Bis(2-chloro-N,N-di­methyl­ethan-1-aminium) tetra­chlorido­cobaltate(II) and tetra­chlorido­zincate(II)

The competition between gauche and anti conformations in 2-chloro­ethyl- or 3-chloro­propyldi­methyl­ammonium cations is investigated for the title tetra­chloro­metallate salts in which the alkyl chain is found to disordered with the gauche conformation dominant.

Key indicators

Structure: cobaltate

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](N-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.030
• wR factor = 0.064
• Data-to-parameter ratio = 18.1

Structure: zincate

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](N-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.033
• wR factor = 0.070
• Data-to-parameter ratio = 25.2

checkCIF/PLATON results

No syntax errors found



Datablock: cobaltate



Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
              Calc: 2(C4 H11 Cl N), Cl4 Co
              Rep.: 2(C4 H11 Cl N 1+), Co Cl4 2-
PLAT234_ALERT_4_C Large Hirshfeld Difference N1       --C1A      .       0.16 Ang.

Alert level G
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd    1)        50% Note
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H4B      ..H2AB     .       1.91 Ang.
                                                      x,y,z  =      1_555 Check
PLAT414_ALERT_2_G Short Intra D-H..H-X       H1       ..H2AA     .       2.11 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H1       ..CL2      .       3.02 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
              H1AA    H1AB    H2AA    H2AB
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
                1  1  0,  -1  1  1,   0  0  2,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          4 Note
                0  0  2,  -1  1  1,   1  1  0,  -1  1  2,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       3.37 Note
              Predicted wR2: Based on SigI   2  1.90 or SHELX Weight  6.06       

   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
  12 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 5 Informative message, check




Datablock: zincate



Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
              Calc: C8 H22 Cl6 N2 Zn
              Rep.: C8 H22 Cl6 N2 Zn1
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
              Calc: 2(C4 H11 Cl N), Cl4 Zn
              Rep.: 2(C4 H11 Cl N 1+), Zn Cl4 2-
PLAT787_ALERT_4_C Change Zn1       into Zn        in SumFormula ..     Please Do

Alert level G
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C1       --C2       .        5.7 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd    1)        50% Note
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H4B      ..H2C      .       1.90 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H1       ..CL2      .       3.03 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
                1  1  0,  -1  1  1,   0  0  2,
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
                0  0  2,
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       62.0 Degree
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       4.66 Note
              Predicted wR2: Based on SigI   2  1.51 or SHELX Weight  6.42       

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

Bis(2-chloro-N,N-dimethylethan-1-aminium) tetrachloridocobaltate(II) (cobaltate)

Crystal data

(C4H11ClN)2[CoCl4]	F(000) = 852
Mr = 417.93	Dx = 1.56 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9986 reflections
a = 12.7521 (6) Å	θ = 2.9–27.4°
b = 8.9648 (4) Å	µ = 1.85 mm^−1
c = 16.6801 (10) Å	T = 295 K
β = 111.057 (1)°	Gem, blue
V = 1779.53 (16) Å^3	0.30 × 0.27 × 0.26 mm
Z = 4

