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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023005509/yz2034sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023005509/yz2034Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023005509/yz2034IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023005509/yz2034IIIsup4.hkl
Contains datablock III

CCDC references: 2271693; 2271692; 2271691

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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 [sigma](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 [sigma](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

Computing details top

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+·Br3F(000) = 404
Mr = 414.98Dx = 1.864 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.9009 (4) ÅCell parameters from 3187 reflections
b = 10.3466 (6) Åθ = 3.0–34.7°
c = 9.4948 (5) ŵ = 8.17 mm1
β = 107.703 (2)°T = 100 K
V = 739.42 (7) Å3Fragment, orange
Z = 20.24 × 0.20 × 0.14 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
2402 reflections with I > 2σ(I)
ω– and φ–scansRint = 0.026
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 35.0°, θmin = 4.5°
Tmin = 0.315, Tmax = 0.394h = 1212
11995 measured reflectionsk = 1616
3239 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.025H-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 reflectionsΔρmax = 0.43 e Å3
73 parametersΔρmin = 0.78 e Å3
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
xyzUiso*/Ueq
Br10.5000000.5000000.5000000.01461 (5)
Br20.26135 (2)0.50973 (2)0.62805 (2)0.02228 (5)
O10.85472 (13)0.45244 (10)0.98120 (11)0.0190 (2)
H11.0000000.5000001.0000000.029*
N10.66034 (15)0.29961 (10)0.87188 (13)0.0153 (2)
C10.80749 (18)0.36364 (12)0.88341 (15)0.0146 (2)
C20.91855 (19)0.33325 (14)0.78479 (16)0.0193 (3)
H2A1.0287240.3836190.8161580.029*
H2B0.8524280.3554100.6824860.029*
H2C0.9471230.2408460.7912280.029*
C30.55467 (19)0.32410 (14)0.97137 (17)0.0198 (3)
H3A0.6247890.3748371.0562420.030*
H3B0.5210000.2416421.0060570.030*
H3C0.4473120.3722480.9185610.030*
C40.5868 (2)0.20268 (14)0.75764 (17)0.0214 (3)
H4A0.6581310.1997380.6893890.032*
H4B0.4640050.2255200.7030180.032*
H4C0.5890380.1177780.8039360.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01420 (9)0.01516 (8)0.01360 (8)0.00133 (6)0.00293 (7)0.00072 (6)
Br20.01914 (8)0.02903 (8)0.02132 (8)0.00196 (6)0.01013 (6)0.00041 (6)
O10.0217 (5)0.0179 (4)0.0149 (5)0.0066 (4)0.0018 (4)0.0020 (4)
N10.0183 (6)0.0141 (5)0.0135 (5)0.0035 (4)0.0050 (5)0.0023 (4)
