In all three title crystals, the cations are linked by O—H

O and/or C—H

O hydrogen bonds. The three-dimensional packing is further consolidated by strong halogen–hydrogen and weak van der Waals interactions.
Supporting information
CCDC references: 2271693; 2271692; 2271691
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.056
- Data-to-parameter ratio = 44.4
Structure: II
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.019
- wR factor = 0.038
- Data-to-parameter ratio = 45.4
Structure: III
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.001 Å
- R factor = 0.008
- wR factor = 0.022
- Data-to-parameter ratio = 33.6
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2 ..BR2 . 4.08 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 6 Note
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report
PLAT303_ALERT_2_G Full Occupancy Atom H1 with # Connections 2.00 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2B ..BR2 . 3.14 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2C ..BR1 . 3.13 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3A ..BR2 . 3.10 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3C ..BR2 . 3.05 Ang.
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 23 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 3.7 Low
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
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
10 ALERT level G = General information/check it is not something unexpected
0 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
7 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Datablock: II
Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min). 15 Note
Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 4 Report
PLAT977_ALERT_2_C Check Negative Difference Density on H4B . -0.33 eA-3
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C8 H19 Br2 I1 N2 O2
Atom count from _chemical_formula_moiety:C8 H19.02 Br2 I1 N2 O2
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 1 ) 15.49 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 2 ) 15.51 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2B ..BR2 . 3.09 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2C ..I1 . 3.18 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3A ..BR2 . 3.07 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H4A ..I1 . 3.31 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H6A ..O1 . 2.64 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H6C ..BR1 . 3.06 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H7B ..BR1 . 2.97 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H8A ..BR1 . 3.05 Ang.
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 39 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.5 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 2 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
1 ALERT level B = A potentially serious problem, consider carefully
2 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
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
3 ALERT type 3 Indicator that the structure quality may be low
