An insight into real and average structure from diffuse X-ray scattering – a case study

Two-dimensional diffuse X-ray scattering from an organic salt [N-(3-(2,6-dimethylanilino)-1-methyl­but-2-enylidene)-2,6-dimethylanilinium chloride, C₂₁H₂₇N₂⁺Cl⁻] was interpreted with the help of an analytical model of diffuse scattering. An analysis of the relationship between symmetry and diffuse scattering for the studied system has been undertaken. The symmetry of the system explains the extinction pattern, taking the form of curves, on the diffuse scattering planes. We have also tested the relationship between the average structure model and scattering intensities. Two models, differing in their representation of overlapping atoms, were used. In the case of diffuse scattering the difference between resulting intensities is immense, while for the Bragg intensities it is much smaller. This sensitivity of diffuse scattering could potentially be used to improve the description of the average structure.

Computing details

For all compounds, data collection: APEX2 v2012.4-3 (Bruker AXS); cell refinement: APEX2 v2012.4-3 (Bruker AXS); data reduction: SAINT V8.18C (Bruker AXS Inc., 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(DP_RT_initial)

Crystal data

Cl·2(C10.5H13.5N)	F(000) = 736
Mr = 342.89	Dx = 1.087 Mg m^−3
Tetragonal, I4/m	Mo Kα radiation, λ = 0.71073 Å
a = 20.2750 (8) Å	µ = 0.19 mm^−1
c = 5.0989 (2) Å	T = 296 K
V = 2096.03 (18) Å^3	Block, clear colourless
Z = 4	0.32 × 0.2 × 0.13 mm

Data collection

Bruker kappa APEX2 area detector diffractometer	737 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	615 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.037
Detector resolution: 7.9 pixels mm^-1	θmax = 22.0°, θmin = 1.4°
ω and φ scans	h = −21→19
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS Inc.)	k = −21→21
Tmin = 0.956, Tmax = 0.976	l = −5→5
8122 measured reflections

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0786P)^2 + 1.3169P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max < 0.001
737 reflections	Δρmax = 0.12 e Å^−3
89 parameters	Δρmin = −0.22 e Å^−3

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)
Cl1	0.58070 (10)	0.62014 (9)	0.5000	0.0736 (7)	0.5
N1	0.55628 (16)	0.69052 (15)	0.0000	0.0667 (9)
H1	0.561 (3)	0.672 (3)	0.146 (8)	0.080*	0.5
C1	0.55176 (17)	0.76079 (15)	0.0000	0.0606 (10)
C2	0.49041 (18)	0.79000 (17)	0.0000	0.0725 (11)
C3	0.4880 (2)	0.8584 (2)	0.0000	0.0852 (12)
H3	0.4473	0.8795	0.0000	0.102*
C4	0.5439 (2)	0.8950 (2)	0.0000	0.0893 (13)
H4	0.5412	0.9408	0.0000	0.107*
C5	0.6035 (2)	0.86526 (19)	0.0000	0.0919 (13)
H5	0.6415	0.8910	0.0000	0.110*
C6	0.60903 (18)	0.79721 (18)	0.0000	0.0738 (11)
C7	0.4286 (2)	0.7495 (2)	0.0000	0.126 (2)
H7A	0.4276	0.7222	−0.1538	0.189*	0.5
H7B	0.3909	0.7782	0.0001	0.189*	0.5
H7C	0.4277	0.7222	0.1537	0.189*	0.5
C8	0.6750 (2)	0.7637 (2)	0.0000	0.1239 (19)
H8A	0.6789	0.7364	0.1530	0.186*	0.5
H8B	0.7093	0.7964	0.0015	0.186*	0.5
H8C	0.6792	0.7370	−0.1545	0.186*	0.5
C9	0.5585 (2)	0.6545 (2)	−0.2568 (8)	0.0470 (11)	0.5
C10	0.5573 (3)	0.6844 (3)	−0.5000	0.0456 (15)	0.5
H10	0.5556	0.7302	−0.5000	0.055*	0.5
C11	0.5623 (2)	0.58243 (19)	−0.2073 (8)	0.0582 (12)	0.5
H11A	0.5644	0.5746	−0.0218	0.087*	0.5
H11B	0.6010	0.5649	−0.2898	0.087*	0.5
H11C	0.5238	0.5613	−0.2781	0.087*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1061 (15)	0.0843 (13)	0.0305 (10)	0.0038 (10)	0.000	0.000
N1	0.0729 (19)	0.055 (2)	0.072 (2)	0.0087 (14)	0.000	0.000
C1	0.071 (2)	0.055 (2)	0.056 (2)	0.0058 (17)	0.000	0.000
C2	0.073 (2)	0.061 (2)	0.083 (3)	0.0087 (18)	0.000	0.000
C3	0.095 (3)	0.075 (3)	0.086 (3)	0.025 (2)	0.000	0.000
C4	0.117 (4)	0.058 (2)	0.093 (3)	0.005 (2)	0.000	0.000
C5	0.096 (3)	0.068 (3)	0.112 (4)	−0.012 (2)	0.000	0.000
C6	0.073 (2)	0.069 (2)	0.079 (3)	0.0028 (19)	0.000	0.000
C7	0.071 (3)	0.095 (3)	0.211 (7)	0.005 (2)	0.000	0.000
C8	0.073 (3)	0.108 (4)	0.190 (6)	0.003 (2)	0.000	0.000
C9	0.052 (2)	0.049 (3)	0.041 (3)	0.0051 (19)	0.001 (2)	−0.005 (2)
C10	0.062 (4)	0.046 (3)	0.029 (3)	0.005 (3)	0.000	0.000
C11	0.084 (3)	0.053 (2)	0.038 (2)	0.007 (2)	0.003 (2)	0.005 (2)

Geometric parameters (Å, º)

