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The room temperature (298 K) structure of the title salt has been redetermined with disordered H atoms for the –NH3 group. Additionally, a twinned monoclinic structure has been identified with lower symmetry at low temperature (100 K) in which the H atoms of the –NH3 groups are ordered to optimize N—H...Cl hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023010812/hb8089sup1.cif
Contains datablocks I_250K, I_100K, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010812/hb8089I_250Ksup2.hkl
Contains datablock I_250K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010812/hb8089I_100Ksup3.hkl
Contains datablock I_100K

CCDC references: 2314991; 2314990

Key indicators

Structure: I_250K
  • Single-crystal X-ray study
  • T = 250 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.102
  • Data-to-parameter ratio = 29.2
Structure: I_100K
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.033
  • wR factor = 0.075
  • Data-to-parameter ratio = 53.6

checkCIF/PLATON results

No syntax errors found



Datablock: I_250K


Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 5.947 Check
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report H1N H2N H3N H4N H5N H6N PLAT300_ALERT_4_G Atom Site Occupancy of H1N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H2N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H3N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H4N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H5N Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H6N Constrained at 0.5 Check PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do ! PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 1 Note 2 0 0, PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 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 1 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 1 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 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: I_100K

Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 18 Report -2 1 1, -2 2 1, -1 2 1, -1 3 1, -1 4 1, -2 0 2, -1 0 2, 0 0 2, -2 1 2, -2 2 2, -1 2 2, -2 3 2, -1 3 2, -1 4 2, -2 5 2, -1 1 3, -1 2 3, -1 3 3,
Alert level G PLAT480_ALERT_4_G Long H...A H-Bond Reported H2 ..CL1 . 2.98 Ang. PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed .. ! Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 266 Note PLAT931_ALERT_5_G CIFcalcFCF Twin Law ( 1 0 0) Est.d BASF 0.44 Check PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 1 Note 0 0 2, PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.4 Low 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 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 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 3 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

