Single-crystal-to-single-crystal photodimerization of 4-chlorocinnamoyl-O,O'-dime­thyl­dopamine

[2+2]Photodimerization of the title compound, C₁₉H₂₀ClNO₃, has been observed in situ by single-crystal X-ray diffraction. Pairs of monomers related by centers of symmetry have parallel C=C bonds at a C...C distance of 4.155 (17) Å. Irradiation of a single crystal with a mercury lamp achieves 100% conversion to the dimer. Redetermination of the structure during the course of the reaction revealed a linear correlation between the percent conversion to the dimer and the decrease in the cell volume. The displacement parameters for the pure dimer structure are substantially smaller than those for the pure monomer structure. The dimerization reaction is also induced by irradiation with X-rays, the induction being stronger with Cu Kα than with Mo Kα radiation.

Computing details

For all compounds, data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(Ia)

Crystal data

C19H20ClNO3	F(000) = 1456.0
Mr = 345.81	Dx = 1.274 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 21.499 (4) Å	Cell parameters from 25 reflections
b = 5.0032 (14) Å	θ = 7.0–11.6°
c = 33.542 (5) Å	µ = 0.23 mm^−1
β = 91.518 (13)°	T = 298 K
V = 3606.6 (13) Å^3	Needle, colourless
Z = 8	0.80 × 0.10 × 0.05 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.035
ω scans	θmax = 25.0°
Absorption correction: integration (Coppens et al., 1965)	h = 0→25
Tmin = 0.970, Tmax = 0.989	k = 0→5
3664 measured reflections	l = −39→39
3165 independent reflections	3 standard reflections every 150 reflections
865 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 0.03P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.142	(Δ/σ)max < 0.001
wR(F^2) = 0.277	Δρmax = 0.37 e Å^−3
S = 2.03	Δρmin = −0.41 e Å^−3
3165 reflections	Extinction correction: SHELXL
217 parameters	Extinction coefficient: none
H-atom parameters not refined

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl	0.4086 (2)	0.5324 (9)	0.1840 (1)	0.156 (2)
O2	0.6379 (5)	0.898 (2)	−0.0218 (3)	0.102 (4)
O3	0.7868 (4)	−0.003 (2)	−0.2055 (2)	0.093 (3)
O4	0.8770 (4)	0.343 (2)	−0.2159 (2)	0.105 (3)
N5	0.6619 (4)	0.474 (2)	−0.0305 (3)	0.079 (3)
C6	0.4481 (6)	0.594 (4)	0.1411 (5)	0.109 (6)
C7	0.4319 (10)	0.803 (4)	0.1167 (6)	0.157 (8)
C8	0.4685 (8)	0.835 (3)	0.0825 (5)	0.117 (5)
C9	0.5197 (6)	0.656 (3)	0.0719 (4)	0.078 (4)
C10	0.5364 (6)	0.463 (3)	0.1000 (4)	0.087 (4)
C11	0.4986 (8)	0.434 (3)	0.1345 (4)	0.120 (6)
C12	0.5575 (6)	0.720 (2)	0.0400 (4)	0.066 (4)
C13	0.5980 (6)	0.571 (2)	0.0220 (4)	0.078 (4)
C14	0.6339 (6)	0.681 (3)	−0.0132 (4)	0.086 (4)
C15	0.7013 (6)	0.498 (3)	−0.0652 (3)	0.102 (5)
C16	0.7546 (6)	0.306 (3)	−0.0679 (3)	0.089 (4)
C17	0.7876 (6)	0.346 (3)	−0.1062 (4)	0.075 (4)
C18	0.7685 (6)	0.146 (2)	−0.1376 (4)	0.073 (4)
C19	0.7973 (6)	0.160 (2)	−0.1716 (5)	0.073 (4)
C20	0.8485 (7)	0.338 (3)	−0.1803 (5)	0.088 (5)
C21	0.8630 (5)	0.520 (3)	−0.1493 (5)	0.088 (4)
C22	0.8341 (6)	0.530 (3)	−0.1117 (3)	0.086 (4)
C23	0.7318 (7)	−0.150 (3)	−0.2017 (4)	0.109 (5)
C24	0.9190 (7)	0.551 (3)	−0.2223 (4)	0.143 (7)
H5	0.6558	0.3008	−0.0195	0.0951*
H7	0.3984	0.9194	0.1224	0.1880*
H8	0.4593	0.9820	0.0653	0.1405*
H10	0.5719	0.3537	0.0965	0.1042*
H11	0.5089	0.2986	0.1535	0.1437*
H12	0.5532	0.8972	0.0301	0.0795*
H13	0.6052	0.3932	0.0308	0.0942*
H15A	0.6754	0.4744	−0.0883	0.1221*
H15B	0.7181	0.6737	−0.0651	0.1221*
H16A	0.7392	0.1278	−0.0668	0.1075*
H16B	0.7830	0.3349	−0.0461	0.1075*
H18	0.7372	0.0162	−0.1331	0.0881*
H21	0.8949	0.6464	−0.1539	0.1061*
H22	0.8461	0.6556	−0.0917	0.1027*
H23A	0.7352	−0.2615	−0.1789	0.1305*
H23B	0.7250	−0.2569	−0.2248	0.1305*
H23C	0.6978	−0.0306	−0.1989	0.1305*
H24A	0.8977	0.7168	−0.2220	0.1713*
H24B	0.9505	0.5494	−0.2018	0.1713*
H24C	0.9377	0.5272	−0.2475	0.1713*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.152 (3)	0.176 (4)	0.142 (3)	−0.017 (4)	0.064 (3)	−0.029 (3)
O2	0.171 (9)	0.038 (6)	0.098 (7)	0.005 (6)	0.019 (6)	0.030 (6)
O3	0.109 (7)	0.078 (7)	0.092 (6)	−0.036 (6)	−0.004 (6)	−0.018 (6)
O4	0.110 (7)	0.146 (10)	0.060 (6)	0.001 (7)	0.020 (5)	0.025 (7)
N5	0.112 (8)	0.072 (8)	0.054 (6)	−0.007 (7)	−0.001 (6)	0.022 (6)
C6	0.049 (9)	0.11 (2)	0.17 (2)	0.001 (10)	0.06 (1)	−0.05 (1)
C7	0.25 (2)	0.07 (1)	0.15 (2)	0.05 (1)	0.01 (2)	0.00 (1)
C8	0.11 (1)	0.13 (1)	0.10 (1)	0.02 (1)	−0.039 (10)	−0.02 (1)
C9	0.052 (9)	0.08 (1)	0.10 (1)	0.011 (9)	−0.012 (8)	−0.01 (1)
C10	0.11 (1)	0.054 (9)	0.09 (1)	0.016 (8)	0.019 (9)	0.026 (8)
C11	0.14 (1)	0.14 (2)	0.080 (10)	−0.02 (1)	−0.01 (1)	0.07 (1)
C12	0.077 (10)	0.050 (9)	0.071 (9)	−0.002 (7)	−0.007 (8)	0.015 (7)
C13	0.089 (10)	0.028 (7)	0.12 (1)	0.021 (8)	0.018 (8)	0.009 (8)
C14	0.11 (1)	0.06 (1)	0.09 (1)	0.02 (1)	0.027 (9)	−0.02 (1)
C15	0.13 (1)	0.10 (1)	0.074 (9)	−0.03 (1)	0.037 (9)	0.037 (9)
C16	0.12 (1)	0.09 (1)	0.062 (8)	0.040 (9)	0.029 (8)	0.009 (8)
C17	0.074 (9)	0.08 (1)	0.076 (10)	0.031 (9)	0.004 (8)	0.041 (9)
C18	0.12 (1)	0.07 (1)	0.034 (7)	−0.004 (8)	0.021 (8)	0.015 (8)
C19	0.060 (9)	0.033 (8)	0.13 (1)	−0.011 (8)	−0.022 (9)	0.018 (9)
C20	0.10 (1)	0.06 (1)	0.10 (1)	0.03 (1)	−0.06 (1)	−0.01 (1)
C21	0.070 (9)	0.08 (1)	0.11 (1)	−0.008 (9)	0.002 (9)	0.04 (1)
C22	0.087 (9)	0.11 (1)	0.059 (9)	−0.049 (9)	−0.010 (8)	0.022 (9)
C23	0.14 (1)	0.07 (1)	0.12 (1)	−0.031 (10)	−0.047 (9)	−0.021 (9)
C24	0.18 (1)	0.12 (1)	0.14 (1)	−0.02 (1)	0.09 (1)	0.04 (1)

Geometric parameters (Å, º)

Cl—C6	1.72 (2)	C13—H13	0.950
O2—C14	1.13 (2)	C15—C16	1.50 (2)
O3—C19	1.41 (2)	C15—H15A	0.951
O3—C23	1.40 (2)	C15—H15B	0.949
O4—C20	1.36 (2)	C16—C17	1.50 (2)
O4—C24	1.40 (2)	C16—H16A	0.949
N5—C14	1.34 (2)	C16—H16B	0.951
N5—C15	1.46 (1)	C17—C18	1.50 (2)
N5—H5	0.950	C17—C22	1.38 (2)
C6—C7	1.37 (3)	C18—C19	1.31 (2)
C6—C11	1.37 (2)	C18—H18	0.951
C7—C8	1.42 (3)	C19—C20	1.45 (2)
C7—H7	0.951	C20—C21	1.41 (2)
C8—C9	1.47 (2)	C21—C22	1.42 (2)
C8—H8	0.951	C21—H21	0.950
C9—C10	1.39 (2)	C22—H22	0.950
C9—C12	1.40 (2)	C23—H23A	0.950
C10—C11	1.44 (2)	C23—H23B	0.950
C10—H10	0.950	C23—H23C	0.950
C11—H11	0.951	C24—H24A	0.949
C12—C13	1.31 (2)	C24—H24B	0.951
C12—H12	0.950	C24—H24C	0.950
C13—C14	1.53 (2)
C19—O3—C23	110.3 (9)	H15A—C15—H15B	109.5
C20—O4—C24	117 (1)	C15—C16—C17	110 (1)
C14—N5—C15	123 (1)	C15—C16—H16A	109.5
C14—N5—H5	118.1	C15—C16—H16B	109.2
C15—N5—H5	118.2	C17—C16—H16A	109.4
Cl—C6—C7	120 (1)	C17—C16—H16B	109.2
Cl—C6—C11	116 (1)	H16A—C16—H16B	109.4
C7—C6—C11	122 (1)	C16—C17—C18	112 (1)
C6—C7—C8	115 (1)	C16—C17—C22	124 (1)
C6—C7—H7	122.0	C18—C17—C22	122 (1)
C8—C7—H7	122.2	C17—C18—C19	116 (1)
C7—C8—C9	123 (1)	C17—C18—H18	121.7
C7—C8—H8	118.0	C19—C18—H18	121.7
C9—C8—H8	118.0	O3—C19—C18	126 (1)
C8—C9—C10	116 (1)	O3—C19—C20	107 (1)
C8—C9—C12	119 (1)	C18—C19—C20	125 (1)
C10—C9—C12	122 (1)	O4—C20—C19	123 (1)
C9—C10—C11	118 (1)	O4—C20—C21	122 (1)
C9—C10—H10	120.8	C19—C20—C21	113 (1)
C11—C10—H10	120.8	C20—C21—C22	125 (1)
C6—C11—C10	122 (1)	C20—C21—H21	117.1
C6—C11—H11	118.8	C22—C21—H21	117.0
C10—C11—H11	118.9	C17—C22—C21	115 (1)
C9—C12—C13	129 (1)	C17—C22—H22	122.2
C9—C12—H12	115.4	C21—C22—H22	122.3
C13—C12—H12	115.4	O3—C23—H23A	109.4
C12—C13—C14	120 (1)	O3—C23—H23B	109.5
C12—C13—H13	119.7	O3—C23—H23C	109.5
C14—C13—H13	119.6	H23A—C23—H23B	109.5
O2—C14—N5	126 (1)	H23A—C23—H23C	109.5
O2—C14—C13	125 (1)	H23B—C23—H23C	109.5
N5—C14—C13	107 (1)	O4—C24—H24A	109.6
N5—C15—C16	116 (1)	O4—C24—H24B	109.4
N5—C15—H15A	107.5	O4—C24—H24C	109.5
N5—C15—H15B	107.7	H24A—C24—H24B	109.5
C16—C15—H15A	107.4	H24A—C24—H24C	109.5
C16—C15—H15B	107.7	H24B—C24—H24C	109.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^i	0.95	2.05	2.942 (13)	155

Symmetry code: (i) x, y−1, z.

