N-[2-(1,3-Benzodioxol-5-yl)eth­yl]-2-chloro­acetamide

The title compound, C₁₁H₁₂ClNO₃, crystallizes with two independent mol­ecules in the asymmetric unit. Inter­molecular N—H...O hydrogen bonds link the mol­ecules related by translation along the b axis into two independent hydrogen-bonded chains. The crystal studied exhibited inversion twinning.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.035
• wR factor = 0.110
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O1

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.470
           From the CIF: _refine_ls_abs_structure_Flack_su    0.080
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               3949
           Count of symmetry unique reflns         2033
           Completeness (_total/calc)            194.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1916
           Fraction of Friedel pairs measured     0.942
           Are heavy atom types Z>Si present        yes
PLAT033_ALERT_4_G Flack Parameter Value Deviates from Zero .......       0.47
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

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

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S1. Comment

The title compound (I) is an important intermediate for the synthesis of3, 4-dihydroisoquinoline and some other heterocyclic compounds (Bernhard & Snieckus, 1971; Ma et al., 2006). In this paper, we report its crystal structure.

Compound (I) crystallizes with two independent molecules in the non-centrosymmetric unit cell (Fig. 1). All bond lengths and angles in (I) are normal (Allen et al., 1987) and in a good agreement with those reported previously (Kuehne et al., 1988). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along b axis into two independent hydrogen-bonded chains.

Related literature

For the crystal structures of related compounds, see: Kuehne et al. (1988). For details of the aplication of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-chloro-acetamide, see: Bernhard & Snieckus (1971); Ma et al. (2006). For bond-length data, see Allen et al. (1987).

S2. Experimental

2-Benzo[1,3]dioxol-5-yl-ethylamine (20 mmol) was dissolved in CH₂Cl₂, and K₂CO₃ (30 mmol) was added, then chloroacetyl chloride (20 mmol) was added during 30 min at 273 K. After 2 h standing at room temperature, the solution was washed with water, the organic layer was separated, dried with Na₂SO₄ and evaporated to obtain the primary product. The pure product was isolated by recrystallization from ethyl acetate (1.50 g, 68%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

S3. Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 or 0.97 Å, N—H=0.86Å and with U_iso(H) = 1.2 times U_eq(C, N).

Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The content of asymmetric unit of (I), with atomic labels and 40% probability displacement ellipsoids for non-H atoms.

N-[2-(1,3-Benzodioxol-5-yl)ethyl]-2-chloroacetamide

Crystal data

C11H12ClNO3	F(000) = 1008
Mr = 241.67	Dx = 1.415 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2501 reflections
a = 14.429 (3) Å	θ = 2.3–25.1°
b = 5.1258 (10) Å	µ = 0.33 mm^−1
c = 30.679 (6) Å	T = 293 K
V = 2269.1 (8) Å^3	Needle, colourless
Z = 8	0.20 × 0.12 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	3949 independent reflections
Radiation source: Rotating Anode	2946 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω oscillation scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.937, Tmax = 0.971	k = −5→6
15836 measured reflections	l = −36→36