4-Methoxyanilinium chloride (I_250K) top
Crystal data top
C7H10NO+·ClDx = 1.304 Mg m3
Mr = 159.61Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9997 reflections
a = 8.8689 (4) Åθ = 3.8–27.4°
b = 8.4361 (3) ŵ = 0.40 mm1
c = 21.7319 (9) ÅT = 250 K
V = 1625.96 (12) Å3Lath fragment, pink
Z = 80.34 × 0.31 × 0.15 mm
F(000) = 672
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2717 independent reflections
Radiation source: fine-focus sealed tube2019 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromatorRint = 0.050
φ and ω scansθmax = 31.6°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1313
Tmin = 0.896, Tmax = 0.942k = 1212
73425 measured reflectionsl = 3232
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0348P)2 + 0.6343P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max = 0.001
S = 1.08Δρmax = 0.24 e Å3
2717 reflectionsΔρmin = 0.21 e Å3
93 parametersExtinction correction: SHELXL-2017/1 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0070 (9)
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)
Cl10.74847 (4)0.51434 (4)0.52125 (2)0.03992 (12)
O10.65326 (14)0.80202 (15)0.20491 (5)0.0514 (3)
N10.52441 (19)0.75043 (18)0.45535 (6)0.0547 (4)
H1N0.5842330.8184220.4759010.082*0.5
H2N0.4272380.7768320.4614810.082*0.5
H3N0.5405740.6512700.4691290.082*0.5
H4N0.4504640.6792600.4617730.082*0.5
H5N0.6074590.7208510.4761930.082*0.5
H6N0.4941230.8464120.4685450.082*0.5
C10.55894 (17)0.75820 (17)0.38936 (7)0.0388 (3)
C20.48090 (17)0.66401 (19)0.34891 (7)0.0427 (3)
H20.4080030.5924620.3635600.051*
C30.51002 (17)0.67476 (19)0.28628 (7)0.0406 (3)
H30.4564730.6109780.2583490.049*
C40.61767 (17)0.77925 (17)0.26521 (6)0.0371 (3)
C50.6976 (2)0.8710 (2)0.30673 (8)0.0481 (4)
H50.7727020.9403790.2924160.058*
C60.6681 (2)0.8615 (2)0.36875 (7)0.0484 (4)
H60.7217760.9249090.3967680.058*
C70.5863 (2)0.6992 (3)0.16061 (8)0.0638 (5)
H7A0.6114850.5901640.1703820.096*
H7B0.6242050.7251230.1199730.096*
H7C0.4776640.7123150.1613430.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03990 (18)0.04090 (19)0.03894 (18)0.00135 (14)0.00086 (16)0.00395 (13)
O10.0576 (7)0.0614 (7)0.0351 (6)0.0028 (6)0.0091 (5)0.0037 (5)
N10.0653 (9)0.0622 (9)0.0364 (7)0.0194 (7)0.0085 (6)0.0064 (6)
C10.0407 (7)0.0429 (7)0.0328 (6)0.0138 (6)0.0038 (6)0.0053 (6)
C20.0373 (7)0.0436 (8)0.0473 (8)0.0006 (6)0.0065 (6)0.0055 (6)
C30.0375 (8)0.0435 (8)0.0407 (7)0.0009 (6)0.0001 (6)0.0035 (6)
C40.0375 (7)0.0391 (7)0.0347 (7)0.0073 (6)0.0040 (6)0.0036 (5)
C50.0484 (9)0.0496 (9)0.0463 (9)0.0129 (7)0.0036 (7)0.0052 (7)
C60.0528 (9)0.0504 (9)0.0419 (8)0.0056 (7)0.0049 (7)0.0028 (7)
