Crystal-to-crystal photodimerization of ­trans-­cinnamamides

Hosomi, H.; Ito, Y.; Ohba, S.

doi:10.1107/S0108768100002329

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Crystal-to-crystal photodimerization of trans-cinnamamides

H. Hosomi, Y. Ito and S. Ohba

In the crystals of trans-4-methylcinnamamide, C₁₀H₁₁NO (I), trans-4-chlorocinnamamide, C₉H₈ClNO (II), trans-3-(2-thienyl)acrylamide, C₇H₇NOS (III), and trans-cinnamamide, C₉H₉NO (IV), the shortest intermolecular C

C distances between the C=C double bonds are 3.670 (2), 3.632 (2), 3.762 (3) and 4.120 (2) Å, respectively, for the pair of molecules related by a center of symmetry. The structure analysis was also carried out for trans-2-(p-chlorophenyl)-cis-4-(p-chlorophenyl)-1-trans-3-diamidocyclobutane, C₁₈H₁₆Cl₂N₂O₂ (V), which is the α-type photodimer of (II). The N—H

O hydrogen-bond networks in (I)–(III) are composed of two-dimensional pleated sheets, and those in (IV) and (V) of one-dimensional flat ribbons. The single crystals of (I), (II) and (IV) were photoirradiated with a 250 W ultra-high-pressure mercury lamp through a band-pass filter or a long-pass filter for 2–5 h. The photodimer was produced in each crystal with retention of the single-crystal form. The populations of the dimers were converged to 86.2 (4), 48.4 (6) and 4.5 (2)% in the refinement of the crystals after photoirradiation, (I $^{\prime}$ ), (II $^{\prime}$ ) and (IV $^{\prime}$ ), respectively. Although the intermolecular N—H

O hydrogen-bond network remained in (I $^{\prime}$ ) and (II $^{\prime}$ ), the network was partly broken in (IV $^{\prime}$ ) in the process of photoreaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100002329/oa0024sup1.cif Contains datablocks amide, I, I', II, II', III, IV, IV', V
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024I'sup3.hkl Contains datablock I'
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IIsup4.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024II'sup5.hkl Contains datablock II'
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IIIsup6.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IVsup7.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024IV'sup8.hkl Contains datablock IV'
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100002329/oa0024Vsup9.hkl Contains datablock V

CCDC references: 148910; 148911; 148912; 148913; 148914; 148915; 148916; 148917

Computing details top

For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top

Crystal data top

C₁₀H₁₁NO	Z = 8
M_r = 161.20	D_x = 1.209 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 23.599 (3) Å	θ = 13.2–15.0°
b = 9.148 (3) Å	µ = 0.08 mm⁻¹
c = 8.208 (3) Å	T = 298 K
β = 87.69 (2)°	Plate-like, colourless
V = 1770.5 (8) Å³	0.8 × 0.5 × 0.2 mm

Data collection top

Rigaku AFC7R diffractometer	θ_max = 27.5°, θ_min = 2.5°
θ–2θ scans	h = 0→31
2080 measured reflections	k = −12→0
2034 independent reflections	l = −11→11
1420 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
R_int = 0.030	intensity decay: none

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.052P)² + 0.6818P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.116	(Δ/σ)_max = 0.0001
S = 1.03	Δρ_max = 0.16 e Å⁻³
2034 reflections	Δρ_min = −0.16 e Å⁻³
165 parameters

Special details top

Refinement. Refinement was based on F² against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F², and conventional R-factor (R) was calculated on F, with F set to zero for negative F². The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.28647 (5)	0.6568 (1)	0.1656 (1)	0.0589 (3)
N2	0.25085 (6)	0.8849 (1)	0.1677 (2)	0.0523 (3)
C3	0.28094 (6)	0.7779 (1)	0.2318 (2)	0.0434 (3)
C4	0.30864 (6)	0.8131 (2)	0.3862 (2)	0.0454 (3)
C5	0.33932 (6)	0.7144 (2)	0.4615 (2)	0.0463 (3)
C6	0.37090 (6)	0.7337 (2)	0.6105 (2)	0.0442 (3)
C7	0.37877 (7)	0.8691 (2)	0.6831 (2)	0.0513 (4)
C8	0.41025 (7)	0.8816 (2)	0.8210 (2)	0.0564 (4)
C9	0.43477 (6)	0.7602 (2)	0.8916 (2)	0.0534 (4)
C10	0.42683 (7)	0.6257 (2)	0.8195 (2)	0.0556 (4)
C11	0.39536 (7)	0.6118 (2)	0.6812 (2)	0.0516 (4)
C12	0.4694 (1)	0.7748 (3)	1.0417 (3)	0.0745 (6)
H2A	0.2341 (7)	0.868 (2)	0.066 (2)	0.07000 (6)*
H2B	0.2434 (7)	0.971 (2)	0.224 (2)	0.07516 (7)*
H4	0.3039 (6)	0.912 (2)	0.424 (2)	0.05154 (5)*
H5	0.3412 (6)	0.616 (2)	0.416 (2)	0.05081 (5)*
H7	0.3628 (7)	0.958 (2)	0.635 (2)	0.06280 (6)*
H8	0.4155 (7)	0.980 (2)	0.865 (2)	0.07000 (6)*
H10	0.4442 (7)	0.537 (2)	0.863 (2)	0.06353 (6)*
H11	0.3902 (7)	0.516 (2)	0.633 (2)	0.06900 (6)*
H12A	0.491 (2)	0.680 (4)	1.063 (4)	0.0534 (1)*	0.50
H12B	0.439 (1)	0.778 (5)	1.135 (5)	0.0573 (1)*	0.50
H12C	0.488 (2)	0.873 (5)	1.045 (5)	0.0673 (1)*	0.50
H12*A	0.458 (2)	0.870 (5)	1.107 (5)	0.0748 (1)*	0.50
H12*B	0.514 (2)	0.771 (5)	1.011 (5)	0.0862 (2)*	0.50
H12*C	0.457 (2)	0.699 (5)	1.123 (6)	0.0856 (2)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0886 (8)	0.0380 (5)	0.0520 (6)	0.0056 (5)	−0.0269 (5)	−0.0031 (4)
N2	0.0692 (8)	0.0396 (6)	0.0497 (7)	0.0046 (6)	−0.0216 (6)	−0.0021 (5)
C3	0.0530 (8)	0.0366 (6)	0.0414 (7)	−0.0046 (6)	−0.0103 (6)	0.0025 (5)
C4	0.0537 (8)	0.0414 (7)	0.0417 (7)	−0.0020 (6)	−0.0092 (6)	−0.0026 (6)
C5	0.0537 (8)	0.0438 (7)	0.0420 (7)	−0.0012 (6)	−0.0099 (6)	−0.0011 (6)
C6	0.0448 (7)	0.0497 (7)	0.0385 (7)	0.0000 (6)	−0.0054 (6)	0.0014 (6)
C7	0.0588 (9)	0.0509 (8)	0.0449 (7)	0.0063 (7)	−0.0122 (6)	−0.0012 (6)
C8	0.0641 (10)	0.0580 (9)	0.0482 (8)	0.0016 (7)	−0.0143 (7)	−0.0088 (7)
C9	0.0496 (8)	0.0690 (10)	0.0424 (7)	0.0015 (7)	−0.0102 (6)	0.0012 (7)
C10	0.0582 (9)	0.0599 (9)	0.0494 (8)	0.0060 (7)	−0.0125 (7)	0.0087 (7)
C11	0.0594 (9)	0.0482 (8)	0.0479 (8)	0.0011 (7)	−0.0096 (6)	0.0019 (6)
C12	0.078 (1)	0.089 (2)	0.059 (1)	0.004 (1)	−0.031 (1)	−0.002 (1)