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 0.2974P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max = 0.001
S = 1.13	Δρmax = 0.34 e Å^−3
3949 reflections	Δρmin = −0.35 e Å^−3
290 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0035 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1304 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.47 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.80437 (6)	0.77974 (17)	0.26938 (4)	0.0660 (3)
Cl2	1.04831 (6)	0.72284 (17)	0.70767 (4)	0.0658 (3)
O1	0.5138 (3)	0.4037 (8)	0.51198 (14)	0.1064 (13)
O2	0.4074 (2)	0.7028 (7)	0.53628 (11)	0.0873 (10)
O3	0.86302 (18)	0.1950 (5)	0.67866 (11)	0.0726 (8)
O4	0.2640 (2)	1.1064 (7)	0.46419 (14)	0.1001 (12)
O5	0.1615 (2)	0.7930 (7)	0.43980 (11)	0.0826 (9)
O6	0.61927 (18)	1.3095 (5)	0.29844 (12)	0.0725 (8)
N1	0.8579 (2)	0.6316 (6)	0.67326 (12)	0.0569 (8)
H1A	0.8872	0.7749	0.6780	0.068*
N2	0.6139 (2)	0.8733 (6)	0.30282 (13)	0.0567 (9)
H2B	0.6428	0.7294	0.2980	0.068*
C1	0.4217 (4)	0.4861 (11)	0.5078 (3)	0.086 (2)
H1B	0.3799	0.3450	0.5154	0.103*
H1C	0.4093	0.5371	0.4779	0.103*
C2	0.6047 (3)	0.9174 (9)	0.60261 (15)	0.0694 (11)
H2A	0.6226	1.0428	0.6228	0.083*
C3	0.5145 (3)	0.9204 (10)	0.58685 (18)	0.0766 (12)
H3A	0.4720	1.0442	0.5964	0.092*
C4	0.4904 (3)	0.7377 (8)	0.55716 (14)	0.0607 (10)
C5	0.5532 (3)	0.5584 (11)	0.5434 (2)	0.0649 (13)
C6	0.6420 (3)	0.5492 (9)	0.5578 (2)	0.0681 (14)
H6A	0.6836	0.4258	0.5473	0.082*
C7	0.6685 (2)	0.7335 (7)	0.58913 (13)	0.0558 (9)
C8	0.7652 (2)	0.7271 (8)	0.60849 (14)	0.0671 (11)
H8A	0.8034	0.6082	0.5917	0.080*
H8B	0.7925	0.8996	0.6064	0.080*
C9	0.7648 (3)	0.6432 (7)	0.65481 (14)	0.0605 (10)
H9A	0.7277	0.7642	0.6717	0.073*
H9B	0.7363	0.4723	0.6569	0.073*
C10	0.8985 (3)	0.4085 (7)	0.68301 (15)	0.0539 (10)
C11	0.9951 (2)	0.4136 (7)	0.70259 (15)	0.0613 (10)
H11A	1.0348	0.3041	0.6848	0.074*
H11B	0.9920	0.3352	0.7313	0.074*
C12	0.1728 (5)	1.0074 (11)	0.4679 (3)	0.088 (2)
H12A	0.1611	0.9539	0.4977	0.105*
H12B	0.1285	1.1426	0.4603	0.105*
C13	0.3619 (3)	0.5967 (9)	0.37410 (14)	0.0662 (11)
H13A	0.3813	0.4735	0.3538	0.079*
C14	0.2717 (3)	0.5835 (10)	0.38929 (18)	0.0748 (12)
H14A	0.2307	0.4562	0.3795	0.090*
C15	0.2458 (3)	0.7656 (8)	0.41918 (13)	0.0605 (10)
C16	0.3067 (3)	0.9502 (10)	0.43397 (19)	0.0592 (12)
C17	0.3958 (3)	0.9658 (9)	0.4176 (2)	0.0668 (15)
H17A	0.4359	1.0969	0.4267	0.080*
C18	0.4239 (3)	0.7821 (7)	0.38744 (12)	0.0560 (9)
C19	0.5200 (3)	0.7908 (9)	0.36873 (14)	0.0670 (11)
H19A	0.5564	0.9174	0.3848	0.080*
H19B	0.5489	0.6214	0.3724	0.080*