C70.0643 (12)0.0896 (14)0.0374 (8)0.0102 (11)0.0031 (8)0.0106 (9)
Geometric parameters (Å, º) top
O1—C41.3615 (17)C2—C31.388 (2)
O1—C71.425 (2)C2—H20.9400
N1—C11.4679 (19)C3—C41.378 (2)
N1—H1N0.9000C3—H30.9400
N1—H2N0.9000C4—C51.384 (2)
N1—H3N0.9000C5—C61.375 (2)
N1—H4N0.9000C5—H50.9400
N1—H5N0.9000C6—H60.9400
N1—H6N0.9000C7—H7A0.9700
C1—C21.372 (2)C7—H7B0.9700
C1—C61.377 (2)C7—H7C0.9700
C4—O1—C7117.88 (14)C4—C3—C2119.77 (14)
C1—N1—H1N109.5C4—C3—H3120.1
C1—N1—H2N109.5C2—C3—H3120.1
H1N—N1—H2N109.5O1—C4—C3124.81 (14)
C1—N1—H3N109.5O1—C4—C5115.46 (14)
H1N—N1—H3N109.5C3—C4—C5119.73 (13)
H2N—N1—H3N109.5C6—C5—C4120.60 (15)
C1—N1—H4N109.5C6—C5—H5119.7
C1—N1—H5N109.5C4—C5—H5119.7
H4N—N1—H5N109.5C5—C6—C1119.28 (15)
C1—N1—H6N109.5C5—C6—H6120.4
H4N—N1—H6N109.5C1—C6—H6120.4
H5N—N1—H6N109.5O1—C7—H7A109.5
C2—C1—C6120.83 (14)O1—C7—H7B109.5
C2—C1—N1119.65 (14)H7A—C7—H7B109.5
C6—C1—N1119.51 (15)O1—C7—H7C109.5
C1—C2—C3119.76 (14)H7A—C7—H7C109.5
C1—C2—H2120.1H7B—C7—H7C109.5
C3—C2—H2120.1
C6—C1—C2—C31.2 (2)C2—C3—C4—C51.0 (2)
N1—C1—C2—C3177.97 (14)O1—C4—C5—C6178.05 (15)
C1—C2—C3—C40.4 (2)C3—C4—C5—C61.5 (2)
C7—O1—C4—C37.0 (2)C4—C5—C6—C10.7 (3)
C7—O1—C4—C5173.48 (15)C2—C1—C6—C50.7 (2)
C2—C3—C4—O1178.58 (14)N1—C1—C6—C5178.52 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl1i0.902.433.3265 (18)174
N1—H2N···Cl1ii0.902.403.1915 (15)147
N1—H3N···CL10.902.453.1570 (16)135
N1—H4N···Cl1iii0.902.433.3323 (18)180
N1—H5N···Cl10.902.363.1570 (15)148
N1—H6N···Cl1ii0.902.493.1915 (17)136
C6—H6···Cl1i0.942.823.6323 (16)145
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x1/2, y+3/2, z+1; (iii) x+1, y+1, z+1.
4-Methoxyanilinium chloride (I_100K) top
Crystal data top
C7H10NO+·ClF(000) = 672
Mr = 159.61Dx = 1.330 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.3039 (6) ÅCell parameters from 9875 reflections
b = 21.6993 (15) Åθ = 3.4–41.5°
c = 8.8495 (6) ŵ = 0.41 mm1
β = 90.077 (2)°T = 100 K
V = 1594.58 (19) Å3Needle fragment, pink
Z = 80.43 × 0.41 × 0.21 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
10832 independent reflections
Radiation source: fine-focus sealed tube9310 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromatorRint = 0.033
φ and ω scansθmax = 41.9°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1515
Tmin = 0.873, Tmax = 0.919k = 4040
48397 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0336P)2 + 0.1702P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
10832 reflectionsΔρmax = 0.47 e Å3
202 parametersΔρmin = 0.28 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.