Geometric parameters (Å, º) top

O1—C3	1.239 (2)	C8—C9	1.390 (2)
N2—C3	1.330 (2)	C8—H8	0.98 (2)
N2—H2A	0.95 (2)	C9—C10	1.381 (2)
N2—H2B	0.92 (2)	C9—C12	1.512 (3)
C3—C4	1.484 (2)	C10—C11	1.387 (2)
C4—C5	1.325 (2)	C10—H10	0.98 (2)
C4—H4	0.96 (2)	C11—H11	0.97 (2)
C5—C6	1.469 (2)	C12—H12A	1.02 (4)
C5—H5	0.97 (2)	C12—H12B	1.02 (4)
C6—C7	1.390 (2)	C12—H12C	1.00 (4)
C6—C11	1.392 (2)	C12—H12*A	1.06 (4)
C7—C8	1.383 (2)	C12—H12*B	1.07 (5)
C7—H7	0.99 (2)	C12—H12*C	1.00 (5)

C3—N2—H2A	118.5 (10)	C8—C9—C10	117.9 (1)
C3—N2—H2B	121.3 (11)	C8—C9—C12	121.1 (2)
H2A—N2—H2B	119.9 (15)	C10—C9—C12	121.0 (2)
O1—C3—N2	122.2 (1)	C9—C10—C11	121.2 (1)
O1—C3—C4	121.8 (1)	C9—C10—H10	121.1 (10)
N2—C3—C4	116.0 (1)	C11—C10—H10	117.7 (10)
C3—C4—C5	121.2 (1)	C6—C11—C10	120.8 (1)
C3—C4—H4	115.6 (9)	C6—C11—H11	119.7 (10)
C5—C4—H4	123.2 (9)	C10—C11—H11	119.5 (10)
C4—C5—C6	127.7 (1)	C9—C12—H12A	111 (2)
C4—C5—H5	118.0 (9)	C9—C12—H12B	103 (2)
C6—C5—H5	114.3 (9)	C9—C12—H12C	111 (2)
C5—C6—C7	123.0 (1)	C9—C12—H12*A	110 (3)
C5—C6—C11	118.9 (1)	C9—C12—H12*B	111 (2)
C7—C6—C11	118.0 (1)	C9—C12—H12*C	109 (3)
C6—C7—C8	120.7 (1)	H12A—C12—H12B	103 (3)
C6—C7—H7	120.3 (10)	H12A—C12—H12C	123 (3)
C8—C7—H7	119.0 (10)	H12B—C12—H12C	104 (3)
C7—C8—C9	121.4 (1)	H12A—C12—H12B	113 (4)
C7—C8—H8	117.5 (10)	H12A—C12—H12C	100 (4)
C9—C8—H8	121.1 (10)	H12B—C12—H12C	113 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.95 (2)	1.99 (2)	2.932 (2)	169.1 (15)
N2—H2B···O1ⁱⁱ	0.92 (2)	2.04 (2)	2.956 (2)	170.4 (16)

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y+1/2, −z+1/2.

(I') top

Crystal data top

C₁₀H₁₁NO	Z = 8
M_r = 161.20	D_x = 1.160 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 22.444 (1) Å	θ = 12.0–14.6°
b = 9.557 (2) Å	µ = 0.08 mm⁻¹
c = 8.632 (1) Å	T = 298 K
β = 94.50 (1)°	Plate-like, colourless
V = 1845.9 (5) Å³	0.7 × 0.4 × 0.2 mm

Data collection top

Rigaku AFC7R diffractometer	θ_max = 27.5°, θ_min = 2.5°
θ–2θ scans	h = 0→29
2404 measured reflections	k = −12→5
2128 independent reflections	l = −11→11
1294 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
R_int = 0.017	intensity decay: none

Refinement top

Refinement on F²	H atoms riding
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.0648P)² + 2.4674P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.212	(Δ/σ)_max = 0.0001
S = 1.19	Δρ_max = 0.30 e Å⁻³
2128 reflections	Δρ_min = −0.22 e Å⁻³
110 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.2865	0.6567	0.1657	0.0574*	0.138 (4)
O1*	0.2713 (1)	0.6544 (2)	0.1924 (2)	0.0493 (7)	0.862 (4)
N2	0.2507	0.8845	0.1679	0.0506*	0.138 (4)
N2*	0.2574 (2)	0.8828 (2)	0.1439 (3)	0.0535 (8)	0.862 (4)
C3	0.2809	0.7782	0.2321	0.0424*	0.138 (4)
C3*	0.2672 (1)	0.7753 (3)	0.2392 (3)	0.0382 (7)	0.862 (4)
C4	0.3086	0.8129	0.3862	0.0443*	0.138 (4)
C4*	0.2701 (1)	0.8123 (3)	0.4104 (3)	0.0391 (8)	0.862 (4)
C5	0.3394	0.7144	0.4614	0.0450*	0.138 (4)
C5*	0.2940 (1)	0.6959 (3)	0.5221 (3)	0.0384 (7)	0.862 (4)
C6	0.3709	0.7337	0.6105	0.0436*	0.138 (4)
C6*	0.3472 (2)	0.7218 (3)	0.6381 (3)	0.0429 (8)	0.862 (4)
C7	0.3788	0.8693	0.6829	0.0502*	0.138 (4)
C7*	0.3657 (2)	0.8512 (3)	0.6893 (4)	0.061 (1)	0.862 (4)
C8	0.4103	0.8819	0.8211	0.0554*	0.138 (4)
C8*	0.4099 (2)	0.8659 (4)	0.8100 (6)	0.083 (1)	0.862 (4)
C9	0.4348	0.7606	0.8916	0.0529*	0.138 (4)
C9*	0.4379 (2)	0.7538 (6)	0.8820 (5)	0.081 (1)	0.862 (4)
C10	0.4269	0.6253	0.8195	0.0547*	0.138 (4)
C10*	0.4200 (2)	0.6247 (5)	0.8307 (5)	0.080 (1)	0.862 (4)
C11	0.3954	0.6115	0.6811	0.0506*	0.138 (4)
C11*	0.3761 (2)	0.6082 (3)	0.7094 (4)	0.0593 (10)	0.862 (4)
C12	0.4696	0.7745	1.0414	0.0750*	0.138 (4)
C12*	0.4859 (2)	0.7711 (4)	1.0137 (5)	0.128 (3)	0.862 (4)
H2A	0.2304	0.8747	0.0664	0.0607*	0.138 (4)
H2B	0.2490	0.9716	0.2227	0.0607*	0.138 (4)
H2*A	0.2550	0.8691	0.0345	0.0623*	0.862 (4)
H2*B	0.2534	0.9747	0.1846	0.0623*	0.862 (4)
H4	0.3044	0.9042	0.4305	0.0532*	0.138 (4)
H4*	0.2896	0.9022	0.4319	0.0441*	0.862 (4)
H5	0.3409	0.6239	0.4137	0.0540*	0.138 (4)
H5*	0.3006	0.6122	0.4642	0.0432*	0.862 (4)
H7	0.3615	0.9507	0.6321	0.0603*	0.138 (4)
H7*	0.3476	0.9326	0.6417	0.0714*	0.862 (4)
H8	0.4159	0.9716	0.8702	0.0664*	0.138 (4)
H8*	0.4211	0.9575	0.8453	0.0986*	0.862 (4)
H10	0.4443	0.5441	0.8706	0.0657*	0.138 (4)
H10*	0.4377	0.5431	0.8796	0.0938*	0.862 (4)
H11	0.3898	0.5217	0.6323	0.0607*	0.138 (4)
H11*	0.3655	0.5160	0.6737	0.0684*	0.862 (4)
H12A	0.4834	0.6840	1.0764	0.0901*	0.138 (4)
H12B	0.5033	0.8345	1.0300	0.0901*	0.138 (4)
H12C	0.4449	0.8141	1.1161	0.0901*	0.138 (4)
H12*A	0.5221	0.7284	0.9873	0.1498*	0.862 (4)
H12*B	0.4734	0.7279	1.1052	0.1498*	0.862 (4)
H12*C	0.4930	0.8679	1.0336	0.1498*	0.862 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1*	0.088 (2)	0.035 (1)	0.0240 (9)	0.003 (1)	0.000 (1)	−0.0004 (8)
N2*	0.098 (2)	0.037 (1)	0.024 (1)	−0.001 (1)	−0.003 (1)	0.003 (1)
C3*	0.050 (2)	0.038 (1)	0.026 (1)	−0.009 (1)	−0.001 (1)	0.004 (1)
C4*	0.058 (2)	0.032 (1)	0.026 (1)	−0.006 (1)	−0.005 (1)	0.000 (1)
C5*	0.056 (2)	0.033 (1)	0.025 (1)	0.001 (1)	−0.006 (1)	−0.001 (1)
C6*	0.052 (2)	0.047 (2)	0.029 (1)	0.001 (1)	−0.001 (1)	0.001 (1)
C7*	0.067 (2)	0.050 (2)	0.062 (2)	−0.002 (2)	−0.019 (2)	−0.006 (2)
C8*	0.080 (3)	0.076 (3)	0.086 (3)	−0.006 (2)	−0.032 (2)	−0.026 (2)
C9*	0.060 (3)	0.114 (4)	0.064 (2)	−0.002 (3)	−0.026 (2)	0.000 (3)
C10*	0.072 (3)	0.090 (3)	0.073 (3)	0.008 (2)	−0.022 (2)	0.028 (2)
C11*	0.066 (2)	0.057 (2)	0.053 (2)	0.001 (2)	−0.008 (2)	0.009 (2)
C12*	0.086 (4)	0.185 (7)	0.102 (4)	−0.006 (4)	−0.058 (3)	−0.006 (4)