12 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Datablock: III
Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 6 Note
Alert level G
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0 0.997 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H1 Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2A Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2B Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2C Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3A Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3B Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3C Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4A Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4B Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4C Constrained at 0.5 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 1 ) 15.50 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A ..CL1 . 2.93 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A ..O1 . 2.61 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2C ..CL1 . 2.96 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3A ..CL1 . 2.95 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3B ..CL1 . 2.89 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3C ..O1 . 2.65 Ang.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 17.30 Deg.
H2C -C2 -H2B 1_555 1_555 6_555 ...... # 21 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 17.30 Deg.
H2B -C2 -H2C 1_555 1_555 6_555 ...... # 25 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 40.10 Deg.
H3C -C3 -H3A 1_555 1_555 6_555 ...... # 38 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 40.10 Deg.
H3B -C3 -H3B 1_555 1_555 6_555 ...... # 41 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 40.10 Deg.
H3A -C3 -H3C 1_555 1_555 6_555 ...... # 45 Check
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 4 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
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
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
28 ALERT level G = General information/check it is not something unexpected
1 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
24 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
For all structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).
N,
N-Dimethylacetamide–1-(dimethyl-
λ4-azanylidene)ethan-1-ol tribromide (1/1) (I)
top
Crystal data top
C4H9NO·C4H10NO+·Br3− | F(000) = 404 |
Mr = 414.98 | Dx = 1.864 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9009 (4) Å | Cell parameters from 3187 reflections |
b = 10.3466 (6) Å | θ = 3.0–34.7° |
c = 9.4948 (5) Å | µ = 8.17 mm−1 |
β = 107.703 (2)° | T = 100 K |
V = 739.42 (7) Å3 | Fragment, orange |
Z = 2 | 0.24 × 0.20 × 0.14 mm |
Data collection top
Bruker Kappa APEXII area-detector diffractometer | 2402 reflections with I > 2σ(I) |
ω– and φ–scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 35.0°, θmin = 4.5° |
Tmin = 0.315, Tmax = 0.394 | h = −12→12 |
11995 measured reflections | k = −16→16 |