N1—H1	0.84 (2)	C6—C8	1.501 (6)
N1—C1	1.428 (4)	C7—H7A	0.9600
N1—C9^i	1.500 (4)	C7—H7B	0.9600
N1—C9	1.500 (4)	C7—H7C	0.9600
C1—C2	1.377 (5)	C8—H8A	0.9600
C1—C6	1.376 (5)	C8—H8B	0.9600
C2—C3	1.388 (5)	C8—H8C	0.9600
C2—C7	1.498 (6)	C9—C10	1.380 (5)
C3—H3	0.9300	C9—C11	1.485 (6)
C3—C4	1.354 (6)	C10—C9^ii	1.380 (5)
C4—H4	0.9300	C10—H10	0.9300
C4—C5	1.351 (6)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C5—C6	1.384 (5)	C11—H11C	0.9600
C1—N1—H1	117 (5)	C2—C7—H7A	109.5
C1—N1—C9^i	119.19 (17)	C2—C7—H7B	109.5
C1—N1—C9	119.19 (17)	C2—C7—H7C	109.5
C9^i—N1—H1	5 (5)	H7A—C7—H7B	109.5
C9—N1—H1	124 (5)	H7A—C7—H7C	109.5
C9^i—N1—C9	121.6 (3)	H7B—C7—H7C	109.5
C2—C1—N1	119.1 (3)	C6—C8—H8A	109.5
C6—C1—N1	118.8 (3)	C6—C8—H8B	109.5
C6—C1—C2	122.1 (3)	C6—C8—H8C	109.5
C1—C2—C3	117.5 (4)	H8A—C8—H8B	109.5
C1—C2—C7	121.3 (3)	H8A—C8—H8C	109.5
C3—C2—C7	121.2 (4)	H8B—C8—H8C	109.5
C2—C3—H3	119.4	C10—C9—N1	124.8 (3)
C4—C3—C2	121.1 (4)	C10—C9—C11	125.8 (4)
C4—C3—H3	119.4	C11—C9—N1	109.4 (3)
C3—C4—H4	119.8	C9^ii—C10—C9	128.0 (5)
C5—C4—C3	120.3 (4)	C9^ii—C10—H10	116.0
C5—C4—H4	119.8	C9—C10—H10	116.0
C4—C5—H5	119.5	C9—C11—H11A	109.5
C4—C5—C6	121.1 (4)	C9—C11—H11B	109.5
C6—C5—H5	119.5	C9—C11—H11C	109.5
C1—C6—C5	117.8 (3)	H11A—C11—H11B	109.5
C1—C6—C8	120.6 (3)	H11A—C11—H11C	109.5
C5—C6—C8	121.5 (4)	H11B—C11—H11C	109.5
N1—C1—C2—C3	180.0	C4—C5—C6—C1	0.0
N1—C1—C2—C7	0.0	C4—C5—C6—C8	180.0
N1—C1—C6—C5	180.0	C6—C1—C2—C3	0.0
N1—C1—C6—C8	0.0	C6—C1—C2—C7	180.0
N1—C9—C10—C9^ii	−179.2 (4)	C7—C2—C3—C4	180.0
C1—N1—C9—C10	1.0 (6)	C9—N1—C1—C2	89.9 (3)
C1—N1—C9—C11	−179.3 (4)	C9^i—N1—C1—C2	−89.9 (3)
C1—C2—C3—C4	0.0	C9—N1—C1—C6	−90.1 (3)
C2—C1—C6—C5	0.0	C9^i—N1—C1—C6	90.1 (3)
C2—C1—C6—C8	180.0	C9^i—N1—C9—C10	−179.3 (3)
C2—C3—C4—C5	0.0	C9^i—N1—C9—C11	0.4 (6)
C3—C4—C5—C6	0.0	C11—C9—C10—C9^ii	1.1 (10)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.84 (2)	2.13 (2)	2.9633 (19)	174 (7)

(DP_RT_final)

Crystal data

Cl·2(C10.5H13.5N)	F(000) = 736
Mr = 342.89	Dx = 1.087 Mg m^−3
Tetragonal, I4/m	Mo Kα radiation, λ = 0.71073 Å
a = 20.2750 (8) Å	µ = 0.19 mm^−1
c = 5.0989 (2) Å	T = 296 K
V = 2096.03 (18) Å^3	Block, clear colourless
Z = 4	0.32 × 0.2 × 0.13 mm

Data collection

Bruker kappa APEX2 area detector diffractometer	737 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	615 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.037
Detector resolution: 7.9 pixels mm^-1	θmax = 22.0°, θmin = 1.4°
ω and φ scans	h = −21→19
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS Inc.)	k = −21→21
Tmin = 0.956, Tmax = 0.976	l = −5→5
8122 measured reflections

Refinement

Refinement on F^2	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.078P)^2 + 1.1345P] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max < 0.001
737 reflections	Δρmax = 0.12 e Å^−3
82 parameters	Δρmin = −0.22 e Å^−3