Geometric parameters (Å, º) top

O1—C3	1.305	C7—H7	0.96
O1—C3	1.229 (4)	C7—C8	1.390 (6)
N2—C3	1.319	C7—H7	0.96
N2—H2A	0.96	C8—C9	1.401
N2—H2B	0.96	C8—H8	0.96
N2—C3	1.324 (4)	C8—C9	1.366 (7)
N2—H2A	0.95	C8—H8	0.95
N2—H2B	0.95	C9—C10	1.440
C3—C4	1.462	C9—C12	1.463
C3—C4	1.516 (4)	C9—C10	1.361 (7)
C4—C5	1.310	C9—C12	1.513 (6)
C4—H4	0.96	C10—C11	1.346
C4—C5	1.540 (4)	C10—H10	0.96
C4—C5ⁱ	1.595 (4)	C10—C11	1.389 (6)
C4—H4	0.98	C10—H10	0.96
C5—C6	1.431	C11—H11	0.96
C5—H5	0.96	C11—H11	0.96
C5—C6	1.517 (4)	C12—H12A	0.96
C5—H5	0.96	C12—H12B	0.96
C6—C7	1.444	C12—H12C	0.96
C6—C11	1.409	C12—H12A	0.95
C6—C7	1.367 (5)	C12—H12B	0.95
C6—C11	1.385 (4)	C12—H12C	0.95
C7—C8	1.344

C3—N2—H2A	120	C6—C7—C8*	121.0 (3)
C3—N2—H2B	120	C6—C7—H7*	119
H2A—N2—H2B	120	C8—C7—H7*	120
C3—N2—H2*A	120	C7—C8—C9	118.2
C3—N2—H2*B	120	C7—C8—H8	121
H2A—N2—H2*B	120	C9—C8—H8	121
O1—C3—N2	124.4	C7—C8—C9*	122.5 (4)
O1—C3—C4	123.6	C7—C8—H8*	119
N2—C3—C4	112.1	C9—C8—H8*	118
O1—C3—N2*	122.6 (2)	C8—C9—C10	121.6
O1—C3—C4*	122.7 (2)	C8—C9—C12	118.2
N2—C3—C4*	114.6 (2)	C10—C9—C12	120.2
C3—C4—C5	117.3	C8—C9—C10*	116.7 (4)
C3—C4—H4	121	C8—C9—C12*	122.1 (4)
C5—C4—H4	121	C10—C9—C12*	121.2 (4)
C3—C4—C5*	115.3 (2)	C9—C10—C11	120.7
C3—C4—C5*ⁱ	112.0 (2)	C9—C10—H10	120
C3—C4—H4*	112	C11—C10—H10	120
C5—C4—C5*ⁱ	90.9 (2)	C9—C10—C11*	121.5 (4)
C5—C4—H4*	113	C9—C10—H10*	120
C5ⁱ—C4—H4*	112	C11—C10—H10*	119
C4—C5—C6	123.9	C6—C11—C10	117.6
C4—C5—H5	118	C6—C11—H11	121
C6—C5—H5	118	C10—C11—H11	121
C4—C5—C4*ⁱ	89.1 (2)	C6—C11—C10*	121.7 (3)
C4—C5—C6*	120.8 (2)	C6—C11—H11*	120
C4—C5—H5*	110	C10—C11—H11*	119
C4ⁱ—C5—C6*	116.9 (2)	C9—C12—H12A	110
C4ⁱ—C5—H5*	109	C9—C12—H12B	110
C6—C5—H5*	110	C9—C12—H12C	109
C5—C6—C7	122.7	H12A—C12—H12B	110
C5—C6—C11	115.5	H12A—C12—H12C	109
C7—C6—C11	121.8	H12B—C12—H12C	110
C5—C6—C7*	124.4 (3)	C9—C12—H12*A	110
C5—C6—C11*	118.9 (3)	C9—C12—H12*B	110
C7—C6—C11*	116.5 (3)	C9—C12—H12*C	110
C6—C7—C8	120.2	H12A—C12—H12*B	109
C6—C7—H7	120	H12A—C12—H12*C	109
C8—C7—H7	120	H12B—C12—H12*C	109

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱⁱ	0.96	2.03	2.961	162
N2—H2B···O1ⁱⁱⁱ	0.96	2.19	3.117	161
N2—H2A···O1*ⁱⁱ	0.95	2.01	2.946 (3)	166
N2—H2B···O1*ⁱⁱⁱ	0.95	2.12	3.049 (3)	166

Symmetry codes: (ii) −x+1/2, −y+3/2, −z; (iii) −x+1/2, y+1/2, −z+1/2.