3239 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.056 | w = 1/[σ2(Fo2) + (0.0249P)2 + 0.0334P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.002 |
3239 reflections | Δρmax = 0.43 e Å−3 |
73 parameters | Δρmin = −0.78 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 | Uiso*/Ueq | |
Br1 | 0.500000 | 0.500000 | 0.500000 | 0.01461 (5) | |
Br2 | 0.26135 (2) | 0.50973 (2) | 0.62805 (2) | 0.02228 (5) | |
O1 | 0.85472 (13) | 0.45244 (10) | 0.98120 (11) | 0.0190 (2) | |
H1 | 1.000000 | 0.500000 | 1.000000 | 0.029* | |
N1 | 0.66034 (15) | 0.29961 (10) | 0.87188 (13) | 0.0153 (2) | |
C1 | 0.80749 (18) | 0.36364 (12) | 0.88341 (15) | 0.0146 (2) | |
C2 | 0.91855 (19) | 0.33325 (14) | 0.78479 (16) | 0.0193 (3) | |
H2A | 1.028724 | 0.383619 | 0.816158 | 0.029* | |
H2B | 0.852428 | 0.355410 | 0.682486 | 0.029* | |
H2C | 0.947123 | 0.240846 | 0.791228 | 0.029* | |
C3 | 0.55467 (19) | 0.32410 (14) | 0.97137 (17) | 0.0198 (3) | |
H3A | 0.624789 | 0.374837 | 1.056242 | 0.030* | |
H3B | 0.521000 | 0.241642 | 1.006057 | 0.030* | |
H3C | 0.447312 | 0.372248 | 0.918561 | 0.030* | |
C4 | 0.5868 (2) | 0.20268 (14) | 0.75764 (17) | 0.0214 (3) | |
H4A | 0.658131 | 0.199738 | 0.689389 | 0.032* | |
H4B | 0.464005 | 0.225520 | 0.703018 | 0.032* | |
H4C | 0.589038 | 0.117778 | 0.803936 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.01420 (9) | 0.01516 (8) | 0.01360 (8) | 0.00133 (6) | 0.00293 (7) | −0.00072 (6) |
Br2 | 0.01914 (8) | 0.02903 (8) | 0.02132 (8) | 0.00196 (6) | 0.01013 (6) | −0.00041 (6) |
O1 | 0.0217 (5) | 0.0179 (4) | 0.0149 (5) | −0.0066 (4) | 0.0018 (4) | −0.0020 (4) |
N1 | 0.0183 (6) | 0.0141 (5) | 0.0135 (5) | −0.0035 (4) | 0.0050 (5) | −0.0023 (4) |
C1 | 0.0168 (6) | 0.0132 (5) | 0.0116 (6) | 0.0002 (5) | 0.0009 (5) | 0.0037 (4) |
C2 | 0.0210 (7) | 0.0196 (6) | 0.0184 (7) | −0.0002 (5) | 0.0078 (6) | 0.0016 (5) |
C3 | 0.0205 (7) | 0.0214 (6) | 0.0200 (7) | −0.0025 (5) | 0.0098 (6) | −0.0021 (5) |
C4 | 0.0255 (7) | 0.0186 (6) | 0.0191 (7) | −0.0073 (5) | 0.0056 (6) | −0.0063 (5) |
Geometric parameters (Å, º) top
Br1—Br2i | 2.5372 (2) | C2—H2B | 0.9800 |
Br1—Br2 | 2.5372 (2) | C2—H2C | 0.9800 |
O1—C1 | 1.2786 (16) | C3—H3A | 0.9800 |
O1—H1 | 1.2112 | C3—H3B | 0.9800 |
N1—C1 | 1.3134 (17) | C3—H3C | 0.9800 |
N1—C3 | 1.4605 (18) | C4—H4A | 0.9800 |
N1—C4 | 1.4618 (18) | C4—H4B | 0.9800 |
C1—C2 | 1.4984 (19) | C4—H4C | 0.9800 |
C2—H2A | 0.9800 | | |
| | | |
Br2i—Br1—Br2 | 180.0 | H2B—C2—H2C | 109.5 |
C1—O1—H1 | 116.95 | N1—C3—H3A | 109.5 |
C1—N1—C3 | 121.62 (11) | N1—C3—H3B | 109.5 |
C1—N1—C4 | 123.36 (12) | H3A—C3—H3B | 109.5 |
C3—N1—C4 | 115.00 (11) | N1—C3—H3C | 109.5 |
O1—C1—N1 | 118.58 (12) | H3A—C3—H3C | 109.5 |
O1—C1—C2 | 120.50 (12) | H3B—C3—H3C | 109.5 |
N1—C1—C2 | 120.92 (12) | N1—C4—H4A | 109.5 |
C1—C2—H2A | 109.5 | N1—C4—H4B | 109.5 |
C1—C2—H2B | 109.5 | H4A—C4—H4B | 109.5 |
H2A—C2—H2B | 109.5 | N1—C4—H4C | 109.5 |
C1—C2—H2C | 109.5 | H4A—C4—H4C | 109.5 |
H2A—C2—H2C | 109.5 | H4B—C4—H4C | 109.5 |
| | | |
C3—N1—C1—O1 | −2.46 (19) | C3—N1—C1—C2 | 177.27 (12) |
C4—N1—C1—O1 | 175.52 (13) | C4—N1—C1—C2 | −4.8 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1ii | 0.98 | 2.52 | 3.2622 (18) | 132 |