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)
Cl1	0.58068 (10)	0.62011 (9)	1.5000	0.0736 (7)	0.5
N1	0.55622 (11)	0.69107 (9)	0.960 (2)	0.051 (2)	0.5
H1	0.5606	0.6691	1.1354	0.061*	0.5
C1	0.55178 (8)	0.76112 (7)	0.969 (3)	0.051 (2)	0.5
C2	0.49031 (9)	0.79005 (8)	1.000 (5)	0.0726 (10)
C3	0.48795 (10)	0.85813 (8)	1.000 (7)	0.0851 (12)
H3	0.4472	0.8791	1.0000	0.102*
C4	0.54352 (12)	0.89455 (7)	1.000 (8)	0.0892 (13)
H4	0.5407	0.9403	1.0000	0.107*
C5	0.60377 (11)	0.86525 (9)	1.000 (7)	0.0915 (13)
H5	0.6416	0.8912	1.0000	0.110*
C6	0.60928 (8)	0.79744 (8)	0.973 (5)	0.067 (3)	0.5
C7	0.42879 (9)	0.74924 (11)	1.000 (7)	0.126 (2)
H7A	0.3912	0.7775	1.0236	0.189*	0.5
H7B	0.4304	0.7186	1.1297	0.189*	0.5
H7C	0.4253	0.7253	0.8240	0.189*	0.5
C8	0.67517 (10)	0.76349 (13)	0.960 (7)	0.109 (6)	0.5
H8A	0.6781	0.7314	1.0974	0.163*	0.5
H8B	0.7096	0.7955	1.0000	0.163*
H8C	0.6799	0.7421	0.7931	0.163*	0.5
C9	0.55844 (17)	0.65471 (18)	0.7433 (8)	0.0470 (10)	0.5
C10	0.5573 (3)	0.6842 (3)	0.5000	0.0459 (14)	0.5
H10	0.5555	0.7301	0.5000	0.055*	0.5
C11	0.5622 (2)	0.58241 (18)	0.7928 (8)	0.0578 (12)	0.5
H11A	0.5642	0.5745	0.9783	0.087*	0.5
H11B	0.6009	0.5648	0.7104	0.087*	0.5
H11C	0.5237	0.5613	0.7217	0.087*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1058 (14)	0.0844 (13)	0.0306 (10)	0.0037 (10)	0.000	0.000
N1	0.0745 (19)	0.0556 (16)	0.022 (6)	0.0087 (12)	−0.0011 (17)	−0.0002 (18)
C1	0.069 (2)	0.0544 (19)	0.030 (5)	0.0054 (15)	−0.002 (2)	−0.009 (3)
C2	0.074 (2)	0.061 (2)	0.083 (3)	0.0087 (17)	0.000	0.000
C3	0.093 (3)	0.075 (3)	0.088 (3)	0.023 (2)	0.000	0.000
C4	0.118 (3)	0.058 (2)	0.092 (3)	0.006 (2)	0.000	0.000
C5	0.096 (3)	0.069 (3)	0.110 (3)	−0.013 (2)	0.000	0.000
C6	0.074 (2)	0.069 (2)	0.058 (9)	0.0037 (18)	−0.007 (4)	−0.011 (5)
C7	0.072 (3)	0.095 (3)	0.211 (6)	0.005 (2)	0.000	0.000
C8	0.073 (3)	0.106 (3)	0.147 (17)	0.002 (2)	−0.008 (6)	−0.009 (7)
C9	0.051 (2)	0.052 (2)	0.038 (3)	0.0050 (17)	0.0004 (18)	−0.004 (2)
C10	0.061 (4)	0.045 (3)	0.031 (3)	0.006 (2)	0.000	0.000
C11	0.084 (3)	0.052 (2)	0.038 (2)	0.006 (2)	0.004 (2)	0.0052 (19)

Geometric parameters (Å, º)