(II) top

Crystal data top

C₉H₈ClNO	Z = 4
M_r = 181.62	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.037 (1) Å	θ = 12.2–14.8°
b = 9.075 (2) Å	µ = 0.39 mm⁻¹
c = 9.042 (2) Å	T = 298 K
β = 108.42 (1)°	Plate-like, colourless
V = 859.3 (2) Å³	0.6 × 0.6 × 0.1 mm

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.015
θ–2θ scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −14→14
T_min = 0.799, T_max = 0.961	k = 0→12
2101 measured reflections	l = −12→0
1977 independent reflections	3 standard reflections every 150 reflections
1360 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0518P)² + 0.3386P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max = 0.0001
S = 1.02	Δρ_max = 0.27 e Å⁻³
1977 reflections	Δρ_min = −0.21 e Å⁻³
141 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.93953 (7)	0.02271 (7)	0.14460 (7)	0.0704 (2)
O2	0.5741 (2)	−0.0971 (2)	0.8706 (2)	0.0534 (4)
N3	0.4869 (2)	0.1302 (2)	0.8370 (2)	0.0488 (4)
C4	0.5552 (2)	0.0230 (2)	0.8019 (2)	0.0410 (4)
C5	0.6096 (2)	0.0568 (2)	0.6750 (2)	0.0423 (4)
C6	0.6905 (2)	−0.0348 (2)	0.6409 (2)	0.0425 (4)
C7	0.7533 (2)	−0.0155 (2)	0.5210 (2)	0.0401 (4)
C8	0.7562 (2)	0.1189 (2)	0.4470 (2)	0.0471 (5)
C9	0.8138 (2)	0.1314 (2)	0.3330 (2)	0.0510 (5)
C10	0.8694 (2)	0.0085 (2)	0.2913 (2)	0.0447 (4)
C11	0.8706 (2)	−0.1247 (2)	0.3635 (2)	0.0475 (5)
C12	0.8127 (2)	−0.1361 (2)	0.4775 (2)	0.0458 (4)
H3A	0.453 (2)	0.112 (2)	0.911 (2)	0.04934 (7)*
H3B	0.469 (2)	0.209 (3)	0.780 (3)	0.05813 (8)*
H5	0.583 (2)	0.148 (2)	0.618 (2)	0.04806 (7)*
H6	0.713 (2)	−0.125 (3)	0.697 (3)	0.05497 (8)*
H8	0.720 (2)	0.203 (3)	0.475 (3)	0.06668 (9)*
H9	0.820 (2)	0.223 (3)	0.284 (2)	0.05567 (8)*
H11	0.908 (2)	−0.209 (3)	0.334 (3)	0.06794 (9)*
H12	0.810 (2)	−0.231 (2)	0.528 (2)	0.05114 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0959 (5)	0.0668 (4)	0.0691 (4)	−0.0169 (3)	0.0557 (4)	−0.0111 (3)
O2	0.077 (1)	0.0363 (7)	0.0594 (9)	0.0067 (7)	0.0394 (8)	0.0056 (6)
N3	0.064 (1)	0.0369 (9)	0.055 (1)	0.0047 (8)	0.0333 (9)	0.0024 (8)
C4	0.0457 (10)	0.0365 (9)	0.0433 (9)	−0.0043 (8)	0.0176 (8)	−0.0046 (8)
C5	0.050 (1)	0.0381 (10)	0.0416 (10)	0.0008 (8)	0.0187 (9)	0.0019 (8)
C6	0.050 (1)	0.0374 (10)	0.0422 (9)	0.0006 (8)	0.0179 (8)	0.0028 (8)
C7	0.0425 (10)	0.0388 (9)	0.0400 (9)	0.0016 (8)	0.0144 (8)	0.0006 (8)
C8	0.058 (1)	0.0368 (10)	0.051 (1)	0.0068 (9)	0.0241 (10)	0.0021 (8)
C9	0.067 (1)	0.040 (1)	0.052 (1)	0.0012 (9)	0.027 (1)	0.0065 (9)
C10	0.050 (1)	0.048 (1)	0.0421 (9)	−0.0062 (9)	0.0227 (8)	−0.0057 (8)
C11	0.054 (1)	0.041 (1)	0.051 (1)	0.0030 (9)	0.0223 (10)	−0.0058 (9)
C12	0.056 (1)	0.0348 (10)	0.051 (1)	0.0053 (8)	0.0219 (9)	0.0037 (8)

Geometric parameters (Å, º) top

Cl1—C10	1.739 (2)	C7—C8	1.396 (3)
O2—C4	1.240 (2)	C7—C12	1.394 (3)
N3—C4	1.329 (3)	C8—C9	1.377 (4)
N3—H3A	0.88 (3)	C8—H8	0.94 (3)
N3—H3B	0.87 (2)	C9—C10	1.382 (3)
C4—C5	1.486 (3)	C9—H9	0.95 (2)
C5—C6	1.326 (3)	C10—C11	1.372 (3)
C5—H5	0.97 (2)	C11—C12	1.378 (4)
C6—C7	1.470 (3)	C11—H11	0.94 (3)
C6—H6	0.95 (2)	C12—H12	0.98 (2)

C4—N3—H3A	117 (1)	C7—C8—C9	121.1 (2)
C4—N3—H3B	120 (2)	C7—C8—H8	121 (2)
H3A—N3—H3B	123 (2)	C9—C8—H8	118 (2)
O2—C4—N3	122.8 (2)	C8—C9—C10	119.2 (2)
O2—C4—C5	121.6 (2)	C8—C9—H9	122 (2)
N3—C4—C5	115.6 (2)	C10—C9—H9	119 (2)
C4—C5—C6	121.1 (2)	Cl1—C10—C9	119.4 (2)
C4—C5—H5	117 (1)	Cl1—C10—C11	119.2 (2)
C6—C5—H5	121 (1)	C9—C10—C11	121.4 (2)
C5—C6—C7	127.3 (2)	C10—C11—C12	119.0 (2)
C5—C6—H6	120 (2)	C10—C11—H11	121 (2)
C7—C6—H6	113 (2)	C12—C11—H11	120 (2)
C6—C7—C8	123.0 (2)	C7—C12—C11	121.5 (2)
C6—C7—C12	119.2 (2)	C7—C12—H12	118 (1)
C8—C7—C12	117.8 (2)	C11—C12—H12	120 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.88 (3)	2.09 (2)	2.941 (3)	163 (2)
N3—H3B···O2ⁱⁱ	0.87 (2)	2.18 (2)	3.050 (2)	178 (2)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y+1/2, −z+3/2.

(II') top

Crystal data top

C₉H₈ClNO	Z = 4
M_r = 181.62	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.398 (3) Å	θ = 10.7–14.8°
b = 9.330 (4) Å	µ = 0.38 mm⁻¹
c = 8.698 (3) Å	T = 298 K
β = 108.95 (2)°	Plate-like, colourless
V = 874.8 (5) Å³	0.6 × 0.6 × 0.1 mm