C2—H2B···Br2i | 0.98 | 3.14 | 4.0788 (15) | 162 |
C2—H2C···Br1iii | 0.98 | 3.13 | 3.9596 (14) | 143 |
C3—H3A···Br2iv | 0.98 | 3.10 | 4.0216 (15) | 158 |
C3—H3C···Br2 | 0.98 | 3.05 | 3.8847 (15) | 143 |
O1—H1···O1ii | 1.21 | 1.21 | 2.4224 (15) | 180 |
C3—H3A···O1 | 0.98 | 2.29 | 2.6940 (19) | 104 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+2. |
N,
N-Dimethylacetamide–1-(dimethyl-
λ4-azanylidene)ethan-1-ol dibromidoiodate (1/1) (II)
top
Crystal data top
C4H9NO·C4H10NO−·Br2I− | Z = 2 |
Mr = 461.97 | F(000) = 440 |
Triclinic, P1 | Dx = 2.004 Mg m−3 |
a = 7.2943 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9544 (4) Å | Cell parameters from 9984 reflections |
c = 13.6097 (7) Å | θ = 2.9–35.2° |
α = 90.645 (2)° | µ = 7.30 mm−1 |
β = 103.651 (2)° | T = 100 K |
γ = 93.656 (2)° | Fragment, orange |
V = 765.51 (6) Å3 | 0.14 × 0.08 × 0.06 mm |
Data collection top
Bruker Kappa APEXII area-detector diffractometer | 5446 reflections with I > 2σ(I) |
ω– and φ–scans | Rint = 0.021 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 35.2°, θmin = 4.3° |
Tmin = 0.515, Tmax = 0.669 | h = −11→11 |
30601 measured reflections | k = −12→12 |
6766 independent reflections | l = −22→21 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.019 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.038 | w = 1/[σ2(Fo2) + (0.0119P)2 + 0.2374P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6766 reflections | Δρmax = 0.52 e Å−3 |
149 parameters | Δρmin = −0.62 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 | Uiso*/Ueq | Occ. (<1) |
I1 | 0.65027 (2) | 0.18015 (2) | 0.21358 (2) | 0.01710 (2) | |
Br1 | 0.80118 (2) | 0.33097 (2) | 0.06912 (2) | 0.02346 (3) | |
Br2 | 0.51412 (2) | 0.02963 (2) | 0.35979 (2) | 0.02157 (3) | |
O1 | 0.20994 (14) | 0.43799 (12) | 0.57436 (7) | 0.01964 (19) | |
H1 | 0.187 (6) | 0.388 (6) | 0.617 (3) | 0.029* | 0.49 (4) |
O2 | 0.10583 (13) | 0.27819 (13) | 0.70454 (7) | 0.02121 (19) | |
H2 | 0.151 (5) | 0.325 (6) | 0.659 (3) | 0.032* | 0.51 (4) |
N1 | 0.22672 (15) | 0.45877 (13) | 0.41323 (8) | 0.01563 (19) | |
N2 | 0.14789 (15) | 0.19762 (14) | 0.86403 (8) | 0.0168 (2) | |
C1 | 0.17805 (16) | 0.37110 (15) | 0.48569 (9) | 0.0147 (2) | |
C2 | 0.08734 (19) | 0.19621 (16) | 0.46499 (10) | 0.0204 (2) | |
H2A | 0.080500 | 0.143984 | 0.529020 | 0.031* | |
H2B | 0.162652 | 0.129403 | 0.430349 | 0.031* | |
H2C | −0.040553 | 0.200696 | 0.422060 | 0.031* | |
C3 | 0.31786 (18) | 0.62905 (16) | 0.43360 (10) | 0.0198 (2) | |
H3A | 0.354648 | 0.651700 | 0.506798 | 0.030* | |
H3B | 0.229380 | 0.711180 | 0.401612 | 0.030* | |
H3C | 0.430563 | 0.638270 | 0.406042 | 0.030* | |
C4 | 0.1909 (2) | 0.39725 (18) | 0.30812 (10) | 0.0215 (3) | |
H4A | 0.104320 | 0.295852 | 0.298507 | 0.032* | |
H4B | 0.310488 | 0.370162 | 0.292695 | 0.032* | |
H4C | 0.134030 | 0.484580 | 0.262824 | 0.032* | |
C5 | 0.21588 (17) | 0.26890 (15) | 0.79243 (9) | 0.0155 (2) | |
C6 | 0.41829 (18) | 0.33486 (16) | 0.81159 (10) | 0.0192 (2) | |
H6A | 0.438604 | 0.396328 | 0.752644 | 0.029* | |
