Crystal structure of 1,4,8,11-tetra­azonia­cyclo­tetra­decane bis­(dichromate) monohydrate from synchrotron data

Moon, D.; Choi, J.-H.

doi:10.1107/S2056989017005771

Crystal structure of 1,4,8,11-tetraazoniacyclotetradecane bis(dichromate) monohydrate from synchrotron data

In the title hydrated salt, (C₁₀H₂₈N₄)⁴⁺·2[Cr₂O₇]²⁻·H₂O, the two unique cations lie about an inversion centre. In the crystal, O—H

O and N—H

O hydrogen bonds connect the anions, cations and water molecule, forming a three-dimensional network

Keywords: crystal structure; 1,4,8,11-tetraazoniacyclotetradecane; dichromate anion; hydrogen bonding; synchrotron radiation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989017005771/wm5385sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989017005771/wm5385Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989017005771/wm5385Isup3.cml Supplementary material

CCDC reference: 1534082

checkCIF report

Key indicators

Single-crystal synchrotron study
T = 200 K
Mean (C-C) = 0.003 Å
R factor = 0.038
wR factor = 0.124
Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2C    --  C5C     ..        8.8 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2D    --  C5D     ..        7.9 s.u.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H5D2   ..  H1O1    ..       1.93 Ang.

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.12 Report
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       2.21 eA-3
PLAT213_ALERT_2_C Atom C3C             has ADP max/min Ratio .....        3.1 prolat
PLAT223_ALERT_4_C Solv./Anion Resd 5   H   Ueq(max)/Ueq(min) Range        4.5 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2D    --  C4D     ..        5.5 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       Cr2B Check
PLAT420_ALERT_2_C D-H Without Acceptor       N1C    --  H2NC   ...     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2C    --  H3NC   ...     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2D    --  H4ND   ...     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3NC   ..  O6A     ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4ND   ..  O2B     ..       2.65 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note
PLAT971_ALERT_2_C Check Calcd Residual Density  0.75A From    Cr1B       1.99 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density  0.98A From     O1W       0.43 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H3C2      -0.34 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H5C1      -0.33 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H5D1      -0.36 eA-3

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          3 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          8 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          1 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1A    ..  C3C     ..       2.74 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1W    ..  C5D     ..       2.79 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3A    ..  C3C     ..       2.77 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3B    ..  C5C     ..       2.80 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4B    ..  C5C     ..       2.84 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O6B    ..  C5D     ..       2.75 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         30 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  25 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
   6 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 & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

1,4,8,11-Tetraazoniacyclotetradecane bis(dichromate) monohydrate top

Crystal data top

(C₁₀H₂₈N₄)[Cr₂O₇]₂·H₂O	F(000) = 1336
M_r = 654.38	D_x = 1.934 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.610 Å
a = 10.428 (2) Å	Cell parameters from 70448 reflections
b = 13.961 (2) Å	θ = 0.4–33.7°
c = 15.490 (2) Å	µ = 1.28 mm⁻¹
β = 94.671 (3)°	T = 200 K
V = 2247.6 (6) Å³	Block, yellow
Z = 4	0.11 × 0.10 × 0.09 mm

Data collection top

ADSC Q210 CCD area detector diffractometer	5804 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnet	R_int = 0.016
ω scan	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: empirical (using intensity measurements) (HKL3000sm Scalepack; Otwinowski & Minor, 1997)	h = −14→14
T_min = 0.942, T_max = 1.000	k = −19→19
12953 measured reflections	l = −21→21
6614 independent reflections

