³
7300 reflections	Δρ_min = −0.40 e Å⁻³
364 parameters	Absolute structure: Twinning involves inversion, so Flack parameter cannot be determined
154 restraints	Absolute structure parameter: 0.5
Primary atom site location: structure-invariant direct methods

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.8290 (2)	0.48239 (16)	0.57523 (16)	0.0129 (4)
C2A	0.8000 (2)	0.57601 (18)	0.6226 (2)	0.0140 (5)
H2A1	0.824879	0.630306	0.578020	0.017*
H2A2	0.848505	0.582406	0.685693	0.017*
C3A	0.6569 (2)	0.57971 (19)	0.6434 (2)	0.0151 (5)
H3A1	0.635556	0.641635	0.677442	0.018*
H3A2	0.609306	0.577543	0.579648	0.018*
O4A	0.6192 (2)	0.49898 (12)	0.70486 (17)	0.0177 (4)
C5A	0.6500 (2)	0.40691 (18)	0.6598 (2)	0.0193 (5)
H5A1	0.601492	0.399677	0.596823	0.023*
H5A2	0.624178	0.353401	0.705039	0.023*
C6A	0.7926 (3)	0.39933 (17)	0.63826 (19)	0.0193 (5)
H6A1	0.841621	0.400702	0.701372	0.023*
H6A2	0.811463	0.337321	0.603486	0.023*
C7A	0.85190 (19)	0.47015 (19)	0.47963 (18)	0.0129 (4)
H7A	0.858586	0.405015	0.456128	0.016*
N8A	0.8664 (2)	0.54034 (17)	0.41380 (18)	0.0172 (4)
H8A1	0.8612 (2)	0.5984 (15)	0.4316 (5)	0.021*
H8A2	0.8807 (4)	0.5267 (3)	0.3543 (14)	0.021*
N1B	0.3318 (4)	0.0173 (3)	0.5727 (3)	0.0140 (6)	0.639 (4)
C2B	0.2939 (4)	0.1008 (2)	0.6349 (3)	0.0194 (7)	0.639 (4)
H2B1	0.311558	0.162540	0.599144	0.023*	0.639 (4)
H2B2	0.343451	0.100825	0.697733	0.023*	0.639 (4)
C3B	0.1518 (4)	0.0928 (3)	0.6575 (3)	0.0215 (7)	0.639 (4)
H3B1	0.126171	0.146548	0.702529	0.026*	0.639 (4)
H3B2	0.102490	0.099394	0.594845	0.026*	0.639 (4)
O4B	0.1222 (3)	0.0012 (2)	0.7034 (2)	0.0191 (6)	0.639 (4)
C5B	0.1604 (5)	−0.0796 (6)	0.6432 (6)	0.0179 (10)	0.639 (4)
H5B1	0.112518	−0.078428	0.579499	0.022*	0.639 (4)
H5B2	0.139565	−0.141230	0.678005	0.022*	0.639 (4)
C6B	0.3031 (4)	−0.0758 (5)	0.6219 (5)	0.0143 (9)	0.639 (4)
H6B1	0.351804	−0.081037	0.684996	0.017*	0.639 (4)
H6B2	0.327946	−0.130785	0.578259	0.017*	0.639 (4)
C7B	0.3530 (3)	0.0287 (2)	0.4776 (2)	0.0149 (6)	0.639 (4)
H7B	0.359065	0.093865	0.454013	0.018*	0.639 (4)
N8B	0.3668 (3)	−0.0406 (2)	0.4117 (3)	0.0192 (6)	0.639 (4)
H8B1	0.3622 (3)	−0.099 (3)	0.4294 (8)	0.023*	0.639 (4)
H8B2	0.3804 (7)	−0.0264 (6)	0.352 (3)	0.023*	0.639 (4)
N1B'	0.1687 (8)	0.0176 (6)	0.6935 (6)	0.0199 (15)	0.361 (4)
C2B'	0.1990 (10)	−0.0769 (9)	0.6440 (12)	0.021 (2)	0.361 (4)
H2C3	0.154138	−0.081905	0.579227	0.025*	0.361 (4)
H2C4	0.172359	−0.132281	0.686577	0.025*	0.361 (4)
C3B'	0.3421 (9)	−0.0779 (10)	0.6288 (11)	0.022 (2)	0.361 (4)
H3C3	0.385858	−0.070707	0.693820	0.027*	0.361 (4)
H3C4	0.368428	−0.140949	0.599215	0.027*	0.361 (4)
O4B'	0.3787 (8)	0.0008 (5)	0.5636 (6)	0.0240 (15)	0.361 (4)
C5B'	0.3445 (8)	0.0923 (6)	0.6060 (7)	0.0241 (17)	0.361 (4)
H5C3	0.367287	0.144961	0.558796	0.029*	0.361 (4)
H5C4	0.394545	0.102477	0.667809	0.029*	0.361 (4)
C6B'	0.2036 (8)	0.0993 (5)	0.6303 (6)	0.0214 (16)	0.361 (4)
H6C3	0.185643	0.161482	0.665102	0.026*	0.361 (4)
H6C4	0.152664	0.097779	0.568073	0.026*	0.361 (4)
C7B'	0.1453 (6)	0.0285 (6)	0.7905 (5)	0.0185 (14)	0.361 (4)
H7B'	0.133998	0.093460	0.813339	0.022*	0.361 (4)
N8B'	0.1362 (7)	−0.0380 (5)	0.8561 (6)	0.0237 (14)	0.361 (4)
H8C3	0.145814	−0.099558	0.839021	0.028*	0.361 (4)
H8C4	0.120303	−0.022593	0.918522	0.028*	0.361 (4)
P1	1.10174 (10)	0.25140 (7)	0.38095 (4)	0.0133 (2)
F1	1.1345 (2)	0.13771 (15)	0.38914 (11)	0.0236 (5)
F2	1.0694 (2)	0.36564 (14)	0.37324 (14)	0.0266 (4)
F3	1.2054 (2)	0.26335 (12)	0.29446 (17)	0.0293 (5)
F4	1.2093 (2)	0.27439 (14)	0.46292 (18)	0.0319 (5)
F5	0.9982 (2)	0.24007 (13)	0.46808 (17)	0.0344 (5)
F6	0.9944 (2)	0.22733 (15)	0.29994 (19)	0.0364 (5)
P1A	0.60169 (10)	0.24864 (7)	0.38572 (4)	0.0148 (2)	0.876 (19)
F1A	0.5698 (2)	0.13505 (16)	0.38354 (13)	0.0355 (6)	0.876 (19)
F2A	0.6341 (2)	0.36245 (16)	0.38891 (11)	0.0230 (5)	0.876 (19)