H6B | 0.500151 | 0.240498 | 0.823484 | 0.029* | |
H6C | 0.448650 | 0.410935 | 0.871198 | 0.029* | |
C7 | −0.0468 (2) | 0.12246 (19) | 0.84285 (11) | 0.0243 (3) | |
H7A | −0.107738 | 0.135459 | 0.771288 | 0.036* | |
H7B | −0.117410 | 0.179306 | 0.884927 | 0.036* | |
H7C | −0.045456 | 0.002396 | 0.858179 | 0.036* | |
C8 | 0.2581 (2) | 0.18213 (19) | 0.96814 (10) | 0.0236 (3) | |
H8A | 0.382190 | 0.242901 | 0.976432 | 0.035* | |
H8B | 0.274782 | 0.062886 | 0.982492 | 0.035* | |
H8C | 0.191026 | 0.230260 | 1.015097 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01763 (4) | 0.01708 (3) | 0.01549 (4) | 0.00366 (3) | 0.00121 (3) | −0.00183 (3) |
Br1 | 0.02527 (7) | 0.02855 (7) | 0.01748 (7) | 0.00332 (5) | 0.00655 (5) | −0.00017 (5) |
Br2 | 0.02328 (7) | 0.01921 (6) | 0.02211 (7) | 0.00054 (5) | 0.00536 (5) | 0.00173 (5) |
O1 | 0.0235 (5) | 0.0221 (4) | 0.0133 (4) | 0.0003 (4) | 0.0045 (4) | 0.0014 (3) |
O2 | 0.0171 (4) | 0.0323 (5) | 0.0145 (4) | 0.0026 (4) | 0.0038 (4) | 0.0061 (4) |
N1 | 0.0139 (5) | 0.0185 (4) | 0.0143 (5) | 0.0007 (4) | 0.0031 (4) | 0.0021 (4) |
N2 | 0.0175 (5) | 0.0207 (5) | 0.0125 (5) | 0.0015 (4) | 0.0040 (4) | 0.0017 (4) |
C1 | 0.0113 (5) | 0.0178 (5) | 0.0146 (5) | 0.0026 (4) | 0.0020 (4) | 0.0022 (4) |
C2 | 0.0220 (6) | 0.0181 (5) | 0.0202 (6) | −0.0019 (5) | 0.0039 (5) | 0.0016 (5) |
C3 | 0.0168 (6) | 0.0189 (5) | 0.0227 (6) | −0.0016 (4) | 0.0030 (5) | 0.0038 (5) |
C4 | 0.0237 (7) | 0.0266 (6) | 0.0148 (6) | 0.0022 (5) | 0.0059 (5) | 0.0006 (5) |
C5 | 0.0164 (5) | 0.0161 (5) | 0.0149 (5) | 0.0043 (4) | 0.0047 (4) | 0.0006 (4) |
C6 | 0.0182 (6) | 0.0213 (5) | 0.0180 (6) | 0.0003 (4) | 0.0043 (5) | 0.0013 (5) |
C7 | 0.0194 (6) | 0.0337 (7) | 0.0208 (7) | −0.0019 (5) | 0.0075 (5) | 0.0031 (5) |
C8 | 0.0270 (7) | 0.0292 (7) | 0.0133 (6) | 0.0001 (5) | 0.0027 (5) | 0.0039 (5) |
Geometric parameters (Å, º) top
I1—Br2 | 2.6860 (2) | C3—H3A | 0.9800 |
I1—Br1 | 2.7243 (2) | C3—H3B | 0.9800 |
O1—C1 | 1.2771 (15) | C3—H3C | 0.9800 |
O1—H1 | 0.75 (5) | C4—H4A | 0.9800 |
O2—C5 | 1.2794 (15) | C4—H4B | 0.9800 |
O2—H2 | 0.85 (5) | C4—H4C | 0.9800 |
N1—C1 | 1.3168 (16) | C5—C6 | 1.4965 (18) |
N1—C3 | 1.4640 (16) | C6—H6A | 0.9800 |
N1—C4 | 1.4648 (17) | C6—H6B | 0.9800 |
N2—C5 | 1.3121 (16) | C6—H6C | 0.9800 |
N2—C8 | 1.4656 (17) | C7—H7A | 0.9800 |
N2—C7 | 1.4673 (17) | C7—H7B | 0.9800 |
C1—C2 | 1.4961 (17) | C7—H7C | 0.9800 |
C2—H2A | 0.9800 | C8—H8A | 0.9800 |
C2—H2B | 0.9800 | C8—H8B | 0.9800 |
C2—H2C | 0.9800 | C8—H8C | 0.9800 |
| | | |
Br2—I1—Br1 | 177.942 (6) | H4A—C4—H4B | 109.5 |
C1—O1—H1 | 120 (3) | N1—C4—H4C | 109.5 |
C5—O2—H2 | 118 (3) | H4A—C4—H4C | 109.5 |
C1—N1—C3 | 120.94 (11) | H4B—C4—H4C | 109.5 |
C1—N1—C4 | 123.49 (11) | O2—C5—N2 | 118.46 (12) |
C3—N1—C4 | 115.55 (10) | O2—C5—C6 | 120.28 (11) |
C5—N2—C8 | 123.75 (11) | N2—C5—C6 | 121.25 (11) |
C5—N2—C7 | 120.94 (11) | C5—C6—H6A | 109.5 |
C8—N2—C7 | 115.28 (11) | C5—C6—H6B | 109.5 |
O1—C1—N1 | 118.77 (11) | H6A—C6—H6B | 109.5 |
O1—C1—C2 | 120.38 (11) | C5—C6—H6C | 109.5 |
N1—C1—C2 | 120.84 (11) | H6A—C6—H6C | 109.5 |