(Ib)

Crystal data

C19H20ClNO3	F(000) = 1456.0
Mr = 345.81	Dx = 1.300 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 21.150 (4) Å	Cell parameters from 25 reflections
b = 4.9724 (10) Å	θ = 10.1–11.8°
c = 33.620 (5) Å	µ = 0.23 mm^−1
β = 91.298 (14)°	T = 297 K
V = 3534.8 (11) Å^3	Needle, colourless
Z = 8	0.45 × 0.20 × 0.07 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.021
ω scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −14→27
Tmin = 0.950, Tmax = 0.984	k = −6→3
6042 measured reflections	l = −43→43
4079 independent reflections	3 standard reflections every 150 reflections
1136 reflections with I > 2σ(I)	intensity decay: 2.6%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.158	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.12 e Å^−3
4079 reflections	Δρmin = −0.12 e Å^−3
263 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl	0.4125 (4)	0.455 (2)	0.1915 (2)	0.183 (3)	0.66
O2	0.6196 (1)	0.8808 (5)	−0.01651 (7)	0.1227 (9)
O3	0.7837 (1)	0.0816 (6)	−0.20296 (8)	0.1183 (8)
O4	0.8726 (1)	0.4270 (5)	−0.20950 (7)	0.1205 (8)
N5	0.6560 (1)	0.4633 (5)	−0.02516 (7)	0.0865 (8)
C6	0.4475 (7)	0.539 (3)	0.1476 (5)	0.118 (7)	0.66
C7	0.4287 (6)	0.747 (2)	0.1227 (4)	0.119 (5)	0.66
C8	0.4612 (5)	0.796 (2)	0.0904 (4)	0.115 (3)	0.66
C9	0.5129 (4)	0.634 (2)	0.0791 (2)	0.088 (2)	0.66
C10	0.5344 (4)	0.434 (2)	0.1044 (3)	0.109 (2)	0.66
C11	0.5010 (7)	0.374 (2)	0.1408 (3)	0.140 (4)	0.66
C12	0.5467 (4)	0.705 (1)	0.0436 (2)	0.094 (2)	0.66
C13	0.5896 (4)	0.557 (1)	0.0258 (2)	0.090 (2)	0.66
C14	0.6180 (2)	0.6436 (9)	−0.0092 (1)	0.101 (1)
C15	0.6986 (2)	0.5343 (6)	−0.0566 (1)	0.103 (1)
C16	0.7475 (2)	0.3346 (9)	−0.0632 (1)	0.135 (1)
C17	0.7822 (2)	0.3648 (9)	−0.1017 (1)	0.104 (1)
C18	0.7660 (2)	0.2052 (7)	−0.1344 (1)	0.100 (1)
C19	0.7964 (2)	0.2308 (9)	−0.1701 (1)	0.093 (1)
C20	0.8443 (2)	0.4198 (9)	−0.1734 (1)	0.097 (1)
C21	0.8598 (2)	0.5819 (7)	−0.1420 (1)	0.109 (1)
C22	0.8285 (2)	0.5529 (8)	−0.1061 (1)	0.114 (1)
C23	0.7288 (2)	−0.0843 (9)	−0.2026 (1)	0.139 (1)
C24	0.9145 (2)	0.6393 (9)	−0.2173 (1)	0.138 (1)
Cl*	0.4294 (7)	0.409 (3)	0.1977 (2)	0.129 (3)	0.34
C6*	0.457 (1)	0.469 (6)	0.1496 (7)	0.0607	0.34
C7*	0.430 (1)	0.661 (5)	0.1304 (7)	0.0691	0.34
C8*	0.4466 (8)	0.718 (3)	0.0887 (5)	0.0619	0.34
C9*	0.4872 (5)	0.579 (2)	0.0699 (3)	0.0443	0.34
C10*	0.5123 (5)	0.384 (3)	0.0915 (3)	0.0594	0.34
C11*	0.4983 (9)	0.336 (3)	0.1290 (5)	0.0682	0.34
C12*	0.4994 (5)	0.628 (2)	0.0258 (3)	0.050 (3)	0.34
C13*	0.5504 (5)	0.463 (2)	0.0052 (3)	0.045 (3)	0.34
H5	0.6553	0.2832	−0.0158	0.1040*
H7	0.3930	0.8544	0.1289	0.1434*	0.66
H8	0.4498	0.9442	0.0741	0.1381*	0.66
H10	0.5707	0.3305	0.0979	0.1301*	0.66
H11	0.5151	0.2405	0.1588	0.1734*	0.66
H12	0.5369	0.8747	0.0320	0.1132*	0.66
H13	0.6014	0.3878	0.0369	0.1079*	0.66
H15A	0.6745	0.5552	−0.0806	0.1233*
H15B	0.7185	0.7002	−0.0499	0.1233*
H16A	0.7777	0.3470	−0.0418	0.1624*
H16B	0.7284	0.1620	−0.0630	0.1624*
H18	0.7333	0.0754	−0.1321	0.1206*
H21	0.8917	0.7146	−0.1445	0.1306*
H22	0.8397	0.6660	−0.0844	0.1368*
H23A	0.6924	0.0244	−0.1992	0.1667*
H23B	0.7250	−0.1789	−0.2271	0.1667*
H23C	0.7325	−0.2095	−0.1813	0.1667*
H24A	0.9486	0.6358	−0.1985	0.1654*
H24B	0.9305	0.6198	−0.2434	0.1654*
H24C	0.8927	0.8058	−0.2155	0.1654*
H7*	0.3995	0.7679	0.1428	0.0830*	0.34
H8*	0.4279	0.8707	0.0768	0.0742*	0.34
H10*	0.5423	0.2725	0.0793	0.0713*	0.34
H11*	0.5198	0.1894	0.1429	0.0818*	0.34
H12*	0.5078	0.8140	0.0220	0.0605*	0.34
H13*	0.5627	0.3151	0.0216	0.0536*	0.34

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.206 (5)	0.181 (4)	0.166 (4)	−0.054 (4)	0.094 (4)	−0.041 (4)
O2	0.194 (2)	0.069 (2)	0.105 (2)	0.033 (2)	0.026 (2)	0.013 (2)
O3	0.120 (2)	0.123 (2)	0.113 (2)	−0.009 (2)	0.024 (2)	0.004 (2)
O4	0.122 (2)	0.134 (2)	0.107 (2)	−0.008 (2)	0.038 (1)	0.018 (2)
N5	0.105 (2)	0.077 (2)	0.079 (2)	0.010 (2)	0.022 (1)	0.008 (1)
C6	0.108 (9)	0.12 (1)	0.127 (7)	−0.010 (9)	0.044 (5)	−0.028 (7)
C7	0.105 (5)	0.104 (8)	0.15 (1)	0.023 (6)	0.007 (5)	0.007 (7)
C8	0.109 (7)	0.103 (8)	0.132 (5)	−0.004 (5)	0.013 (5)	−0.006 (6)
C9	0.076 (5)	0.088 (5)	0.099 (5)	0.004 (4)	0.004 (4)	−0.020 (4)
C10	0.101 (6)	0.103 (5)	0.123 (6)	0.007 (5)	0.016 (5)	0.000 (5)
C11	0.188 (8)	0.141 (7)	0.093 (7)	−0.003 (6)	0.057 (7)	−0.003 (6)
C12	0.108 (6)	0.073 (4)	0.103 (4)	0.013 (4)	0.006 (5)	0.003 (3)
C13	0.103 (5)	0.077 (4)	0.091 (4)	0.003 (4)	0.006 (4)	0.008 (4)
C14	0.143 (3)	0.086 (3)	0.075 (2)	0.031 (3)	0.028 (2)	0.007 (2)
C15	0.116 (3)	0.071 (2)	0.122 (3)	0.007 (2)	0.036 (2)	−0.001 (2)
C16	0.146 (3)	0.159 (4)	0.102 (3)	0.058 (3)	0.049 (2)	0.039 (2)
C17	0.116 (3)	0.099 (3)	0.099 (3)	0.041 (3)	0.028 (3)	0.026 (3)
C18	0.106 (3)	0.089 (3)	0.107 (3)	0.021 (2)	0.033 (2)	0.030 (3)
C19	0.092 (3)	0.088 (3)	0.100 (3)	0.012 (2)	0.014 (2)	0.018 (3)
C20	0.096 (3)	0.106 (3)	0.091 (3)	0.012 (3)	0.022 (2)	0.021 (3)
C21	0.110 (3)	0.099 (3)	0.119 (3)	0.008 (2)	0.018 (3)	0.010 (3)
C22	0.135 (3)	0.112 (3)	0.096 (3)	0.023 (3)	0.016 (3)	0.006 (2)
C23	0.131 (4)	0.137 (4)	0.148 (4)	0.001 (3)	0.007 (3)	−0.016 (3)
C24	0.137 (3)	0.155 (4)	0.123 (3)	−0.009 (3)	0.033 (2)	0.041 (3)
Cl*	0.188 (7)	0.157 (5)	0.043 (2)	−0.032 (5)	0.027 (3)	0.003 (3)
C6*	0.0706	0.0710	0.0409	−0.0126	0.0119	−0.0043
C7*	0.0734	0.0831	0.0517	0.0119	0.0183	−0.0119
C8*	0.0749	0.0629	0.0484	0.0149	0.0135	−0.0040
C9*	0.0507	0.0420	0.0406	−0.0015	0.0074	−0.0041
C10*	0.0717	0.0608	0.0463	0.0118	0.0122	0.0030
C11*	0.0871	0.0683	0.0492	0.0100	0.0043	0.0135
C12*	0.039 (6)	0.046 (5)	0.065 (6)	0.002 (5)	0.007 (5)	0.001 (4)
C13*	0.040 (6)	0.047 (5)	0.046 (5)	0.005 (5)	0.008 (5)	0.003 (4)

Geometric parameters (Å, º)

Cl—C6	1.72 (2)	C17—C18	1.391 (6)
O2—C14	1.205 (5)	C17—C22	1.365 (6)
O3—C19	1.354 (5)	C18—C19	1.380 (6)
O3—C23	1.424 (5)	C18—H18	0.950
O4—C20	1.365 (5)	C19—C20	1.389 (6)
O4—C24	1.407 (5)	C20—C21	1.362 (6)
N5—C14	1.325 (5)	C21—C22	1.396 (6)
N5—C15	1.449 (4)	C21—H21	0.949
N5—H5	0.950	C22—H22	0.949
C6—C7	1.38 (2)	C23—H23A	0.950
C6—C11	1.42 (2)	C23—H23B	0.950
C7—C8	1.32 (2)	C23—H23C	0.950
C7—H7	0.951	C24—H24A	0.950
C8—C9	1.42 (1)	C24—H24B	0.950
C8—H8	0.945	C24—H24C	0.950
C9—C10	1.38 (1)	Cl*—C6*	1.76 (3)
C9—C12	1.45 (1)	C6*—C7*	1.28 (4)
C10—C11	1.46 (1)	C6*—C11*	1.31 (3)
C10—H10	0.954	C7*—C8*	1.48 (3)
C11—H11	0.942	C7*—H7*	0.947
C12—C13	1.33 (1)	C8*—C9*	1.28 (2)
C12—H12	0.950	C8*—H8*	0.940
C13—C14	1.401 (8)	C9*—C10*	1.32 (2)
C13—H13	0.950	C9*—C12*	1.53 (1)
C14—C13*	1.77 (1)	C10*—C11*	1.32 (2)
C15—C16	1.454 (5)	C10*—H10*	0.942
C15—H15A	0.950	C11*—H11*	0.973
C15—H15B	0.951	C12*—C13*	1.53 (1)
C16—C17	1.510 (6)	C12*—C13*^i	1.53 (1)
C16—H16A	0.952	C12*—H12*	0.951
C16—H16B	0.949	C13*—H13*	0.950
C19—O3—C23	117.2 (3)	C19—C20—C21	120.1 (4)
C20—O4—C24	118.4 (3)	C20—C21—C22	119.9 (4)
C14—N5—C15	121.6 (3)	C20—C21—H21	120.1
C14—N5—H5	119.3	C22—C21—H21	120.1
C15—N5—H5	119.2	C17—C22—C21	121.4 (4)
Cl—C6—C7	125 (1)	C17—C22—H22	119.3
Cl—C6—C11	111 (1)	C21—C22—H22	119.3
C7—C6—C11	123 (1)	O3—C23—H23A	109.5
C6—C7—C8	119 (1)	O3—C23—H23B	109.5
C6—C7—H7	120.4	O3—C23—H23C	109.5
C8—C7—H7	120.4	H23A—C23—H23B	109.5
C7—C8—C9	122.2 (10)	H23A—C23—H23C	109.5
C7—C8—H8	119.4	H23B—C23—H23C	109.4
C9—C8—H8	118.4	O4—C24—H24A	109.5
C8—C9—C10	119.5 (8)	O4—C24—H24B	109.5
C8—C9—C12	118.7 (8)	O4—C24—H24C	109.5
C10—C9—C12	121.4 (7)	H24A—C24—H24B	109.4
C9—C10—C11	120.4 (8)	H24A—C24—H24C	109.4
C9—C10—H10	120.3	H24B—C24—H24C	109.5
C11—C10—H10	119.3	Cl*—C6*—C7*	116 (2)
C6—C11—C10	114 (1)	Cl*—C6*—C11*	130 (2)
C6—C11—H11	123.1	C7*—C6*—C11*	113 (2)
C10—C11—H11	122.0	C6*—C7*—C8*	120 (2)
C9—C12—C13	126.4 (6)	C6*—C7*—H7*	119.8
C9—C12—H12	116.7	C8*—C7*—H7*	119.3
C13—C12—H12	116.9	C7*—C8*—C9*	122 (1)
C12—C13—C14	121.3 (6)	C7*—C8*—H8*	116.8
C12—C13—H13	119.3	C9*—C8*—H8*	120.6
C14—C13—H13	119.4	C8*—C9*—C10*	113 (1)
O2—C14—N5	124.1 (3)	C8*—C9*—C12*	121 (1)
O2—C14—C13	119.2 (4)	C10*—C9*—C12*	125.2 (10)
N5—C14—C13	114.0 (4)	C9*—C10*—C11*	124 (1)
N5—C15—C16	113.6 (3)	C9*—C10*—H10*	117.3
N5—C15—H15A	108.5	C11*—C10*—H10*	118.5
N5—C15—H15B	108.4	C6*—C11*—C10*	125 (1)
C16—C15—H15A	108.4	C6*—C11*—H11*	115.7
C16—C15—H15B	108.5	C10*—C11*—H11*	118.7
H15A—C15—H15B	109.4	C9*—C12*—C13*	119.2 (8)
C15—C16—C17	115.0 (3)	C9*—C12*—C13*^i	118.9 (8)
C15—C16—H16A	108.1	C9*—C12*—H12*	108.9
C15—C16—H16B	108.2	C13*—C12*—C13*^i	90.8 (7)
C17—C16—H16A	108.0	C13*—C12*—H12*	108.9
C17—C16—H16B	108.1	C13*^i—C12*—H12*	108.7
H16A—C16—H16B	109.4	C14—C13*—C12*	115.6 (6)
C16—C17—C18	120.3 (4)	C14—C13*—C12*^i	120.8 (7)
C16—C17—C22	121.7 (4)	C14—C13*—H13*	109.8
C18—C17—C22	118.0 (4)	C12*—C13*—C12*^i	89.2 (7)
C17—C18—C19	121.5 (4)	C12*—C13*—H13*	109.8
C17—C18—H18	119.3	C12*^i—C13*—H13*	110.0
C19—C18—H18	119.2	C9*—C12*—C13*^i	118.9 (8)
O3—C19—C18	124.9 (4)	C13*—C12*—C13*^i	90.8 (7)
O3—C19—C20	115.9 (4)	H12*—C12*—C13*^i	108.7
C18—C19—C20	119.2 (4)	C12*—C13*—C12*^i	89.2 (8)
O4—C20—C19	115.1 (4)	H13*—C13*—C12*^i	110.0
O4—C20—C21	124.9 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^ii	0.95	2.14	3.013 (3)	152