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −14→14
T_min = 0.812, T_max = 0.962	k = 0→12
2138 measured reflections	l = −12→0
2006 independent reflections	3 standard reflections every 150 reflections
1148 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	H atoms riding
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0526P)² + 0.2095P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max = 0.0001
S = 1.11	Δρ_max = 0.15 e Å⁻³
2006 reflections	Δρ_min = −0.14 e Å⁻³
218 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.9389 (6)	0.0251 (6)	0.1346 (6)	0.105 (2)	0.516 (6)
Cl1*	0.9768 (5)	0.0172 (8)	0.1967 (7)	0.114 (2)	0.484 (6)
O2	0.545 (1)	−0.089 (1)	0.831 (1)	0.055 (2)	0.516 (6)
O2*	0.580 (2)	−0.101 (2)	0.874 (2)	0.072 (3)	0.484 (6)
N3	0.511 (1)	0.1298 (5)	0.859 (1)	0.077 (3)	0.516 (6)
N3*	0.4989 (7)	0.1395 (6)	0.8377 (7)	0.070 (4)	0.484 (6)
C4	0.548 (1)	0.027 (2)	0.793 (1)	0.066 (6)	0.516 (6)
C4*	0.551 (1)	0.026 (1)	0.790 (2)	0.063 (6)	0.484 (6)
C5	0.6165 (7)	0.0586 (4)	0.6765 (7)	0.054 (1)	0.516 (6)
C5*	0.5415 (7)	0.0651 (5)	0.6105 (8)	0.056 (2)	0.484 (6)
C6	0.6908 (5)	−0.0347 (4)	0.6373 (6)	0.059 (2)	0.516 (6)
C6*	0.5906 (5)	−0.0544 (4)	0.5241 (6)	0.054 (2)	0.484 (6)
C7	0.7531 (7)	−0.0158 (9)	0.5191 (8)	0.052 (2)	0.516 (6)
C7*	0.7013 (8)	−0.029 (1)	0.4628 (9)	0.053 (2)	0.484 (6)
C8	0.766 (2)	0.101 (1)	0.457 (2)	0.070 (4)	0.516 (6)
C8*	0.739 (2)	0.1194 (9)	0.428 (2)	0.052 (3)	0.484 (6)
C9	0.822 (2)	0.1216 (9)	0.346 (3)	0.087 (7)	0.516 (6)
C9*	0.824 (2)	0.1288 (8)	0.340 (2)	0.065 (6)	0.484 (6)
C10	0.859 (2)	0.004 (3)	0.278 (2)	0.054 (3)	0.516 (6)
C10*	0.889 (2)	0.007 (4)	0.316 (2)	0.060 (4)	0.484 (6)
C11	0.846 (2)	−0.119 (2)	0.327 (2)	0.073 (4)	0.516 (6)
C11*	0.862 (2)	−0.134 (2)	0.367 (2)	0.060 (3)	0.484 (6)
C12	0.803 (2)	−0.131 (1)	0.468 (2)	0.075 (3)	0.516 (6)
C12*	0.763 (2)	−0.1493 (9)	0.426 (2)	0.074 (4)	0.484 (6)
H3A	0.4664	0.1115	0.9338	0.1013*	0.516 (6)
H3B	0.5373	0.2248	0.8454	0.1013*	0.516 (6)
H3*A	0.4944	0.1406	0.9460	0.0760*	0.484 (6)
H3*B	0.4653	0.2172	0.7648	0.0760*	0.484 (6)
H5	0.6146	0.1556	0.6383	0.0620*	0.516 (6)
H5*	0.5826	0.1540	0.6068	0.0710*	0.484 (6)
H6	0.7018	−0.1263	0.6898	0.0627*	0.516 (6)
H6*	0.6045	−0.1402	0.5878	0.0685*	0.484 (6)
H8	0.7363	0.1866	0.4940	0.0679*	0.516 (6)
H8*	0.7032	0.2018	0.4621	0.0579*	0.484 (6)
H9	0.8499	0.2180	0.3397	0.1231*	0.516 (6)
H9*	0.8353	0.2184	0.2930	0.0650*	0.484 (6)
H11	0.8691	−0.2072	0.2855	0.0759*	0.516 (6)
H11*	0.9150	−0.2141	0.3670	0.1080*	0.484 (6)
H12	0.8091	−0.2194	0.5263	0.0882*	0.516 (6)
H12*	0.7382	−0.2440	0.4460	0.0846*	0.484 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.143 (4)	0.104 (2)	0.110 (3)	−0.014 (2)	0.097 (3)	−0.007 (2)
Cl1*	0.100 (3)	0.153 (3)	0.123 (4)	−0.012 (2)	0.085 (3)	−0.005 (3)
O2	0.088 (7)	0.044 (3)	0.043 (4)	0.005 (4)	0.035 (4)	0.004 (3)
O2*	0.097 (9)	0.065 (4)	0.070 (7)	0.015 (4)	0.049 (6)	0.019 (4)
N3	0.149 (8)	0.050 (5)	0.049 (4)	−0.007 (4)	0.055 (4)	−0.003 (3)
N3*	0.082 (5)	0.077 (7)	0.079 (6)	0.004 (4)	0.063 (5)	−0.003 (4)
C4	0.10 (1)	0.08 (1)	0.040 (5)	−0.043 (6)	0.049 (6)	−0.019 (5)
C4*	0.071 (9)	0.038 (7)	0.09 (1)	0.006 (6)	0.042 (7)	−0.013 (6)
C5	0.074 (4)	0.047 (2)	0.052 (3)	−0.006 (3)	0.035 (3)	0.001 (2)
C5*	0.073 (4)	0.059 (3)	0.049 (3)	−0.013 (3)	0.038 (3)	−0.013 (2)
C6	0.079 (4)	0.054 (2)	0.059 (3)	−0.004 (2)	0.039 (3)	0.002 (2)
C6*	0.079 (4)	0.049 (2)	0.049 (3)	−0.004 (2)	0.039 (3)	0.002 (2)
C7	0.070 (5)	0.051 (3)	0.039 (4)	−0.001 (4)	0.025 (3)	−0.002 (3)
C7*	0.073 (6)	0.054 (3)	0.034 (4)	−0.009 (4)	0.021 (3)	−0.007 (3)
C8	0.099 (9)	0.069 (6)	0.050 (6)	0.037 (4)	0.035 (7)	0.012 (5)
C8*	0.067 (6)	0.041 (3)	0.059 (7)	0.018 (4)	0.034 (6)	0.024 (3)
C9	0.10 (2)	0.07 (1)	0.09 (2)	−0.009 (10)	0.03 (1)	0.001 (10)
C9*	0.08 (1)	0.064 (9)	0.08 (1)	−0.006 (8)	0.06 (1)	0.006 (8)
C10	0.040 (7)	0.080 (6)	0.046 (7)	−0.008 (6)	0.019 (6)	−0.006 (7)
C10*	0.044 (8)	0.093 (7)	0.040 (7)	−0.018 (7)	0.007 (5)	−0.012 (7)
C11	0.092 (8)	0.081 (7)	0.058 (9)	0.013 (5)	0.042 (6)	0.000 (6)
C11*	0.080 (6)	0.060 (4)	0.045 (7)	0.009 (4)	0.026 (5)	−0.002 (5)
C12	0.12 (1)	0.052 (4)	0.069 (6)	0.001 (4)	0.048 (6)	0.002 (4)
C12*	0.11 (1)	0.053 (4)	0.087 (8)	−0.011 (4)	0.066 (7)	−0.018 (4)

Geometric parameters (Å, º) top

Cl1—C10	1.78 (2)	C7—C8	1.24 (2)
Cl1—C10	1.67 (2)	C7—C12	1.36 (2)
O2—C4	1.14 (2)	C7—C8	1.51 (2)
O2—C4	1.38 (2)	C7—C12	1.41 (2)
N3—C4	1.26 (2)	C8—C9	1.35 (3)
N3—H3A	0.96	C8—H8	0.96
N3—H3B	0.96	C8—C9	1.41 (3)
N3—C4	1.35 (2)	C8—H8	0.96
N3—H3A	0.96	C9—C10	1.37 (3)
N3—H3B	0.96	C9—H9	0.96
C4—C5	1.50 (2)	C9—C10	1.41 (4)
C4—C5	1.57 (2)	C9—H9	0.96
C5—C6	1.334 (9)	C10—C11	1.25 (3)
C5—H5	0.96	C10—C11	1.45 (4)
C5—C6	1.548 (9)	C11—C12	1.47 (3)
C5—C6ⁱ	1.582 (8)	C11—H11	0.96
C5—H5	0.96	C11—C12	1.39 (3)
C6—C7	1.44 (1)	C11—H11	0.96
C6—H6	0.96	C12—H12	0.96
C6—C7	1.54 (1)	C12—H12	0.96
C6—H6	0.96