C1—C2—H2A | 109.5 | H6B—C6—H6C | 109.5 |
C1—C2—H2B | 109.5 | N2—C7—H7A | 109.5 |
H2A—C2—H2B | 109.5 | N2—C7—H7B | 109.5 |
C1—C2—H2C | 109.5 | H7A—C7—H7B | 109.5 |
H2A—C2—H2C | 109.5 | N2—C7—H7C | 109.5 |
H2B—C2—H2C | 109.5 | H7A—C7—H7C | 109.5 |
N1—C3—H3A | 109.5 | H7B—C7—H7C | 109.5 |
N1—C3—H3B | 109.5 | N2—C8—H8A | 109.5 |
H3A—C3—H3B | 109.5 | N2—C8—H8B | 109.5 |
N1—C3—H3C | 109.5 | H8A—C8—H8B | 109.5 |
H3A—C3—H3C | 109.5 | N2—C8—H8C | 109.5 |
H3B—C3—H3C | 109.5 | H8A—C8—H8C | 109.5 |
N1—C4—H4A | 109.5 | H8B—C8—H8C | 109.5 |
N1—C4—H4B | 109.5 | | |
| | | |
C3—N1—C1—O1 | 0.75 (17) | C8—N2—C5—O2 | −178.76 (12) |
C4—N1—C1—O1 | −177.75 (11) | C7—N2—C5—O2 | 3.09 (18) |
C3—N1—C1—C2 | −179.15 (11) | C8—N2—C5—C6 | 2.56 (19) |
C4—N1—C1—C2 | 2.35 (18) | C7—N2—C5—C6 | −175.59 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.75 (5) | 1.69 (5) | 2.4278 (13) | 173 (4) |
O2—H2···O1 | 0.85 (5) | 1.59 (5) | 2.4278 (14) | 170 (4) |
C2—H2A···O2 | 0.98 | 2.57 | 3.2872 (17) | 130 |
C2—H2B···Br2 | 0.98 | 3.09 | 4.0105 (14) | 158 |
C2—H2C···I1i | 0.98 | 3.18 | 4.0838 (14) | 155 |
C3—H3A···Br2ii | 0.98 | 3.07 | 3.8153 (14) | 134 |
C3—H3B···O2iii | 0.98 | 2.54 | 3.3481 (16) | 140 |
C4—H4A···I1i | 0.98 | 3.31 | 4.1081 (14) | 140 |
C6—H6A···O1 | 0.98 | 2.64 | 3.3630 (16) | 131 |
C6—H6C···Br1ii | 0.98 | 3.06 | 3.7331 (14) | 128 |
C7—H7B···Br1iv | 0.98 | 2.97 | 3.8980 (15) | 159 |
C8—H8A···Br1v | 0.98 | 3.05 | 3.9722 (15) | 157 |
C3—H3A···O1 | 0.98 | 2.26 | 2.6878 (16) | 105 |
C7—H7A···O2 | 0.98 | 2.24 | 2.6801 (18) | 106 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z+1; (v) x, y, z+1. |
N,
N-Dimethylacetamide–1-(dimethyl-
λ4-azanylidene)ethan-1-ol dichloridoiodate (1/1) (III)
top
Crystal data top
C4H9NO·C4H10NO−·Cl2I− | F(000) = 368 |
Mr = 373.05 | Dx = 1.683 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5264 (3) Å | Cell parameters from 9986 reflections |
b = 6.7261 (2) Å | θ = 3.6–35.1° |
c = 10.8124 (3) Å | µ = 2.53 mm−1 |
β = 105.950 (1)° | T = 100 K |
V = 736.06 (4) Å3 | Fragment, orange |
Z = 2 | 0.20 × 0.18 × 0.14 mm |
Data collection top
Bruker Kappa APEXII area-detector diffractometer | 1745 reflections with I > 2σ(I) |
ω– and φ–scans | Rint = 0.014 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 35.2°, θmin = 4.4° |
Tmin = 0.630, Tmax = 0.719 | h = −16→16 |
13071 measured reflections | k = −10→10 |
1745 independent reflections | l = −17→16 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.008 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.022 | w = 1/[σ2(Fo2) + (0.0153P)2 + 0.0381P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.003 |
1745 reflections | Δρmax = 0.46 e Å−3 |
52 parameters | Δρmin = −0.25 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 | Uiso*/Ueq | Occ. (<1) |
I1 | 0.500000 | 0.500000 | 0.500000 | 0.01617 (2) | |
Cl1 | 0.60222 (2) | 0.500000 | 0.74187 (2) | 0.02093 (3) | |
O1 | 0.60066 (6) | 0.000000 | 0.96603 (6) | 0.02505 (10) | |
H1 | 0.543 (3) | 0.000000 | 0.977 (3) | 0.038* | 0.5 |
N1 | 0.70175 (6) | 0.000000 | 0.81090 (6) | 0.01741 (9) | |
C1 | 0.59151 (7) | 0.000000 | 0.84597 (6) | 0.01742 (10) | |