N1—N1^i	0.41 (2)	C6—C6^i	0.28 (5)
N1—C9	1.329 (10)	C6—C1^i	1.411 (6)
N1—C1	1.4238	C6—C8	1.5043
N1—C1^i	1.469 (7)	C6—C8^i	1.542 (16)
N1—C9^i	1.683 (9)	C7—H7A	0.9606
N1—H1	1.0028	C7—H7B	0.9076
C1—C1^i	0.32 (3)	C7—H7C	1.0225
C1—C6	1.3791	C8—C8^i	0.41 (7)
C1—C2	1.3867	C8—C6^i	1.542 (11)
C1—C6^i	1.411 (11)	C8—H8A	0.9591
C1—N1^i	1.469 (5)	C8—H8B	0.9745
C2—C3	1.3812	C8—H8C	0.9588
C2—C1^i	1.387 (3)	C9—C10	1.378 (5)
C2—C7	1.4968	C9—C11	1.489 (5)
C3—C4	1.3471	C9—N1^i	1.683 (9)
C3—H3	0.9293	C10—C9^ii	1.378 (5)
C4—C5	1.3584	C10—H10	0.9300
C4—H4	0.9284	C11—H11A	0.9600
C5—C6	1.3865	C11—H11B	0.9600
C5—C6^i	1.386 (5)	C11—H11C	0.9600
C5—H5	0.9294
N1^i—N1—C9	146.2 (3)	C1—C6—C5	117.6
N1^i—N1—C1	88.2 (6)	C6^i—C6—C1^i	77.7 (12)
C9—N1—C1	125.5 (8)	C1—C6—C1^i	13.1 (11)
N1^i—N1—C1^i	75.7 (7)	C5—C6—C1^i	115.4 (2)
C9—N1—C1^i	138.1 (9)	C6^i—C6—C8	92.48 (12)
C1—N1—C1^i	12.6 (10)	C1—C6—C8	120.4
N1^i—N1—C9^i	26.03 (19)	C5—C6—C8	121.99 (5)
C9—N1—C9^i	120.2 (3)	C1^i—C6—C8	120.28 (8)
C1—N1—C9^i	114.3 (7)	C6^i—C6—C8^i	77 (3)
C1^i—N1—C9^i	101.7 (8)	C1—C6—C8^i	119.8 (3)
N1^i—N1—H1	26.9	C5—C6—C8^i	119.3 (6)
C9—N1—H1	119.5	C1^i—C6—C8^i	115.8 (11)
C1—N1—H1	114.9	C8—C6—C8^i	15 (2)
C1^i—N1—H1	102.3	C2—C7—H7A	109.3
C9^i—N1—H1	3.6	C2—C7—H7B	110.4
C1^i—C1—C6	89.16 (8)	H7A—C7—H7B	110.2
C1^i—C1—C2	83.37 (6)	C2—C7—H7C	108.6
C6—C1—C2	122.2	H7A—C7—H7C	109.8
C1^i—C1—C6^i	78 (2)	H7B—C7—H7C	108.5
C6—C1—C6^i	11 (2)	C8^i—C8—C6	87.5
C2—C1—C6^i	119.8 (5)	C8^i—C8—C6^i	77.1 (19)
C1^i—C1—N1	91.8	C6—C8—C6^i	10.4 (18)
C6—C1—N1	118.7	C8^i—C8—H8A	42.9
C2—C1—N1	118.8	C6—C8—H8A	109.4
C6^i—C1—N1	118.35 (17)	C6^i—C8—H8A	101.1
C1^i—C1—N1^i	75.7 (8)	C8^i—C8—H8B	77.8
C6—C1—N1^i	117.4 (2)	C6—C8—H8B	108.8
C2—C1—N1^i	115.8 (3)	C6^i—C8—H8B	106.1
C6^i—C1—N1^i	113.7 (7)	H8A—C8—H8B	104.7
N1—C1—N1^i	16.1 (8)	C8^i—C8—H8C	152.4
C3—C2—C1	117.0	C6—C8—H8C	109.5
C3—C2—C1^i	116.99 (6)	C6^i—C8—H8C	119.1
C1—C2—C1^i	13.3 (11)	H8A—C8—H8C	109.6
C3—C2—C7	121.6	H8B—C8—H8C	114.6
C1—C2—C7	121.0	N1—C9—C10	120.5 (4)
C1^i—C2—C7	121.01 (8)	N1—C9—C11	114.0 (4)
C4—C3—C2	121.3	C10—C9—C11	125.5 (4)
C4—C3—H3	119.6	N1—C9—N1^i	7.7 (4)
C2—C3—H3	119.2	C10—C9—N1^i	128.2 (4)
C3—C4—C5	120.8	C11—C9—N1^i	106.3 (3)
C3—C4—H4	119.7	C9—C10—C9^ii	128.4 (5)
C5—C4—H4	119.5	C9—C10—H10	115.8
C4—C5—C6	120.4	C9^ii—C10—H10	115.8
C4—C5—C6^i	120.41 (14)	C9—C11—H11A	109.5
C6—C5—C6^i	12 (2)	C9—C11—H11B	109.5
C4—C5—H5	119.7	H11A—C11—H11B	109.5
C6—C5—H5	119.6	C9—C11—H11C	109.5
C6^i—C5—H5	119.6	H11A—C11—H11C	109.5
C6^i—C6—C1	90.8	H11B—C11—H11C	109.5
C6^i—C6—C5	84.2
N1^i—N1—C1—C1^i	0.0 (7)	N1^i—C1—C6—C5	−157.2 (9)
C9—N1—C1—C1^i	179.9 (8)	C2—C1—C6—C1^i	81.6
C9^i—N1—C1—C1^i	0.1 (7)	C6^i—C1—C6—C1^i	−0.02 (6)
N1^i—N1—C1—C6	90.0 (7)	N1—C1—C6—C1^i	−91.6
C9—N1—C1—C6	−90.1 (8)	N1^i—C1—C6—C1^i	−73.3 (9)
C1^i—N1—C1—C6	90.0	C1^i—C1—C6—C8	93.4
C9^i—N1—C1—C6	90.1 (7)	C2—C1—C6—C8	175.0
N1^i—N1—C1—C2	−83.4 (7)	C6^i—C1—C6—C8	93.4
C9—N1—C1—C2	96.5 (8)	N1—C1—C6—C8	1.8
C1^i—N1—C1—C2	−83.4	N1^i—C1—C6—C8	20.0 (9)
C9^i—N1—C1—C2	−83.3 (7)	C1^i—C1—C6—C8^i	76 (3)
N1^i—N1—C1—C6^i	77.0 (19)	C2—C1—C6—C8^i	157 (3)
C9—N1—C1—C6^i	−103.1 (19)	C6^i—C1—C6—C8^i	76 (3)
C1^i—N1—C1—C6^i	77 (2)	N1—C1—C6—C8^i	−16 (3)
C9^i—N1—C1—C6^i	77.1 (19)	N1^i—C1—C6—C8^i	2 (3)
C9—N1—C1—N1^i	180 (100)	C4—C5—C6—C6^i	−93.43 (7)
C1^i—N1—C1—N1^i	0.0 (7)	C4—C5—C6—C1	−5.5
C9^i—N1—C1—N1^i	0.07 (17)	C6^i—C5—C6—C1	87.9
C1^i—C1—C2—C3	93.4	C4—C5—C6—C1^i	−20.0 (12)
C6—C1—C2—C3	8.6	C6^i—C5—C6—C1^i	73.5 (11)
C6^i—C1—C2—C3	22 (2)	C4—C5—C6—C8	177.3
N1—C1—C2—C3	−178.2	C6^i—C5—C6—C8	−89.3
N1^i—C1—C2—C3	163.9 (9)	C4—C5—C6—C8^i	−165 (3)
C6—C1—C2—C1^i	−84.81 (5)	C6^i—C5—C6—C8^i	−72 (3)
C6^i—C1—C2—C1^i	−72 (2)	C6^i—C6—C8—C8^i	0.0
N1—C1—C2—C1^i	88.4	C1—C6—C8—C8^i	−92.4
N1^i—C1—C2—C1^i	70.5 (9)	C5—C6—C8—C8^i	84.7
C1^i—C1—C2—C7	−94.0	C1^i—C6—C8—C8^i	−77.2 (12)
C6—C1—C2—C7	−178.8	C1—C6—C8—C6^i	−92.4
C6^i—C1—C2—C7	−166 (2)	C5—C6—C8—C6^i	84.73 (12)
N1—C1—C2—C7	−5.6	C1^i—C6—C8—C6^i	−77.2 (12)
N1^i—C1—C2—C7	−23.5 (9)	C8^i—C6—C8—C6^i	0.0 (2)
C1—C2—C3—C4	−7.4	N1^i—N1—C9—C10	−179.4 (3)
C1^i—C2—C3—C4	7.4 (12)	C1—N1—C9—C10	0.8 (5)
C7—C2—C3—C4	180.0	C1^i—N1—C9—C10	0.8 (6)
C2—C3—C4—C5	0.0	C9^i—N1—C9—C10	−179.4 (3)
C3—C4—C5—C6	6.7	N1^i—N1—C9—C11	0.6 (5)
C3—C4—C5—C6^i	−7 (2)	C1—N1—C9—C11	−179.3 (2)
C1^i—C1—C6—C6^i	0.0	C1^i—N1—C9—C11	−179.2 (4)
C2—C1—C6—C6^i	81.7	C9^i—N1—C9—C11	0.6 (5)
N1—C1—C6—C6^i	−91.6	C1—N1—C9—N1^i	−179.8 (4)
N1^i—C1—C6—C6^i	−73.3 (9)	C1^i—N1—C9—N1^i	−179.8 (6)
C1^i—C1—C6—C5	−83.9	C9^i—N1—C9—N1^i	0.00 (4)
C2—C1—C6—C5	−2.3	N1—C9—C10—C9^ii	−179.2 (4)
C6^i—C1—C6—C5	−83.9	C11—C9—C10—C9^ii	0.8 (9)
N1—C1—C6—C5	−175.5	N1^i—C9—C10—C9^ii	−179.3 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	1.00 (2)	2.15 (2)	3.15 (9)	174 (7)

(DP_100K_initial)