C10.0168 (6)0.0132 (5)0.0116 (6)0.0002 (5)0.0009 (5)0.0037 (4)
C20.0210 (7)0.0196 (6)0.0184 (7)0.0002 (5)0.0078 (6)0.0016 (5)
C30.0205 (7)0.0214 (6)0.0200 (7)0.0025 (5)0.0098 (6)0.0021 (5)
C40.0255 (7)0.0186 (6)0.0191 (7)0.0073 (5)0.0056 (6)0.0063 (5)
Geometric parameters (Å, º) top
Br1—Br2i2.5372 (2)C2—H2B0.9800
Br1—Br22.5372 (2)C2—H2C0.9800
O1—C11.2786 (16)C3—H3A0.9800
O1—H11.2112C3—H3B0.9800
N1—C11.3134 (17)C3—H3C0.9800
N1—C31.4605 (18)C4—H4A0.9800
N1—C41.4618 (18)C4—H4B0.9800
C1—C21.4984 (19)C4—H4C0.9800
C2—H2A0.9800
Br2i—Br1—Br2180.0H2B—C2—H2C109.5
C1—O1—H1116.95N1—C3—H3A109.5
C1—N1—C3121.62 (11)N1—C3—H3B109.5
C1—N1—C4123.36 (12)H3A—C3—H3B109.5
C3—N1—C4115.00 (11)N1—C3—H3C109.5
O1—C1—N1118.58 (12)H3A—C3—H3C109.5
O1—C1—C2120.50 (12)H3B—C3—H3C109.5
N1—C1—C2120.92 (12)N1—C4—H4A109.5
C1—C2—H2A109.5N1—C4—H4B109.5
C1—C2—H2B109.5H4A—C4—H4B109.5
H2A—C2—H2B109.5N1—C4—H4C109.5
C1—C2—H2C109.5H4A—C4—H4C109.5
H2A—C2—H2C109.5H4B—C4—H4C109.5
C3—N1—C1—O12.46 (19)C3—N1—C1—C2177.27 (12)
C4—N1—C1—O1175.52 (13)C4—N1—C1—C24.8 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1ii0.982.523.2622 (18)132
C2—H2B···Br2i0.983.144.0788 (15)162
C2—H2C···Br1iii0.983.133.9596 (14)143
C3—H3A···Br2iv0.983.104.0216 (15)158
C3—H3C···Br20.983.053.8847 (15)143
O1—H1···O1ii1.211.212.4224 (15)180
C3—H3A···O10.982.292.6940 (19)104
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+2; (iii) x+3/2, y1/2, 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·Br2IZ = 2
Mr = 461.97F(000) = 440
Triclinic, P1Dx = 2.004 Mg m3
a = 7.2943 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.9544 (4) ÅCell parameters from 9984 reflections
c = 13.6097 (7) Åθ = 2.9–35.2°
α = 90.645 (2)°µ = 7.30 mm1
β = 103.651 (2)°T = 100 K
γ = 93.656 (2)°Fragment, orange
V = 765.51 (6) Å30.14 × 0.08 × 0.06 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
5446 reflections with I > 2σ(I)
ω– and φ–scansRint = 0.021
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 35.2°, θmin = 4.3°
Tmin = 0.515, Tmax = 0.669h = 1111
30601 measured reflectionsk = 1212
6766 independent reflectionsl = 2221
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.019H 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 reflectionsΔρmax = 0.52 e Å3
149 parametersΔρmin = 0.62 e Å3
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
xyzUiso*/UeqOcc. (<1)
I10.65027 (2)0.18015 (2)0.21358 (2)0.01710 (2)
Br10.80118 (2)0.33097 (2)0.06912 (2)0.02346 (3)
Br20.51412 (2)0.02963 (2)0.35979 (2)0.02157 (3)
O10.20994 (14)0.43799 (12)0.57436 (7)0.01964 (19)