C2 | 0.45979 (7) | 0.000000 | 0.74807 (8) | 0.02291 (12) | |
H2A | 0.390193 | −0.021971 | 0.790959 | 0.034* | 0.5 |
H2B | 0.457166 | −0.106447 | 0.685527 | 0.034* | 0.5 |
H2C | 0.445707 | 0.128418 | 0.703565 | 0.034* | 0.5 |
C3 | 0.82909 (8) | 0.000000 | 0.90856 (8) | 0.02547 (13) | |
H3A | 0.824028 | 0.085866 | 0.980273 | 0.038* | 0.5 |
H3B | 0.897594 | 0.049926 | 0.870861 | 0.038* | 0.5 |
H3C | 0.851076 | −0.135792 | 0.940046 | 0.038* | 0.5 |
C4 | 0.70493 (8) | 0.000000 | 0.67698 (7) | 0.02212 (12) | |
H4A | 0.622560 | 0.056849 | 0.623015 | 0.033* | 0.5 |
H4B | 0.714477 | −0.136724 | 0.649508 | 0.033* | 0.5 |
H4C | 0.779897 | 0.079874 | 0.668365 | 0.033* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01526 (3) | 0.01688 (3) | 0.01778 (3) | 0.000 | 0.00693 (2) | 0.000 |
Cl1 | 0.02127 (7) | 0.02325 (7) | 0.01802 (6) | 0.000 | 0.00499 (5) | 0.000 |
O1 | 0.0226 (2) | 0.0357 (3) | 0.0204 (2) | 0.000 | 0.01195 (19) | 0.000 |
N1 | 0.0170 (2) | 0.0189 (2) | 0.0187 (2) | 0.000 | 0.00881 (18) | 0.000 |
C1 | 0.0173 (2) | 0.0164 (2) | 0.0208 (2) | 0.000 | 0.0090 (2) | 0.000 |
C2 | 0.0176 (3) | 0.0254 (3) | 0.0260 (3) | 0.000 | 0.0065 (2) | 0.000 |
C3 | 0.0172 (3) | 0.0356 (4) | 0.0242 (3) | 0.000 | 0.0067 (2) | 0.000 |
C4 | 0.0235 (3) | 0.0260 (3) | 0.0201 (3) | 0.000 | 0.0113 (2) | 0.000 |
Geometric parameters (Å, º) top
I1—Cl1 | 2.5398 (2) | C2—H2Cii | 0.980 (10) |
I1—Cl1i | 2.5398 (2) | C3—H3A | 0.9800 |
O1—C1 | 1.2750 (8) | C3—H3B | 0.9800 |
O1—H1 | 0.64 (3) | C3—H3C | 0.9800 |
N1—C1 | 1.3161 (8) | C3—H3Aii | 0.980 (9) |
N1—C4 | 1.4576 (9) | C3—H3Bii | 0.980 (6) |
N1—C3 | 1.4608 (10) | C3—H3Cii | 0.980 (3) |
C1—C2 | 1.4955 (10) | C4—H4A | 0.9800 |
C2—H2A | 0.9800 | C4—H4B | 0.9800 |
C2—H2B | 0.9800 | C4—H4C | 0.9800 |
C2—H2C | 0.9800 | C4—H4Aii | 0.980 (7) |
C2—H2Aii | 0.980 (5) | C4—H4Bii | 0.9800 (17) |
C2—H2Bii | 0.980 (15) | C4—H4Cii | 0.980 (8) |
| | | |
Cl1—I1—Cl1i | 180.0 | H3A—C3—H3Aii | 72.2 |
C1—O1—H1 | 112 (3) | H3B—C3—H3Aii | 137.5 |
C1—N1—C4 | 123.30 (6) | H3C—C3—H3Aii | 40.1 |
C1—N1—C3 | 119.89 (6) | N1—C3—H3Bii | 109.47 (14) |
C4—N1—C3 | 116.81 (6) | H3A—C3—H3Bii | 137.5 |
O1—C1—N1 | 117.87 (7) | H3B—C3—H3Bii | 40.1 |
O1—C1—C2 | 121.10 (6) | H3C—C3—H3Bii | 72.2 |
N1—C1—C2 | 121.02 (6) | H3Aii—C3—H3Bii | 109.5 |
C1—C2—H2A | 109.5 | N1—C3—H3Cii | 109.47 (6) |
C1—C2—H2B | 109.5 | H3A—C3—H3Cii | 40.1 |
H2A—C2—H2B | 109.5 | H3B—C3—H3Cii | 72.2 |
C1—C2—H2C | 109.5 | H3C—C3—H3Cii | 137.5 |
H2A—C2—H2C | 109.5 | H3Aii—C3—H3Cii | 109.5 |
H2B—C2—H2C | 109.5 | H3Bii—C3—H3Cii | 109.5 |
C1—C2—H2Aii | 109.47 (11) | N1—C4—H4A | 109.5 |
H2B—C2—H2Aii | 123.6 | N1—C4—H4B | 109.5 |
H2C—C2—H2Aii | 93.9 | H4A—C4—H4B | 109.5 |
C1—C2—H2Bii | 109.5 (3) | N1—C4—H4C | 109.5 |
H2A—C2—H2Bii | 123.6 | H4A—C4—H4C | 109.5 |
H2B—C2—H2Bii | 93.9 | H4B—C4—H4C | 109.5 |
H2C—C2—H2Bii | 17.3 | N1—C4—H4Aii | 109.47 (15) |
H2Aii—C2—H2Bii | 109.5 | H4A—C4—H4Aii | 45.9 |
C1—C2—H2Cii | 109.5 (2) | H4B—C4—H4Aii | 66.5 |
H2A—C2—H2Cii | 93.9 | H4C—C4—H4Aii | 139.6 |
H2B—C2—H2Cii | 17.3 | N1—C4—H4Bii | 109.47 (3) |