Refinement. Refined as a 2-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.46961 (2)0.52412 (2)0.74414 (2)0.01433 (3)
Cl21.00704 (2)0.51981 (2)0.75416 (2)0.01431 (3)
O10.81503 (9)0.79863 (3)0.36295 (8)0.01972 (12)
N10.75005 (10)0.54837 (3)0.50236 (8)0.01524 (11)
H11N0.8313 (18)0.5382 (6)0.5613 (16)0.023*
H12N0.7496 (18)0.5254 (6)0.4219 (16)0.023*
H13N0.6580 (18)0.5390 (6)0.5566 (17)0.023*
C10.75955 (9)0.61391 (3)0.46333 (8)0.01282 (11)
C20.66656 (10)0.65590 (4)0.54219 (9)0.01463 (13)
H20.5929160.6420480.6168990.018*
C30.68159 (10)0.71877 (4)0.51130 (9)0.01510 (12)
H30.6189850.7479030.5657340.018*
C40.78835 (10)0.73857 (3)0.40075 (9)0.01439 (12)
C50.87901 (11)0.69542 (4)0.31922 (10)0.01746 (14)
H50.9498890.7089350.2418330.021*
C60.86556 (10)0.63310 (4)0.35115 (10)0.01644 (13)
H60.9280090.6038200.2970510.020*
C70.71299 (15)0.84409 (4)0.43121 (12)0.02472 (19)
H7A0.6001930.8346170.4082140.037*
H7B0.7399870.8848930.3911230.037*
H7C0.7290580.8438090.5409400.037*
O20.69262 (8)0.20673 (3)0.82982 (8)0.01905 (11)
N20.73702 (9)0.45944 (3)0.94929 (8)0.01440 (11)
H21N0.7316 (18)0.4677 (6)1.0489 (16)0.022*
H22N0.6576 (18)0.4795 (6)0.9008 (16)0.022*
H23N0.8253 (18)0.4776 (6)0.9085 (16)0.022*
C80.72962 (9)0.39304 (3)0.91915 (8)0.01249 (11)
C90.82458 (10)0.35313 (4)1.00292 (9)0.01498 (12)
H90.8951130.3687381.0783680.018*
C100.81599 (10)0.28992 (3)0.97583 (9)0.01480 (12)
H100.8802480.2622351.0331860.018*
C110.71267 (9)0.26745 (3)0.86417 (9)0.01383 (12)
C120.61959 (10)0.30835 (4)0.77920 (10)0.01777 (14)
H120.5507150.2930620.7020260.021*
C130.62716 (10)0.37124 (4)0.80690 (10)0.01671 (13)
H130.5630530.3990670.7498070.020*
C140.80131 (12)0.16348 (4)0.89757 (11)0.02172 (16)
H14A0.9123390.1747340.8722500.033*
H14B0.7782110.1220360.8592470.033*
H14C0.7877210.1640901.0075470.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01254 (6)0.01532 (6)0.01511 (7)0.00041 (5)0.00015 (8)0.00016 (6)
Cl20.01256 (6)0.01453 (6)0.01584 (7)0.00127 (5)0.00072 (8)0.00022 (6)
O10.0248 (3)0.0133 (2)0.0211 (3)0.0012 (2)0.0017 (2)0.0031 (2)
N10.0200 (3)0.0126 (2)0.0132 (3)0.0018 (2)0.0019 (2)0.00002 (19)
C10.0144 (3)0.0126 (2)0.0114 (3)0.0006 (2)0.0012 (2)0.0003 (2)
C20.0154 (3)0.0155 (3)0.0130 (3)0.0001 (2)0.0007 (2)0.0002 (2)
C30.0168 (3)0.0149 (3)0.0136 (3)0.0019 (2)0.0001 (2)0.0010 (2)
C40.0158 (3)0.0133 (3)0.0140 (3)0.0011 (2)0.0034 (2)0.0009 (2)
C50.0187 (3)0.0169 (3)0.0168 (3)0.0015 (3)0.0047 (3)0.0013 (3)
C60.0182 (3)0.0150 (3)0.0161 (3)0.0007 (2)0.0037 (3)0.0010 (2)
C70.0372 (6)0.0143 (3)0.0226 (4)0.0052 (3)0.0034 (4)0.0003 (3)
O20.0220 (3)0.0129 (2)0.0222 (3)0.0016 (2)0.0008 (2)0.0029 (2)
N20.0182 (3)0.0126 (2)0.0124 (3)0.0008 (2)0.0008 (2)0.00002 (19)
C80.0136 (3)0.0124 (2)0.0115 (3)0.0012 (2)0.0008 (2)0.0003 (2)
C90.0166 (3)0.0149 (3)0.0134 (3)0.0003 (2)0.0026 (3)0.0014 (2)
C100.0169 (3)0.0139 (3)0.0136 (3)0.0007 (2)0.0013 (2)0.0006 (2)
C110.0147 (3)0.0129 (3)0.0139 (3)0.0023 (2)0.0023 (2)0.0014 (2)
C120.0193 (3)0.0160 (3)0.0180 (4)0.0021 (2)0.0055 (3)0.0018 (2)
C130.0181 (3)0.0153 (3)0.0167 (3)0.0010 (2)0.0050 (3)0.0011 (2)