Symmetry code: (ii) x, y−1, z.

(II)

Crystal data

C38H40Cl2N2O6	F(000) = 1456.0
Mr = 691.62	Dx = 1.332 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 20.835 (3) Å	Cell parameters from 25 reflections
b = 4.9657 (10) Å	θ = 10.1–13.9°
c = 33.352 (3) Å	µ = 0.24 mm^−1
β = 92.166 (9)°	T = 297 K
V = 3448.1 (9) Å^3	Needle, colourless
Z = 4	0.45 × 0.20 × 0.07 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.017
ω scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −14→27
Tmin = 0.948, Tmax = 0.984	k = −6→3
5877 measured reflections	l = −43→43
3951 independent reflections	3 standard reflections every 150 reflections
1805 reflections with I > 2σ(I)	intensity decay: 0.8%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 1.860P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.19 e Å^−3
3951 reflections	Δρmin = −0.23 e Å^−3
217 parameters

Special details

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl	0.43417 (4)	0.3456 (2)	0.19711 (2)	0.0970 (3)
O2	0.60664 (8)	0.8679 (3)	−0.01459 (5)	0.0562 (4)
O3	0.78102 (9)	0.1693 (4)	−0.20197 (6)	0.0816 (6)
O4	0.87070 (9)	0.5192 (4)	−0.20785 (5)	0.0805 (6)
N5	0.65527 (9)	0.4692 (4)	−0.02370 (5)	0.0510 (5)
C6	0.4566 (1)	0.4331 (6)	0.14907 (7)	0.0606 (7)
C7	0.4283 (1)	0.6467 (6)	0.12983 (8)	0.0690 (8)
C8	0.4451 (1)	0.7104 (5)	0.09113 (7)	0.0618 (7)
C9	0.4893 (1)	0.5556 (5)	0.07105 (6)	0.0443 (5)
C10	0.5180 (1)	0.3474 (5)	0.09164 (7)	0.0593 (7)
C11	0.5023 (1)	0.2860 (6)	0.13066 (7)	0.0682 (8)
C12	0.5014 (1)	0.6219 (4)	0.02773 (6)	0.0433 (5)
C13	0.5520 (1)	0.4626 (4)	0.00509 (6)	0.0425 (5)
C14	0.6071 (1)	0.6217 (5)	−0.01099 (6)	0.0424 (5)
C15	0.7019 (1)	0.5710 (5)	−0.05156 (8)	0.0624 (7)
C16	0.7537 (1)	0.3745 (6)	−0.05876 (8)	0.0767 (9)
C17	0.7868 (1)	0.4223 (6)	−0.09782 (7)	0.0596 (7)
C18	0.7679 (1)	0.2718 (5)	−0.13140 (8)	0.0600 (7)
C19	0.7963 (1)	0.3088 (5)	−0.16789 (8)	0.0580 (7)
C20	0.8447 (1)	0.5024 (6)	−0.17076 (7)	0.0587 (7)
C21	0.8627 (1)	0.6534 (6)	−0.13791 (8)	0.0649 (7)
C22	0.8338 (1)	0.6123 (6)	−0.10165 (7)	0.0649 (7)
C23	0.7259 (2)	−0.0005 (7)	−0.2022 (1)	0.094 (1)
C24	0.9149 (2)	0.7289 (7)	−0.21436 (9)	0.091 (1)
H5	0.6593	0.2891	−0.0143	0.0615*
H7	0.3971	0.7513	0.1429	0.0828*
H8	0.4261	0.8627	0.0781	0.0745*
H10	0.5493	0.2413	0.0789	0.0712*
H11	0.5234	0.1422	0.1446	0.0818*
H12	0.5099	0.8091	0.0254	0.0519*
H13	0.5668	0.3115	0.0202	0.0510*
H15A	0.7206	0.7310	−0.0407	0.0751*
H15B	0.6801	0.6110	−0.0764	0.0751*
H16A	0.7357	0.1990	−0.0594	0.0922*
H16B	0.7849	0.3868	−0.0373	0.0922*
H18	0.7348	0.1410	−0.1293	0.0719*
H21	0.8951	0.7873	−0.1400	0.0778*
H22	0.8470	0.7172	−0.0790	0.0783*
H23A	0.6890	0.1041	−0.1972	0.1128*
H23B	0.7315	−0.1336	−0.1819	0.1128*
H23C	0.7208	−0.0860	−0.2276	0.1128*
H24A	0.9294	0.7177	−0.2410	0.1090*
H24B	0.9506	0.7119	−0.1959	0.1090*
H24C	0.8946	0.8976	−0.2106	0.1090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1300 (7)	0.1155 (7)	0.0475 (4)	−0.0216 (6)	0.0279 (4)	−0.0001 (4)
O2	0.065 (1)	0.0382 (10)	0.067 (1)	0.0022 (9)	0.0182 (8)	0.0026 (8)
O3	0.080 (1)	0.092 (2)	0.074 (1)	−0.018 (1)	0.013 (1)	−0.014 (1)
O4	0.085 (1)	0.100 (2)	0.059 (1)	−0.018 (1)	0.0244 (10)	0.004 (1)
N5	0.057 (1)	0.042 (1)	0.055 (1)	0.009 (1)	0.0194 (10)	0.0097 (9)
C6	0.071 (2)	0.071 (2)	0.041 (1)	−0.013 (2)	0.012 (1)	−0.004 (1)
C7	0.073 (2)	0.083 (2)	0.052 (1)	0.012 (2)	0.018 (1)	−0.012 (2)
C8	0.075 (2)	0.063 (2)	0.048 (1)	0.015 (1)	0.013 (1)	−0.004 (1)
C9	0.051 (1)	0.042 (1)	0.041 (1)	−0.002 (1)	0.007 (1)	−0.004 (1)
C10	0.072 (2)	0.061 (2)	0.046 (1)	0.012 (1)	0.012 (1)	0.003 (1)
C11	0.087 (2)	0.068 (2)	0.049 (1)	0.010 (2)	0.004 (1)	0.013 (1)
C12	0.052 (1)	0.034 (1)	0.045 (1)	0.004 (1)	0.011 (1)	0.001 (1)
C13	0.050 (1)	0.038 (1)	0.040 (1)	0.006 (1)	0.010 (1)	0.003 (1)
C14	0.048 (1)	0.040 (1)	0.039 (1)	0.006 (1)	0.0037 (10)	0.000 (1)
C15	0.064 (2)	0.054 (2)	0.071 (2)	0.003 (1)	0.028 (1)	0.005 (1)
C16	0.073 (2)	0.094 (2)	0.065 (2)	0.029 (2)	0.026 (1)	0.024 (2)
C17	0.058 (2)	0.065 (2)	0.057 (2)	0.021 (1)	0.018 (1)	0.013 (1)
C18	0.053 (2)	0.056 (2)	0.072 (2)	0.005 (1)	0.016 (1)	0.010 (1)
C19	0.057 (2)	0.060 (2)	0.057 (2)	0.006 (1)	0.007 (1)	0.001 (1)
C20	0.057 (2)	0.066 (2)	0.053 (1)	0.002 (1)	0.014 (1)	0.008 (1)
C21	0.060 (2)	0.070 (2)	0.065 (2)	−0.003 (2)	0.012 (1)	0.000 (2)
C22	0.070 (2)	0.070 (2)	0.056 (1)	0.009 (2)	0.009 (1)	−0.003 (1)
C23	0.086 (2)	0.096 (3)	0.100 (2)	−0.013 (2)	−0.002 (2)	−0.016 (2)
C24	0.091 (2)	0.105 (3)	0.079 (2)	−0.013 (2)	0.030 (2)	0.027 (2)

Geometric parameters (Å, º)

Cl—C6	1.741 (3)	C13—C14	1.509 (3)
O2—C14	1.228 (3)	C13—H13	0.949
O3—C19	1.359 (3)	C15—C16	1.482 (4)
O3—C23	1.425 (4)	C15—H15A	0.951
O4—C20	1.372 (3)	C15—H15B	0.949
O4—C24	1.413 (4)	C16—C17	1.515 (4)
N5—C14	1.340 (3)	C16—H16A	0.949
N5—C15	1.459 (3)	C16—H16B	0.950
N5—H5	0.950	C17—C18	1.390 (4)
C6—C7	1.362 (4)	C17—C22	1.370 (4)
C6—C11	1.365 (4)	C18—C19	1.386 (4)
C7—C8	1.386 (4)	C18—H18	0.951
C7—H7	0.950	C19—C20	1.398 (4)
C8—C9	1.392 (3)	C20—C21	1.368 (4)
C8—H8	0.951	C21—C22	1.386 (4)
C9—C10	1.366 (3)	C21—H21	0.952
C9—C12	1.512 (3)	C22—H22	0.951
C10—C11	1.388 (3)	C23—H23A	0.948
C10—H10	0.951	C23—H23B	0.951
C11—H11	0.951	C23—H23C	0.950
C12—C13	1.538 (3)	C24—H24A	0.950
C12—C13^i	1.587 (3)	C24—H24B	0.951
C12—H12	0.951	C24—H24C	0.949
C19—O3—C23	118.0 (2)	N5—C15—H15B	108.7
C20—O4—C24	117.8 (2)	C16—C15—H15A	108.8
C14—N5—C15	122.0 (2)	C16—C15—H15B	108.8
C14—N5—H5	119.0	H15A—C15—H15B	109.5
C15—N5—H5	119.0	C15—C16—C17	113.2 (2)
Cl—C6—C7	120.1 (2)	C15—C16—H16A	108.5
Cl—C6—C11	119.8 (2)	C15—C16—H16B	108.5
C7—C6—C11	120.1 (2)	C17—C16—H16A	108.6
C6—C7—C8	119.8 (3)	C17—C16—H16B	108.5
C6—C7—H7	120.1	H16A—C16—H16B	109.5
C8—C7—H7	120.2	C16—C17—C18	119.0 (2)
C7—C8—C9	121.1 (2)	C16—C17—C22	122.6 (2)
C7—C8—H8	119.4	C18—C17—C22	118.4 (2)
C9—C8—H8	119.5	C17—C18—C19	121.3 (2)
C8—C9—C10	117.5 (2)	C17—C18—H18	119.4
C8—C9—C12	118.5 (2)	C19—C18—H18	119.4
C10—C9—C12	124.0 (2)	O3—C19—C18	124.9 (2)
C9—C10—C11	121.6 (2)	O3—C19—C20	116.1 (2)
C9—C10—H10	119.3	C18—C19—C20	119.0 (2)
C11—C10—H10	119.2	O4—C20—C19	114.5 (2)
C6—C11—C10	119.9 (2)	O4—C20—C21	125.7 (2)
C6—C11—H11	120.1	C19—C20—C21	119.9 (2)
C10—C11—H11	120.1	C20—C21—C22	120.2 (2)
C9—C12—C13	119.9 (2)	C20—C21—H21	119.9
C9—C12—C13^i	117.6 (2)	C22—C21—H21	119.9
C9—C12—H12	109.3	C17—C22—C21	121.2 (2)
C13—C12—C13^i	90.0 (2)	C17—C22—H22	119.3
C13—C12—H12	109.2	C21—C22—H22	119.5
C13^i—C12—H12	109.2	O3—C23—H23A	109.5
C12—C13—C12^i	90.0 (2)	O3—C23—H23B	109.3
C12—C13—C14	116.7 (2)	O3—C23—H23C	109.4
C12—C13—H13	111.2	H23A—C23—H23B	109.6
C12^i—C13—C14	114.6 (2)	H23A—C23—H23C	109.7
C12^i—C13—H13	111.3	H23B—C23—H23C	109.4
C14—C13—H13	111.4	O4—C24—H24A	109.5
O2—C14—N5	122.3 (2)	O4—C24—H24B	109.4
O2—C14—C13	123.6 (2)	O4—C24—H24C	109.5
N5—C14—C13	113.9 (2)	H24A—C24—H24B	109.4
N5—C15—C16	112.4 (2)	H24A—C24—H24C	109.6
N5—C15—H15A	108.6	H24B—C24—H24C	109.5

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^ii	0.95	2.36	3.171 (2)	143

Symmetry code: (ii) x, y−1, z.