Data collection

Bruker D8 Quest Eco diffractometer	1676 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.042
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 27.5°, θmin = 3.4°
Tmin = 0.696, Tmax = 0.746	h = −16→16
23748 measured reflections	k = −11→11
2041 independent reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0202P)^2 + 2.2595P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.064	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.38 e Å^−3
2041 reflections	Δρmin = −0.29 e Å^−3
113 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b)
1 restraint	Extinction coefficient: 0.0038 (3)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.5	0.77754 (4)	0.25	0.03399 (13)
Cl1	0.63314 (4)	0.92047 (6)	0.34886 (3)	0.04269 (15)
Cl2	0.40423 (5)	0.65066 (7)	0.31892 (4)	0.05376 (18)
N1	0.84438 (16)	0.6926 (2)	0.36634 (12)	0.0402 (4)
H1	0.775 (2)	0.725 (3)	0.3517 (17)	0.066 (8)*
C1	0.8515 (7)	0.5245 (5)	0.3673 (6)	0.0395 (13)	0.707 (2)
H1A	0.929586	0.496545	0.381431	0.047*	0.707 (2)
H1B	0.810217	0.488369	0.309775	0.047*	0.707 (2)
C2	0.8069 (3)	0.4440 (4)	0.4297 (2)	0.0465 (8)	0.707 (2)
H2A	0.848364	0.477204	0.487909	0.056*	0.707 (2)
H2B	0.818475	0.337488	0.427118	0.056*	0.707 (2)
Cl3	0.66156 (8)	0.48055 (11)	0.40385 (6)	0.0581 (3)	0.707 (2)
C1A	0.8273 (19)	0.5310 (12)	0.3788 (17)	0.055 (5)	0.293 (2)
H1AA	0.800336	0.479291	0.324113	0.066*	0.293 (2)
H1AB	0.897006	0.48509	0.415285	0.066*	0.293 (2)
C2A	0.7424 (9)	0.5258 (10)	0.4203 (6)	0.051 (2)	0.293 (2)
H2AA	0.672082	0.570241	0.383851	0.061*	0.293 (2)
H2AB	0.768918	0.576965	0.475201	0.061*	0.293 (2)
Cl3A	0.7270 (3)	0.3331 (3)	0.43356 (19)	0.0799 (11)	0.293 (2)
C3	0.8885 (2)	0.7413 (3)	0.29966 (17)	0.0572 (7)
H3A	0.885462	0.848115	0.295397	0.086*
H3B	0.843773	0.698591	0.245341	0.086*
H3C	0.964987	0.708767	0.315027	0.086*
C4	0.9070 (3)	0.7654 (3)	0.44973 (17)	0.0687 (8)
H4A	0.984779	0.737603	0.468255	0.103*
H4B	0.876356	0.733971	0.491816	0.103*
H4C	0.900302	0.871732	0.443083	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0301 (2)	0.0362 (2)	0.0354 (2)	0	0.01147 (16)	0
Cl1	0.0383 (3)	0.0475 (3)	0.0375 (3)	−0.0055 (2)	0.0078 (2)	−0.0033 (2)
Cl2	0.0611 (4)	0.0447 (3)	0.0666 (4)	−0.0097 (3)	0.0364 (3)	0.0013 (3)
N1	0.0339 (9)	0.0456 (11)	0.0413 (10)	0.0079 (8)	0.0137 (8)	−0.0021 (8)
C1	0.043 (4)	0.040 (2)	0.042 (3)	−0.0033 (16)	0.023 (2)	0.0027 (16)
C2	0.0492 (19)	0.0449 (19)	0.0467 (19)	0.0064 (16)	0.0188 (15)	0.0019 (16)
Cl3	0.0479 (6)	0.0665 (6)	0.0663 (6)	−0.0018 (4)	0.0280 (4)	−0.0007 (5)
C1A	0.038 (9)	0.086 (10)	0.047 (9)	−0.015 (6)	0.024 (5)	0.001 (6)
C2A	0.062 (6)	0.047 (5)	0.048 (5)	0.004 (5)	0.025 (4)	0.009 (4)
Cl3A	0.113 (2)	0.0584 (16)	0.0850 (19)	−0.0153 (14)	0.0554 (17)	0.0128 (13)
C3	0.0704 (17)	0.0520 (15)	0.0552 (15)	−0.0085 (13)	0.0297 (13)	0.0012 (12)
C4	0.081 (2)	0.0703 (19)	0.0485 (15)	0.0016 (15)	0.0150 (14)	−0.0161 (14)

Geometric parameters (Å, º)