F3A	0.7033 (5)	0.2329 (2)	0.2977 (4)	0.0302 (8)	0.876 (19)
F4A	0.7122 (4)	0.2274 (3)	0.4658 (4)	0.0308 (7)	0.876 (19)
F5A	0.5008 (5)	0.2645 (2)	0.4755 (4)	0.0295 (8)	0.876 (19)
F6A	0.4912 (5)	0.2708 (3)	0.3067 (4)	0.0333 (8)	0.876 (19)
P1B	0.60169 (10)	0.24864 (7)	0.38572 (4)	0.0148 (2)	0.124 (19)
F1B	0.5698 (2)	0.13505 (16)	0.38354 (13)	0.0355 (6)	0.124 (19)
F2B	0.6341 (2)	0.36245 (16)	0.38891 (11)	0.0230 (5)	0.124 (19)
F3B	0.723 (2)	0.2384 (16)	0.3217 (19)	0.022 (4)*	0.124 (19)
F4B	0.690 (2)	0.2428 (18)	0.4841 (18)	0.022 (4)*	0.124 (19)
F5B	0.4767 (16)	0.2571 (11)	0.4483 (16)	0.013 (3)*	0.124 (19)
F6B	0.517 (2)	0.2531 (16)	0.2880 (14)	0.018 (4)*	0.124 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0147 (9)	0.0120 (9)	0.0119 (9)	0.0017 (8)	0.0010 (8)	0.0001 (8)
C2A	0.0165 (12)	0.0132 (10)	0.0123 (10)	0.0002 (9)	−0.0010 (10)	−0.0029 (8)
C3A	0.0165 (12)	0.0139 (11)	0.0150 (11)	0.0013 (8)	0.0013 (9)	0.0003 (9)
O4A	0.0202 (9)	0.0196 (10)	0.0134 (8)	−0.0006 (7)	0.0041 (9)	0.0005 (6)
C5A	0.0232 (14)	0.0156 (12)	0.0192 (13)	−0.0044 (9)	0.0054 (9)	0.0008 (10)
C6A	0.0241 (14)	0.0143 (11)	0.0194 (13)	0.0023 (10)	0.0014 (10)	0.0061 (8)
C7A	0.0096 (9)	0.0144 (11)	0.0148 (10)	0.0003 (7)	0.0004 (7)	−0.0015 (9)
N8A	0.0219 (10)	0.0173 (10)	0.0123 (10)	−0.0012 (8)	0.0035 (9)	−0.0004 (9)
N1B	0.0179 (17)	0.0127 (13)	0.0114 (12)	−0.0012 (12)	0.0011 (13)	−0.0010 (10)
C2B	0.029 (2)	0.0117 (13)	0.0179 (17)	−0.0032 (14)	0.0032 (14)	−0.0058 (11)
C3B	0.029 (2)	0.0192 (16)	0.0169 (16)	0.0056 (14)	0.0024 (14)	−0.0024 (12)
O4B	0.0243 (17)	0.0200 (14)	0.0129 (11)	0.0027 (12)	0.0056 (12)	0.0022 (9)
C5B	0.018 (2)	0.0200 (18)	0.0155 (18)	0.000 (2)	0.009 (2)	0.0006 (13)
C6B	0.018 (2)	0.0133 (15)	0.0117 (15)	0.0008 (19)	−0.0031 (19)	0.0007 (11)
C7B	0.0128 (13)	0.0166 (13)	0.0153 (13)	0.0000 (10)	0.0009 (10)	−0.0001 (10)
N8B	0.0199 (14)	0.0193 (14)	0.0185 (14)	0.0009 (11)	0.0033 (12)	−0.0012 (11)
N1B'	0.024 (4)	0.017 (3)	0.019 (3)	−0.003 (3)	0.003 (3)	0.001 (2)
C2B'	0.028 (5)	0.011 (3)	0.024 (4)	−0.003 (4)	0.009 (5)	−0.001 (3)
C3B'	0.021 (5)	0.024 (4)	0.023 (5)	−0.002 (4)	0.001 (4)	0.002 (3)
O4B'	0.028 (4)	0.021 (3)	0.024 (3)	−0.005 (3)	0.008 (3)	−0.004 (2)
C5B'	0.030 (4)	0.023 (4)	0.020 (4)	−0.002 (3)	0.006 (3)	0.002 (3)
C6B'	0.029 (4)	0.014 (3)	0.021 (4)	0.002 (3)	0.012 (3)	0.002 (3)
C7B'	0.017 (3)	0.020 (3)	0.019 (3)	−0.003 (2)	0.001 (2)	−0.005 (3)
N8B'	0.033 (4)	0.023 (3)	0.014 (3)	−0.001 (3)	0.005 (3)	−0.001 (3)
P1	0.0120 (5)	0.0128 (4)	0.0152 (4)	0.0003 (3)	0.00030 (18)	−0.00023 (16)
F1	0.0264 (12)	0.0121 (10)	0.0323 (13)	0.0020 (9)	−0.0029 (6)	0.0027 (5)
F2	0.0299 (11)	0.0138 (9)	0.0360 (8)	0.0056 (8)	0.0105 (7)	0.0027 (6)
F3	0.0357 (12)	0.0234 (8)	0.0287 (11)	0.0025 (7)	0.0191 (9)	0.0025 (8)
F4	0.0334 (11)	0.0295 (9)	0.0328 (11)	−0.0075 (8)	−0.0162 (9)	−0.0048 (8)
F5	0.0306 (11)	0.0319 (10)	0.0408 (14)	0.0003 (9)	0.0209 (11)	0.0066 (9)
F6	0.0336 (11)	0.0311 (9)	0.0445 (14)	−0.0029 (8)	−0.0246 (11)	0.0029 (9)
P1A	0.0115 (5)	0.0135 (4)	0.0193 (6)	−0.0004 (3)	−0.00038 (17)	0.00138 (15)
F1A	0.0291 (12)	0.0153 (10)	0.0620 (16)	−0.0064 (9)	0.0038 (8)	−0.0005 (7)
F2A	0.0240 (12)	0.0152 (11)	0.0297 (12)	−0.0021 (9)	0.0008 (5)	−0.0001 (5)
F3A	0.0329 (17)	0.0286 (12)	0.0290 (16)	−0.0004 (10)	0.0151 (14)	−0.0042 (11)
F4A	0.0258 (13)	0.0334 (13)	0.0333 (16)	0.0055 (10)	−0.0139 (11)	0.0052 (12)
F5A	0.0275 (14)	0.0349 (12)	0.0262 (16)	−0.0025 (10)	0.0128 (14)	−0.0002 (11)
F6A	0.0281 (14)	0.0353 (13)	0.0366 (15)	0.0069 (11)	−0.0193 (12)	−0.0072 (12)
P1B	0.0115 (5)	0.0135 (4)	0.0193 (6)	−0.0004 (3)	−0.00038 (17)	0.00138 (15)
F1B	0.0291 (12)	0.0153 (10)	0.0620 (16)	−0.0064 (9)	0.0038 (8)	−0.0005 (7)
F2B	0.0240 (12)	0.0152 (11)	0.0297 (12)	−0.0021 (9)	0.0008 (5)	−0.0001 (5)