C4—N3—H3A	120	C6—C7—C8*	122.0 (10)
C4—N3—H3B	119	C6—C7—C12*	118.6 (9)
H3A—N3—H3B	121	C8—C7—C12*	119 (1)
C4—N3—H3*A	119	C7—C8—C9	126 (1)
C4—N3—H3*B	121	C7—C8—H8	119
H3A—N3—H3*B	120	C9—C8—H8	115
O2—C4—N3	122 (1)	C7—C8—C9*	117 (1)
O2—C4—C5	117 (1)	C7—C8—H8*	119
N3—C4—C5	118 (1)	C9—C8—H8*	124
O2—C4—N3*	124 (1)	C8—C9—C10	118 (1)
O2—C4—C5*	131 (1)	C8—C9—H9	115
N3—C4—C5*	103.3 (9)	C10—C9—H9	125
C4—C5—C6	123.9 (7)	C8—C9—C10*	120 (1)
C4—C5—H5	118	C8—C9—H9*	120
C6—C5—H5	118	C10—C9—H9*	119
C4—C5—C6*	113.3 (6)	Cl1—C10—C9	120 (2)
C4—C5—C6*ⁱ	117.7 (8)	Cl1—C10—C11	118 (2)
C4—C5—H5*	111	C9—C10—C11	120 (2)
C6—C5—C6*ⁱ	90.2 (4)	Cl1—C10—C9*	119 (2)
C6—C5—H5*	110	Cl1—C10—C11*	118 (2)
C6ⁱ—C5—H5*	113	C9—C10—C11*	120 (1)
C5—C6—C7	127.2 (5)	C10—C11—C12	117 (1)
C5—C6—H6	117	C10—C11—H11	125
C7—C6—H6	116	C12—C11—H11	117
C5—C6—C5*ⁱ	89.8 (4)	C10—C11—C12*	118 (1)
C5—C6—C7*	121.6 (5)	C10—C11—H11*	120.3
C5—C6—H6*	110	C12—C11—H11*	120.6
C5ⁱ—C6—C7*	116.3 (5)	C7—C12—C11	120 (1)
C5ⁱ—C6—H6*	108	C7—C12—H12	118
C7—C6—H6*	109	C11—C12—H12	121
C6—C7—C8	124 (1)	C7—C12—C11*	121 (1)
C6—C7—C12	119.6 (9)	C7—C12—H12*	120
C8—C7—C12	115 (1)	C11—C12—H12*	119

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱⁱ	0.96	2.10	2.98 (2)	153
N3—H3B···O2ⁱⁱⁱ	0.96	2.30	3.06 (1)	135
N3—H3A···O2*ⁱⁱ	0.96	2.04	2.94 (2)	157
N3—H3B···O2*ⁱⁱⁱ	0.96	2.05	3.00 (2)	171

Symmetry codes: (ii) −x+1, −y, −z+2; (iii) −x+1, y+1/2, −z+3/2.

(III) top

Crystal data top

C₇H₇NOS	D_x = 1.359 Mg m⁻³
M_r = 153.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
Hall symbol: -P 2ac 2ab	θ = 14.3–14.9°
a = 20.243 (3) Å	µ = 0.36 mm⁻¹
b = 9.087 (2) Å	T = 298 K
c = 8.137 (2) Å	Plate-like, colorless
V = 1496.9 (4) Å³	0.7 × 0.3 × 0.05 mm
Z = 8

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.024
θ–2θ scans	θ_max = 30°, θ_min = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −14→28
T_min = 0.735, T_max = 0.975	k = 0→12
2476 measured reflections	l = 0→11
2188 independent reflections	3 standard reflections every 150 reflections
1074 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	H atoms: see text
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0521P)² + 0.5253P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.142	(Δ/σ)_max = 0.0001
S = 0.99	Δρ_max = 0.21 e Å⁻³
2188 reflections	Δρ_min = −0.17 e Å⁻³
116 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.14123 (4)	0.36940 (8)	0.2684 (1)	0.0751 (3)	0.825 (3)
S1*	0.1854 (1)	0.6366 (2)	0.2971 (2)	0.0751 (8)	0.175 (3)
O2	0.04607 (9)	0.5978 (2)	0.8368 (2)	0.0613 (5)
N3	−0.0005 (1)	0.3727 (2)	0.8248 (3)	0.0556 (5)
C4	0.0372 (1)	0.4794 (2)	0.7633 (3)	0.0491 (5)
C5	0.0685 (1)	0.4496 (3)	0.6026 (3)	0.0504 (5)
C6	0.1091 (1)	0.5451 (3)	0.5332 (3)	0.0512 (5)
C7	0.1437 (1)	0.5264 (2)	0.3782 (3)	0.0513 (5)
C8	0.1889 (2)	0.4360 (4)	0.1204 (4)	0.090 (1)
C9	0.2089 (2)	0.5724 (4)	0.1476 (4)	0.0841 (9)
C10	0.1854 (1)	0.6366 (2)	0.2971 (2)	0.0751 (8)	0.825 (3)
C10*	0.14123 (4)	0.36940 (8)	0.2684 (1)	0.0751 (3)	0.175 (3)
H3A	−0.020 (1)	0.382 (3)	0.925 (3)	0.0745 (1)*
H3B	−0.013 (1)	0.286 (3)	0.766 (3)	0.0899 (1)*
H5	0.058 (1)	0.355 (3)	0.552 (3)	0.05255 (8)*
H6	0.118 (1)	0.634 (3)	0.585 (3)	0.06064 (9)*
H8	0.200 (2)	0.377 (3)	0.034 (4)	0.1098 (1)*
H9	0.238 (2)	0.624 (4)	0.077 (4)	0.1233 (2)*
H10	0.1946	0.7325	0.3371	0.0901*	0.825 (3)
H10*	0.1203	0.2770	0.2852	0.0901*	0.175 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0862 (6)	0.0618 (5)	0.0773 (6)	−0.0042 (4)	0.0240 (5)	−0.0149 (4)
S1*	0.084 (1)	0.073 (1)	0.069 (1)	−0.002 (1)	0.0009 (10)	0.0079 (10)
O2	0.088 (1)	0.0424 (8)	0.0530 (9)	−0.0058 (8)	0.0110 (9)	−0.0035 (7)
N3	0.070 (1)	0.0427 (10)	0.054 (1)	−0.0030 (10)	0.013 (1)	−0.0010 (10)
C4	0.059 (1)	0.0397 (10)	0.049 (1)	0.0068 (10)	−0.001 (1)	0.0029 (10)
C5	0.060 (1)	0.042 (1)	0.049 (1)	0.004 (1)	0.000 (1)	−0.0015 (10)
C6	0.056 (1)	0.048 (1)	0.050 (1)	0.002 (1)	−0.002 (1)	−0.002 (1)
C7	0.050 (1)	0.055 (1)	0.049 (1)	0.003 (1)	−0.003 (1)	0.003 (1)
C8	0.103 (2)	0.098 (2)	0.068 (2)	0.025 (2)	0.019 (2)	−0.011 (2)
C9	0.081 (2)	0.102 (2)	0.069 (2)	0.002 (2)	0.016 (2)	0.023 (2)
C10	0.084 (1)	0.073 (1)	0.069 (1)	−0.002 (1)	0.0009 (10)	0.0079 (10)
C10*	0.0862 (6)	0.0618 (5)	0.0773 (6)	−0.0042 (4)	0.0240 (5)	−0.0149 (4)