H2C—C2—H2Cii | 123.6 | H4A—C4—H4Bii | 66.5 |
H2Aii—C2—H2Cii | 109.5 | H4B—C4—H4Bii | 139.6 |
H2Bii—C2—H2Cii | 109.5 | H4C—C4—H4Bii | 45.9 |
N1—C3—H3A | 109.5 | H4Aii—C4—H4Bii | 109.5 |
N1—C3—H3B | 109.5 | N1—C4—H4Cii | 109.47 (18) |
H3A—C3—H3B | 109.5 | H4A—C4—H4Cii | 139.6 |
N1—C3—H3C | 109.5 | H4B—C4—H4Cii | 45.9 |
H3A—C3—H3C | 109.5 | H4C—C4—H4Cii | 66.5 |
H3B—C3—H3C | 109.5 | H4Aii—C4—H4Cii | 109.5 |
N1—C3—H3Aii | 109.5 (2) | H4Bii—C4—H4Cii | 109.5 |
| | | |
C4—N1—C1—O1 | 180.000 (1) | C4—N1—C1—C2 | 0.000 (1) |
C3—N1—C1—O1 | 0.000 (1) | C3—N1—C1—C2 | 180.000 (1) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1iii | 0.64 (3) | 1.79 (3) | 2.4261 (11) | 170 (4) |
C2—H2A···Cl1iv | 0.98 | 2.93 | 3.7461 (8) | 141 |
C2—H2A···O1iii | 0.98 | 2.61 | 3.3230 (9) | 130 |
C2—H2C···Cl1 | 0.98 | 2.96 | 3.6902 (3) | 132 |
C3—H3A···Cl1v | 0.98 | 2.95 | 3.6479 (9) | 129 |
C3—H3B···Cl1vi | 0.98 | 2.89 | 3.7897 (8) | 153 |
C3—H3C···O1vii | 0.98 | 2.65 | 3.6256 (4) | 176 |
Symmetry codes: (iii) −x+1, −y, −z+2; (iv) x−1/2, y−1/2, z; (v) −x+3/2, −y+1/2, −z+2; (vi) x+1/2, y−1/2, z; (vii) −x+3/2, −y−1/2, −z+2. |
Summary of short interatomic contacts (Å) in (I),
(II) and (III) topContact | Distance | Symmetry operation |
(I) | | |
H1···O1 | 1.61 | -x+2, -y+1, -z+2 |
O1···H4B | 2.73 | x+1/2, -y+1/2, z+1/2 |
C2···H4C | 3.06 | -x+3/2, y+1/2, -z+3/2 |
C2···H3B | 3.09 | x+1/2, -y+1/2, z-1/2 |
H2A···Br2 | 3.21 | x+1, y, z |
H3C···Br2 | 3.05 | x, y, z |
H2C···Br1 | 3.13 | -x+3/2, y-1/2, -z+3/2 |
H3A···Br2 | 3.09 | -x+1, -y+1, -z+2 |
H4C···Br2 | 3.23 | -x+1/2, y-1/2, -z+3/2 |
Br2···H2B | 3.14 | -x+1, -y+1, -z+1 |
| | |
(II) | | |
H1···H2 | 0.86 | x, y, z |
C1···O1 | 3.24 | -x, -y+1, -z+1 |
H3C···O1 | 2.68 | -x+1, -y+1, -z+1 |
H2A···H2A | 2.54 | -x, -y, -z+1 |
H3C···Br2 | 3.23 | x, y+1, z |
H2B···Br2 | 3.09 | x, y, z |
H2C···I1 | 3.18 | x-1, y, z |
H3A···Br2 | 3.07 | -x+1, -y+1, -z+1 |
H3C···H6A | 2.58 | -x+1, -y+1, -z+1 |
O2···H3B | 2.54 | -x, -y+1, -z+1 |
H8B···Br1 | 3.19 | -x+1, -y, -z+1 |
H6C···Br1 | 3.06 | -x+1, -y+1, -z+1 |
H8A···Br1 | 3.05 | x, y, z+1 |
H7B···Br1 | 2.97 | x-1, y, z+1 |
| | |
(III) | | |
H1···O1 | 1.79 | -x+1, y, -z+2 |
H3C···O1 | 2.65 | -x+3/2, y-1/2, -z+2 |
H4B···Cl1 | 3.00 | x, y-1, z |
H2C···Cl1 | 2.96 | x, y, z |
C3···C3 | 2.60 | -x+2, y, -z+2 |
H3A···Cl1 | 2.95 | -x+3/2, y-1/2, -z+2 |
H2A···Cl1 | 2.93 | x-1/2, y-1/2, z |
H2C···H4C | 2.58 | x-1/2, y+1/2, z |
H3B···Cl1 | 2.89 | x+1/2, y-1/2, z |
I1···H4A | 3.37 | -x+1, y, -z+1 |
I1···H4C | 3.36 | -x+3/2, y+1/2, -z+1 |
Percentage contributions of interatomic contacts to the
Hirshfeld surface for (I), (II) and (III) topContact | (I) (%) | (II) (%) | (III) (%) |
H···H | 57.5 | 60.3 | 88.9 |
Br···H/H···Br | 24.0 | 15.2 | - |
O···H/H···O | 13.3 | 12.0 | 6.5 |
C···H/H···C | 3.0 | 2.7 | 2.0 |
Br···N/N···Br | 1.0 | - | - |
N···H/H···N | 0.9 | 2.4 | 0.8 |
Br···C/C···Br | 0.5 | - | - |
I···H/H···I | - | 4.7 | - |
O···C/C···O | - | 2.2 | - |
O···N/N···O | - | 0.3 | - |
O···O | - | 0.1 | - |
Cl···N/N···Cl | - | - | 0.8 |
Cl···C/C···Cl | - | - | 0.7 |
Cl···H/H···Cl | - | - | 0.4 |