Geometric parameters (Å, º) top

N1A—C7A	1.315 (3)	N1B'—C7B'	1.333 (10)
N1A—C2A	1.465 (3)	N1B'—C6B'	1.452 (10)
N1A—C6A	1.469 (3)	N1B'—C2B'	1.492 (14)
C2A—C3A	1.522 (3)	C2B'—C3B'	1.509 (12)
C2A—H2A1	0.9900	C2B'—H2C3	0.9900
C2A—H2A2	0.9900	C2B'—H2C4	0.9900
C3A—O4A	1.436 (3)	C3B'—O4B'	1.442 (13)
C3A—H3A1	0.9900	C3B'—H3C3	0.9900
C3A—H3A2	0.9900	C3B'—H3C4	0.9900
O4A—C5A	1.437 (3)	O4B'—C5B'	1.424 (10)
C5A—C6A	1.521 (3)	C5B'—C6B'	1.511 (10)
C5A—H5A1	0.9900	C5B'—H5C3	0.9900
C5A—H5A2	0.9900	C5B'—H5C4	0.9900
C6A—H6A1	0.9900	C6B'—H6C3	0.9900
C6A—H6A2	0.9900	C6B'—H6C4	0.9900
C7A—N8A	1.315 (3)	C7B'—N8B'	1.271 (10)
C7A—H7A	0.9500	C7B'—H7B'	0.9500
N8A—H8A1	0.83 (2)	N8B'—H8C3	0.8800
N8A—H8A2	0.83 (2)	N8B'—H8C4	0.8800
N1B—C7B	1.304 (5)	P1—F3	1.596 (2)
N1B—C6B	1.468 (7)	P1—F6	1.596 (2)
N1B—C2B	1.472 (5)	P1—F1	1.600 (2)
C2B—C3B	1.519 (6)	P1—F5	1.601 (2)
C2B—H2B1	0.9900	P1—F4	1.604 (2)
C2B—H2B2	0.9900	P1—F2	1.606 (2)
C3B—O4B	1.433 (5)	P1A—F6A	1.597 (3)
C3B—H3B1	0.9900	P1A—F1A	1.594 (2)
C3B—H3B2	0.9900	P1A—F3A	1.602 (3)
O4B—C5B	1.428 (8)	P1A—F2A	1.598 (2)
C5B—C6B	1.519 (7)	P1A—F4A	1.604 (3)
C5B—H5B1	0.9900	P1A—F5A	1.615 (3)
C5B—H5B2	0.9900	P1B—F4B	1.61 (2)
C6B—H6B1	0.9900	P1B—F3B	1.54 (2)
C6B—H6B2	0.9900	P1B—F5B	1.558 (15)
C7B—N8B	1.306 (4)	P1B—F6B	1.583 (18)
C7B—H7B	0.9500	P1B—F1B	1.594 (2)
N8B—H8B1	0.84 (4)	P1B—F2B	1.598 (2)
N8B—H8B2	0.84 (4)