Geometric parameters (Å, º) top

S1—C7	1.684 (2)	C6—C7	1.452 (3)
S1—C8	1.658 (4)	C6—H6	0.93 (2)
S1*—C7	1.466 (3)	C7—C10	1.466 (3)
S1*—C9	1.431 (4)	C7—C10*	1.684 (2)
O2—C4	1.244 (3)	C8—C9	1.322 (5)
N3—C4	1.331 (3)	C8—C10*	1.658 (4)
N3—H3A	0.91 (3)	C8—H8	0.91 (3)
N3—H3B	0.96 (3)	C9—H9	0.94 (3)
C4—C5	1.478 (3)	C9—C10	1.431 (4)
C5—C6	1.321 (3)	C10—H10	0.95
C5—H5	0.98 (2)	C10—H10	0.95

C7—S1—C8	93.4 (2)	S1*—C7—C6	126.1 (2)
C7—S1*—C9	107.2 (2)	C10—C7—C6	126.1 (2)
C4—N3—H3A	121 (1)	S1—C8—C9	113.5 (3)
C4—N3—H3B	124 (1)	C10*—C8—C9	113.5 (3)
H3A—N3—H3B	114 (2)	S1—C8—H8	118 (2)
O2—C4—N3	122.1 (2)	C10*—C8—H8	118 (2)
O2—C4—C5	121.4 (2)	C9—C8—H8	127 (2)
N3—C4—C5	116.5 (2)	S1*—C9—C8	115.0 (3)
C4—C5—C6	121.7 (2)	C10—C9—C8	115.0 (3)
C4—C5—H5	116 (1)	S1*—C9—H9	121 (2)
C6—C5—H5	122 (1)	C10—C9—H9	121 (2)
C5—C6—C7	126.5 (2)	C8—C9—H9	123 (2)
C5—C6—H6	119 (1)	C7—C10—C9	107.2 (2)
C7—C6—H6	113 (1)	C7—C10—H10	126
S1—C7—C10	110.9 (2)	C9—C10—H10	127
S1—C7—C10	110.9 (2)	C7—C10*—C8	93.4 (2)
S1—C7—C6	123.0 (2)	C7—C10—H10	133
C10*—C7—C6	123.0 (2)	C8—C10—H10	133

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.91 (3)	2.01 (3)	2.916 (3)	169 (2)
N3—H3B···O2ⁱⁱ	0.96 (3)	2.02 (3)	2.970 (3)	173 (2)

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, y−1/2, −z+3/2.

(IV) top

Crystal data top

C₉H₉NO	Z = 4
M_r = 147.18	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 25 reflections
a = 16.047 (2) Å	θ = 12.2–14.8°
b = 5.084 (2) Å	µ = 0.08 mm⁻¹
c = 9.584 (2) Å	T = 298 K
β = 94.06 (1)°	Prism, colourless
V = 779.9 (3) Å³	0.8 × 0.3 × 0.2 mm

Data collection top

Rigaku AFC7R diffractometer	θ_max = 27.5°, θ_min = 2.5°
θ–2θ scans	h = 0→21
1857 measured reflections	k = −7→0
1790 independent reflections	l = −12→12
1259 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
R_int = 0.007	intensity decay: 0.8%

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.0639P)² + 0.0958P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.040	(Δ/σ)_max = 0.0001
wR(F²) = 0.121	Δρ_max = 0.12 e Å⁻³
S = 1.02	Δρ_min = −0.15 e Å⁻³
1790 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
137 parameters	Extinction coefficient: 0.066 (8)
All H-atom parameters refined

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.95690 (8)	0.7028 (2)	1.3471 (1)	0.0679 (4)
N2	0.93750 (9)	0.2729 (3)	1.3872 (1)	0.0549 (4)
C3	0.93202 (9)	0.4845 (3)	1.3059 (1)	0.0475 (4)
C4	0.8932 (1)	0.4470 (3)	1.1619 (1)	0.0489 (4)
C5	0.89926 (9)	0.6276 (3)	1.0648 (1)	0.0477 (3)
C6	0.86334 (8)	0.6225 (3)	0.9191 (1)	0.0452 (3)
C7	0.8039 (1)	0.4387 (3)	0.8718 (2)	0.0552 (4)
C8	0.7713 (1)	0.4412 (4)	0.7342 (2)	0.0669 (5)
C9	0.7979 (1)	0.6235 (4)	0.6423 (2)	0.0689 (5)
C10	0.8554 (1)	0.8082 (4)	0.6870 (2)	0.0731 (5)
C11	0.8882 (1)	0.8088 (4)	0.8249 (2)	0.0619 (4)
H2A	0.968 (1)	0.287 (4)	1.469 (2)	0.07089 (6)*
H2B	0.929 (1)	0.114 (4)	1.351 (2)	0.06032 (6)*
H4	0.8634 (10)	0.281 (3)	1.145 (2)	0.05960 (6)*
H5	0.931 (1)	0.784 (4)	1.090 (2)	0.06950 (6)*
H7	0.787 (1)	0.302 (4)	0.934 (2)	0.06765 (6)*
H8	0.732 (1)	0.306 (5)	0.706 (2)	0.09891 (9)*
H9	0.774 (1)	0.621 (4)	0.542 (3)	0.09725 (8)*
H10	0.878 (1)	0.938 (5)	0.629 (2)	0.09681 (9)*
H11	0.929 (1)	0.932 (4)	0.858 (2)	0.07250 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1073 (9)	0.0379 (5)	0.0536 (6)	−0.0013 (6)	−0.0285 (6)	−0.0027 (5)
N2	0.0786 (9)	0.0416 (7)	0.0419 (6)	−0.0036 (6)	−0.0137 (6)	0.0005 (5)
C3	0.0600 (8)	0.0378 (7)	0.0432 (7)	0.0027 (6)	−0.0079 (6)	−0.0032 (6)
C4	0.0617 (8)	0.0414 (7)	0.0419 (7)	−0.0012 (6)	−0.0081 (6)	−0.0023 (6)
C5	0.0506 (8)	0.0458 (7)	0.0454 (7)	−0.0019 (6)	−0.0057 (6)	−0.0009 (6)
C6	0.0477 (7)	0.0475 (7)	0.0399 (7)	0.0056 (6)	0.0008 (5)	0.0031 (6)
C7	0.0645 (9)	0.0594 (9)	0.0408 (7)	−0.0075 (7)	−0.0020 (6)	0.0026 (7)
C8	0.078 (1)	0.075 (1)	0.0460 (8)	−0.0083 (9)	−0.0092 (8)	−0.0040 (8)
C9	0.081 (1)	0.086 (1)	0.0383 (8)	0.009 (1)	−0.0037 (7)	0.0048 (8)
C10	0.080 (1)	0.087 (1)	0.0524 (9)	0.002 (1)	0.0068 (8)	0.0271 (9)
C11	0.0614 (9)	0.066 (1)	0.0578 (9)	−0.0067 (8)	−0.0016 (7)	0.0151 (8)