C20	0.5208 (2)	0.8615 (7)	0.32136 (14)	0.0602 (10)
H20A	0.4848	0.7339	0.3053	0.072*
H20B	0.4912	1.0299	0.3177	0.072*
C21	0.6554 (2)	1.0929 (7)	0.29311 (13)	0.0506 (9)
C22	0.7510 (3)	1.0888 (7)	0.27470 (15)	0.0627 (10)
H22A	0.7901	1.1967	0.2930	0.075*
H22B	0.7491	1.1696	0.2461	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0492 (5)	0.0504 (5)	0.0983 (7)	0.0069 (4)	0.0175 (5)	0.0016 (6)
Cl2	0.0504 (5)	0.0516 (5)	0.0956 (7)	−0.0081 (4)	−0.0166 (5)	0.0014 (6)
O1	0.076 (2)	0.131 (3)	0.112 (3)	0.006 (2)	−0.031 (2)	−0.054 (3)
O2	0.0487 (16)	0.124 (3)	0.089 (2)	0.0023 (16)	−0.0162 (16)	0.001 (2)
O3	0.0640 (17)	0.0391 (13)	0.115 (2)	−0.0078 (11)	−0.0205 (16)	−0.0023 (16)
O4	0.075 (2)	0.103 (2)	0.122 (3)	−0.007 (2)	0.037 (2)	−0.041 (3)
O5	0.0531 (16)	0.107 (2)	0.087 (2)	−0.0059 (15)	0.0207 (16)	−0.0081 (19)
O6	0.0626 (17)	0.0394 (13)	0.115 (2)	0.0078 (11)	0.0219 (16)	−0.0040 (16)
N1	0.0437 (16)	0.0416 (16)	0.085 (2)	−0.0045 (13)	−0.0175 (16)	0.0032 (17)
N2	0.0424 (16)	0.0411 (17)	0.087 (3)	0.0053 (13)	0.0127 (16)	−0.0041 (17)
C1	0.066 (3)	0.122 (5)	0.069 (5)	−0.019 (3)	−0.030 (4)	0.005 (3)
C2	0.059 (2)	0.075 (3)	0.074 (3)	0.006 (2)	−0.009 (2)	−0.012 (3)
C3	0.059 (3)	0.090 (3)	0.080 (3)	0.026 (2)	−0.005 (3)	−0.013 (3)
C4	0.042 (2)	0.081 (3)	0.058 (2)	−0.0002 (19)	−0.0040 (17)	0.007 (2)
C5	0.055 (3)	0.072 (2)	0.067 (3)	−0.007 (2)	−0.005 (2)	−0.010 (3)
C6	0.053 (3)	0.078 (3)	0.073 (4)	0.009 (2)	−0.004 (2)	−0.010 (3)
C7	0.0438 (18)	0.068 (2)	0.056 (2)	−0.0028 (17)	−0.0025 (17)	0.004 (2)
C8	0.042 (2)	0.093 (3)	0.067 (3)	−0.0042 (18)	−0.0033 (17)	−0.001 (2)
C9	0.040 (2)	0.057 (2)	0.085 (3)	−0.0035 (15)	−0.0128 (17)	0.007 (2)
C10	0.052 (2)	0.039 (2)	0.071 (3)	−0.0008 (17)	0.001 (2)	−0.001 (2)
C11	0.0459 (19)	0.0435 (19)	0.094 (3)	0.0010 (15)	−0.016 (2)	0.005 (2)
C12	0.072 (4)	0.103 (5)	0.087 (6)	0.010 (2)	0.007 (4)	0.003 (3)
C13	0.061 (3)	0.069 (3)	0.068 (3)	−0.005 (2)	0.013 (2)	−0.005 (3)
C14	0.065 (3)	0.086 (3)	0.074 (3)	−0.025 (2)	0.012 (2)	−0.008 (3)
C15	0.046 (2)	0.075 (2)	0.061 (3)	0.0012 (19)	0.0091 (17)	0.010 (2)
C16	0.053 (3)	0.067 (2)	0.058 (3)	0.003 (2)	0.009 (2)	−0.001 (2)
C17	0.057 (3)	0.074 (3)	0.070 (4)	−0.011 (2)	0.012 (3)	−0.012 (2)
C18	0.049 (2)	0.066 (2)	0.054 (2)	0.0020 (17)	0.0007 (18)	0.0051 (19)
C19	0.044 (2)	0.088 (3)	0.068 (3)	0.001 (2)	0.0021 (17)	−0.003 (2)
C20	0.040 (2)	0.060 (2)	0.080 (3)	0.0049 (16)	0.0119 (17)	0.006 (2)
C21	0.0473 (19)	0.038 (2)	0.067 (2)	0.0004 (15)	0.0091 (19)	−0.002 (2)
C22	0.054 (2)	0.0424 (19)	0.092 (3)	0.0005 (16)	0.015 (2)	−0.003 (2)