C7A—N1A—C2A	124.9 (2)	N1B'—C2B'—H2C4	110.5
C7A—N1A—C6A	120.6 (2)	C3B'—C2B'—H2C4	110.5
C2A—N1A—C6A	112.1 (2)	H2C3—C2B'—H2C4	108.7
N1A—C2A—C3A	108.1 (2)	O4B'—C3B'—C2B'	109.8 (9)
N1A—C2A—H2A1	110.1	O4B'—C3B'—H3C3	109.7
C3A—C2A—H2A1	110.1	C2B'—C3B'—H3C3	109.7
N1A—C2A—H2A2	110.1	O4B'—C3B'—H3C4	109.7
C3A—C2A—H2A2	110.1	C2B'—C3B'—H3C4	109.7
H2A1—C2A—H2A2	108.4	H3C3—C3B'—H3C4	108.2
O4A—C3A—C2A	110.4 (2)	C5B'—O4B'—C3B'	110.5 (9)
O4A—C3A—H3A1	109.6	O4B'—C5B'—C6B'	112.8 (7)
C2A—C3A—H3A1	109.6	O4B'—C5B'—H5C3	109.0
O4A—C3A—H3A2	109.6	C6B'—C5B'—H5C3	109.0
C2A—C3A—H3A2	109.6	O4B'—C5B'—H5C4	109.0
H3A1—C3A—H3A2	108.1	C6B'—C5B'—H5C4	109.0
C3A—O4A—C5A	112.0 (2)	H5C3—C5B'—H5C4	107.8
O4A—C5A—C6A	111.1 (2)	N1B'—C6B'—C5B'	108.7 (7)
O4A—C5A—H5A1	109.4	N1B'—C6B'—H6C3	109.9
C6A—C5A—H5A1	109.4	C5B'—C6B'—H6C3	109.9
O4A—C5A—H5A2	109.4	N1B'—C6B'—H6C4	109.9
C6A—C5A—H5A2	109.4	C5B'—C6B'—H6C4	109.9
H5A1—C5A—H5A2	108.0	H6C3—C6B'—H6C4	108.3
N1A—C6A—C5A	108.1 (2)	N8B'—C7B'—N1B'	127.6 (8)
N1A—C6A—H6A1	110.1	N8B'—C7B'—H7B'	116.2
C5A—C6A—H6A1	110.1	N1B'—C7B'—H7B'	116.2
N1A—C6A—H6A2	110.1	C7B'—N8B'—H8C3	120.0
C5A—C6A—H6A2	110.1	C7B'—N8B'—H8C4	120.0
H6A1—C6A—H6A2	108.4	H8C3—N8B'—H8C4	120.0
N8A—C7A—N1A	125.6 (2)	F3—P1—F6	90.19 (14)
N8A—C7A—H7A	117.2	F3—P1—F1	90.29 (10)
N1A—C7A—H7A	117.2	F6—P1—F1	89.73 (11)
C7A—N8A—H8A1	120.0	F3—P1—F5	179.60 (14)
C7A—N8A—H8A2	120.0	F6—P1—F5	90.11 (17)
H8A1—N8A—H8A2	120.0	F1—P1—F5	89.99 (11)
C7B—N1B—C6B	125.4 (4)	F3—P1—F4	90.14 (15)
C7B—N1B—C2B	120.4 (3)	F6—P1—F4	179.35 (13)
C6B—N1B—C2B	111.5 (4)	F1—P1—F4	89.70 (11)
N1B—C2B—C3B	108.7 (3)	F5—P1—F4	89.57 (13)
N1B—C2B—H2B1	110.0	F3—P1—F2	89.75 (10)
C3B—C2B—H2B1	110.0	F6—P1—F2	90.58 (12)
N1B—C2B—H2B2	110.0	F1—P1—F2	179.68 (14)
C3B—C2B—H2B2	110.0	F5—P1—F2	89.97 (10)
H2B1—C2B—H2B2	108.3	F4—P1—F2	89.99 (12)
O4B—C3B—C2B	111.1 (3)	F6A—P1A—F1A	91.31 (16)
O4B—C3B—H3B1	109.4	F6A—P1A—F3A	90.92 (18)
C2B—C3B—H3B1	109.4	F1A—P1A—F3A	89.64 (15)
O4B—C3B—H3B2	109.4	F6A—P1A—F2A	89.14 (15)
C2B—C3B—H3B2	109.4	F1A—P1A—F2A	179.49 (12)
H3B1—C3B—H3B2	108.0	F3A—P1A—F2A	90.60 (15)
C5B—O4B—C3B	112.2 (4)	F6A—P1A—F4A	179.36 (17)
O4B—C5B—C6B	110.7 (5)	F1A—P1A—F4A	89.15 (16)
O4B—C5B—H5B1	109.5	F3A—P1A—F4A	89.5 (2)
C6B—C5B—H5B1	109.5	F2A—P1A—F4A	90.40 (16)
O4B—C5B—H5B2	109.5	F6A—P1A—F5A	89.85 (18)
C6B—C5B—H5B2	109.5	F1A—P1A—F5A	90.47 (15)
H5B1—C5B—H5B2	108.1	F3A—P1A—F5A	179.22 (18)
N1B—C6B—C5B	108.4 (4)	F2A—P1A—F5A	89.28 (15)
N1B—C6B—H6B1	110.0	F4A—P1A—F5A	89.69 (16)
C5B—C6B—H6B1	110.0	F4B—P1B—F3B	88.9 (10)
N1B—C6B—H6B2	110.0	F4B—P1B—F5B	92.3 (9)
C5B—C6B—H6B2	110.0	F3B—P1B—F5B	178.4 (8)
H6B1—C6B—H6B2	108.4	F4B—P1B—F6B	178.9 (9)
N1B—C7B—N8B	126.4 (3)	F3B—P1B—F6B	90.2 (9)
N1B—C7B—H7B	116.8	F5B—P1B—F6B	88.6 (7)
N8B—C7B—H7B	116.8	F4B—P1B—F1B	94.9 (9)
C7B—N8B—H8B1	120.0	F3B—P1B—F1B	94.2 (8)
C7B—N8B—H8B2	120.0	F5B—P1B—F1B	84.7 (6)
H8B1—N8B—H8B2	120.0	F6B—P1B—F1B	84.6 (7)
C7B'—N1B'—C6B'	122.1 (8)	F4B—P1B—F2B	84.6 (8)
C7B'—N1B'—C2B'	124.8 (10)	F3B—P1B—F2B	85.9 (8)
C6B'—N1B'—C2B'	111.0 (8)	F5B—P1B—F2B	95.2 (6)
N1B'—C2B'—C3B'	106.2 (9)	F6B—P1B—F2B	95.9 (7)
N1B'—C2B'—H2C3	110.5	F1B—P1B—F2B	179.49 (12)
C3B'—C2B'—H2C3	110.5