H10.187 (6)0.388 (6)0.617 (3)0.029*0.49 (4)
O20.10583 (13)0.27819 (13)0.70454 (7)0.02121 (19)
H20.151 (5)0.325 (6)0.659 (3)0.032*0.51 (4)
N10.22672 (15)0.45877 (13)0.41323 (8)0.01563 (19)
N20.14789 (15)0.19762 (14)0.86403 (8)0.0168 (2)
C10.17805 (16)0.37110 (15)0.48569 (9)0.0147 (2)
C20.08734 (19)0.19621 (16)0.46499 (10)0.0204 (2)
H2A0.0805000.1439840.5290200.031*
H2B0.1626520.1294030.4303490.031*
H2C0.0405530.2006960.4220600.031*
C30.31786 (18)0.62905 (16)0.43360 (10)0.0198 (2)
H3A0.3546480.6517000.5067980.030*
H3B0.2293800.7111800.4016120.030*
H3C0.4305630.6382700.4060420.030*
C40.1909 (2)0.39725 (18)0.30812 (10)0.0215 (3)
H4A0.1043200.2958520.2985070.032*
H4B0.3104880.3701620.2926950.032*
H4C0.1340300.4845800.2628240.032*
C50.21588 (17)0.26890 (15)0.79243 (9)0.0155 (2)
C60.41829 (18)0.33486 (16)0.81159 (10)0.0192 (2)
H6A0.4386040.3963280.7526440.029*
H6B0.5001510.2404980.8234840.029*
H6C0.4486500.4109350.8711980.029*
C70.0468 (2)0.12246 (19)0.84285 (11)0.0243 (3)
H7A0.1077380.1354590.7712880.036*
H7B0.1174100.1793060.8849270.036*
H7C0.0454560.0023960.8581790.036*
C80.2581 (2)0.18213 (19)0.96814 (10)0.0236 (3)
H8A0.3821900.2429010.9764320.035*
H8B0.2747820.0628860.9824920.035*
H8C0.1910260.2302601.0150970.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01763 (4)0.01708 (3)0.01549 (4)0.00366 (3)0.00121 (3)0.00183 (3)
Br10.02527 (7)0.02855 (7)0.01748 (7)0.00332 (5)0.00655 (5)0.00017 (5)
Br20.02328 (7)0.01921 (6)0.02211 (7)0.00054 (5)0.00536 (5)0.00173 (5)
O10.0235 (5)0.0221 (4)0.0133 (4)0.0003 (4)0.0045 (4)0.0014 (3)
O20.0171 (4)0.0323 (5)0.0145 (4)0.0026 (4)0.0038 (4)0.0061 (4)
N10.0139 (5)0.0185 (4)0.0143 (5)0.0007 (4)0.0031 (4)0.0021 (4)
N20.0175 (5)0.0207 (5)0.0125 (5)0.0015 (4)0.0040 (4)0.0017 (4)
C10.0113 (5)0.0178 (5)0.0146 (5)0.0026 (4)0.0020 (4)0.0022 (4)
C20.0220 (6)0.0181 (5)0.0202 (6)0.0019 (5)0.0039 (5)0.0016 (5)
C30.0168 (6)0.0189 (5)0.0227 (6)0.0016 (4)0.0030 (5)0.0038 (5)
C40.0237 (7)0.0266 (6)0.0148 (6)0.0022 (5)0.0059 (5)0.0006 (5)
C50.0164 (5)0.0161 (5)0.0149 (5)0.0043 (4)0.0047 (4)0.0006 (4)
C60.0182 (6)0.0213 (5)0.0180 (6)0.0003 (4)0.0043 (5)0.0013 (5)
C70.0194 (6)0.0337 (7)0.0208 (7)0.0019 (5)0.0075 (5)0.0031 (5)
C80.0270 (7)0.0292 (7)0.0133 (6)0.0001 (5)0.0027 (5)0.0039 (5)
Geometric parameters (Å, º) top
I1—Br22.6860 (2)C3—H3A0.9800
I1—Br12.7243 (2)C3—H3B0.9800
O1—C11.2771 (15)C3—H3C0.9800
O1—H10.75 (5)C4—H4A0.9800
O2—C51.2794 (15)C4—H4B0.9800
O2—H20.85 (5)C4—H4C0.9800
N1—C11.3168 (16)C5—C61.4965 (18)
N1—C31.4640 (16)C6—H6A0.9800