Crystal data

Cl·2(C10.5H13.5N)	F(000) = 736
Mr = 342.89	Dx = 1.128 Mg m^−3
Tetragonal, I4/m	Mo Kα radiation, λ = 0.71073 Å
a = 19.924 (10) Å	µ = 0.19 mm^−1
c = 5.088 (3) Å	T = 100 K
V = 2020 (2) Å^3	Block, clear colourless
Z = 4	0.32 × 0.2 × 0.13 mm

Data collection

Bruker kappa APEX2 area detector diffractometer	1611 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	1391 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.041
Detector resolution: 7.9 pixels mm^-1	θmax = 29.9°, θmin = 1.5°
ω and φ scans	h = −27→23
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS Inc.)	k = −27→18
Tmin = 0.955, Tmax = 0.975	l = −6→7
9109 measured reflections

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 1.0663P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
1611 reflections	Δρmax = 0.42 e Å^−3
88 parameters	Δρmin = −0.22 e Å^−3

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)
Cl1	0.58670 (4)	0.61813 (3)	0.5000	0.02109 (19)	0.5
N1	0.55627 (7)	0.68996 (6)	0.0000	0.0285 (3)
H1	0.5617 (15)	0.6683 (14)	0.141 (4)	0.034*	0.5
C1	0.55205 (7)	0.76183 (7)	0.0000	0.0225 (3)
C2	0.48895 (7)	0.79240 (7)	0.0000	0.0251 (3)
C3	0.48666 (8)	0.86248 (7)	0.0000	0.0239 (3)
H3	0.4444	0.8846	0.0000	0.029*
C4	0.54491 (8)	0.89999 (7)	0.0000	0.0248 (3)
H4	0.5425	0.9476	0.0000	0.030*
C5	0.60714 (8)	0.86843 (7)	0.0000	0.0249 (3)
H5	0.6469	0.8947	0.0000	0.030*
C6	0.61172 (7)	0.79866 (7)	0.0000	0.0216 (3)
C7	0.42559 (8)	0.75112 (9)	0.0000	0.0430 (5)
H7A	0.4245	0.7227	−0.1573	0.064*	0.5
H7B	0.3865	0.7810	0.0000	0.064*	0.5
H7C	0.4245	0.7227	0.1573	0.064*	0.5
C8	0.67843 (8)	0.76337 (9)	0.0000	0.0340 (4)
H8A	0.6820	0.7351	0.1571	0.051*	0.5
H8B	0.7146	0.7967	0.0003	0.051*	0.5
H8C	0.6821	0.7353	−0.1574	0.051*	0.5
C9	0.55938 (9)	0.65381 (9)	−0.2550 (4)	0.0141 (3)	0.5
C10	0.55798 (13)	0.68498 (12)	−0.5000	0.0151 (5)	0.5
H10	0.5558	0.7326	−0.5000	0.018*	0.5
C11	0.56383 (9)	0.57974 (9)	−0.2070 (4)	0.0180 (4)	0.5
H11A	0.5685	0.5714	−0.0180	0.027*
H11B	0.6029	0.5615	−0.2995	0.027*	0.5
H11C	0.5230	0.5579	−0.2719	0.027*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0302 (4)	0.0232 (3)	0.0099 (3)	0.0033 (2)	0.000	0.000
N1	0.0215 (6)	0.0149 (6)	0.0490 (9)	0.0022 (4)	0.000	0.000
C1	0.0212 (6)	0.0151 (6)	0.0312 (8)	0.0026 (5)	0.000	0.000
C2	0.0195 (6)	0.0201 (6)	0.0356 (9)	0.0024 (5)	0.000	0.000
C3	0.0256 (7)	0.0208 (6)	0.0252 (7)	0.0065 (5)	0.000	0.000
C4	0.0316 (7)	0.0170 (6)	0.0258 (7)	0.0022 (5)	0.000	0.000
C5	0.0254 (7)	0.0214 (7)	0.0279 (8)	−0.0028 (5)	0.000	0.000
C6	0.0201 (6)	0.0214 (6)	0.0233 (7)	0.0021 (5)	0.000	0.000
C7	0.0198 (7)	0.0267 (8)	0.0823 (16)	0.0003 (6)	0.000	0.000
C8	0.0199 (7)	0.0304 (8)	0.0516 (11)	0.0030 (6)	0.000	0.000
C9	0.0139 (7)	0.0160 (7)	0.0123 (7)	0.0004 (6)	0.0010 (6)	−0.0006 (6)
C10	0.0182 (11)	0.0136 (10)	0.0134 (11)	0.0002 (8)	0.000	0.000
C11	0.0261 (8)	0.0148 (7)	0.0133 (9)	0.0016 (6)	0.0013 (7)	0.0014 (6)

Geometric parameters (Å, º)