Geometric parameters (Å, º)

Cl1—C22	1.769 (4)	C7—C8	1.517 (5)
Cl2—C11	1.768 (4)	C8—C9	1.485 (6)
O1—C5	1.372 (7)	C8—H8A	0.9700
O1—C1	1.401 (7)	C8—H8B	0.9700
O2—C4	1.370 (5)	C9—H9A	0.9700
O2—C1	1.428 (7)	C9—H9B	0.9700
O3—C10	1.216 (4)	C10—C11	1.518 (5)
O4—C16	1.371 (6)	C11—H11A	0.9700
O4—C12	1.416 (7)	C11—H11B	0.9700
O5—C15	1.378 (5)	C12—H12A	0.9700
O5—C12	1.405 (7)	C12—H12B	0.9700
O6—C21	1.237 (4)	C13—C18	1.367 (6)
N1—C10	1.319 (5)	C13—C14	1.384 (6)
N1—C9	1.458 (4)	C13—H13A	0.9300
N1—H1A	0.8600	C14—C15	1.361 (6)
N2—C21	1.309 (5)	C14—H14A	0.9300
N2—C20	1.459 (4)	C15—C16	1.368 (6)
N2—H2B	0.8600	C16—C17	1.383 (6)
C1—H1B	0.9700	C17—C18	1.381 (6)
C1—H1C	0.9700	C17—H17A	0.9300
C2—C7	1.381 (6)	C18—C19	1.501 (5)
C2—C3	1.388 (6)	C19—C20	1.498 (6)
C2—H2A	0.9300	C19—H19A	0.9700
C3—C4	1.352 (7)	C19—H19B	0.9700
C3—H3A	0.9300	C20—H20A	0.9700
C4—C5	1.358 (7)	C20—H20B	0.9700
C5—C6	1.355 (6)	C21—C22	1.491 (5)
C6—C7	1.401 (7)	C22—H22A	0.9700
C6—H6A	0.9300	C22—H22B	0.9700
C5—O1—C1	106.5 (4)	C10—C11—H11A	108.1
C4—O2—C1	105.1 (4)	Cl2—C11—H11A	108.1
C16—O4—C12	105.2 (4)	C10—C11—H11B	108.1
C15—O5—C12	105.0 (4)	Cl2—C11—H11B	108.1
C10—N1—C9	122.2 (3)	H11A—C11—H11B	107.3
C10—N1—H1A	118.9	O5—C12—O4	109.8 (6)
C9—N1—H1A	118.9	O5—C12—H12A	109.7
C21—N2—C20	123.0 (3)	O4—C12—H12A	109.7
C21—N2—H2B	118.5	O5—C12—H12B	109.7
C20—N2—H2B	118.5	O4—C12—H12B	109.7
O1—C1—O2	108.4 (5)	H12A—C12—H12B	108.2
O1—C1—H1B	110.0	C18—C13—C14	123.2 (4)
O2—C1—H1B	110.0	C18—C13—H13A	118.4
O1—C1—H1C	110.0	C14—C13—H13A	118.4
O2—C1—H1C	110.0	C15—C14—C13	116.8 (4)
H1B—C1—H1C	108.4	C15—C14—H14A	121.6
C7—C2—C3	121.8 (4)	C13—C14—H14A	121.6
C7—C2—H2A	119.1	C14—C15—C16	121.4 (4)
C3—C2—H2A	119.1	C14—C15—O5	128.4 (4)
C4—C3—C2	117.9 (4)	C16—C15—O5	110.1 (4)
C4—C3—H3A	121.0	C15—C16—O4	109.9 (4)
C2—C3—H3A	121.0	C15—C16—C17	121.1 (5)
C3—C4—C5	120.4 (4)	O4—C16—C17	129.0 (5)
C3—C4—O2	129.1 (4)	C18—C17—C16	118.5 (4)
C5—C4—O2	110.5 (4)	C18—C17—H17A	120.8
C6—C5—C4	123.6 (5)	C16—C17—H17A	120.8
C6—C5—O1	126.9 (5)	C13—C18—C17	118.9 (4)
C4—C5—O1	109.4 (4)	C13—C18—C19	120.7 (4)
C5—C6—C7	117.2 (5)	C17—C18—C19	120.4 (4)
C5—C6—H6A	121.4	C20—C19—C18	112.7 (3)
C7—C6—H6A	121.4	C20—C19—H19A	109.0