N1—C41.4648 (17)C6—H6B0.9800
N2—C51.3121 (16)C6—H6C0.9800
N2—C81.4656 (17)C7—H7A0.9800
N2—C71.4673 (17)C7—H7B0.9800
C1—C21.4961 (17)C7—H7C0.9800
C2—H2A0.9800C8—H8A0.9800
C2—H2B0.9800C8—H8B0.9800
C2—H2C0.9800C8—H8C0.9800
Br2—I1—Br1177.942 (6)H4A—C4—H4B109.5
C1—O1—H1120 (3)N1—C4—H4C109.5
C5—O2—H2118 (3)H4A—C4—H4C109.5
C1—N1—C3120.94 (11)H4B—C4—H4C109.5
C1—N1—C4123.49 (11)O2—C5—N2118.46 (12)
C3—N1—C4115.55 (10)O2—C5—C6120.28 (11)
C5—N2—C8123.75 (11)N2—C5—C6121.25 (11)
C5—N2—C7120.94 (11)C5—C6—H6A109.5
C8—N2—C7115.28 (11)C5—C6—H6B109.5
O1—C1—N1118.77 (11)H6A—C6—H6B109.5
O1—C1—C2120.38 (11)C5—C6—H6C109.5
N1—C1—C2120.84 (11)H6A—C6—H6C109.5
C1—C2—H2A109.5H6B—C6—H6C109.5
C1—C2—H2B109.5N2—C7—H7A109.5
H2A—C2—H2B109.5N2—C7—H7B109.5
C1—C2—H2C109.5H7A—C7—H7B109.5
H2A—C2—H2C109.5N2—C7—H7C109.5
H2B—C2—H2C109.5H7A—C7—H7C109.5
N1—C3—H3A109.5H7B—C7—H7C109.5
N1—C3—H3B109.5N2—C8—H8A109.5
H3A—C3—H3B109.5N2—C8—H8B109.5
N1—C3—H3C109.5H8A—C8—H8B109.5
H3A—C3—H3C109.5N2—C8—H8C109.5
H3B—C3—H3C109.5H8A—C8—H8C109.5
N1—C4—H4A109.5H8B—C8—H8C109.5
N1—C4—H4B109.5
C3—N1—C1—O10.75 (17)C8—N2—C5—O2178.76 (12)
C4—N1—C1—O1177.75 (11)C7—N2—C5—O23.09 (18)
C3—N1—C1—C2179.15 (11)C8—N2—C5—C62.56 (19)
C4—N1—C1—C22.35 (18)C7—N2—C5—C6175.59 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.75 (5)1.69 (5)2.4278 (13)173 (4)
O2—H2···O10.85 (5)1.59 (5)2.4278 (14)170 (4)
C2—H2A···O20.982.573.2872 (17)130
C2—H2B···Br20.983.094.0105 (14)158
C2—H2C···I1i0.983.184.0838 (14)155
C3—H3A···Br2ii0.983.073.8153 (14)134
C3—H3B···O2iii0.982.543.3481 (16)140
C4—H4A···I1i0.983.314.1081 (14)140
C6—H6A···O10.982.643.3630 (16)131
C6—H6C···Br1ii0.983.063.7331 (14)128
C7—H7B···Br1iv0.982.973.8980 (15)159
C8—H8A···Br1v0.983.053.9722 (15)157
C3—H3A···O10.982.262.6878 (16)105
C7—H7A···O20.982.242.6801 (18)106
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z+1; (iv) x1, 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·Cl2IF(000) = 368
Mr = 373.05Dx = 1.683 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
a = 10.5264 (3) ÅCell parameters from 9986 reflections
b = 6.7261 (2) Åθ = 3.6–35.1°
c = 10.8124 (3) ŵ = 2.53 mm1
β = 105.950 (1)°T = 100 K
V = 736.06 (4) Å3Fragment, orange
Z = 20.20 × 0.18 × 0.14 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
1745 reflections with I > 2σ(I)
ω– and φ–scansRint = 0.014
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 35.2°, θmin = 4.4°
Tmin = 0.630, Tmax = 0.719h = 1616
13071 measured reflectionsk = 1010