(Ic)

Crystal data

C19H20ClNO3	F(000) = 1456.0
Mr = 345.82	Dx = 1.290 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 21.233 (5) Å	Cell parameters from 25 reflections
b = 4.9827 (14) Å	θ = 10.2–13.6°
c = 33.664 (5) Å	µ = 0.23 mm^−1
β = 91.313 (14)°	T = 297 K
V = 3560.6 (14) Å^3	Needle, colourless
Z = 8	0.40 × 0.20 × 0.05 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.014
ω scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −10→27
Tmin = 0.952, Tmax = 0.989	k = −6→6
5130 measured reflections	l = −43→43
4109 independent reflections	3 standard reflections every 150 reflections
1133 reflections with I > 2σ(I)	intensity decay: 1.8%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.160	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.13 e Å^−3
4109 reflections	Δρmin = −0.13 e Å^−3
264 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl	0.4105 (3)	0.478 (2)	0.1897 (2)	0.167 (2)	0.78
Cl*	0.433 (1)	0.427 (5)	0.1977 (4)	0.139 (6)	0.22
O2	0.6257 (1)	0.8849 (5)	−0.01773 (7)	0.1250 (10)
O3	0.7841 (1)	0.0534 (5)	−0.20353 (7)	0.1115 (8)
O4	0.8737 (1)	0.3992 (5)	−0.21116 (7)	0.1179 (8)
N5	0.6581 (1)	0.4627 (5)	−0.02679 (7)	0.0903 (8)
C6	0.4483 (3)	0.549 (2)	0.1466 (3)	0.098 (3)	0.78
C6*	0.465 (1)	0.459 (5)	0.1504 (7)	0.0607	0.22
C7	0.4298 (4)	0.755 (2)	0.1215 (3)	0.118 (4)	0.78
C7*	0.435 (2)	0.676 (7)	0.131 (1)	0.0691	0.22
C8	0.4641 (4)	0.798 (2)	0.0878 (3)	0.121 (3)	0.78
C8*	0.446 (1)	0.748 (6)	0.0890 (9)	0.0619	0.22
C9	0.5155 (3)	0.645 (1)	0.0777 (2)	0.088 (2)	0.78
C9*	0.4876 (8)	0.589 (3)	0.0696 (4)	0.0443	0.22
C10	0.5347 (3)	0.448 (1)	0.1032 (2)	0.102 (2)	0.78
C10*	0.5128 (8)	0.383 (4)	0.0919 (5)	0.0594	0.22
C11	0.5018 (4)	0.392 (2)	0.1389 (2)	0.122 (3)	0.78
C11*	0.500 (1)	0.351 (5)	0.1256 (7)	0.0682	0.22
C12	0.5505 (3)	0.7111 (9)	0.0418 (1)	0.085 (2)	0.78
C12*	0.5021 (8)	0.632 (2)	0.0257 (5)	0.052 (5)	0.22
C13	0.5917 (3)	0.5621 (9)	0.0246 (2)	0.082 (2)	0.78
C13*	0.5491 (8)	0.460 (2)	0.0045 (4)	0.052 (4)	0.22
C14	0.6235 (2)	0.6498 (8)	−0.0095 (1)	0.094 (1)
C15	0.6990 (2)	0.5256 (6)	−0.0597 (1)	0.103 (1)
C16	0.7484 (2)	0.3246 (8)	−0.0649 (1)	0.129 (1)
C17	0.7828 (2)	0.3518 (9)	−0.1038 (1)	0.096 (1)
C18	0.7667 (2)	0.1875 (7)	−0.1354 (1)	0.096 (1)
C19	0.7966 (2)	0.2048 (8)	−0.1711 (1)	0.088 (1)
C20	0.8450 (2)	0.3942 (8)	−0.1751 (1)	0.095 (1)
C21	0.8604 (2)	0.5613 (7)	−0.1441 (1)	0.105 (1)
C22	0.8294 (2)	0.5421 (8)	−0.1080 (1)	0.111 (1)
C23	0.7300 (2)	−0.1122 (8)	−0.2026 (1)	0.126 (1)
C24	0.9158 (2)	0.6135 (9)	−0.2191 (1)	0.143 (2)
H5	0.6562	0.2831	−0.0174	0.1083*
H7	0.3943	0.8633	0.1273	0.1419*	0.78
H8	0.4516	0.9410	0.0706	0.1447*	0.78
H10	0.5707	0.3441	0.0971	0.1226*	0.78
H11	0.5153	0.2552	0.1566	0.1468*	0.78
H12	0.5419	0.8809	0.0300	0.1021*	0.78
H13	0.6008	0.3892	0.0351	0.0991*	0.78
H15A	0.7183	0.6947	−0.0548	0.1241*
H15B	0.6741	0.5350	−0.0834	0.1241*
H16A	0.7296	0.1517	−0.0641	0.1549*
H16B	0.7782	0.3419	−0.0436	0.1549*
H18	0.7341	0.0587	−0.1324	0.1150*
H21	0.8926	0.6920	−0.1472	0.1263*
H22	0.8403	0.6587	−0.0865	0.1334*
H23A	0.7338	−0.2336	−0.1809	0.1515*
H23B	0.7262	−0.2102	−0.2267	0.1515*
H23C	0.6936	−0.0037	−0.1995	0.1515*
H24A	0.8936	0.7790	−0.2182	0.1713*
H24B	0.9327	0.5903	−0.2448	0.1713*
H24C	0.9490	0.6143	−0.1998	0.1713*
H7*	0.4059	0.7817	0.1457	0.0829*	0.22
H8*	0.4250	0.8945	0.0764	0.0742*	0.22
H10*	0.5415	0.2637	0.0798	0.0713*	0.22
H11*	0.5228	0.2016	0.1369	0.0818*	0.22
H12*	0.5113	0.8160	0.0213	0.0627*	0.22
H13*	0.5606	0.3130	0.0211	0.0618*	0.22

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.167 (4)	0.172 (3)	0.165 (4)	−0.036 (3)	0.082 (3)	−0.035 (3)
Cl*	0.20 (2)	0.17 (1)	0.051 (3)	−0.05 (1)	0.021 (5)	0.003 (4)
O2	0.200 (3)	0.063 (2)	0.112 (2)	0.032 (2)	0.020 (2)	0.009 (2)
O3	0.122 (2)	0.110 (2)	0.103 (2)	−0.011 (2)	0.012 (2)	−0.001 (2)
O4	0.121 (2)	0.131 (2)	0.103 (2)	−0.009 (2)	0.030 (2)	0.019 (2)
N5	0.125 (2)	0.063 (2)	0.083 (2)	0.015 (2)	0.019 (2)	0.009 (1)
C6	0.086 (5)	0.091 (5)	0.117 (5)	0.005 (4)	0.018 (4)	−0.018 (4)
C6*	0.0706	0.0710	0.0409	−0.0126	0.0119	−0.0043
C7	0.091 (4)	0.125 (7)	0.139 (9)	0.025 (5)	0.010 (4)	−0.012 (5)
C7*	0.0734	0.0831	0.0517	0.0119	0.0183	−0.0119
C8	0.088 (6)	0.138 (7)	0.136 (5)	0.005 (5)	0.004 (5)	−0.005 (5)
C8*	0.0749	0.0629	0.0484	0.0149	0.0135	−0.0040
C9	0.072 (4)	0.089 (4)	0.104 (4)	0.006 (3)	−0.009 (3)	−0.026 (3)
C9*	0.0507	0.0420	0.0406	−0.0015	0.0074	−0.0041
C10	0.100 (5)	0.086 (4)	0.121 (5)	0.004 (4)	0.018 (4)	0.006 (4)
C10*	0.0717	0.0608	0.0463	0.0118	0.0122	0.0030
C11	0.152 (5)	0.128 (5)	0.088 (5)	0.005 (4)	0.052 (5)	−0.002 (4)
C11*	0.0871	0.0683	0.0492	0.0100	0.0043	0.0135
C12	0.102 (5)	0.064 (3)	0.089 (3)	0.011 (3)	−0.010 (3)	0.001 (3)
C12*	0.05 (1)	0.038 (7)	0.070 (9)	0.000 (7)	0.017 (8)	−0.004 (7)
C13	0.110 (5)	0.054 (3)	0.084 (3)	0.002 (3)	0.008 (3)	0.002 (3)
C13*	0.07 (1)	0.036 (7)	0.048 (8)	−0.013 (8)	0.010 (8)	0.001 (6)
C14	0.141 (3)	0.068 (2)	0.074 (2)	0.022 (3)	0.007 (2)	0.008 (2)
C15	0.121 (3)	0.072 (2)	0.118 (3)	0.008 (2)	0.025 (2)	0.009 (2)
C16	0.155 (4)	0.137 (3)	0.097 (3)	0.052 (3)	0.027 (3)	0.028 (2)
C17	0.116 (3)	0.089 (3)	0.084 (3)	0.032 (3)	0.010 (2)	0.018 (2)
C18	0.103 (3)	0.088 (3)	0.098 (3)	0.016 (2)	0.020 (2)	0.022 (2)
C19	0.095 (3)	0.076 (2)	0.093 (3)	0.009 (2)	0.007 (2)	0.010 (2)
C20	0.100 (3)	0.093 (3)	0.094 (3)	0.013 (3)	0.014 (2)	0.015 (2)
C21	0.105 (3)	0.095 (3)	0.116 (3)	0.003 (2)	0.001 (3)	0.008 (3)
C22	0.134 (4)	0.103 (3)	0.096 (3)	0.015 (3)	−0.003 (3)	0.006 (2)
C23	0.122 (3)	0.132 (3)	0.125 (3)	−0.009 (3)	−0.004 (3)	−0.009 (3)
C24	0.129 (3)	0.163 (4)	0.139 (3)	−0.020 (3)	0.042 (3)	0.042 (3)

Geometric parameters (Å, º)