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)] = 0.038	w = 1/[σ²(F_o²) + (0.0712P)² + 4.2149P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.124	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 2.21 e Å⁻³
6614 reflections	Δρ_min = −1.04 e Å⁻³
307 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0096 (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
Cr1A	0.94583 (4)	0.25171 (3)	0.36481 (2)	0.00893 (10)
Cr2A	0.97052 (4)	0.12932 (3)	0.18519 (2)	0.01054 (10)
O1A	0.94853 (19)	0.23337 (12)	0.25072 (11)	0.0152 (3)
O2A	0.9464 (2)	0.16272 (14)	0.08541 (12)	0.0215 (4)
O3A	0.8720 (2)	0.04430 (14)	0.20636 (13)	0.0198 (4)
O4A	1.1160 (2)	0.09255 (16)	0.20477 (14)	0.0239 (4)
O5A	1.05842 (18)	0.18684 (14)	0.41408 (13)	0.0198 (4)
O6A	0.80867 (18)	0.22499 (15)	0.39940 (13)	0.0207 (4)
O7A	0.9714 (2)	0.36520 (13)	0.37925 (12)	0.0189 (4)
Cr1B	0.49741 (4)	0.58036 (3)	0.18882 (2)	0.01299 (10)
Cr2B	0.45749 (4)	0.72591 (3)	0.35345 (2)	0.01274 (10)
O1B	0.5392 (2)	0.66545 (16)	0.27369 (13)	0.0226 (4)
O2B	0.3859 (2)	0.51137 (17)	0.21811 (15)	0.0283 (5)
O3B	0.6245 (2)	0.51689 (16)	0.17659 (13)	0.0244 (4)
O4B	0.4512 (2)	0.63565 (15)	0.09915 (13)	0.0225 (4)
O5B	0.5562 (3)	0.8034 (2)	0.39672 (19)	0.0485 (8)
O6B	0.4180 (2)	0.65172 (15)	0.42912 (13)	0.0222 (4)
O7B	0.3338 (3)	0.7803 (2)	0.31136 (17)	0.0442 (7)
N1C	1.1608 (2)	0.48518 (17)	0.07746 (16)	0.0207 (4)
H1NC	1.192696	0.527486	0.118455	0.025*
H2NC	1.084404	0.508441	0.053719	0.025*
N2C	0.8491 (2)	0.38005 (16)	0.07391 (15)	0.0179 (4)
H3NC	0.905802	0.373982	0.032598	0.021*
H4NC	0.829751	0.320363	0.092561	0.021*
C1C	1.2545 (2)	0.47649 (17)	0.00725 (15)	0.0133 (4)
H1C1	1.338852	0.453735	0.033274	0.016*
H1C2	1.221515	0.428903	−0.036475	0.016*
C2C	1.1387 (2)	0.38925 (17)	0.11984 (15)	0.0129 (4)
H2C1	1.110865	0.341470	0.074936	0.016*
H2C2	1.219961	0.366488	0.150578	0.016*
C3C	1.0374 (2)	0.39918 (15)	0.18280 (12)	0.0071 (3)
H3C1	1.022978	0.335164	0.207745	0.008*
H3C2	1.072279	0.440867	0.230818	0.008*
C4C	0.9100 (2)	0.43839 (17)	0.14937 (15)	0.0125 (4)
H4C1	0.920930	0.505402	0.130394	0.015*
H4C2	0.851635	0.438789	0.196698	0.015*
C5C	0.72907 (19)	0.42821 (15)	0.03596 (13)	0.0068 (3)
H5C1	0.671037	0.437307	0.082792	0.008*
H5C2	0.685296	0.384273	−0.007113	0.008*
N1D	0.74042 (19)	0.43291 (15)	0.45783 (13)	0.0124 (4)
H1ND	0.797863	0.387321	0.444322	0.015*
H2ND	0.694753	0.408892	0.500537	0.015*
N2D	0.6336 (2)	0.57400 (17)	0.58080 (16)	0.0213 (5)
H3ND	0.589300	0.521117	0.561168	0.026*
H4ND	0.676852	0.559214	0.632478	0.026*
C1D	0.5652 (2)	0.36748 (17)	0.35112 (15)	0.0139 (4)
H1D1	0.527317	0.380206	0.291539	0.017*
H1D2	0.619964	0.309743	0.348804	0.017*
C2D	0.6505 (2)	0.45172 (18)	0.38007 (15)	0.0131 (4)
H2D1	0.701386	0.470585	0.331598	0.016*
H2D2	0.594811	0.506624	0.392587	0.016*
C3D	0.8139 (2)	0.52031 (18)	0.49225 (16)	0.0144 (4)
H3D1	0.870329	0.542564	0.447912	0.017*
H3D2	0.869859	0.501556	0.544205	0.017*