C2—C7—C6	119.0 (4)	C18—C19—H19A	109.0
C2—C7—C8	120.7 (4)	C20—C19—H19B	109.0
C6—C7—C8	120.3 (4)	C18—C19—H19B	109.0
C9—C8—C7	112.2 (3)	H19A—C19—H19B	107.8
C9—C8—H8A	109.2	N2—C20—C19	113.3 (3)
C7—C8—H8A	109.2	N2—C20—H20A	108.9
C9—C8—H8B	109.2	C19—C20—H20A	108.9
C7—C8—H8B	109.2	N2—C20—H20B	108.9
H8A—C8—H8B	107.9	C19—C20—H20B	108.9
N1—C9—C8	112.4 (3)	H20A—C20—H20B	107.7
N1—C9—H9A	109.1	O6—C21—N2	123.3 (3)
C8—C9—H9A	109.1	O6—C21—C22	116.9 (3)
N1—C9—H9B	109.1	N2—C21—C22	119.8 (3)
C8—C9—H9B	109.1	C21—C22—Cl1	116.8 (3)
H9A—C9—H9B	107.9	C21—C22—H22A	108.1
O3—C10—N1	124.7 (4)	Cl1—C22—H22A	108.1
O3—C10—C11	116.4 (3)	C21—C22—H22B	108.1
N1—C10—C11	118.9 (3)	Cl1—C22—H22B	108.1
C10—C11—Cl2	116.7 (3)	H22A—C22—H22B	107.3
C5—O1—C1—O2	2.5 (7)	C15—O5—C12—O4	−0.5 (7)
C4—O2—C1—O1	−1.5 (6)	C16—O4—C12—O5	0.0 (7)
C7—C2—C3—C4	−0.7 (8)	C18—C13—C14—C15	−0.5 (7)
C2—C3—C4—C5	−0.2 (8)	C13—C14—C15—C16	−1.0 (7)
C2—C3—C4—O2	−178.6 (4)	C13—C14—C15—O5	−178.8 (4)
C1—O2—C4—C3	178.5 (6)	C12—O5—C15—C14	178.8 (6)
C1—O2—C4—C5	−0.1 (5)	C12—O5—C15—C16	0.8 (5)
C3—C4—C5—C6	−0.2 (9)	C14—C15—C16—O4	−179.0 (5)
O2—C4—C5—C6	178.5 (5)	O5—C15—C16—O4	−0.9 (6)
C3—C4—C5—O1	−177.1 (5)	C14—C15—C16—C17	2.9 (8)
O2—C4—C5—O1	1.6 (6)	O5—C15—C16—C17	−178.9 (5)
C1—O1—C5—C6	−179.3 (6)	C12—O4—C16—C15	0.5 (7)
C1—O1—C5—C4	−2.5 (7)	C12—O4—C16—C17	178.4 (6)
C4—C5—C6—C7	1.3 (9)	C15—C16—C17—C18	−3.2 (9)
O1—C5—C6—C7	177.6 (6)	O4—C16—C17—C18	179.1 (5)
C3—C2—C7—C6	1.7 (7)	C14—C13—C18—C17	0.1 (7)
C3—C2—C7—C8	−177.1 (5)	C14—C13—C18—C19	−178.2 (4)
C5—C6—C7—C2	−2.0 (8)	C16—C17—C18—C13	1.7 (8)
C5—C6—C7—C8	176.9 (5)	C16—C17—C18—C19	180.0 (5)
C2—C7—C8—C9	69.1 (5)	C13—C18—C19—C20	66.7 (5)
C6—C7—C8—C9	−109.7 (5)	C17—C18—C19—C20	−111.5 (5)
C10—N1—C9—C8	−109.7 (5)	C21—N2—C20—C19	−106.4 (5)
C7—C8—C9—N1	178.8 (3)	C18—C19—C20—N2	179.4 (3)
C9—N1—C10—O3	−1.6 (6)	C20—N2—C21—O6	−0.6 (6)
C9—N1—C10—C11	−179.3 (4)	C20—N2—C21—C22	179.3 (4)
O3—C10—C11—Cl2	178.4 (3)	O6—C21—C22—Cl1	177.3 (3)
N1—C10—C11—Cl2	−3.7 (6)	N2—C21—C22—Cl1	−2.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.86	2.18	2.894 (4)	140
N2—H2B···O6^ii	0.86	2.18	2.894 (4)	140

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