Cl—C6	1.71 (1)	C17—C22	1.380 (6)
O2—C14	1.205 (5)	C18—C19	1.378 (6)
O3—C19	1.347 (5)	C18—H18	0.950
O3—C23	1.415 (5)	C19—C20	1.404 (6)
O4—C20	1.371 (4)	C20—C21	1.369 (6)
O4—C24	1.421 (5)	C21—C22	1.401 (6)
N5—C14	1.329 (5)	C21—H21	0.950
N5—C15	1.457 (4)	C22—H22	0.950
N5—H5	0.950	C23—H23A	0.950
C6—C7	1.38 (1)	C23—H23B	0.950
C6—C11	1.41 (1)	C23—H23C	0.950
C7—C8	1.38 (1)	C24—H24A	0.950
C7—H7	0.951	C24—H24B	0.950
C8—C9	1.38 (1)	C24—H24C	0.950
C8—H8	0.952	Cl*—C6*	1.75 (3)
C9—C10	1.361 (9)	C6*—C7*	1.41 (4)
C9—C12	1.470 (8)	C6*—C11*	1.25 (4)
C10—C11	1.43 (1)	C7*—C8*	1.49 (5)
C10—H10	0.950	C7*—H7*	0.947
C11—H11	0.945	C8*—C9*	1.37 (3)
C12—C13	1.295 (8)	C8*—H8*	0.946
C12—H12	0.950	C9*—C10*	1.37 (2)
C13—C14	1.415 (6)	C9*—C12*	1.53 (2)
C13—H13	0.950	C10*—C11*	1.19 (3)
C15—C16	1.462 (5)	C10*—H10*	0.950
C15—H15A	0.950	C11*—H11*	0.964
C15—H15B	0.950	C12*—C13*	1.51 (2)
C16—C17	1.520 (5)	C12*—C13*^i	1.54 (2)
C16—H16A	0.950	C12*—H12*	0.950
C16—H16B	0.950	C13*—H13*	0.950
C17—C18	1.379 (6)
C19—O3—C23	117.0 (3)	O3—C19—C20	115.6 (3)
C20—O4—C24	118.3 (3)	C18—C19—C20	118.6 (3)
C14—N5—C15	121.8 (3)	O4—C20—C19	115.9 (3)
C14—N5—H5	119.1	O4—C20—C21	124.1 (4)
C15—N5—H5	119.1	C19—C20—C21	120.0 (4)
Cl—C6—C7	122.6 (7)	C20—C21—C22	120.8 (4)
Cl—C6—C11	116.0 (7)	C20—C21—H21	119.6
C7—C6—C11	121.3 (8)	C22—C21—H21	119.6
C6—C7—C8	118.1 (8)	C17—C22—C21	119.2 (3)
C6—C7—H7	120.9	C17—C22—H22	120.4
C8—C7—H7	121.0	C21—C22—H22	120.4
C7—C8—C9	123.5 (9)	O3—C23—H23A	109.5
C7—C8—H8	118.2	O3—C23—H23B	109.5
C9—C8—H8	118.3	O3—C23—H23C	109.4
C8—C9—C10	118.1 (7)	H23A—C23—H23B	109.5
C8—C9—C12	119.8 (7)	H23A—C23—H23C	109.5
C10—C9—C12	121.9 (6)	H23B—C23—H23C	109.5
C9—C10—C11	121.6 (6)	O4—C24—H24A	109.5
C9—C10—H10	119.3	O4—C24—H24B	109.4
C11—C10—H10	119.2	O4—C24—H24C	109.5
C6—C11—C10	117.3 (7)	H24A—C24—H24B	109.5
C6—C11—H11	121.3	H24A—C24—H24C	109.5
C10—C11—H11	121.4	H24B—C24—H24C	109.5
C9—C12—C13	126.9 (5)	Cl*—C6*—C7*	108 (2)
C9—C12—H12	116.6	Cl*—C6*—C11*	144 (2)
C13—C12—H12	116.6	C7*—C6*—C11*	107 (2)
C12—C13—C14	121.8 (4)	C6*—C7*—C8*	122 (2)
C12—C13—H13	119.1	C6*—C7*—H7*	118.6
C14—C13—H13	119.1	C8*—C7*—H7*	118.5
O2—C14—N5	123.8 (3)	C7*—C8*—C9*	115 (2)
O2—C14—C13	120.6 (4)	C7*—C8*—H8*	122.0
N5—C14—C13	114.7 (4)	C9*—C8*—H8*	122.3
N5—C15—C16	112.6 (3)	C8*—C9*—C10*	115 (1)
N5—C15—H15A	108.7	C8*—C9*—C12*	121 (1)
N5—C15—H15B	108.7	C10*—C9*—C12*	123 (1)
C16—C15—H15A	108.7	C9*—C10*—C11*	121 (1)
C16—C15—H15B	108.7	C9*—C10*—H10*	118.8
H15A—C15—H15B	109.5	C11*—C10*—H10*	119.4
C15—C16—C17	113.7 (3)	C6*—C11*—C10*	137 (2)
C15—C16—H16A	108.4	C6*—C11*—H11*	111.9
C15—C16—H16B	108.4	C10*—C11*—H11*	110.8
C17—C16—H16A	108.4	C9*—C12*—C13*	121 (1)
C17—C16—H16B	108.4	C9*—C12*—C13*^i	116 (1)
H16A—C16—H16B	109.5	C9*—C12*—H12*	109.4
C16—C17—C18	119.7 (4)	C13*—C12*—C13*^i	89 (1)
C16—C17—C22	120.6 (3)	C13*—C12*—H12*	109.4
C18—C17—C22	119.7 (4)	C13*^i—C12*—H12*	109.3
C17—C18—C19	121.7 (3)	C12*—C13*—C12*^i	90 (1)
C17—C18—H18	119.1	C12*—C13*—H13*	108.9
C19—C18—H18	119.1	C12*^i—C13*—H13*	109.0
O3—C19—C18	125.8 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^ii	0.95	2.09	2.977 (3)	155

Symmetry code: (ii) x, y−1, z.

(Id)

Crystal data

C19H20ClNO3	F(000) = 1456.0
Mr = 345.82	Dx = 1.292 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 21.210 (4) Å	Cell parameters from 25 reflections
b = 4.9818 (12) Å	θ = 10.0–11.7°
c = 33.657 (4) Å	µ = 0.23 mm^−1
β = 91.313 (12)°	T = 298 K
V = 3554.7 (12) Å^3	Needle, colourless
Z = 8	0.40 × 0.20 × 0.05 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.018
ω scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −10→27
Tmin = 0.952, Tmax = 0.989	k = −6→2
5123 measured reflections	l = −43→43
4103 independent reflections	3 standard reflections every 150 reflections
1093 reflections with I > 2σ(I)	intensity decay: 1.9%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0719P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.190	(Δ/σ)max = 0.002
S = 0.94	Δρmax = 0.11 e Å^−3
4103 reflections	Δρmin = −0.13 e Å^−3
264 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl	0.4106 (4)	0.472 (2)	0.1897 (2)	0.179 (2)	0.74
Cl*	0.4296 (9)	0.432 (4)	0.1974 (2)	0.129 (5)	0.26
O2	0.6246 (2)	0.8848 (6)	−0.01723 (8)	0.126 (1)
O3	0.7841 (1)	0.0592 (6)	−0.20338 (9)	0.1141 (9)
O4	0.8733 (1)	0.4031 (6)	−0.21090 (8)	0.1191 (9)
N5	0.6577 (1)	0.4625 (6)	−0.02631 (8)	0.0896 (9)
C6	0.4501 (7)	0.547 (2)	0.1471 (5)	0.111 (5)	0.74
C6*	0.456 (1)	0.468 (6)	0.1499 (8)	0.0607	0.26
C7	0.4297 (4)	0.753 (2)	0.1223 (3)	0.108 (3)	0.74
C7*	0.433 (1)	0.650 (7)	0.1313 (8)	0.0691	0.26
C8	0.4628 (5)	0.805 (2)	0.0890 (3)	0.115 (3)	0.74
C8*	0.448 (1)	0.726 (4)	0.0884 (6)	0.0619	0.26
C9	0.5148 (4)	0.642 (1)	0.0781 (2)	0.087 (2)	0.74
C9*	0.4877 (7)	0.591 (3)	0.0696 (4)	0.0443	0.26
C10	0.5350 (4)	0.445 (1)	0.1034 (3)	0.104 (2)	0.74
C10*	0.5125 (8)	0.383 (4)	0.0918 (5)	0.0594	0.26
C11	0.5054 (6)	0.387 (3)	0.1373 (5)	0.132 (3)	0.74
C11*	0.490 (1)	0.350 (6)	0.1338 (8)	0.0682	0.26
C12	0.5497 (4)	0.712 (1)	0.0425 (2)	0.088 (2)	0.74
C12*	0.5021 (8)	0.634 (2)	0.0258 (4)	0.057 (5)	0.26
C13	0.5914 (3)	0.560 (1)	0.0247 (2)	0.084 (2)	0.74
C13*	0.5490 (7)	0.459 (2)	0.0049 (4)	0.054 (4)	0.26
C14	0.6224 (2)	0.6479 (9)	−0.0094 (1)	0.100 (1)
C15	0.6989 (2)	0.5286 (7)	−0.0589 (1)	0.102 (1)
C16	0.7477 (2)	0.3275 (10)	−0.0645 (1)	0.132 (2)
C17	0.7824 (2)	0.3549 (10)	−0.1029 (1)	0.100 (1)
C18	0.7664 (2)	0.1911 (8)	−0.1352 (2)	0.101 (1)
C19	0.7969 (2)	0.2091 (9)	−0.1710 (1)	0.089 (1)
C20	0.8447 (2)	0.4005 (10)	−0.1747 (1)	0.097 (1)
C21	0.8600 (2)	0.5648 (9)	−0.1438 (2)	0.109 (1)
C22	0.8286 (2)	0.5416 (9)	−0.1077 (1)	0.112 (1)
C23	0.7297 (2)	−0.1067 (10)	−0.2023 (1)	0.127 (2)
C24	0.9150 (2)	0.617 (1)	−0.2184 (1)	0.140 (2)
H5	0.6562	0.2828	−0.0169	0.1076*
H7	0.3935	0.8553	0.1284	0.1294*	0.74
H7*	0.4033	0.7587	0.1444	0.0829*	0.26
H8	0.4507	0.9529	0.0727	0.1386*	0.74
H8*	0.4270	0.8720	0.0759	0.0742*	0.26
H10	0.5713	0.3438	0.0968	0.1250*	0.74
H10*	0.5427	0.2651	0.0811	0.0713*	0.26
H11	0.5199	0.2475	0.1543	0.1592*	0.74
H11*	0.5089	0.2049	0.1483	0.0818*	0.26
H12	0.5415	0.8833	0.0311	0.1053*	0.74
H12*	0.5118	0.8175	0.0214	0.0688*	0.26
H13	0.6008	0.3873	0.0351	0.1005*	0.74
H13*	0.5605	0.3128	0.0216	0.0647*	0.26
H15A	0.6741	0.5416	−0.0827	0.1227*
H15B	0.7185	0.6966	−0.0535	0.1227*
H16A	0.7776	0.3424	−0.0431	0.1581*
H16B	0.7287	0.1552	−0.0640	0.1581*
H18	0.7336	0.0630	−0.1325	0.1210*
H21	0.8921	0.6960	−0.1466	0.1306*
H22	0.8396	0.6579	−0.0863	0.1341*
H23A	0.6934	0.0021	−0.1992	0.1529*
H23B	0.7258	−0.2051	−0.2264	0.1529*
H23C	0.7336	−0.2279	−0.1806	0.1529*
H24A	0.9485	0.6149	−0.1992	0.1685*
H24B	0.9317	0.5966	−0.2442	0.1685*
H24C	0.8930	0.7822	−0.2169	0.1685*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.181 (4)	0.183 (4)	0.179 (4)	−0.042 (3)	0.090 (4)	−0.040 (4)
Cl*	0.20 (1)	0.151 (7)	0.039 (3)	−0.055 (8)	0.028 (3)	−0.003 (3)
O2	0.204 (3)	0.067 (2)	0.108 (2)	0.033 (2)	0.017 (2)	0.008 (2)
O3	0.123 (2)	0.114 (2)	0.106 (2)	−0.012 (2)	0.011 (2)	0.000 (2)
O4	0.121 (2)	0.129 (2)	0.109 (2)	−0.011 (2)	0.034 (2)	0.019 (2)
N5	0.121 (3)	0.067 (2)	0.082 (2)	0.012 (2)	0.019 (2)	0.008 (2)
C6	0.117 (7)	0.092 (9)	0.125 (6)	−0.017 (7)	0.022 (4)	−0.006 (7)
C6*	0.0706	0.0710	0.0409	−0.0126	0.0119	−0.0043
C7	0.088 (4)	0.098 (6)	0.138 (8)	0.015 (5)	0.017 (4)	0.001 (5)
C7*	0.0734	0.0831	0.0517	0.0119	0.0183	−0.0119
C8	0.112 (7)	0.091 (7)	0.143 (6)	−0.005 (5)	−0.001 (5)	−0.007 (5)
C8*	0.0749	0.0629	0.0484	0.0149	0.0135	−0.0040
C9	0.079 (5)	0.081 (4)	0.102 (5)	0.009 (4)	−0.010 (4)	−0.023 (4)
C9*	0.0507	0.0420	0.0406	−0.0015	0.0074	−0.0041
C10	0.098 (6)	0.086 (5)	0.130 (6)	0.003 (4)	0.024 (4)	−0.002 (4)
C10*	0.0717	0.0608	0.0463	0.0118	0.0122	0.0030
C11	0.112 (9)	0.130 (7)	0.157 (8)	−0.005 (6)	0.043 (7)	0.015 (6)
C11*	0.0871	0.0683	0.0492	0.0100	0.0043	0.0135
C12	0.101 (5)	0.071 (4)	0.090 (4)	0.003 (4)	−0.012 (4)	0.004 (3)
C12*	0.07 (1)	0.041 (7)	0.066 (9)	0.011 (7)	0.022 (8)	−0.005 (6)
C13	0.109 (5)	0.062 (3)	0.080 (4)	0.004 (4)	0.005 (4)	0.003 (3)
C13*	0.070 (10)	0.045 (7)	0.048 (7)	−0.006 (7)	0.016 (7)	−0.001 (6)
C14	0.148 (4)	0.077 (3)	0.074 (3)	0.027 (3)	0.009 (2)	0.005 (2)
C15	0.113 (3)	0.074 (3)	0.121 (3)	0.008 (2)	0.026 (3)	0.005 (2)
C16	0.156 (4)	0.146 (4)	0.095 (3)	0.055 (4)	0.039 (3)	0.035 (3)
C17	0.116 (4)	0.092 (3)	0.093 (3)	0.034 (3)	0.017 (3)	0.027 (3)
C18	0.109 (3)	0.089 (3)	0.105 (3)	0.021 (2)	0.028 (3)	0.031 (3)
C19	0.095 (3)	0.080 (3)	0.091 (3)	0.011 (3)	0.002 (3)	0.016 (2)
C20	0.100 (3)	0.095 (3)	0.095 (3)	0.011 (3)	0.013 (3)	0.019 (3)
C21	0.100 (3)	0.099 (3)	0.128 (4)	0.001 (3)	0.006 (3)	0.012 (3)
C22	0.128 (4)	0.112 (4)	0.095 (3)	0.022 (3)	0.005 (3)	0.008 (3)
C23	0.123 (4)	0.127 (4)	0.132 (3)	−0.006 (3)	−0.003 (3)	−0.012 (3)
C24	0.131 (4)	0.159 (4)	0.132 (3)	−0.013 (4)	0.036 (3)	0.042 (3)