1745 independent reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.008H 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 reflectionsΔρmax = 0.46 e Å3
52 parametersΔρmin = 0.25 e Å3
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
xyzUiso*/UeqOcc. (<1)
I10.5000000.5000000.5000000.01617 (2)
Cl10.60222 (2)0.5000000.74187 (2)0.02093 (3)
O10.60066 (6)0.0000000.96603 (6)0.02505 (10)
H10.543 (3)0.0000000.977 (3)0.038*0.5
N10.70175 (6)0.0000000.81090 (6)0.01741 (9)
C10.59151 (7)0.0000000.84597 (6)0.01742 (10)
C20.45979 (7)0.0000000.74807 (8)0.02291 (12)
H2A0.3901930.0219710.7909590.034*0.5
H2B0.4571660.1064470.6855270.034*0.5
H2C0.4457070.1284180.7035650.034*0.5
C30.82909 (8)0.0000000.90856 (8)0.02547 (13)
H3A0.8240280.0858660.9802730.038*0.5
H3B0.8975940.0499260.8708610.038*0.5
H3C0.8510760.1357920.9400460.038*0.5
C40.70493 (8)0.0000000.67698 (7)0.02212 (12)
H4A0.6225600.0568490.6230150.033*0.5
H4B0.7144770.1367240.6495080.033*0.5
H4C0.7798970.0798740.6683650.033*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01526 (3)0.01688 (3)0.01778 (3)0.0000.00693 (2)0.000
Cl10.02127 (7)0.02325 (7)0.01802 (6)0.0000.00499 (5)0.000
O10.0226 (2)0.0357 (3)0.0204 (2)0.0000.01195 (19)0.000
N10.0170 (2)0.0189 (2)0.0187 (2)0.0000.00881 (18)0.000
C10.0173 (2)0.0164 (2)0.0208 (2)0.0000.0090 (2)0.000
C20.0176 (3)0.0254 (3)0.0260 (3)0.0000.0065 (2)0.000
C30.0172 (3)0.0356 (4)0.0242 (3)0.0000.0067 (2)0.000
C40.0235 (3)0.0260 (3)0.0201 (3)0.0000.0113 (2)0.000
Geometric parameters (Å, º) top
I1—Cl12.5398 (2)C2—H2Cii0.980 (10)
I1—Cl1i2.5398 (2)C3—H3A0.9800
O1—C11.2750 (8)C3—H3B0.9800
O1—H10.64 (3)C3—H3C0.9800
N1—C11.3161 (8)C3—H3Aii0.980 (9)
N1—C41.4576 (9)C3—H3Bii0.980 (6)
N1—C31.4608 (10)C3—H3Cii0.980 (3)
C1—C21.4955 (10)C4—H4A0.9800
C2—H2A0.9800C4—H4B0.9800
C2—H2B0.9800C4—H4C0.9800
C2—H2C0.9800C4—H4Aii0.980 (7)
C2—H2Aii0.980 (5)C4—H4Bii0.9800 (17)
C2—H2Bii0.980 (15)C4—H4Cii0.980 (8)
Cl1—I1—Cl1i180.0H3A—C3—H3Aii72.2
C1—O1—H1112 (3)H3B—C3—H3Aii137.5
C1—N1—C4123.30 (6)H3C—C3—H3Aii40.1
C1—N1—C3119.89 (6)N1—C3—H3Bii109.47 (14)
C4—N1—C3116.81 (6)H3A—C3—H3Bii137.5
O1—C1—N1117.87 (7)H3B—C3—H3Bii40.1
O1—C1—C2121.10 (6)H3C—C3—H3Bii72.2
N1—C1—C2121.02 (6)H3Aii—C3—H3Bii109.5
C1—C2—H2A109.5N1—C3—H3Cii109.47 (6)
C1—C2—H2B109.5H3A—C3—H3Cii40.1
H2A—C2—H2B109.5H3B—C3—H3Cii72.2
C1—C2—H2C109.5H3C—C3—H3Cii137.5
H2A—C2—H2C109.5H3Aii—C3—H3Cii109.5
H2B—C2—H2C109.5H3Bii—C3—H3Cii109.5
C1—C2—H2Aii109.47 (11)N1—C4—H4A109.5
H2B—C2—H2Aii123.6N1—C4—H4B109.5
H2C—C2—H2Aii93.9H4A—C4—H4B109.5
C1—C2—H2Bii109.5 (3)N1—C4—H4C109.5
H2A—C2—H2Bii123.6H4A—C4—H4C109.5
H2B—C2—H2Bii93.9H4B—C4—H4C109.5