C7A—N1A—C2A—C3A	103.6 (3)	C7B—N1B—C6B—C5B	−102.8 (6)
C6A—N1A—C2A—C3A	−59.2 (3)	C2B—N1B—C6B—C5B	58.6 (6)
N1A—C2A—C3A—O4A	57.4 (3)	O4B—C5B—C6B—N1B	−57.7 (7)
C2A—C3A—O4A—C5A	−58.2 (3)	C6B—N1B—C7B—N8B	−8.3 (6)
C3A—O4A—C5A—C6A	57.9 (3)	C2B—N1B—C7B—N8B	−168.2 (3)
C7A—N1A—C6A—C5A	−105.2 (3)	C7B'—N1B'—C2B'—C3B'	−101.5 (12)
C2A—N1A—C6A—C5A	58.4 (3)	C6B'—N1B'—C2B'—C3B'	62.1 (13)
O4A—C5A—C6A—N1A	−56.3 (3)	N1B'—C2B'—C3B'—O4B'	−62.4 (14)
C2A—N1A—C7A—N8A	7.9 (4)	C2B'—C3B'—O4B'—C5B'	60.8 (13)
C6A—N1A—C7A—N8A	169.3 (2)	C3B'—O4B'—C5B'—C6B'	−56.5 (10)
C7B—N1B—C2B—C3B	104.8 (4)	C7B'—N1B'—C6B'—C5B'	106.4 (9)
C6B—N1B—C2B—C3B	−57.8 (4)	C2B'—N1B'—C6B'—C5B'	−57.7 (10)
N1B—C2B—C3B—O4B	55.8 (4)	O4B'—C5B'—C6B'—N1B'	54.5 (10)
C2B—C3B—O4B—C5B	−57.4 (5)	C6B'—N1B'—C7B'—N8B'	−166.6 (8)
C3B—O4B—C5B—C6B	58.3 (7)	C2B'—N1B'—C7B'—N8B'	−4.9 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2A1···F4ⁱ	0.99	2.36	3.115 (3)	133
C2A—H2A2···F3ⁱⁱ	0.99	2.63	3.189 (3)	116
C6A—H6A2···F4B	0.99	2.42	3.17 (2)	132
C7A—H7A···F2	0.95	2.53	3.043 (3)	114
N8A—H8A1···F4ⁱ	0.83	2.40	3.096 (3)	142
N8A—H8A1···F5Aⁱⁱⁱ	0.83	2.45	3.135 (4)	140
N8A—H8A1···F5Bⁱⁱⁱ	0.83	2.33	3.043 (15)	144
N8A—H8A2···O4A^iv	0.83	2.04	2.864 (3)	169
N8B—H8B1···F5^v	0.84	2.45	3.153 (4)	141
N8B—H8B2···O4B^vi	0.84	2.02	2.855 (5)	169
N8B′—H8C3···F6^vii	0.88	2.34	3.028 (8)	135
N8B′—H8C4···O4B′^viii	0.88	1.97	2.839 (12)	168