Geometric parameters (Å, º)

Cl—C6	1.72 (2)	C17—C22	1.364 (7)
O2—C14	1.210 (5)	C18—C19	1.385 (7)
O3—C19	1.343 (5)	C18—H18	0.950
O3—C23	1.421 (6)	C19—C20	1.400 (6)
O4—C20	1.374 (5)	C20—C21	1.356 (7)
O4—C24	1.412 (6)	C21—C22	1.403 (7)
N5—C14	1.325 (5)	C21—H21	0.950
N5—C15	1.457 (5)	C22—H22	0.950
N5—H5	0.950	C23—H23A	0.950
C6—C7	1.38 (2)	C23—H23B	0.950
C6—C11	1.46 (2)	C23—H23C	0.950
C7—C8	1.36 (1)	C24—H24A	0.950
C7—H7	0.950	C24—H24B	0.950
C8—C9	1.42 (1)	C24—H24C	0.950
C8—H8	0.951	Cl*—C6*	1.71 (3)
C9—C10	1.36 (1)	C6*—C7*	1.20 (4)
C9—C12	1.464 (9)	C6*—C11*	1.09 (4)
C10—C11	1.35 (2)	C7*—C8*	1.53 (4)
C10—H10	0.951	C7*—H7*	0.953
C11—H11	0.948	C8*—C9*	1.26 (3)
C12—C13	1.319 (9)	C8*—H8*	0.945
C12—H12	0.950	C9*—C10*	1.37 (2)
C13—C14	1.404 (7)	C9*—C12*	1.53 (2)
C13—H13	0.950	C10*—C11*	1.51 (3)
C15—C16	1.456 (6)	C10*—H10*	0.948
C15—H15A	0.950	C11*—H11*	0.954
C15—H15B	0.950	C12*—C13*	1.51 (2)
C16—C17	1.506 (6)	C12*—C13*^i	1.55 (2)
C16—H16A	0.951	C12*—H12*	0.950
C16—H16B	0.949	C13*—H13*	0.950
C17—C18	1.394 (7)
C19—O3—C23	116.8 (3)	O3—C19—C20	116.1 (4)
C20—O4—C24	117.2 (3)	C18—C19—C20	118.3 (4)
C14—N5—C15	121.4 (3)	O4—C20—C19	114.8 (4)
C14—N5—H5	119.3	O4—C20—C21	124.9 (4)
C15—N5—H5	119.3	C19—C20—C21	120.3 (4)
Cl—C6—C7	120 (1)	C20—C21—C22	120.2 (4)
Cl—C6—C11	118 (1)	C20—C21—H21	119.9
C7—C6—C11	120 (1)	C22—C21—H21	119.9
C6—C7—C8	118.6 (10)	C17—C22—C21	121.1 (4)
C6—C7—H7	120.7	C17—C22—H22	119.4
C8—C7—H7	120.7	C21—C22—H22	119.5
C7—C8—C9	121.4 (8)	O3—C23—H23A	109.5
C7—C8—H8	119.1	O3—C23—H23B	109.5
C9—C8—H8	119.5	O3—C23—H23C	109.5
C8—C9—C10	119.0 (7)	H23A—C23—H23B	109.4
C8—C9—C12	119.1 (7)	H23A—C23—H23C	109.5
C10—C9—C12	121.5 (7)	H23B—C23—H23C	109.5
C9—C10—C11	122.5 (9)	O4—C24—H24A	109.4
C9—C10—H10	118.8	O4—C24—H24B	109.4
C11—C10—H10	118.7	O4—C24—H24C	109.4
C6—C11—C10	117 (1)	H24A—C24—H24B	109.5
C6—C11—H11	121.0	H24A—C24—H24C	109.5
C10—C11—H11	121.2	H24B—C24—H24C	109.5
C9—C12—C13	126.5 (6)	Cl*—C6*—C7*	115 (2)
C9—C12—H12	116.7	Cl*—C6*—C11*	130 (2)
C13—C12—H12	116.8	C7*—C6*—C11*	114 (3)
C12—C13—C14	121.7 (5)	C6*—C7*—C8*	126 (2)
C12—C13—H13	119.2	C6*—C7*—H7*	116.9
C14—C13—H13	119.1	C8*—C7*—H7*	116.5
O2—C14—N5	124.1 (4)	C7*—C8*—C9*	119 (1)
O2—C14—C13	120.1 (4)	C7*—C8*—H8*	120.4
N5—C14—C13	114.4 (4)	C9*—C8*—H8*	120.1
N5—C15—C16	112.5 (3)	C8*—C9*—C10*	112 (1)
N5—C15—H15A	108.7	C8*—C9*—C12*	124 (1)
N5—C15—H15B	108.7	C10*—C9*—C12*	123 (1)
C16—C15—H15A	108.7	C9*—C10*—C11*	117 (1)
C16—C15—H15B	108.8	C9*—C10*—H10*	120.9
H15A—C15—H15B	109.5	C11*—C10*—H10*	121.2
C15—C16—C17	114.2 (4)	C6*—C11*—C10*	129 (2)
C15—C16—H16A	108.2	C6*—C11*—H11*	115.5
C15—C16—H16B	108.4	C10*—C11*—H11*	115.1
C17—C16—H16A	108.2	C9*—C12*—C13*	121 (1)
C17—C16—H16B	108.3	C9*—C12*—C13*^i	116 (1)
H16A—C16—H16B	109.5	C9*—C12*—H12*	109.5
C16—C17—C18	120.1 (4)	C13*—C12*—C13*^i	88 (1)
C16—C17—C22	122.0 (4)	C13*—C12*—H12*	109.6
C18—C17—C22	117.9 (4)	C13*^i—C12*—H12*	109.6
C17—C18—C19	122.1 (4)	C12*—C13*—C12*^i	91 (1)
C17—C18—H18	118.9	C12*—C13*—H13*	109.3
C19—C18—H18	118.9	C12*^i—C13*—H13*	109.4
O3—C19—C18	125.5 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^ii	0.95	2.09	2.979 (4)	155

Symmetry code: (ii) x, y−1, z.

(Ie)

Crystal data

C19H20ClNO3	F(000) = 1456.0
Mr = 345.82	Dx = 1.294 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 21.195 (3) Å	Cell parameters from 25 reflections
b = 4.9784 (11) Å	θ = 10.1–11.8°
c = 33.646 (4) Å	µ = 0.23 mm^−1
β = 91.292 (10)°	T = 298 K
V = 3549.3 (10) Å^3	Needle, colourless
Z = 8	0.40 × 0.20 × 0.05 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.016
ω scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −10→27
Tmin = 0.952, Tmax = 0.989	k = −6→2
5116 measured reflections	l = −43→43
4096 independent reflections	3 standard reflections every 150 reflections
1066 reflections with I > 2σ(I)	intensity decay: 1.7%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0727P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.195	(Δ/σ)max = 0.001
S = 0.93	Δρmax = 0.12 e Å^−3
4096 reflections	Δρmin = −0.11 e Å^−3
264 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl	0.4112 (4)	0.466 (2)	0.1899 (2)	0.183 (3)	0.72
Cl*	0.4287 (9)	0.429 (4)	0.1977 (3)	0.132 (5)	0.28
O2	0.6232 (2)	0.8837 (6)	−0.01696 (8)	0.128 (1)
O3	0.7839 (2)	0.0637 (7)	−0.20335 (9)	0.1151 (9)
O4	0.8729 (1)	0.4107 (6)	−0.21051 (8)	0.121 (1)
N5	0.6572 (2)	0.4636 (6)	−0.02611 (8)	0.0909 (10)
C6	0.4475 (5)	0.544 (2)	0.1474 (4)	0.105 (4)	0.72
C6*	0.462 (1)	0.461 (5)	0.1504 (6)	0.0607	0.28
C7	0.4284 (4)	0.750 (2)	0.1223 (4)	0.112 (4)	0.72
C7*	0.435 (1)	0.658 (6)	0.1314 (8)	0.0691	0.28
C8	0.4620 (6)	0.801 (2)	0.0896 (4)	0.121 (3)	0.72
C8*	0.447 (1)	0.735 (5)	0.0884 (6)	0.0619	0.28
C9	0.5140 (4)	0.642 (2)	0.0783 (2)	0.087 (2)	0.72
C9*	0.4882 (6)	0.581 (3)	0.0702 (4)	0.0443	0.28
C10	0.5349 (4)	0.442 (2)	0.1043 (3)	0.104 (2)	0.72
C10*	0.5133 (7)	0.383 (3)	0.0916 (4)	0.0594	0.28
C11	0.5024 (6)	0.385 (2)	0.1398 (3)	0.139 (4)	0.72
C11*	0.498 (1)	0.345 (4)	0.1286 (7)	0.0682	0.28
C12	0.5488 (4)	0.711 (1)	0.0431 (2)	0.093 (2)	0.72
C12*	0.5019 (8)	0.631 (2)	0.0258 (4)	0.058 (4)	0.28
C13	0.5910 (4)	0.564 (1)	0.0253 (2)	0.087 (2)	0.72
C13*	0.5510 (7)	0.460 (2)	0.0055 (4)	0.047 (4)	0.28
C14	0.6210 (2)	0.647 (1)	−0.0092 (1)	0.103 (1)
C15	0.6991 (2)	0.5292 (8)	−0.0584 (1)	0.104 (1)
C16	0.7475 (2)	0.328 (1)	−0.0644 (1)	0.133 (2)
C17	0.7821 (2)	0.357 (1)	−0.1028 (1)	0.103 (1)
C18	0.7665 (2)	0.1945 (8)	−0.1351 (2)	0.101 (1)
C19	0.7962 (2)	0.2135 (9)	−0.1711 (1)	0.093 (1)
C20	0.8447 (2)	0.404 (1)	−0.1742 (1)	0.099 (1)
C21	0.8604 (2)	0.5702 (9)	−0.1430 (2)	0.110 (1)
C22	0.8284 (2)	0.544 (1)	−0.1074 (1)	0.112 (1)
C23	0.7292 (2)	−0.102 (1)	−0.2023 (1)	0.131 (2)
C24	0.9149 (2)	0.624 (1)	−0.2181 (1)	0.142 (2)
H5	0.6557	0.2835	−0.0168	0.1091*
H7	0.3922	0.8537	0.1282	0.1346*	0.72
H8	0.4500	0.9500	0.0733	0.1453*	0.72
H10	0.5715	0.3410	0.0983	0.1245*	0.72
H11	0.5163	0.2484	0.1576	0.1668*	0.72
H12	0.5401	0.8820	0.0317	0.1116*	0.72
H13	0.6015	0.3934	0.0363	0.1042*	0.72
H15A	0.7190	0.6959	−0.0526	0.1253*
H15B	0.6746	0.5451	−0.0822	0.1253*
H16A	0.7283	0.1565	−0.0640	0.1597*
H16B	0.7775	0.3417	−0.0430	0.1597*
H18	0.7340	0.0649	−0.1323	0.1206*
H21	0.8926	0.7013	−0.1456	0.1324*
H22	0.8391	0.6602	−0.0859	0.1350*
H23A	0.6930	0.0065	−0.1987	0.1572*
H23B	0.7333	−0.2259	−0.1809	0.1572*
H23C	0.7249	−0.1982	−0.2266	0.1572*
H24A	0.9310	0.6053	−0.2442	0.1708*
H24B	0.9489	0.6204	−0.1992	0.1708*
H24C	0.8932	0.7903	−0.2163	0.1708*
H7*	0.4061	0.7631	0.1455	0.0830*	0.28
H8*	0.4265	0.8809	0.0757	0.0743*	0.28
H10*	0.5427	0.2652	0.0798	0.0713*	0.28
H11*	0.5202	0.1993	0.1410	0.0818*	0.28
H12*	0.5113	0.8154	0.0220	0.0695*	0.28
H13*	0.5629	0.3133	0.0221	0.0558*	0.28