C4D	0.7290 (2)	0.60301 (18)	0.51601 (16)	0.0142 (4)
H4D1	0.680965	0.627588	0.462816	0.017*
H4D2	0.783948	0.655524	0.541016	0.017*
C5D	0.5418 (2)	0.65411 (15)	0.59291 (14)	0.0084 (4)
H5D1	0.503368	0.674117	0.535164	0.010*
H5D2	0.591171	0.709254	0.618333	0.010*
O1W	0.7376 (2)	0.75592 (18)	0.19670 (18)	0.0313 (5)
H1O1	0.749 (13)	0.723 (5)	0.152 (4)	0.30 (8)*
H2O1	0.708 (5)	0.718 (3)	0.232 (3)	0.066 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1A	0.01239 (17)	0.00745 (17)	0.00736 (17)	0.00232 (12)	0.00323 (12)	0.00134 (12)
Cr2A	0.01754 (19)	0.00764 (17)	0.00646 (17)	0.00091 (13)	0.00113 (12)	−0.00038 (12)
O1A	0.0271 (9)	0.0096 (7)	0.0094 (7)	0.0002 (7)	0.0048 (6)	−0.0016 (6)
O2A	0.0375 (11)	0.0171 (9)	0.0098 (8)	0.0022 (8)	0.0012 (7)	0.0016 (7)
O3A	0.0267 (10)	0.0128 (8)	0.0197 (9)	−0.0043 (7)	−0.0002 (7)	0.0030 (7)
O4A	0.0219 (9)	0.0260 (10)	0.0238 (10)	0.0072 (8)	0.0012 (8)	−0.0015 (8)
O5A	0.0186 (9)	0.0214 (9)	0.0194 (9)	0.0085 (7)	0.0013 (7)	0.0053 (7)
O6A	0.0161 (8)	0.0260 (10)	0.0209 (9)	0.0013 (7)	0.0059 (7)	0.0078 (8)
O7A	0.0306 (10)	0.0104 (8)	0.0159 (8)	0.0000 (7)	0.0036 (7)	−0.0028 (6)
Cr1B	0.01447 (19)	0.01425 (19)	0.01028 (18)	0.00271 (13)	0.00115 (13)	−0.00104 (13)
Cr2B	0.0189 (2)	0.01113 (18)	0.00895 (17)	0.00155 (13)	0.00592 (13)	0.00160 (13)
O1B	0.0241 (9)	0.0264 (10)	0.0181 (9)	−0.0004 (8)	0.0067 (7)	−0.0098 (8)
O2B	0.0254 (10)	0.0306 (11)	0.0292 (11)	−0.0093 (9)	0.0038 (8)	0.0042 (9)
O3B	0.0250 (10)	0.0290 (11)	0.0194 (9)	0.0134 (8)	0.0023 (7)	−0.0046 (8)
O4B	0.0276 (10)	0.0218 (10)	0.0171 (9)	0.0010 (8)	−0.0051 (7)	0.0036 (7)
O5B	0.0656 (19)	0.0379 (14)	0.0446 (15)	−0.0317 (14)	0.0206 (14)	−0.0224 (12)
O6B	0.0291 (10)	0.0231 (10)	0.0149 (8)	−0.0037 (8)	0.0040 (7)	0.0079 (7)
O7B	0.0396 (14)	0.0612 (18)	0.0347 (13)	0.0314 (13)	0.0199 (11)	0.0275 (13)
N1C	0.0239 (11)	0.0177 (10)	0.0207 (10)	0.0008 (9)	0.0035 (8)	0.0042 (9)
N2C	0.0230 (11)	0.0143 (10)	0.0165 (10)	−0.0009 (8)	0.0028 (8)	−0.0007 (8)
C1C	0.0150 (10)	0.0110 (10)	0.0140 (10)	0.0001 (8)	0.0020 (8)	0.0013 (8)
C2C	0.0151 (10)	0.0113 (10)	0.0125 (9)	0.0006 (8)	0.0011 (8)	0.0028 (8)
C3C	0.0131 (9)	0.0052 (8)	0.0028 (8)	−0.0017 (7)	0.0005 (7)	0.0022 (6)
C4C	0.0161 (10)	0.0119 (10)	0.0098 (9)	0.0001 (8)	0.0019 (8)	−0.0017 (8)
C5C	0.0083 (8)	0.0076 (8)	0.0046 (8)	−0.0029 (7)	0.0020 (6)	0.0005 (7)
N1D	0.0140 (9)	0.0138 (9)	0.0096 (8)	0.0049 (7)	0.0021 (7)	0.0015 (7)
N2D	0.0226 (11)	0.0189 (11)	0.0228 (11)	0.0038 (9)	0.0039 (9)	0.0000 (9)
C1D	0.0164 (10)	0.0149 (10)	0.0106 (10)	0.0037 (8)	0.0017 (8)	−0.0030 (8)
C2D	0.0136 (10)	0.0159 (10)	0.0098 (9)	0.0021 (8)	0.0000 (7)	0.0024 (8)
C3D	0.0108 (9)	0.0183 (11)	0.0141 (10)	0.0000 (8)	0.0021 (8)	0.0024 (9)
C4D	0.0148 (10)	0.0128 (10)	0.0152 (10)	−0.0017 (8)	0.0019 (8)	−0.0002 (8)
C5D	0.0107 (9)	0.0054 (8)	0.0093 (9)	0.0017 (7)	0.0018 (7)	−0.0019 (7)
O1W	0.0229 (10)	0.0311 (12)	0.0405 (13)	0.0049 (9)	0.0053 (9)	0.0165 (10)