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

Pyrrolidinoformamidinium hexafluorophosphate (2) top

Crystal data top

C₅H₁₁N₂⁺·PF₆⁻	F(000) = 992
M_r = 244.13	D_x = 1.733 Mg m⁻³
Monoclinic, Cc	Cu Kα radiation, λ = 1.54178 Å
a = 12.3588 (3) Å	Cell parameters from 9886 reflections
b = 12.7942 (3) Å	θ = 3.7–74.5°
c = 12.2759 (3) Å	µ = 3.28 mm⁻¹
β = 105.400 (1)°	T = 130 K
V = 1871.38 (8) Å³	Block, colourless
Z = 8	0.21 × 0.21 × 0.11 mm

Data collection top

Bruker D8 with PHOTON III area detector diffractometer	3450 reflections with I > 2σ(I)
Radiation source: microfocus	R_int = 0.035
φ and ω shutterless scans	θ_max = 74.6°, θ_min = 5.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −15→14
T_min = 0.639, T_max = 0.754	k = −15→15
17935 measured reflections	l = −15→15
3467 independent reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.085P)² + 2.020P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.049	(Δ/σ)_max = 0.004
wR(F²) = 0.135	Δρ_max = 0.37 e Å⁻³
S = 1.07	Δρ_min = −0.35 e Å⁻³
3467 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
257 parameters	Extinction coefficient: 0.0014 (4)
2 restraints	Absolute structure: Refined as an inversion twin
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.49 (4)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
N1	0.3206 (4)	0.7280 (3)	0.7550 (3)	0.0306 (9)
C2	0.3205 (5)	0.8419 (4)	0.7666 (5)	0.0359 (11)
H2A	0.291759	0.876189	0.692152	0.054*
H2B	0.396755	0.868571	0.802754	0.054*
C3	0.2414 (5)	0.8601 (4)	0.8420 (4)	0.0397 (11)
H3A	0.283785	0.863514	0.922572	0.059*
H3B	0.198412	0.925707	0.821178	0.059*
C4	0.1646 (4)	0.7661 (4)	0.8193 (4)	0.0358 (9)
H4A	0.105798	0.773984	0.747162	0.054*
H4B	0.128245	0.755416	0.881246	0.054*
C5	0.2435 (4)	0.6762 (4)	0.8132 (4)	0.0337 (10)
H5A	0.284091	0.651192	0.889404	0.050*
H5B	0.202882	0.617023	0.768457	0.050*
C6	0.3770 (4)	0.6777 (4)	0.6965 (4)	0.0347 (10)
H6	0.370295	0.603790	0.691284	0.042*
N7	0.4439 (4)	0.7258 (3)	0.6435 (4)	0.0409 (10)
H7A	0.4509 (6)	0.792 (4)	0.6473 (4)	0.049*
H7B	0.480 (2)	0.690 (2)	0.606 (2)	0.049*
N11	0.7698 (3)	0.2303 (3)	0.3159 (3)	0.0252 (7)
C12	0.7633 (4)	0.3449 (4)	0.2985 (4)	0.0321 (10)
H12A	0.793006	0.382648	0.370603	0.048*
H12B	0.684995	0.367475	0.264147	0.048*
C13	0.8362 (4)	0.3633 (4)	0.2184 (4)	0.0374 (11)
H13A	0.805789	0.420775	0.165124	0.056*
H13B	0.914031	0.380689	0.260727	0.056*
C14	0.8322 (4)	0.2588 (4)	0.1552 (4)	0.0349 (9)
H14A	0.761520	0.251673	0.094543	0.052*
H14B	0.896670	0.251823	0.122180	0.052*
C15	0.8383 (4)	0.1797 (4)	0.2476 (4)	0.0340 (10)
H15A	0.805607	0.111878	0.216390	0.051*
H15B	0.916660	0.168610	0.292739	0.051*
C16	0.7173 (4)	0.1803 (4)	0.3774 (4)	0.0314 (10)
H16	0.722967	0.106294	0.380722	0.038*
N17	0.6562 (4)	0.2270 (3)	0.4358 (4)	0.0385 (9)
H17A	0.6505 (5)	0.289 (4)	0.4342 (4)	0.046*
H17B	0.6253 (18)	0.194 (2)	0.473 (2)	0.046*
P1	0.52748 (8)	0.48090 (9)	0.50675 (8)	0.0281 (3)
F1	0.5597 (3)	0.6020 (2)	0.5039 (3)	0.0491 (8)
F2	0.4952 (3)	0.3602 (2)	0.5089 (3)	0.0473 (8)
F3	0.5479 (6)	0.4896 (4)	0.6384 (4)	0.0758 (15)
F4	0.6561 (3)	0.4490 (3)	0.5209 (4)	0.0666 (11)
F5	0.5090 (5)	0.4728 (3)	0.3746 (4)	0.0730 (14)
F6	0.4008 (3)	0.5132 (3)	0.4886 (5)	0.0678 (13)