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.193 (4)	0.190 (4)	0.170 (4)	−0.040 (3)	0.093 (4)	−0.037 (4)
Cl*	0.20 (1)	0.153 (7)	0.042 (3)	−0.067 (8)	0.025 (4)	−0.006 (3)
O2	0.207 (3)	0.070 (2)	0.110 (2)	0.033 (2)	0.025 (2)	0.012 (2)
O3	0.123 (2)	0.116 (2)	0.106 (2)	−0.008 (2)	0.017 (2)	−0.003 (2)
O4	0.121 (2)	0.133 (3)	0.109 (2)	−0.011 (2)	0.035 (2)	0.022 (2)
N5	0.120 (3)	0.072 (2)	0.081 (2)	0.012 (2)	0.019 (2)	0.009 (2)
C6	0.092 (6)	0.100 (8)	0.126 (7)	0.006 (5)	0.029 (5)	−0.006 (6)
C6*	0.0706	0.0710	0.0409	−0.0126	0.0119	−0.0043
C7	0.087 (5)	0.109 (7)	0.141 (9)	0.033 (5)	0.014 (4)	−0.002 (6)
C7*	0.0734	0.0831	0.0517	0.0119	0.0183	−0.0119
C8	0.101 (7)	0.115 (9)	0.147 (6)	−0.007 (5)	−0.002 (6)	−0.011 (6)
C8*	0.0749	0.0629	0.0484	0.0149	0.0135	−0.0040
C9	0.070 (5)	0.084 (5)	0.107 (5)	−0.007 (4)	−0.003 (4)	−0.027 (4)
C9*	0.0507	0.0420	0.0406	−0.0015	0.0074	−0.0041
C10	0.096 (6)	0.087 (5)	0.128 (6)	0.007 (4)	0.011 (5)	−0.001 (5)
C10*	0.0717	0.0608	0.0463	0.0118	0.0122	0.0030
C11	0.167 (8)	0.150 (8)	0.102 (8)	−0.008 (6)	0.067 (8)	−0.009 (6)
C11*	0.0871	0.0683	0.0492	0.0100	0.0043	0.0135
C12	0.104 (6)	0.075 (4)	0.100 (5)	0.014 (4)	−0.001 (4)	−0.002 (4)
C12*	0.07 (1)	0.045 (7)	0.059 (8)	0.007 (7)	0.015 (8)	0.004 (6)
C13	0.110 (5)	0.065 (4)	0.085 (4)	−0.002 (4)	−0.002 (4)	0.001 (3)
C13*	0.066 (9)	0.031 (6)	0.045 (7)	−0.001 (6)	0.025 (6)	0.002 (5)
C14	0.153 (4)	0.084 (3)	0.074 (3)	0.025 (3)	0.016 (3)	0.007 (3)
C15	0.118 (3)	0.076 (3)	0.121 (3)	0.010 (3)	0.031 (3)	0.007 (2)
C16	0.150 (4)	0.154 (4)	0.098 (3)	0.052 (4)	0.040 (3)	0.033 (3)
C17	0.117 (4)	0.099 (3)	0.095 (3)	0.037 (3)	0.017 (3)	0.031 (3)
C18	0.112 (3)	0.086 (3)	0.105 (3)	0.024 (2)	0.028 (3)	0.028 (3)
C19	0.094 (3)	0.088 (3)	0.097 (3)	0.009 (3)	0.013 (3)	0.015 (3)
C20	0.098 (3)	0.103 (3)	0.097 (3)	0.018 (3)	0.014 (3)	0.026 (3)
C21	0.109 (3)	0.098 (3)	0.124 (4)	0.004 (3)	0.007 (3)	0.007 (3)
C22	0.127 (4)	0.113 (4)	0.098 (3)	0.022 (3)	0.007 (3)	0.007 (3)
C23	0.123 (4)	0.129 (4)	0.140 (4)	−0.003 (4)	−0.001 (3)	−0.010 (3)
C24	0.136 (4)	0.163 (5)	0.129 (4)	−0.013 (4)	0.031 (3)	0.043 (3)

Geometric parameters (Å, º)

Cl—C6	1.69 (1)	C17—C22	1.366 (7)
O2—C14	1.208 (6)	C18—C19	1.383 (7)
O3—C19	1.336 (6)	C18—H18	0.950
O3—C23	1.425 (6)	C19—C20	1.403 (7)
O4—C20	1.372 (5)	C20—C21	1.372 (7)
O4—C24	1.413 (6)	C21—C22	1.396 (7)
N5—C14	1.329 (6)	C21—H21	0.950
N5—C15	1.456 (5)	C22—H22	0.950
N5—H5	0.950	C23—H23A	0.950
C6—C7	1.38 (2)	C23—H23B	0.950
C6—C11	1.43 (2)	C23—H23C	0.950
C7—C8	1.35 (2)	C24—H24A	0.951
C7—H7	0.950	C24—H24B	0.950
C8—C9	1.42 (1)	C24—H24C	0.950
C8—H8	0.953	Cl*—C6*	1.76 (3)
C9—C10	1.39 (1)	C6*—C7*	1.29 (4)
C9—C12	1.45 (1)	C6*—C11*	1.22 (3)
C10—C11	1.42 (1)	C7*—C8*	1.52 (3)
C10—H10	0.950	C7*—H7*	0.949
C11—H11	0.948	C8*—C9*	1.32 (3)
C12—C13	1.31 (1)	C8*—H8*	0.944
C12—H12	0.951	C9*—C10*	1.32 (2)
C13—C14	1.399 (8)	C9*—C12*	1.55 (2)
C13—H13	0.950	C10*—C11*	1.30 (3)
C15—C16	1.450 (7)	C10*—H10*	0.949
C15—H15A	0.949	C11*—H11*	0.952
C15—H15B	0.950	C12*—C13*	1.52 (2)
C16—C17	1.508 (7)	C12*—C13*^i	1.59 (2)
C16—H16A	0.949	C12*—H12*	0.950
C16—H16B	0.951	C13*—H13*	0.950
C17—C18	1.389 (7)
C19—O3—C23	116.6 (4)	O3—C19—C20	116.5 (4)
C20—O4—C24	118.0 (4)	C18—C19—C20	117.4 (4)
C14—N5—C15	122.2 (3)	O4—C20—C19	114.7 (4)
C14—N5—H5	118.9	O4—C20—C21	124.2 (4)
C15—N5—H5	118.9	C19—C20—C21	121.1 (4)
Cl—C6—C7	123.7 (9)	C20—C21—C22	119.2 (4)
Cl—C6—C11	114.3 (9)	C20—C21—H21	120.4
C7—C6—C11	121 (1)	C22—C21—H21	120.4
C6—C7—C8	119.0 (10)	C17—C22—C21	121.6 (4)
C6—C7—H7	120.3	C17—C22—H22	119.2
C8—C7—H7	120.7	C21—C22—H22	119.2
C7—C8—C9	122 (1)	O3—C23—H23A	109.4
C7—C8—H8	118.4	O3—C23—H23B	109.5
C9—C8—H8	118.8	O3—C23—H23C	109.5
C8—C9—C10	118.1 (8)	H23A—C23—H23B	109.4
C8—C9—C12	119.9 (8)	H23A—C23—H23C	109.5
C10—C9—C12	121.6 (7)	H23B—C23—H23C	109.5
C9—C10—C11	121.2 (8)	O4—C24—H24A	109.5
C9—C10—H10	119.4	O4—C24—H24B	109.6
C11—C10—H10	119.4	O4—C24—H24C	109.5
C6—C11—C10	116.8 (10)	H24A—C24—H24B	109.4
C6—C11—H11	121.7	H24A—C24—H24C	109.4
C10—C11—H11	121.5	H24B—C24—H24C	109.5
C9—C12—C13	127.2 (6)	Cl*—C6*—C7*	109 (2)
C9—C12—H12	116.4	Cl*—C6*—C11*	140 (2)
C13—C12—H12	116.4	C7*—C6*—C11*	109 (2)
C12—C13—C14	122.7 (6)	C6*—C7*—C8*	125 (2)
C12—C13—H13	118.6	C6*—C7*—H7*	117.3
C14—C13—H13	118.7	C8*—C7*—H7*	117.0
O2—C14—N5	123.5 (4)	C7*—C8*—C9*	114 (1)
O2—C14—C13	119.3 (5)	C7*—C8*—H8*	122.9
N5—C14—C13	115.4 (5)	C9*—C8*—H8*	122.6
N5—C15—C16	113.2 (3)	C8*—C9*—C10*	116 (1)
N5—C15—H15A	108.6	C8*—C9*—C12*	119 (1)
N5—C15—H15B	108.5	C10*—C9*—C12*	124 (1)
C16—C15—H15A	108.6	C9*—C10*—C11*	121 (1)
C16—C15—H15B	108.4	C9*—C10*—H10*	119.2
H15A—C15—H15B	109.5	C11*—C10*—H10*	119.2
C15—C16—C17	114.5 (4)	C6*—C11*—C10*	132 (2)
C15—C16—H16A	108.3	C6*—C11*—H11*	113.7
C15—C16—H16B	108.1	C10*—C11*—H11*	113.8
C17—C16—H16A	108.3	C9*—C12*—C13*	119 (1)
C17—C16—H16B	108.1	C9*—C12*—C13*^i	116 (1)
H16A—C16—H16B	109.5	C9*—C12*—H12*	109.4
C16—C17—C18	120.3 (4)	C13*—C12*—C13*^i	91.3 (10)
C16—C17—C22	121.7 (4)	C13*—C12*—H12*	109.4
C18—C17—C22	117.9 (4)	C13*^i—C12*—H12*	109.4
C17—C18—C19	122.8 (4)	C12*—C13*—C12*^i	88.7 (10)
C17—C18—H18	118.6	C12*—C13*—H13*	110.1
C19—C18—H18	118.6	C12*^i—C13*—H13*	110.1
O3—C19—C18	126.1 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^ii	0.95	2.11	2.993 (4)	155

Symmetry code: (ii) x, y−1, z.

(If)