Geometric parameters (Å, º) top

Cr1A—O6A	1.6114 (19)	C3C—C4C	1.491 (3)
Cr1A—O7A	1.6192 (19)	C3C—H3C1	0.9900
Cr1A—O5A	1.6233 (19)	C3C—H3C2	0.9900
Cr1A—O1A	1.7882 (18)	C4C—H4C1	0.9900
Cr2A—O4A	1.607 (2)	C4C—H4C2	0.9900
Cr2A—O2A	1.6143 (19)	C5C—H5C1	0.9900
Cr2A—O3A	1.6209 (19)	C5C—H5C2	0.9900
Cr2A—O1A	1.7975 (18)	N1D—C2D	1.489 (3)
Cr1B—O2B	1.603 (2)	N1D—C3D	1.515 (3)
Cr1B—O3B	1.618 (2)	N1D—H1ND	0.9100
Cr1B—O4B	1.627 (2)	N1D—H2ND	0.9100
Cr1B—O1B	1.799 (2)	N2D—C5D	1.494 (3)
Cr2B—O7B	1.590 (2)	N2D—C4D	1.524 (3)
Cr2B—O5B	1.602 (3)	N2D—H3ND	0.9100
Cr2B—O6B	1.6417 (19)	N2D—H4ND	0.9100
Cr2B—O1B	1.7711 (19)	C1D—C5Dⁱⁱ	1.498 (3)
N1C—C2C	1.517 (3)	C1D—C2D	1.520 (3)
N1C—C1C	1.524 (3)	C1D—H1D1	0.9900
N1C—H1NC	0.9100	C1D—H1D2	0.9900
N1C—H2NC	0.9100	C2D—H2D1	0.9900
N2C—C5C	1.498 (3)	C2D—H2D2	0.9900
N2C—C4C	1.521 (3)	C3D—C4D	1.519 (3)
N2C—H3NC	0.9100	C3D—H3D1	0.9900
N2C—H4NC	0.9100	C3D—H3D2	0.9900
C1C—C5Cⁱ	1.506 (3)	C4D—H4D1	0.9900
C1C—H1C1	0.9900	C4D—H4D2	0.9900
C1C—H1C2	0.9900	C5D—H5D1	0.9900
C2C—C3C	1.501 (3)	C5D—H5D2	0.9900
C2C—H2C1	0.9900	O1W—H1O1	0.844 (10)
C2C—H2C2	0.9900	O1W—H2O1	0.844 (10)