P2	0.55335 (8)	0.97931 (9)	0.55060 (8)	0.0294 (3)
F1A	0.5774 (4)	0.9564 (4)	0.6830 (3)	0.0566 (9)
F2A	0.5294 (5)	1.0049 (3)	0.4195 (3)	0.0607 (11)
F3A	0.4242 (3)	0.9567 (3)	0.5382 (3)	0.0530 (9)
F4A	0.5735 (4)	0.8594 (3)	0.5287 (4)	0.0611 (11)
F5A	0.6830 (3)	1.0047 (3)	0.5650 (4)	0.0552 (10)
F6A	0.5350 (3)	1.1002 (2)	0.5742 (3)	0.0440 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0326 (19)	0.032 (2)	0.0275 (17)	0.0026 (15)	0.0078 (14)	−0.0001 (14)
C2	0.044 (3)	0.025 (2)	0.041 (2)	−0.0009 (18)	0.017 (2)	0.0006 (18)
C3	0.051 (3)	0.037 (2)	0.039 (2)	0.004 (2)	0.025 (2)	0.002 (2)
C4	0.032 (2)	0.043 (2)	0.0352 (19)	0.0038 (18)	0.0133 (16)	0.0034 (18)
C5	0.040 (3)	0.033 (2)	0.029 (2)	−0.001 (2)	0.0112 (19)	0.0001 (18)
C6	0.036 (2)	0.032 (2)	0.037 (2)	0.0017 (17)	0.0116 (19)	0.0001 (17)
N7	0.046 (2)	0.038 (2)	0.048 (2)	0.0020 (17)	0.0283 (18)	−0.0008 (17)
N11	0.0262 (17)	0.0227 (19)	0.0269 (15)	0.0001 (13)	0.0071 (13)	−0.0027 (13)
C12	0.037 (2)	0.023 (2)	0.037 (2)	−0.0015 (17)	0.013 (2)	0.0007 (17)
C13	0.043 (3)	0.027 (2)	0.043 (3)	−0.003 (2)	0.013 (2)	0.003 (2)
C14	0.035 (2)	0.040 (2)	0.0323 (19)	−0.0024 (17)	0.0131 (16)	−0.0027 (17)
C15	0.034 (2)	0.027 (2)	0.043 (3)	0.0035 (18)	0.013 (2)	−0.0013 (19)
C16	0.035 (2)	0.0262 (19)	0.032 (2)	0.0009 (17)	0.0079 (17)	0.0040 (16)
N17	0.045 (2)	0.035 (2)	0.044 (2)	0.0030 (16)	0.0280 (18)	0.0047 (16)
P1	0.0305 (6)	0.0272 (5)	0.0297 (6)	−0.0008 (4)	0.0135 (4)	−0.0002 (4)
F1	0.066 (2)	0.0324 (14)	0.0631 (19)	−0.0144 (15)	0.0411 (17)	−0.0115 (15)
F2	0.0448 (16)	0.0285 (14)	0.075 (2)	0.0023 (12)	0.0280 (15)	0.0067 (13)
F3	0.125 (5)	0.073 (3)	0.033 (2)	0.002 (3)	0.027 (2)	0.0007 (15)
F4	0.0359 (18)	0.054 (2)	0.112 (3)	−0.0018 (17)	0.0221 (19)	−0.021 (2)
F5	0.131 (4)	0.055 (2)	0.036 (2)	−0.010 (2)	0.028 (2)	−0.0084 (15)
F6	0.0331 (19)	0.0443 (19)	0.124 (4)	0.0071 (14)	0.018 (2)	−0.002 (2)
P2	0.0316 (6)	0.0291 (6)	0.0310 (6)	0.0036 (4)	0.0144 (4)	0.0005 (4)
F1A	0.066 (2)	0.068 (2)	0.0366 (17)	−0.0045 (19)	0.0160 (15)	0.0150 (16)
F2A	0.092 (3)	0.062 (2)	0.0289 (18)	−0.004 (2)	0.0164 (18)	0.0007 (14)
F3A	0.0310 (17)	0.0565 (19)	0.072 (2)	−0.0083 (15)	0.0144 (15)	−0.0127 (17)
F4A	0.089 (3)	0.0304 (15)	0.087 (3)	0.0103 (17)	0.064 (2)	−0.0006 (16)
F5A	0.0379 (19)	0.061 (2)	0.075 (3)	0.0070 (16)	0.0291 (18)	0.0190 (18)
F6A	0.0541 (18)	0.0309 (13)	0.0541 (17)	0.0011 (13)	0.0269 (13)	−0.0058 (13)

Geometric parameters (Å, º) top

N1—C6	1.296 (7)	C13—C14	1.540 (7)
N1—C5	1.490 (7)	C13—H13A	0.9900
N1—C2	1.465 (5)	C13—H13B	0.9900
C2—C3	1.531 (7)	C14—C15	1.506 (7)
C2—H2A	0.9900	C14—H14A	0.9900
C2—H2B	0.9900	C14—H14B	0.9900
C3—C4	1.512 (7)	C15—H15A	0.9900
C3—H3A	0.9900	C15—H15B	0.9900
C3—H3B	0.9900	C16—N17	1.315 (6)
C4—C5	1.523 (6)	C16—H16	0.9500
C4—H4A	0.9900	N17—H17A	0.79 (5)
C4—H4B	0.9900	N17—H17B	0.79 (5)
C5—H5A	0.9900	P1—F5	1.580 (4)
C5—H5B	0.9900	P1—F3	1.572 (4)
C6—N7	1.331 (7)	P1—F6	1.576 (4)
C6—H6	0.9500	P1—F2	1.597 (3)
N7—H7A	0.86 (5)	P1—F4	1.606 (4)
N7—H7B	0.86 (5)	P1—F1	1.602 (3)
N11—C16	1.289 (6)	P2—F3A	1.589 (3)
N11—C12	1.481 (5)	P2—F2A	1.591 (4)
N11—C15	1.489 (6)	P2—F5A	1.598 (4)
C12—C13	1.517 (7)	P2—F1A	1.600 (3)
C12—H12A	0.9900	P2—F4A	1.588 (3)
C12—H12B	0.9900	P2—F6A	1.601 (3)