Crystal data

C19H20ClNO3	F(000) = 1456.0
Mr = 345.82	Dx = 1.296 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 21.180 (4) Å	Cell parameters from 25 reflections
b = 4.9770 (12) Å	θ = 10.1–11.8°
c = 33.642 (4) Å	µ = 0.23 mm^−1
β = 91.290 (11)°	T = 298 K
V = 3545.3 (11) Å^3	Needle, colourless
Z = 8	0.40 × 0.20 × 0.05 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.017
ω scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −10→27
Tmin = 0.952, Tmax = 0.989	k = −6→2
5109 measured reflections	l = −43→43
4089 independent reflections	3 standard reflections every 150 reflections
1078 reflections with I > 2σ(I)	intensity decay: 2.1%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0787P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.201	(Δ/σ)max = 0.004
S = 0.93	Δρmax = 0.12 e Å^−3
4089 reflections	Δρmin = −0.13 e Å^−3
264 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl	0.4138 (3)	0.459 (2)	0.1908 (2)	0.187 (2)	0.71
Cl*	0.4252 (7)	0.425 (4)	0.1980 (2)	0.154 (4)	0.29
O2	0.6220 (2)	0.8840 (6)	−0.01682 (8)	0.129 (1)
O3	0.7839 (2)	0.0712 (7)	−0.2032 (1)	0.120 (1)
O4	0.8732 (1)	0.4161 (6)	−0.21004 (8)	0.121 (1)
N5	0.6568 (2)	0.4624 (6)	−0.02576 (8)	0.0903 (10)
C6	0.4468 (8)	0.531 (4)	0.1467 (5)	0.123 (7)	0.71
C6*	0.459 (2)	0.486 (7)	0.1509 (7)	0.0607	0.29
C7	0.4285 (6)	0.747 (2)	0.1223 (4)	0.118 (5)	0.71
C7*	0.434 (1)	0.670 (6)	0.1317 (8)	0.0691	0.29
C8	0.4627 (5)	0.798 (3)	0.0899 (4)	0.126 (3)	0.71
C8*	0.4458 (10)	0.735 (4)	0.0889 (6)	0.0619	0.29
C9	0.5137 (4)	0.639 (2)	0.0789 (2)	0.088 (2)	0.71
C9*	0.4877 (6)	0.578 (3)	0.0698 (4)	0.0443	0.29
C10	0.5338 (4)	0.442 (2)	0.1043 (3)	0.111 (2)	0.71
C10*	0.5143 (7)	0.379 (3)	0.0910 (4)	0.0594	0.29
C11	0.501 (1)	0.384 (4)	0.1378 (6)	0.156 (5)	0.71
C11*	0.498 (2)	0.339 (6)	0.1333 (9)	0.0682	0.29
C12	0.5480 (4)	0.709 (1)	0.0432 (2)	0.097 (2)	0.71
C12*	0.4998 (6)	0.629 (2)	0.0257 (3)	0.048 (4)	0.29
C13	0.5899 (4)	0.556 (1)	0.0249 (2)	0.090 (2)	0.71
C13*	0.5486 (6)	0.459 (2)	0.0041 (3)	0.054 (4)	0.29
C14	0.6201 (2)	0.647 (1)	−0.0095 (1)	0.101 (1)
C15	0.6989 (2)	0.5327 (7)	−0.0576 (1)	0.106 (1)
C16	0.7477 (2)	0.332 (1)	−0.0636 (1)	0.134 (2)
C17	0.7817 (2)	0.358 (1)	−0.1026 (1)	0.103 (1)
C18	0.7661 (2)	0.1973 (9)	−0.1350 (2)	0.100 (1)
C19	0.7963 (2)	0.2197 (9)	−0.1704 (1)	0.092 (1)
C20	0.8447 (2)	0.411 (1)	−0.1739 (1)	0.097 (1)
C21	0.8598 (2)	0.5739 (9)	−0.1429 (2)	0.109 (1)
C22	0.8282 (2)	0.547 (1)	−0.1068 (1)	0.115 (1)
C23	0.7292 (2)	−0.095 (1)	−0.2025 (1)	0.136 (2)
C24	0.9155 (2)	0.629 (1)	−0.2175 (1)	0.141 (2)
H5	0.6555	0.2821	−0.0165	0.1082*
H7	0.3930	0.8544	0.1285	0.1427*	0.71
H8	0.4514	0.9468	0.0737	0.1524*	0.71
H10	0.5710	0.3428	0.0988	0.1337*	0.71
H11	0.5140	0.2437	0.1552	0.1870*	0.71
H12	0.5396	0.8810	0.0319	0.1168*	0.71
H13	0.5995	0.3827	0.0352	0.1083*	0.71
H15A	0.7186	0.6993	−0.0513	0.1273*
H15B	0.6747	0.5508	−0.0816	0.1273*
H16A	0.7287	0.1593	−0.0627	0.1602*
H16B	0.7781	0.3474	−0.0425	0.1602*
H18	0.7335	0.0675	−0.1325	0.1203*
H21	0.8917	0.7067	−0.1455	0.1309*
H22	0.8393	0.6604	−0.0850	0.1379*
H23A	0.6929	0.0134	−0.1990	0.1636*
H23B	0.7332	−0.2193	−0.1811	0.1636*
H23C	0.7252	−0.1901	−0.2269	0.1636*
H24A	0.9317	0.6109	−0.2434	0.1697*
H24B	0.9493	0.6242	−0.1984	0.1697*
H24C	0.8938	0.7956	−0.2155	0.1697*
H7*	0.4046	0.7813	0.1452	0.0830*	0.29
H8*	0.4247	0.8813	0.0758	0.0743*	0.29
H10*	0.5437	0.2634	0.0789	0.0713*	0.29
H11*	0.5188	0.1960	0.1472	0.0818*	0.29
H12*	0.5089	0.8138	0.0218	0.0586*	0.29
H13*	0.5604	0.3101	0.0203	0.0647*	0.29

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.213 (4)	0.188 (4)	0.165 (4)	−0.054 (3)	0.114 (3)	−0.041 (4)
Cl*	0.26 (1)	0.159 (8)	0.048 (3)	−0.070 (7)	0.010 (4)	0.001 (3)
O2	0.208 (3)	0.072 (2)	0.106 (2)	0.035 (2)	0.023 (2)	0.010 (2)
O3	0.125 (3)	0.121 (2)	0.114 (2)	−0.013 (2)	0.027 (2)	0.003 (2)
O4	0.124 (2)	0.131 (3)	0.110 (2)	−0.010 (2)	0.035 (2)	0.016 (2)
N5	0.114 (2)	0.073 (2)	0.085 (2)	0.015 (2)	0.024 (2)	0.008 (2)
C6	0.10 (1)	0.12 (1)	0.144 (9)	−0.004 (9)	0.031 (7)	−0.011 (7)
C6*	0.0706	0.0710	0.0409	−0.0126	0.0119	−0.0043
C7	0.100 (6)	0.117 (9)	0.14 (1)	0.025 (6)	0.007 (5)	−0.009 (6)
C7*	0.0734	0.0831	0.0517	0.0119	0.0183	−0.0119
C8	0.099 (8)	0.139 (10)	0.141 (6)	0.001 (6)	0.018 (6)	−0.004 (6)
C8*	0.0749	0.0629	0.0484	0.0149	0.0135	−0.0040
C9	0.086 (6)	0.076 (5)	0.103 (5)	−0.007 (4)	0.006 (4)	−0.022 (4)
C9*	0.0507	0.0420	0.0406	−0.0015	0.0074	−0.0041
C10	0.123 (7)	0.098 (5)	0.115 (6)	0.004 (5)	0.018 (5)	−0.001 (5)
C10*	0.0717	0.0608	0.0463	0.0118	0.0122	0.0030
C11	0.179 (9)	0.14 (1)	0.16 (1)	0.007 (7)	0.067 (8)	0.015 (8)
C11*	0.0871	0.0683	0.0492	0.0100	0.0043	0.0135
C12	0.116 (6)	0.076 (4)	0.099 (5)	0.005 (4)	−0.006 (5)	0.005 (4)
C12*	0.040 (7)	0.045 (6)	0.060 (7)	−0.002 (5)	0.008 (6)	−0.009 (5)
C13	0.108 (6)	0.071 (4)	0.092 (4)	0.003 (4)	0.014 (4)	0.008 (4)
C13*	0.059 (8)	0.052 (7)	0.050 (7)	−0.016 (6)	0.017 (6)	−0.005 (6)
C14	0.140 (4)	0.089 (3)	0.075 (3)	0.025 (3)	0.020 (2)	0.005 (3)
C15	0.118 (3)	0.073 (3)	0.128 (3)	0.005 (3)	0.030 (3)	0.001 (2)
C16	0.145 (4)	0.157 (4)	0.101 (3)	0.056 (4)	0.038 (3)	0.038 (3)
C17	0.120 (4)	0.090 (3)	0.101 (3)	0.037 (3)	0.027 (3)	0.030 (3)
C18	0.111 (3)	0.085 (3)	0.106 (3)	0.019 (2)	0.029 (3)	0.023 (3)
C19	0.095 (3)	0.085 (3)	0.096 (3)	0.016 (3)	0.012 (3)	0.014 (3)
C20	0.099 (3)	0.105 (3)	0.090 (3)	0.012 (3)	0.018 (3)	0.015 (3)
C21	0.114 (3)	0.094 (3)	0.120 (3)	0.007 (3)	0.013 (3)	0.013 (3)
C22	0.134 (4)	0.113 (4)	0.098 (3)	0.032 (3)	0.015 (3)	0.010 (3)
C23	0.131 (4)	0.126 (4)	0.151 (4)	0.001 (4)	0.010 (3)	−0.007 (3)
C24	0.145 (4)	0.148 (4)	0.132 (4)	−0.014 (4)	0.037 (3)	0.039 (3)

Geometric parameters (Å, º)

Cl—C6	1.69 (2)	C17—C22	1.371 (7)
O2—C14	1.207 (6)	C18—C19	1.368 (7)
O3—C19	1.349 (6)	C18—H18	0.951
O3—C23	1.423 (6)	C19—C20	1.406 (7)
O4—C20	1.369 (5)	C20—C21	1.355 (7)
O4—C24	1.413 (6)	C21—C22	1.406 (7)
N5—C14	1.329 (6)	C21—H21	0.950
N5—C15	1.452 (5)	C22—H22	0.950
N5—H5	0.951	C23—H23A	0.950
C6—C7	1.40 (2)	C23—H23B	0.950
C6—C11	1.39 (3)	C23—H23C	0.950
C7—C8	1.35 (2)	C24—H24A	0.949
C7—H7	0.949	C24—H24B	0.950
C8—C9	1.39 (1)	C24—H24C	0.951
C8—H8	0.948	Cl*—C6*	1.78 (3)
C9—C10	1.37 (1)	C6*—C7*	1.23 (4)
C9—C12	1.46 (1)	C6*—C11*	1.27 (5)
C10—C11	1.37 (2)	C7*—C8*	1.50 (4)
C10—H10	0.951	C7*—H7*	0.955
C11—H11	0.951	C8*—C9*	1.35 (2)
C12—C13	1.33 (1)	C8*—H8*	0.957
C12—H12	0.950	C9*—C10*	1.34 (2)
C13—C14	1.409 (8)	C9*—C12*	1.53 (2)
C13—H13	0.950	C10*—C11*	1.48 (3)
C15—C16	1.455 (7)	C10*—H10*	0.949
C15—H15A	0.950	C11*—H11*	0.949
C15—H15B	0.951	C12*—C13*	1.53 (2)
C16—C17	1.517 (7)	C12*—C13*^i	1.48 (2)
C16—H16A	0.949	C12*—H12*	0.950
C16—H16B	0.950	C13*—H13*	0.949
C17—C18	1.386 (7)
C19—O3—C23	116.7 (4)	O3—C19—C20	115.5 (4)
C20—O4—C24	117.7 (4)	C18—C19—C20	119.0 (4)
C14—N5—C15	120.9 (3)	O4—C20—C19	115.2 (4)
C14—N5—H5	119.6	O4—C20—C21	124.9 (4)
C15—N5—H5	119.6	C19—C20—C21	119.9 (4)
Cl—C6—C7	124 (1)	C20—C21—C22	120.1 (4)
Cl—C6—C11	115 (1)	C20—C21—H21	120.0
C7—C6—C11	119 (1)	C22—C21—H21	119.9
C6—C7—C8	118 (1)	C17—C22—C21	120.8 (4)
C6—C7—H7	121.0	C17—C22—H22	119.6
C8—C7—H7	120.9	C21—C22—H22	119.7
C7—C8—C9	122 (1)	O3—C23—H23A	109.4
C7—C8—H8	118.7	O3—C23—H23B	109.4
C9—C8—H8	118.4	O3—C23—H23C	109.4
C8—C9—C10	118.2 (9)	H23A—C23—H23B	109.5
C8—C9—C12	119.1 (8)	H23A—C23—H23C	109.6
C10—C9—C12	122.2 (7)	H23B—C23—H23C	109.5
C9—C10—C11	120 (1)	O4—C24—H24A	109.5
C9—C10—H10	120.0	O4—C24—H24B	109.5
C11—C10—H10	119.5	O4—C24—H24C	109.4
C6—C11—C10	120 (1)	H24A—C24—H24B	109.5
C6—C11—H11	119.4	H24A—C24—H24C	109.5
C10—C11—H11	120.6	H24B—C24—H24C	109.4
C9—C12—C13	126.3 (6)	Cl*—C6*—C7*	114 (2)
C9—C12—H12	116.9	Cl*—C6*—C11*	126 (2)
C13—C12—H12	116.8	C7*—C6*—C11*	117 (2)
C12—C13—C14	121.0 (6)	C6*—C7*—C8*	125 (2)
C12—C13—H13	119.5	C6*—C7*—H7*	117.4
C14—C13—H13	119.5	C8*—C7*—H7*	117.1
O2—C14—N5	124.6 (4)	C7*—C8*—C9*	117 (1)
O2—C14—C13	119.9 (5)	C7*—C8*—H8*	121.2
N5—C14—C13	113.5 (5)	C9*—C8*—H8*	121.6
N5—C15—C16	112.7 (3)	C8*—C9*—C10*	116 (1)
N5—C15—H15A	108.6	C8*—C9*—C12*	119 (1)
N5—C15—H15B	108.7	C10*—C9*—C12*	124 (1)
C16—C15—H15A	108.7	C9*—C10*—C11*	120 (1)
C16—C15—H15B	108.7	C9*—C10*—H10*	119.5
H15A—C15—H15B	109.4	C11*—C10*—H10*	119.7
C15—C16—C17	114.3 (4)	C6*—C11*—C10*	122 (2)
C15—C16—H16A	108.3	C6*—C11*—H11*	119.7
C15—C16—H16B	108.2	C10*—C11*—H11*	117.9
C17—C16—H16A	108.3	C9*—C12*—C13*	119.9 (9)
C17—C16—H16B	108.2	C9*—C12*—C13*^i	118 (1)
H16A—C16—H16B	109.5	C9*—C12*—H12*	109.5
C16—C17—C18	121.5 (4)	C13*—C12*—C13*^i	88.8 (9)
C16—C17—C22	120.3 (4)	C13*—C12*—H12*	109.2
C18—C17—C22	118.2 (4)	C13*^i—C12*—H12*	109.2
C17—C18—C19	122.0 (4)	C12*—C13*—C12*^i	91.2 (9)
C17—C18—H18	119.0	C12*—C13*—H13*	109.2
C19—C18—H18	119.0	C12*^i—C13*—H13*	109.2
O3—C19—C18	125.5 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^ii	0.95	2.10	2.989 (4)	154

Symmetry code: (ii) x, y−1, z.