H2C—C2—H2Bii17.3N1—C4—H4Aii109.47 (15)
H2Aii—C2—H2Bii109.5H4A—C4—H4Aii45.9
C1—C2—H2Cii109.5 (2)H4B—C4—H4Aii66.5
H2A—C2—H2Cii93.9H4C—C4—H4Aii139.6
H2B—C2—H2Cii17.3N1—C4—H4Bii109.47 (3)
H2C—C2—H2Cii123.6H4A—C4—H4Bii66.5
H2Aii—C2—H2Cii109.5H4B—C4—H4Bii139.6
H2Bii—C2—H2Cii109.5H4C—C4—H4Bii45.9
N1—C3—H3A109.5H4Aii—C4—H4Bii109.5
N1—C3—H3B109.5N1—C4—H4Cii109.47 (18)
H3A—C3—H3B109.5H4A—C4—H4Cii139.6
N1—C3—H3C109.5H4B—C4—H4Cii45.9
H3A—C3—H3C109.5H4C—C4—H4Cii66.5
H3B—C3—H3C109.5H4Aii—C4—H4Cii109.5
N1—C3—H3Aii109.5 (2)H4Bii—C4—H4Cii109.5
C4—N1—C1—O1180.000 (1)C4—N1—C1—C20.000 (1)
C3—N1—C1—O10.000 (1)C3—N1—C1—C2180.000 (1)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1iii0.64 (3)1.79 (3)2.4261 (11)170 (4)
C2—H2A···Cl1iv0.982.933.7461 (8)141
C2—H2A···O1iii0.982.613.3230 (9)130
C2—H2C···Cl10.982.963.6902 (3)132
C3—H3A···Cl1v0.982.953.6479 (9)129
C3—H3B···Cl1vi0.982.893.7897 (8)153
C3—H3C···O1vii0.982.653.6256 (4)176
Symmetry codes: (iii) x+1, y, z+2; (iv) x1/2, y1/2, z; (v) x+3/2, y+1/2, z+2; (vi) x+1/2, y1/2, z; (vii) x+3/2, y1/2, z+2.
Summary of short interatomic contacts (Å) in (I), (II) and (III) top
ContactDistanceSymmetry operation
(I)
H1···O11.61-x+2, -y+1, -z+2
O1···H4B2.73x+1/2, -y+1/2, z+1/2
C2···H4C3.06-x+3/2, y+1/2, -z+3/2
C2···H3B3.09x+1/2, -y+1/2, z-1/2
H2A···Br23.21x+1, y, z
H3C···Br23.05x, y, z
H2C···Br13.13-x+3/2, y-1/2, -z+3/2
H3A···Br23.09-x+1, -y+1, -z+2
H4C···Br23.23-x+1/2, y-1/2, -z+3/2
Br2···H2B3.14-x+1, -y+1, -z+1
(II)
H1···H20.86x, y, z
C1···O13.24-x, -y+1, -z+1
H3C···O12.68-x+1, -y+1, -z+1
H2A···H2A2.54-x, -y, -z+1
H3C···Br23.23x, y+1, z
H2B···Br23.09x, y, z
H2C···I13.18x-1, y, z
H3A···Br23.07-x+1, -y+1, -z+1
H3C···H6A2.58-x+1, -y+1, -z+1
O2···H3B2.54-x, -y+1, -z+1
H8B···Br13.19-x+1, -y, -z+1
H6C···Br13.06-x+1, -y+1, -z+1
H8A···Br13.05x, y, z+1
H7B···Br12.97x-1, y, z+1
(III)
H1···O11.79-x+1, y, -z+2
H3C···O12.65-x+3/2, y-1/2, -z+2
H4B···Cl13.00x, y-1, z
H2C···Cl12.96x, y, z
C3···C32.60-x+2, y, -z+2
H3A···Cl12.95-x+3/2, y-1/2, -z+2
H2A···Cl12.93x-1/2, y-1/2, z
H2C···H4C2.58x-1/2, y+1/2, z
H3B···Cl12.89x+1/2, y-1/2, z
I1···H4A3.37-x+1, y, -z+1
I1···H4C3.36-x+3/2, y+1/2, -z+1
Percentage contributions of interatomic contacts to the Hirshfeld surface for (I), (II) and (III) top
Contact(I) (%)(II) (%)(III) (%)
H···H57.560.388.9
Br···H/H···Br24.015.2-
O···H/H···O13.312.06.5
C···H/H···C3.02.72.0
Br···N/N···Br1.0--
N···H/H···N0.92.40.8
Br···C/C···Br0.5--
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
 

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