C140.0280 (4)0.0136 (3)0.0236 (4)0.0022 (3)0.0032 (3)0.0011 (3)
Geometric parameters (Å, º) top
O1—C41.3636 (10)O2—C111.3624 (9)
O1—C71.4343 (12)O2—C141.4330 (11)
N1—C11.4655 (10)N2—C81.4667 (10)
N1—H11N0.880 (15)N2—H21N0.901 (14)
N1—H12N0.870 (14)N2—H22N0.899 (14)
N1—H13N0.926 (15)N2—H23N0.907 (15)
C1—C21.3838 (11)C8—C91.3856 (11)
C1—C61.3915 (11)C8—C131.3900 (11)
C2—C31.3971 (11)C9—C101.3941 (11)
C2—H20.9500C9—H90.9500
C3—C41.3893 (12)C10—C111.3957 (11)
C3—H30.9500C10—H100.9500
C4—C51.4020 (12)C11—C121.3961 (11)
C5—C61.3860 (11)C12—C131.3879 (11)
C5—H50.9500C12—H120.9500
C6—H60.9500C13—H130.9500
C7—H7A0.9800C14—H14A0.9800
C7—H7B0.9800C14—H14B0.9800
C7—H7C0.9800C14—H14C0.9800
C4—O1—C7117.24 (7)C11—O2—C14117.60 (7)
C1—N1—H11N109.9 (9)C8—N2—H21N111.7 (8)
C1—N1—H12N111.4 (9)C8—N2—H22N111.0 (8)
H11N—N1—H12N110.1 (13)H21N—N2—H22N109.5 (12)
C1—N1—H13N112.4 (8)C8—N2—H23N112.8 (8)
H11N—N1—H13N105.7 (12)H21N—N2—H23N110.2 (13)
H12N—N1—H13N107.2 (13)H22N—N2—H23N101.1 (12)
C2—C1—C6121.11 (7)C9—C8—C13121.13 (7)
C2—C1—N1119.33 (7)C9—C8—N2119.54 (7)
C6—C1—N1119.53 (7)C13—C8—N2119.32 (7)
C1—C2—C3119.63 (8)C8—C9—C10119.60 (7)
C1—C2—H2120.2C8—C9—H9120.2
C3—C2—H2120.2C10—C9—H9120.2
C4—C3—C2119.81 (7)C9—C10—C11119.78 (7)
C4—C3—H3120.1C9—C10—H10120.1
C2—C3—H3120.1C11—C10—H10120.1
O1—C4—C3124.91 (7)O2—C11—C10124.79 (7)
O1—C4—C5115.12 (7)O2—C11—C12115.29 (7)
C3—C4—C5119.96 (7)C10—C11—C12119.91 (7)
C6—C5—C4120.22 (8)C13—C12—C11120.33 (7)
C6—C5—H5119.9C13—C12—H12119.8
C4—C5—H5119.9C11—C12—H12119.8
C5—C6—C1119.26 (7)C12—C13—C8119.23 (7)
C5—C6—H6120.4C12—C13—H13120.4
C1—C6—H6120.4C8—C13—H13120.4
O1—C7—H7A109.5O2—C14—H14A109.5
O1—C7—H7B109.5O2—C14—H14B109.5
H7A—C7—H7B109.5H14A—C14—H14B109.5
O1—C7—H7C109.5O2—C14—H14C109.5
H7A—C7—H7C109.5H14A—C14—H14C109.5
H7B—C7—H7C109.5H14B—C14—H14C109.5
C6—C1—C2—C31.43 (12)C13—C8—C9—C100.84 (12)
N1—C1—C2—C3176.47 (7)N2—C8—C9—C10179.11 (7)
C1—C2—C3—C40.67 (12)C8—C9—C10—C110.36 (12)
C7—O1—C4—C36.94 (12)C14—O2—C11—C109.35 (12)
C7—O1—C4—C5173.41 (8)C14—O2—C11—C12171.16 (8)
C2—C3—C4—O1178.79 (8)C9—C10—C11—O2178.87 (8)
C2—C3—C4—C50.84 (12)C9—C10—C11—C120.60 (12)
O1—C4—C5—C6178.02 (8)O2—C11—C12—C13178.42 (8)
C3—C4—C5—C61.65 (12)C10—C11—C12—C131.10 (13)
C4—C5—C6—C10.91 (13)C11—C12—C13—C80.63 (13)
C2—C1—C6—C50.63 (12)C9—C8—C13—C120.35 (13)
N1—C1—C6—C5177.26 (8)N2—C8—C13—C12179.60 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11N···Cl20.880 (15)2.279 (15)3.1450 (8)167.7 (13)
N1—H12N···Cl1i0.870 (14)2.573 (14)3.2480 (7)135.2 (13)
N1—H12N···Cl2ii0.870 (14)2.735 (15)3.3797 (8)132.1 (12)
N1—H13N···Cl10.926 (15)2.304 (16)3.2080 (8)165.0 (13)
N2—H21N···Cl1iii0.901 (14)2.487 (15)3.2318 (8)140.3 (12)
N2—H21N···Cl2iv0.901 (14)2.795 (14)3.4047 (8)126.2 (11)
N2—H22N···Cl10.899 (14)2.300 (15)3.1916 (8)171.3 (12)
N2—H23N···Cl20.907 (15)2.234 (15)3.1201 (8)165.5 (13)
C2—H2···Cl10.952.983.7487 (8)139
C6—H6···Cl2ii0.952.773.6055 (8)147
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x+2, y+1, z+2.
 

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