O6A—Cr1A—O7A	108.74 (11)	C3C—C4C—N2C	112.02 (19)
O6A—Cr1A—O5A	110.00 (10)	C3C—C4C—H4C1	109.2
O7A—Cr1A—O5A	112.10 (11)	N2C—C4C—H4C1	109.2
O6A—Cr1A—O1A	112.41 (10)	C3C—C4C—H4C2	109.2
O7A—Cr1A—O1A	105.13 (9)	N2C—C4C—H4C2	109.2
O5A—Cr1A—O1A	108.41 (9)	H4C1—C4C—H4C2	107.9
O4A—Cr2A—O2A	110.11 (11)	N2C—C5C—C1Cⁱ	116.69 (18)
O4A—Cr2A—O3A	109.41 (11)	N2C—C5C—H5C1	108.1
O2A—Cr2A—O3A	110.70 (11)	C1Cⁱ—C5C—H5C1	108.1
O4A—Cr2A—O1A	108.27 (10)	N2C—C5C—H5C2	108.1
O2A—Cr2A—O1A	106.87 (9)	C1Cⁱ—C5C—H5C2	108.1
O3A—Cr2A—O1A	111.43 (10)	H5C1—C5C—H5C2	107.3
Cr1A—O1A—Cr2A	133.37 (11)	C2D—N1D—C3D	114.21 (19)
O2B—Cr1B—O3B	108.89 (13)	C2D—N1D—H1ND	108.7
O2B—Cr1B—O4B	110.81 (11)	C3D—N1D—H1ND	108.7
O3B—Cr1B—O4B	110.38 (11)	C2D—N1D—H2ND	108.7
O2B—Cr1B—O1B	109.15 (11)	C3D—N1D—H2ND	108.7
O3B—Cr1B—O1B	107.16 (10)	H1ND—N1D—H2ND	107.6
O4B—Cr1B—O1B	110.35 (11)	C5D—N2D—C4D	110.1 (2)
O7B—Cr2B—O5B	108.74 (19)	C5D—N2D—H3ND	109.6
O7B—Cr2B—O6B	110.59 (12)	C4D—N2D—H3ND	109.6
O5B—Cr2B—O6B	108.50 (14)	C5D—N2D—H4ND	109.6
O7B—Cr2B—O1B	111.22 (12)	C4D—N2D—H4ND	109.6
O5B—Cr2B—O1B	106.51 (13)	H3ND—N2D—H4ND	108.2
O6B—Cr2B—O1B	111.12 (11)	C5Dⁱⁱ—C1D—C2D	115.47 (19)
Cr2B—O1B—Cr1B	136.28 (12)	C5Dⁱⁱ—C1D—H1D1	108.4
C2C—N1C—C1C	111.5 (2)	C2D—C1D—H1D1	108.4
C2C—N1C—H1NC	109.3	C5Dⁱⁱ—C1D—H1D2	108.4
C1C—N1C—H1NC	109.3	C2D—C1D—H1D2	108.4
C2C—N1C—H2NC	109.3	H1D1—C1D—H1D2	107.5
C1C—N1C—H2NC	109.3	N1D—C2D—C1D	114.7 (2)
H1NC—N1C—H2NC	108.0	N1D—C2D—H2D1	108.6
C5C—N2C—C4C	110.15 (18)	C1D—C2D—H2D1	108.6
C5C—N2C—H3NC	109.6	N1D—C2D—H2D2	108.6
C4C—N2C—H3NC	109.6	C1D—C2D—H2D2	108.6
C5C—N2C—H4NC	109.6	H2D1—C2D—H2D2	107.6
C4C—N2C—H4NC	109.6	N1D—C3D—C4D	114.17 (19)
H3NC—N2C—H4NC	108.1	N1D—C3D—H3D1	108.7
C5Cⁱ—C1C—N1C	110.47 (19)	C4D—C3D—H3D1	108.7
C5Cⁱ—C1C—H1C1	109.6	N1D—C3D—H3D2	108.7
N1C—C1C—H1C1	109.6	C4D—C3D—H3D2	108.7
C5Cⁱ—C1C—H1C2	109.6	H3D1—C3D—H3D2	107.6
N1C—C1C—H1C2	109.6	C3D—C4D—N2D	112.5 (2)
H1C1—C1C—H1C2	108.1	C3D—C4D—H4D1	109.1
C3C—C2C—N1C	109.84 (19)	N2D—C4D—H4D1	109.1
C3C—C2C—H2C1	109.7	C3D—C4D—H4D2	109.1
N1C—C2C—H2C1	109.7	N2D—C4D—H4D2	109.1
C3C—C2C—H2C2	109.7	H4D1—C4D—H4D2	107.8
N1C—C2C—H2C2	109.7	N2D—C5D—C1Dⁱⁱ	115.92 (19)
H2C1—C2C—H2C2	108.2	N2D—C5D—H5D1	108.3
C4C—C3C—C2C	117.56 (18)	C1Dⁱⁱ—C5D—H5D1	108.3
C4C—C3C—H3C1	107.9	N2D—C5D—H5D2	108.3
C2C—C3C—H3C1	107.9	C1Dⁱⁱ—C5D—H5D2	108.3
C4C—C3C—H3C2	107.9	H5D1—C5D—H5D2	107.4
C2C—C3C—H3C2	107.9	H1O1—O1W—H2O1	106 (3)
H3C1—C3C—H3C2	107.2