N1—H1	0.845 (10)	C6—C8	1.504 (2)
N1—C1	1.4345 (19)	C7—H7A	0.9800
N1—C9^i	1.485 (2)	C7—H7B	0.9800
N1—C9	1.485 (2)	C7—H7C	0.9800
C1—C2	1.397 (2)	C8—H8A	0.9800
C1—C6	1.397 (2)	C8—H8B	0.9800
C2—C3	1.397 (2)	C8—H8C	0.9800
C2—C7	1.507 (2)	C9—C10	1.393 (2)
C3—H3	0.9500	C9—C11	1.499 (2)
C3—C4	1.380 (2)	C10—C9^ii	1.393 (2)
C4—H4	0.9500	C10—H10	0.9500
C4—C5	1.390 (2)	C11—H11A	0.9800
C5—H5	0.9500	C11—H11B	0.9800
C5—C6	1.393 (2)	C11—H11C	0.9800
C1—N1—H1	121 (2)	C2—C7—H7A	109.5
C1—N1—C9	119.11 (8)	C2—C7—H7B	109.5
C1—N1—C9^i	119.11 (8)	C2—C7—H7C	109.5
C9^i—N1—H1	5 (2)	H7A—C7—H7B	109.5
C9—N1—H1	119 (2)	H7A—C7—H7C	109.5
C9—N1—C9^i	121.76 (16)	H7B—C7—H7C	109.5
C2—C1—N1	119.21 (13)	C6—C8—H8A	109.5
C2—C1—C6	122.48 (13)	C6—C8—H8B	109.5
C6—C1—N1	118.31 (12)	C6—C8—H8C	109.5
C1—C2—C3	117.71 (13)	H8A—C8—H8B	109.5
C1—C2—C7	121.07 (13)	H8A—C8—H8C	109.5
C3—C2—C7	121.21 (13)	H8B—C8—H8C	109.5
C2—C3—H3	119.5	N1—C9—C11	109.72 (14)
C4—C3—C2	120.90 (13)	C10—C9—N1	124.38 (15)
C4—C3—H3	119.5	C10—C9—C11	125.91 (17)
C3—C4—H4	119.8	C9^ii—C10—C9	127.0 (2)
C3—C4—C5	120.33 (13)	C9^ii—C10—H10	116.5
C5—C4—H4	119.8	C9—C10—H10	116.5
C4—C5—H5	119.7	C9—C11—H11A	109.5
C4—C5—C6	120.65 (14)	C9—C11—H11B	109.5
C6—C5—H5	119.7	C9—C11—H11C	109.5
C1—C6—C8	120.44 (13)	H11A—C11—H11B	109.5
C5—C6—C1	117.92 (13)	H11A—C11—H11C	109.5
C5—C6—C8	121.64 (14)	H11B—C11—H11C	109.5
N1—C1—C2—C3	180.0	C4—C5—C6—C1	0.0
N1—C1—C2—C7	0.0	C4—C5—C6—C8	180.0
N1—C1—C6—C5	180.0	C6—C1—C2—C3	0.0
N1—C1—C6—C8	0.0	C6—C1—C2—C7	180.0
N1—C9—C10—C9^ii	−178.62 (15)	C7—C2—C3—C4	180.0
C1—N1—C9—C10	−0.5 (2)	C9^i—N1—C1—C2	−90.85 (12)
C1—N1—C9—C11	179.77 (14)	C9—N1—C1—C2	90.86 (12)
C1—C2—C3—C4	0.0	C9^i—N1—C1—C6	89.15 (12)
C2—C1—C6—C5	0.0	C9—N1—C1—C6	−89.14 (12)
C2—C1—C6—C8	180.0	C9^i—N1—C9—C10	−178.74 (14)
C2—C3—C4—C5	0.0	C9^i—N1—C9—C11	1.5 (2)
C3—C4—C5—C6	0.0	C11—C9—C10—C9^ii	1.1 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.85 (1)	2.14 (1)	2.9812 (15)	174 (3)

(DP_100K_final)

Crystal data

Cl·2(C10.5H13.5N)	F(000) = 736
Mr = 342.89	Dx = 1.128 Mg m^−3
Tetragonal, I4/m	Mo Kα radiation, λ = 0.71073 Å
a = 19.924 (10) Å	µ = 0.19 mm^−1
c = 5.088 (3) Å	T = 100 K
V = 2020 (2) Å^3	Block, clear colourless
Z = 4	0.32 × 0.2 × 0.13 mm

Data collection

Bruker kappa APEX2 area detector diffractometer	1611 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	1391 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.041
Detector resolution: 7.9 pixels mm^-1	θmax = 29.9°, θmin = 1.5°
ω and φ scans	h = −27→23
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS Inc.)	k = −27→18
Tmin = 0.955, Tmax = 0.975	l = −6→7
9109 measured reflections

Refinement

Refinement on F^2	40 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.7757P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.002
1611 reflections	Δρmax = 0.48 e Å^−3
88 parameters	Δρmin = −0.16 e Å^−3

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)
Cl1	0.58669 (3)	0.61812 (3)	1.5000	0.02093 (19)	0.5
N1	0.55626 (8)	0.68995 (7)	0.9657 (9)	0.0162 (8)	0.5
H1	0.5604 (14)	0.6730 (13)	1.121 (3)	0.019*	0.5
C1	0.55203 (8)	0.76197 (7)	0.9732 (16)	0.0154 (10)	0.5
C2	0.48894 (8)	0.79240 (8)	0.9728 (16)	0.0177 (10)	0.5
C3	0.48664 (7)	0.86250 (7)	1.0000	0.0237 (3)
H3	0.4439 (9)	0.8850 (9)	1.0000	0.028*
C4	0.54492 (8)	0.90000 (7)	1.0000	0.0247 (3)
H4	0.5418 (9)	0.9498 (9)	1.0000	0.030*
C5	0.60716 (7)	0.86842 (7)	1.0000	0.0248 (3)
H5	0.6472 (10)	0.8967 (9)	1.0000	0.030*
C6	0.61171 (7)	0.79865 (7)	1.0000	0.0214 (3)
C7	0.42561 (9)	0.75119 (10)	0.9640 (17)	0.0297 (16)	0.5
H7A	0.420 (2)	0.7249 (16)	0.806 (5)	0.044*	0.5
H7B	0.3871 (9)	0.7823 (10)	0.959 (8)	0.044*	0.5
H7C	0.425 (2)	0.7199 (15)	1.108 (5)	0.044*	0.5
C8	0.67831 (8)	0.76335 (9)	1.0000	0.0338 (4)
H8A	0.684 (4)	0.7308 (19)	1.140 (7)	0.051*	0.5
H8B	0.7156 (10)	0.7942 (11)	1.0000	0.051*
H8C	0.685 (4)	0.740 (2)	0.833 (6)	0.051*	0.5
C9	0.55939 (8)	0.65379 (8)	0.7454 (3)	0.0138 (3)	0.5
C10	0.55798 (12)	0.68496 (12)	0.5000	0.0146 (4)	0.5
H10	0.5559	0.7316	0.5000	0.018*	0.5
C11	0.56383 (9)	0.57976 (8)	0.7930 (3)	0.0179 (4)	0.5
H11A	0.5684	0.5715	0.9781	0.027*	0.5
H11B	0.6021	0.5619	0.7023	0.027*	0.5
H11C	0.5238	0.5584	0.7293	0.027*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0300 (3)	0.0230 (3)	0.0098 (3)	0.0033 (2)	0.000	0.000
N1	0.0224 (6)	0.0159 (6)	0.010 (3)	0.0024 (4)	−0.0001 (7)	0.0018 (6)
C1	0.0211 (6)	0.0154 (5)	0.010 (3)	0.0024 (4)	0.0000 (8)	−0.0025 (8)
C2	0.0195 (6)	0.0199 (6)	0.014 (3)	0.0023 (5)	0.0000 (8)	−0.0004 (8)
C3	0.0256 (7)	0.0204 (6)	0.0251 (7)	0.0063 (5)	0.000	0.000
C4	0.0311 (7)	0.0172 (6)	0.0257 (7)	0.0022 (5)	0.000	0.000
C5	0.0253 (7)	0.0212 (6)	0.0278 (7)	−0.0026 (5)	0.000	0.000
C6	0.0198 (6)	0.0210 (6)	0.0232 (7)	0.0019 (5)	0.000	0.000
C7	0.0204 (7)	0.0259 (8)	0.043 (5)	0.0001 (6)	0.0003 (10)	0.0007 (11)
C8	0.0196 (7)	0.0302 (8)	0.0517 (11)	0.0031 (5)	0.000	0.000
C9	0.0134 (7)	0.0153 (7)	0.0128 (7)	0.0006 (5)	0.0010 (6)	−0.0003 (6)
C10	0.0179 (10)	0.0133 (10)	0.0127 (11)	0.0001 (8)	0.000	0.000
C11	0.0259 (8)	0.0146 (7)	0.0134 (8)	0.0015 (6)	0.0016 (6)	0.0014 (6)