C6—N1—C5	123.5 (4)	C15—C14—C13	102.5 (4)
C6—N1—C2	124.2 (5)	C15—C14—H14A	111.3
C5—N1—C2	112.2 (4)	C13—C14—H14A	111.3
N1—C2—C3	103.1 (4)	C15—C14—H14B	111.3
N1—C2—H2A	111.1	C13—C14—H14B	111.3
C3—C2—H2A	111.1	H14A—C14—H14B	109.2
N1—C2—H2B	111.1	N11—C15—C14	102.1 (4)
C3—C2—H2B	111.1	N11—C15—H15A	111.4
H2A—C2—H2B	109.1	C14—C15—H15A	111.4
C4—C3—C2	103.8 (4)	N11—C15—H15B	111.4
C4—C3—H3A	111.0	C14—C15—H15B	111.4
C2—C3—H3A	111.0	H15A—C15—H15B	109.2
C4—C3—H3B	111.0	N11—C16—N17	123.1 (5)
C2—C3—H3B	111.0	N11—C16—H16	118.5
H3A—C3—H3B	109.0	N17—C16—H16	118.5
C3—C4—C5	103.3 (4)	C16—N17—H17A	120.0
C3—C4—H4A	111.1	C16—N17—H17B	120.0
C5—C4—H4A	111.1	H17A—N17—H17B	120.0
C3—C4—H4B	111.1	F5—P1—F3	179.1 (4)
C5—C4—H4B	111.1	F5—P1—F6	90.3 (3)
H4A—C4—H4B	109.1	F3—P1—F6	90.5 (3)
N1—C5—C4	100.8 (4)	F5—P1—F2	89.2 (2)
N1—C5—H5A	111.6	F3—P1—F2	91.4 (2)
C4—C5—H5A	111.6	F6—P1—F2	90.73 (19)
N1—C5—H5B	111.6	F5—P1—F4	87.9 (3)
C4—C5—H5B	111.6	F3—P1—F4	91.3 (3)
H5A—C5—H5B	109.4	F6—P1—F4	178.1 (3)
N1—C6—N7	122.4 (5)	F2—P1—F4	89.8 (2)
N1—C6—H6	118.8	F5—P1—F1	90.5 (2)
N7—C6—H6	118.8	F3—P1—F1	88.9 (2)
C6—N7—H7A	120.0	F6—P1—F1	89.2 (2)
C6—N7—H7B	120.0	F2—P1—F1	179.7 (2)
H7A—N7—H7B	120.0	F4—P1—F1	90.2 (2)
C16—N11—C12	124.0 (4)	F3A—P2—F2A	91.6 (3)
C16—N11—C15	124.4 (4)	F3A—P2—F5A	178.5 (2)
C12—N11—C15	111.5 (4)	F2A—P2—F5A	88.9 (3)
N11—C12—C13	103.2 (4)	F3A—P2—F1A	88.5 (2)
N11—C12—H12A	111.1	F2A—P2—F1A	178.7 (3)
C13—C12—H12A	111.1	F5A—P2—F1A	90.8 (2)
N11—C12—H12B	111.1	F3A—P2—F4A	90.4 (2)
C13—C12—H12B	111.1	F2A—P2—F4A	91.3 (2)
H12A—C12—H12B	109.1	F5A—P2—F4A	91.0 (2)
C14—C13—C12	104.3 (4)	F1A—P2—F4A	90.0 (2)
C14—C13—H13A	110.9	F3A—P2—F6A	90.4 (2)
C12—C13—H13A	110.9	F2A—P2—F6A	89.3 (2)
C14—C13—H13B	110.9	F5A—P2—F6A	88.3 (2)
C12—C13—H13B	110.9	F1A—P2—F6A	89.4 (2)
H13A—C13—H13B	108.9	F4A—P2—F6A	179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7B···F1	0.86	2.11	2.966 (5)	177
N7—H7A···F3A	0.86	2.47	3.207 (6)	145
N7—H7A···F4A	0.86	2.51	2.945 (6)	112
C16—H16···F6ⁱ	0.95	2.54	3.153 (6)	122
N17—H17A···F2	0.79	2.51	2.935 (5)	115
N17—H17A···F4	0.79	2.30	3.026 (6)	152
N17—H17B···F6Aⁱⁱ	0.79	2.23	3.019 (5)	179

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

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

Crystal structures of two formamidinium hexa­fluorido­phosphate salts, one with batch-dependent disorder

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structures of two formamidinium hexafluoridophosphate salts, one with batch-dependent disorder