Co1—Cl1	2.2873 (6)	C1—H1B	0.97
Co1—Cl2	2.2618 (6)	C1—C2	1.534 (6)
N1—C3	1.482 (3)	C2—H2A	0.97
C3—H3A	0.96	C2—H2B	0.97
C3—H3B	0.96	C2—Cl3	1.776 (3)
C3—H3C	0.96	N1—C1A	1.490 (10)
N1—C4	1.483 (3)	C1A—H1AA	0.97
C4—H4A	0.96	C1A—H1AB	0.97
C4—H4B	0.96	C1A—C2A	1.480 (15)
C4—H4C	0.96	C2A—H2AA	0.97
N1—H1	0.87 (3)	C2A—H2AB	0.97
N1—C1	1.509 (5)	C2A—Cl3A	1.762 (9)
C1—H1A	0.97
Cl1^i—Co1—Cl1	111.86 (3)	C2—C1—H1A	108.2
Cl1—Co1—Cl2	108.17 (2)	N1—C1—H1B	108.2
Cl1—Co1—Cl2^i	104.58 (2)	C2—C1—H1B	108.2
Cl2^i—Co1—Cl2	119.62 (4)	H1A—C1—H1B	107.4
C3—N1—C4	110.6 (2)	C1—C2—Cl3	111.0 (4)
N1—C3—H3A	109.5	C1—C2—H2A	109.4
N1—C3—H3B	109.5	Cl3—C2—H2A	109.4
H3A—C3—H3B	109.5	C1—C2—H2B	109.4
N1—C3—H3C	109.5	Cl3—C2—H2B	109.4
H3A—C3—H3C	109.5	H2A—C2—H2B	108
H3B—C3—H3C	109.5	C3—N1—C1A	120.4 (7)
N1—C4—H4A	109.5	C4—N1—C1A	110.7 (11)
N1—C4—H4B	109.5	C2A—C1A—N1	105.3 (9)
H4A—C4—H4B	109.5	C2A—C1A—H1AA	110.7
N1—C4—H4C	109.5	N1—C1A—H1AA	110.7
H4A—C4—H4C	109.5	C2A—C1A—H1AB	110.7
H4B—C4—H4C	109.5	N1—C1A—H1AB	110.7
C3—N1—C1	105.4 (3)	H1AA—C1A—H1AB	108.8
C4—N1—C1	114.8 (4)	C1A—C2A—Cl3A	102.9 (7)
C3—N1—H1	108.0 (18)	C1A—C2A—H2AA	111.2
C4—N1—H1	105.3 (18)	Cl3A—C2A—H2AA	111.2
C1A—N1—H1	100 (2)	C1A—C2A—H2AB	111.2
C1—N1—H1	112.6 (19)	Cl3A—C2A—H2AB	111.2
N1—C1—C2	116.2 (5)	H2AA—C2A—H2AB	109.1
N1—C1—H1A	108.2
C3—N1—C1—C2	−178.1 (5)	C3—N1—C1A—C2A	−156.9 (10)
C4—N1—C1—C2	59.9 (7)	C4—N1—C1A—C2A	71.9 (16)
N1—C1—C2—Cl3	61.6 (7)	N1—C1A—C2A—Cl3A	−179.7 (13)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.87 (3)	2.51 (3)	3.3093 (19)	152 (2)
N1—H1···Cl2^i	0.87 (3)	3.02 (3)	3.564 (2)	122 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Bis(2-chloro-N,N-dimethylethan-1-aminium) tetrachloridozincate(II) (zincate)

Crystal data

(C4H11ClN)2[ZnCl4]	F(000) = 864
Mr = 424.34	Dx = 1.584 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9979 reflections
a = 12.7297 (7) Å	θ = 2.8–33.7°
b = 8.9784 (5) Å	µ = 2.26 mm^−1
c = 16.6837 (11) Å	T = 295 K
β = 111.062 (2)°	Irregular, colourless
V = 1779.43 (18) Å^3	0.39 × 0.38 × 0.29 mm
Z = 4

Data collection

Bruker D8 Quest Eco diffractometer	2479 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.036
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 31.0°, θmin = 3.4°
Tmin = 0.472, Tmax = 0.560	h = −18→18
46381 measured reflections	k = −12→12
2843 independent reflections	l = −24→24