Geometric parameters (Å, º)

N1—N1^i	0.350 (9)	C5—C6	1.393 (2)
N1—C9	1.334 (4)	C5—H5	0.977 (19)
N1—C1	1.438 (2)	C6—C1^i	1.402 (2)
N1—C1^i	1.471 (3)	C6—C8	1.502 (2)
N1—C9^i	1.638 (5)	C7—C7^i	0.366 (17)
N1—H1	0.865 (10)	C7—C2^i	1.539 (4)
C1—C1^i	0.273 (16)	C7—H7A	0.966 (18)
C1—C2	1.396 (2)	C7—H7B	0.985 (16)
C1—C6	1.402 (2)	C7—H7C	0.964 (18)
C1—C2^i	1.423 (3)	C8—H8A	0.971 (18)
C1—N1^i	1.471 (3)	C8—H8B	0.964 (16)
C2—C2^i	0.276 (16)	C8—H8C	0.983 (18)
C2—C3	1.404 (2)	C9—C10	1.395 (2)
C2—C1^i	1.423 (3)	C9—C11	1.497 (2)
C2—C7	1.506 (3)	C9—N1^i	1.638 (5)
C2—C7^i	1.539 (4)	C10—C9^ii	1.395 (2)
C3—C4	1.381 (2)	C10—H10	0.9300
C3—C2^i	1.404 (2)	C11—H11A	0.9600
C3—H3	0.963 (18)	C11—H11B	0.9600
C4—C5	1.391 (2)	C11—H11C	0.9600
C4—H4	0.995 (19)
N1^i—N1—C9	147.16 (13)	C2^i—C3—H3	119.5 (11)
N1^i—N1—C1	88.5 (4)	C3—C4—C5	120.34 (13)
C9—N1—C1	124.4 (5)	C3—C4—H4	119.2 (11)
N1^i—N1—C1^i	77.8 (3)	C5—C4—H4	120.5 (11)
C9—N1—C1^i	135.0 (4)	C4—C5—C6	120.62 (13)
C1—N1—C1^i	10.7 (6)	C4—C5—H5	117.9 (11)
N1^i—N1—C9^i	26.19 (10)	C6—C5—H5	121.5 (11)
C9—N1—C9^i	120.98 (16)	C5—C6—C1^i	117.71 (13)
C1—N1—C9^i	114.6 (4)	C5—C6—C1	117.71 (13)
C1^i—N1—C9^i	104.0 (4)	C1^i—C6—C1	11.2 (7)
N1^i—N1—H1	24 (2)	C5—C6—C8	121.65 (13)
C9—N1—H1	123.7 (19)	C1^i—C6—C8	120.34 (13)
C1—N1—H1	112 (2)	C1—C6—C8	120.34 (13)
C1^i—N1—H1	101 (2)	C7^i—C7—C2	88.3 (5)
C9^i—N1—H1	4.4 (19)	C7^i—C7—C2^i	77.9 (4)
C1^i—C1—C2	90.1 (5)	C2—C7—C2^i	10.3 (6)
C1^i—C1—C6	84.4 (3)	C7^i—C7—H7A	146 (2)
C2—C1—C6	122.50 (16)	C2—C7—H7A	115 (3)
C1^i—C1—C2^i	78.9 (5)	C2^i—C7—H7A	124 (3)
C2—C1—C2^i	11.2 (7)	C7^i—C7—H7B	92 (2)
C6—C1—C2^i	120.6 (2)	C2—C7—H7B	108.0 (13)
C1^i—C1—N1	91.5 (4)	C2^i—C7—H7B	107.9 (14)
C2—C1—N1	119.10 (15)	H7A—C7—H7B	103 (3)
C6—C1—N1	118.23 (14)	C7^i—C7—H7C	40 (2)
C2^i—C1—N1	118.84 (18)	C2—C7—H7C	110 (3)
C1^i—C1—N1^i	77.8 (4)	C2^i—C7—H7C	101 (2)
C2—C1—N1^i	118.4 (2)	H7A—C7—H7C	106 (2)
C6—C1—N1^i	116.1 (2)	H7B—C7—H7C	115 (3)
C2^i—C1—N1^i	115.2 (3)	C6—C8—H8A	114 (4)
N1—C1—N1^i	13.7 (4)	C6—C8—H8B	112.5 (14)
C2^i—C2—C1	89.9 (5)	H8A—C8—H8B	110 (4)
C2^i—C2—C3	84.4 (3)	C6—C8—H8C	110 (4)
C1—C2—C3	117.48 (16)	H8A—C8—H8C	107.5 (19)
C2^i—C2—C1^i	78.9 (5)	H8B—C8—H8C	102 (4)
C1—C2—C1^i	11.0 (7)	N1—C9—C10	120.71 (19)
C3—C2—C1^i	115.7 (2)	N1—C9—C11	113.50 (18)
C2^i—C2—C7	91.7 (5)	C10—C9—C11	125.79 (16)
C1—C2—C7	121.18 (15)	N1—C9—N1^i	6.64 (17)
C3—C2—C7	121.19 (16)	C10—C9—N1^i	127.35 (15)
C1^i—C2—C7	120.91 (19)	C11—C9—N1^i	106.86 (15)
C2^i—C2—C7^i	77.9 (4)	C9^ii—C10—C9	127.1 (2)
C1—C2—C7^i	120.4 (2)	C9^ii—C10—H10	116.5
C3—C2—C7^i	118.9 (2)	C9—C10—H10	116.5