O6A—Cr1A—O1A—Cr2A	−81.13 (17)	C2C—N1C—C1C—C5Cⁱ	177.91 (19)
O7A—Cr1A—O1A—Cr2A	160.74 (15)	C1C—N1C—C2C—C3C	−175.00 (19)
O5A—Cr1A—O1A—Cr2A	40.70 (18)	N1C—C2C—C3C—C4C	55.8 (3)
O4A—Cr2A—O1A—Cr1A	−67.38 (18)	C2C—C3C—C4C—N2C	56.8 (3)
O2A—Cr2A—O1A—Cr1A	174.04 (15)	C5C—N2C—C4C—C3C	−173.51 (18)
O3A—Cr2A—O1A—Cr1A	52.99 (18)	C4C—N2C—C5C—C1Cⁱ	65.9 (2)
O7B—Cr2B—O1B—Cr1B	−53.2 (2)	C3D—N1D—C2D—C1D	−173.36 (19)
O5B—Cr2B—O1B—Cr1B	−171.5 (2)	C5Dⁱⁱ—C1D—C2D—N1D	73.5 (3)
O6B—Cr2B—O1B—Cr1B	70.5 (2)	C2D—N1D—C3D—C4D	57.5 (3)
O2B—Cr1B—O1B—Cr2B	−32.7 (2)	N1D—C3D—C4D—N2D	55.5 (3)
O3B—Cr1B—O1B—Cr2B	−150.48 (18)	C5D—N2D—C4D—C3D	−172.66 (19)
O4B—Cr1B—O1B—Cr2B	89.3 (2)	C4D—N2D—C5D—C1Dⁱⁱ	174.65 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1C—H1NC···O2Bⁱⁱⁱ	0.91	2.45	3.091 (3)	128
N1D—H1ND···O6A	0.91	2.38	3.140 (3)	142
N1D—H1ND···O7A	0.91	2.16	2.942 (3)	143
N1D—H2ND···O6Bⁱⁱ	0.91	1.87	2.768 (3)	169
N2C—H3NC···O6A^iv	0.91	2.62	3.074 (3)	112
N2C—H4NC···O7B^v	0.91	2.42	3.047 (3)	126
N2C—H4NC···O2A	0.91	2.52	3.200 (3)	132
N2D—H3ND···O6Bⁱⁱ	0.91	2.42	3.198 (3)	144
N2D—H4ND···O2Bⁱⁱ	0.91	2.65	3.357 (3)	136
O1W—H1O1···O5A^vi	0.84 (1)	2.38 (10)	2.999 (3)	130 (11)
O1W—H2O1···O1B	0.84 (1)	2.05 (4)	2.774 (3)	143 (5)

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

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Crystal structure of 1,4,8,11-tetra­azonia­cyclo­tetra­decane bis­(dichromate) monohydrate from synchrotron data

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Crystal structure of 1,4,8,11-tetraazoniacyclotetradecane bis(dichromate) monohydrate from synchrotron data