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0155P)^2 + 3.2372P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.070	(Δ/σ)max = 0.001
S = 1.12	Δρmax = 0.57 e Å^−3
2843 reflections	Δρmin = −0.40 e Å^−3
113 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b)
1 restraint	Extinction coefficient: 0.0035 (3)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.5	0.72176 (4)	0.25	0.03333 (10)
Cl1	0.63307 (4)	0.57810 (6)	0.34859 (3)	0.04085 (12)
Cl2	0.40494 (5)	0.84939 (6)	0.31868 (4)	0.05219 (15)
N1	0.15576 (15)	0.8071 (2)	0.13379 (11)	0.0396 (4)
H1	0.223 (2)	0.770 (3)	0.1486 (17)	0.055 (7)*
C1	0.1482 (5)	0.9756 (5)	0.1328 (5)	0.0393 (10)	0.697 (2)
H1A	0.189643	1.011624	0.190345	0.047*	0.697 (2)
H1B	0.069934	1.003059	0.118912	0.047*	0.697 (2)
C2	0.1923 (3)	1.0567 (4)	0.0703 (2)	0.0451 (7)	0.697 (2)
H2A	0.180985	1.163084	0.073337	0.054*	0.697 (2)
H2B	0.15046	1.024182	0.012066	0.054*	0.697 (2)
Cl3	0.33801 (8)	1.01959 (11)	0.09585 (6)	0.0569 (3)	0.697 (2)
C1A	0.1726 (14)	0.9672 (11)	0.1224 (12)	0.052 (4)	0.303 (2)
H1C	0.200388	1.01761	0.177512	0.063*	0.303 (2)
H1D	0.102578	1.01361	0.086803	0.063*	0.303 (2)
C2A	0.2568 (7)	0.9742 (9)	0.0801 (5)	0.0480 (18)	0.303 (2)
H2C	0.229594	0.923437	0.025068	0.058*	0.303 (2)
H2D	0.32746	0.929578	0.115896	0.058*	0.303 (2)
Cl3A	0.2728 (3)	1.1668 (3)	0.06669 (18)	0.0773 (9)	0.303 (2)
C3	0.1113 (2)	0.7582 (3)	0.20017 (16)	0.0552 (6)
H3A	0.034943	0.791657	0.185019	0.083*
H3B	0.156482	0.799774	0.254694	0.083*
H3C	0.113532	0.65148	0.203863	0.083*
C4	0.0928 (3)	0.7347 (3)	0.05022 (17)	0.0675 (8)
H4A	0.10053	0.628507	0.056467	0.101*
H4B	0.122638	0.767543	0.007913	0.101*
H4C	0.014696	0.761126	0.032261	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02977 (15)	0.03496 (17)	0.03503 (17)	0	0.01136 (12)	0
Cl1	0.0366 (2)	0.0455 (3)	0.0358 (2)	0.00580 (19)	0.00738 (18)	0.00353 (19)
Cl2	0.0601 (3)	0.0429 (3)	0.0653 (4)	0.0098 (2)	0.0367 (3)	−0.0012 (2)
N1	0.0331 (8)	0.0453 (10)	0.0401 (9)	0.0091 (7)	0.0129 (7)	−0.0022 (7)
C1	0.042 (3)	0.0422 (18)	0.040 (2)	−0.0022 (15)	0.0234 (18)	0.0028 (14)
C2	0.0476 (16)	0.0459 (17)	0.0437 (16)	0.0085 (14)	0.0186 (13)	0.0044 (13)
Cl3	0.0477 (5)	0.0645 (6)	0.0649 (6)	−0.0009 (4)	0.0280 (4)	0.0002 (4)
C1A	0.042 (7)	0.083 (8)	0.043 (6)	−0.022 (5)	0.027 (4)	−0.003 (5)
C2A	0.055 (5)	0.052 (4)	0.042 (4)	0.001 (4)	0.023 (3)	0.008 (3)
Cl3A	0.110 (2)	0.0557 (13)	0.0823 (17)	−0.0148 (13)	0.0536 (16)	0.0132 (12)
C3	0.0694 (16)	0.0485 (13)	0.0532 (13)	−0.0096 (11)	0.0288 (12)	0.0008 (10)
C4	0.0780 (19)	0.0693 (18)	0.0481 (13)	0.0019 (15)	0.0139 (13)	−0.0172 (13)