C1^i—C2—C7^i	117.2 (3)	C9—C11—H11A	109.5
C7—C2—C7^i	13.8 (7)	C9—C11—H11B	109.5
C4—C3—C2	120.71 (13)	H11A—C11—H11B	109.5
C4—C3—C2^i	120.72 (13)	C9—C11—H11C	109.5
C2—C3—C2^i	11.3 (7)	H11A—C11—H11C	109.5
C4—C3—H3	119.4 (11)	H11B—C11—H11C	109.5
C2—C3—H3	119.5 (11)
N1^i—N1—C1—C1^i	0.01 (3)	C1—C2—C3—C2^i	−87.0 (7)
C9—N1—C1—C1^i	−178.94 (16)	C1^i—C2—C3—C2^i	−74.8 (6)
C9^i—N1—C1—C1^i	−0.76 (12)	C7—C2—C3—C2^i	88.6 (7)
N1^i—N1—C1—C2	−90.9 (7)	C7^i—C2—C3—C2^i	72.9 (6)
C9—N1—C1—C2	90.1 (7)	C2—C3—C4—C5	−6.6 (4)
C1^i—N1—C1—C2	−91.0 (7)	C2^i—C3—C4—C5	6.6 (4)
C9^i—N1—C1—C2	−91.7 (7)	C3—C4—C5—C6	0.0
N1^i—N1—C1—C6	84.5 (6)	C4—C5—C6—C1^i	−6.3 (4)
C9—N1—C1—C6	−94.5 (6)	C4—C5—C6—C1	6.3 (4)
C1^i—N1—C1—C6	84.5 (6)	C4—C5—C6—C8	180.0
C9^i—N1—C1—C6	83.7 (6)	C1^i—C1—C6—C5	−92.94 (18)
N1^i—N1—C1—C2^i	−78.1 (7)	C2—C1—C6—C5	−6.4 (9)
C9—N1—C1—C2^i	102.9 (7)	C2^i—C1—C6—C5	−19.4 (8)
C1^i—N1—C1—C2^i	−78.1 (7)	N1—C1—C6—C5	178.3 (4)
C9^i—N1—C1—C2^i	−78.9 (7)	N1^i—C1—C6—C5	−166.4 (4)
C9—N1—C1—N1^i	−179 (100)	C2—C1—C6—C1^i	86.5 (7)
C1^i—N1—C1—N1^i	−0.01 (4)	C2^i—C1—C6—C1^i	73.6 (6)
C9^i—N1—C1—N1^i	−0.78 (12)	N1—C1—C6—C1^i	−88.7 (6)
C1^i—C1—C2—C2^i	−0.02 (3)	N1^i—C1—C6—C1^i	−73.5 (5)
C6—C1—C2—C2^i	−83.4 (6)	C1^i—C1—C6—C8	93.3 (2)
N1—C1—C2—C2^i	91.8 (7)	C2—C1—C6—C8	179.8 (6)
N1^i—C1—C2—C2^i	76.1 (6)	C2^i—C1—C6—C8	166.8 (5)
C1^i—C1—C2—C3	83.6 (6)	N1—C1—C6—C8	4.5 (8)
C6—C1—C2—C3	0.2 (11)	N1^i—C1—C6—C8	19.8 (7)
C2^i—C1—C2—C3	83.6 (6)	C2^i—C2—C7—C7^i	−0.001 (10)
N1—C1—C2—C3	175.4 (6)	C1—C2—C7—C7^i	90.9 (7)
N1^i—C1—C2—C3	159.7 (5)	C3—C2—C7—C7^i	−84.4 (6)
C6—C1—C2—C1^i	−83.4 (6)	C1^i—C2—C7—C7^i	78.0 (7)
C2^i—C1—C2—C1^i	0.02 (4)	C1—C2—C7—C2^i	90.9 (8)
N1—C1—C2—C1^i	91.8 (7)	C3—C2—C7—C2^i	−84.4 (6)
N1^i—C1—C2—C1^i	76.1 (6)	C1^i—C2—C7—C2^i	78.0 (7)
C1^i—C1—C2—C7	−92.0 (7)	C7^i—C2—C7—C2^i	0.00 (2)
C6—C1—C2—C7	−175.4 (7)	N1^i—N1—C9—C10	−178.78 (14)
C2^i—C1—C2—C7	−91.9 (8)	C1—N1—C9—C10	−0.7 (3)
N1—C1—C2—C7	−0.2 (12)	C1^i—N1—C9—C10	−1.0 (3)
N1^i—C1—C2—C7	−15.8 (11)	C9^i—N1—C9—C10	−178.78 (14)
C1^i—C1—C2—C7^i	−76.0 (7)	N1^i—N1—C9—C11	1.6 (3)
C6—C1—C2—C7^i	−159.4 (6)	C1—N1—C9—C11	179.71 (15)
C2^i—C1—C2—C7^i	−75.9 (7)	C1^i—N1—C9—C11	179.43 (18)
N1—C1—C2—C7^i	15.9 (11)	C9^i—N1—C9—C11	1.6 (2)
N1^i—C1—C2—C7^i	0.2 (11)	C1—N1—C9—N1^i	178 (100)
C2^i—C2—C3—C4	93.4 (2)	C1^i—N1—C9—N1^i	178 (100)
C1—C2—C3—C4	6.4 (8)	C9^i—N1—C9—N1^i	0.00 (2)
C1^i—C2—C3—C4	18.6 (8)	N1—C9—C10—C9^ii	−178.51 (16)
C7—C2—C3—C4	−178.1 (5)	C11—C9—C10—C9^ii	1.0 (4)
C7^i—C2—C3—C4	166.3 (5)	N1^i—C9—C10—C9^ii	−178.69 (15)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.87 (1)	2.28 (1)	3.132 (15)	170 (1)