Geometric parameters (Å, º)

Zn1—Cl2	2.2553 (5)	C2—H2B	0.97
Zn1—Cl2^i	2.2554 (5)	C1A—C2A	1.481 (12)
Zn1—Cl1^i	2.2883 (5)	C1A—H1C	0.97
Zn1—Cl1	2.2883 (5)	C1A—H1D	0.97
N1—C1A	1.476 (9)	C2A—Cl3A	1.765 (8)
N1—C3	1.480 (3)	C2A—H2C	0.97
N1—C4	1.485 (3)	C2A—H2D	0.97
N1—C1	1.515 (5)	C3—H3A	0.96
N1—H1	0.87 (3)	C3—H3B	0.96
C1—C2	1.535 (5)	C3—H3C	0.96
C1—H1A	0.97	C4—H4A	0.96
C1—H1B	0.97	C4—H4B	0.96
C2—Cl3	1.779 (3)	C4—H4C	0.96
C2—H2A	0.97
Cl2—Zn1—Cl2^i	118.93 (3)	H2A—C2—H2B	108.1
Cl2—Zn1—Cl1^i	104.94 (2)	N1—C1A—C2A	105.4 (7)
Cl2^i—Zn1—Cl1^i	108.36 (2)	N1—C1A—H1C	110.7
Cl2—Zn1—Cl1	108.36 (2)	C2A—C1A—H1C	110.7
Cl2^i—Zn1—Cl1	104.94 (2)	N1—C1A—H1D	110.7
Cl1^i—Zn1—Cl1	111.38 (3)	C2A—C1A—H1D	110.7
C1A—N1—C3	119.8 (5)	H1C—C1A—H1D	108.8
C1A—N1—C4	111.1 (8)	C1A—C2A—Cl3A	103.8 (6)
C3—N1—C4	110.5 (2)	C1A—C2A—H2C	111
C3—N1—C1	105.3 (2)	Cl3A—C2A—H2C	111
C4—N1—C1	114.6 (3)	C1A—C2A—H2D	111
C1A—N1—H1	103.7 (19)	Cl3A—C2A—H2D	111
C3—N1—H1	106.0 (18)	H2C—C2A—H2D	109
C4—N1—H1	104.1 (18)	N1—C3—H3A	109.5
C1—N1—H1	116.1 (18)	N1—C3—H3B	109.5
N1—C1—C2	116.3 (4)	H3A—C3—H3B	109.5
N1—C1—H1A	108.2	N1—C3—H3C	109.5
C2—C1—H1A	108.2	H3A—C3—H3C	109.5
N1—C1—H1B	108.2	H3B—C3—H3C	109.5
C2—C1—H1B	108.2	N1—C4—H4A	109.5
H1A—C1—H1B	107.4	N1—C4—H4B	109.5
C1—C2—Cl3	110.7 (3)	H4A—C4—H4B	109.5
C1—C2—H2A	109.5	N1—C4—H4C	109.5
Cl3—C2—H2A	109.5	H4A—C4—H4C	109.5
C1—C2—H2B	109.5	H4B—C4—H4C	109.5
Cl3—C2—H2B	109.5
C3—N1—C1—C2	178.5 (4)	C3—N1—C1A—C2A	157.7 (7)
C4—N1—C1—C2	−59.9 (6)	C4—N1—C1A—C2A	−71.4 (12)
N1—C1—C2—Cl3	−61.3 (6)	N1—C1A—C2A—Cl3A	179.3 (9)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1^i	0.87 (3)	2.51 (3)	3.3124 (18)	156 (2)
N1—H1···Cl2	0.87 (3)	3.03 (3)	3.5620 (19)	121 (2)

Symmetry code: (i) −x+1, y, −z+1/2.