Geometric parameters (Å, º) top

O1—C3	1.235 (2)	C6—C11	1.387 (2)
N2—C3	1.327 (2)	C7—C8	1.384 (2)
N2—H2A	0.90 (2)	C7—H7	0.97 (2)
N2—H2B	0.89 (2)	C8—C9	1.368 (3)
C3—C4	1.485 (2)	C8—H8	0.96 (2)
C4—C5	1.316 (2)	C9—C10	1.363 (3)
C4—H4	0.98 (2)	C9—H9	1.01 (2)
C5—C6	1.472 (2)	C10—C11	1.389 (2)
C5—H5	0.97 (2)	C10—H10	0.95 (2)
C6—C7	1.388 (2)	C11—H11	0.94 (2)

C3—N2—H2A	117 (1)	C6—C7—C8	120.7 (2)
C3—N2—H2B	120 (1)	C6—C7—H7	119 (1)
H2A—N2—H2B	118 (1)	C8—C7—H7	119 (1)
O1—C3—N2	122.3 (1)	C7—C8—C9	120.3 (2)
O1—C3—C4	121.2 (1)	C7—C8—H8	117 (1)
N2—C3—C4	116.6 (1)	C9—C8—H8	122 (1)
C3—C4—C5	121.4 (1)	C8—C9—C10	120.0 (2)
C3—C4—H4	115.6 (10)	C8—C9—H9	119 (1)
C5—C4—H4	123.1 (10)	C10—C9—H9	120 (1)
C4—C5—C6	127.9 (1)	C9—C10—C11	120.2 (2)
C4—C5—H5	117 (1)	C9—C10—H10	124 (1)
C6—C5—H5	114 (1)	C11—C10—H10	114 (1)
C5—C6—C7	122.4 (1)	C6—C11—C10	120.7 (2)
C5—C6—C11	119.6 (1)	C6—C11—H11	117 (1)
C7—C6—C11	118.0 (1)	C10—C11—H11	121 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.90 (2)	2.07 (2)	2.960 (2)	176 (2)
N2—H2B···O1ⁱⁱ	0.89 (2)	2.14 (2)	3.943 (2)	151 (1)

Symmetry codes: (i) −x+2, −y+1, −z+3; (ii) x, y−1, z.

(IV') top

Crystal data top

C₉H₉NO	Z = 4
M_r = 147.18	D_x = 1.252 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 25 reflections
a = 16.191 (2) Å	θ = 12.2–14.6°
b = 5.079 (2) Å	µ = 0.08 mm⁻¹
c = 9.509 (2) Å	T = 298 K
β = 93.37 (2)°	Prism, colourless
V = 780.7 (4) Å³	0.8 × 0.3 × 0.2 mm

Data collection top

Rigaku AFC7R diffractometer	θ_max = 27.5°, θ_min = 2.5°
θ–2θ scans	h = 0→21
1859 measured reflections	k = −7→0
1793 independent reflections	l = −12→12
1163 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
R_int = 0.008	intensity decay: 1.3%

Refinement top

Refinement on F²	H atoms: see text
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0927P)² + 0.0444P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.160	(Δ/σ)_max = 0.0001
S = 1.05	Δρ_max = 0.20 e Å⁻³
1793 reflections	Δρ_min = −0.18 e Å⁻³
137 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.9573 (1)	0.7022 (2)	1.3477 (2)	0.0760 (5)	0.955 (2)
O1*	0.9763	0.7104	1.2757	0.0757*	0.045 (2)
N2	0.9383 (1)	0.2719 (3)	1.3887 (2)	0.0630 (5)	0.955 (2)
N2*	0.9577	0.2972	1.3333	0.0629*	0.045 (2)
C3	0.9326 (1)	0.4837 (3)	1.3065 (2)	0.0553 (5)	0.955 (2)
C3*	0.9588	0.4830	1.2321	0.0551*	0.045 (2)
C4	0.8940 (1)	0.4463 (3)	1.1627 (2)	0.0559 (5)	0.955 (2)
C4*	0.9579	0.4199	1.0802	0.0558*	0.045 (2)
C5	0.8997 (1)	0.6275 (3)	1.0647 (2)	0.0543 (4)	0.955 (2)
C5*	0.9535	0.6426	0.9734	0.0542*	0.045 (2)
C6	0.8634 (1)	0.6220 (3)	0.9189 (2)	0.0518 (4)	0.955 (2)
C6*	0.8860	0.6680	0.8628	0.0519*	0.045 (2)
C7	0.8037 (1)	0.4398 (4)	0.8733 (2)	0.0633 (5)	0.955 (2)
C7*	0.8359	0.4448	0.8652	0.0632*	0.045 (2)
C8	0.7709 (2)	0.4445 (5)	0.7351 (2)	0.0773 (7)	0.955 (2)
C8*	0.7677	0.4204	0.7693	0.0772*	0.045 (2)
C9	0.7972 (2)	0.6257 (5)	0.6420 (2)	0.0804 (7)	0.955 (2)
C9*	0.7496	0.6192	0.6711	0.0803*	0.045 (2)
C10	0.8552 (2)	0.8078 (6)	0.6856 (2)	0.0840 (7)	0.955 (2)
C10*	0.7997	0.8425	0.6687	0.0840*	0.045 (2)
C11	0.8882 (2)	0.8089 (5)	0.8230 (2)	0.0701 (6)	0.955 (2)
C11*	0.8679	0.8669	0.7646	0.0700*	0.045 (2)
H2A	0.967 (1)	0.287 (4)	1.476 (3)	0.06603 (7)*	0.955 (2)
H2B	0.931 (1)	0.117 (5)	1.348 (2)	0.06755 (7)*	0.955 (2)
H2*A	0.9583	0.3479	1.4306	0.0755*	0.045 (2)
H2*B	0.9562	0.1142	1.3080	0.0755*	0.045 (2)
H4	0.862 (1)	0.283 (5)	1.146 (2)	0.07358 (8)*	0.955 (2)
H4*	0.9193	0.2844	1.0553	0.0670*	0.045 (2)
H5	0.932 (1)	0.778 (5)	1.091 (2)	0.07779 (8)*	0.955 (2)
H5*	0.9572	0.8040	1.0239	0.0650*	0.045 (2)
H7	0.789 (1)	0.319 (4)	0.936 (2)	0.06496 (7)*	0.955 (2)
H7*	0.8483	0.3079	0.9327	0.0759*	0.045 (2)
H8	0.738 (2)	0.311 (6)	0.709 (3)	0.1086 (1)*	0.955 (2)
H8*	0.7332	0.2667	0.7710	0.0927*	0.045 (2)
H9	0.771 (2)	0.626 (6)	0.541 (3)	0.1138 (1)*	0.955 (2)
H9*	0.7027	0.6024	0.6052	0.0963*	0.045 (2)
H10	0.875 (2)	0.925 (6)	0.629 (3)	0.1029 (1)*	0.955 (2)
H10*	0.7872	0.9793	0.6012	0.1008*	0.045 (2)
H11	0.933 (2)	0.924 (5)	0.856 (3)	0.08534 (9)*	0.955 (2)
H11*	0.9023	1.0205	0.7629	0.0841*	0.045 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.126 (1)	0.0330 (6)	0.0644 (8)	−0.0019 (7)	−0.0329 (8)	−0.0027 (5)
N2	0.099 (1)	0.0357 (7)	0.0521 (8)	−0.0034 (7)	−0.0146 (8)	0.0008 (6)
C3	0.078 (1)	0.0344 (8)	0.0520 (10)	0.0028 (7)	−0.0106 (8)	−0.0030 (6)
C4	0.076 (1)	0.0389 (8)	0.0511 (9)	−0.0018 (8)	−0.0104 (8)	−0.0027 (7)
C5	0.064 (1)	0.0431 (8)	0.0548 (9)	−0.0026 (8)	−0.0086 (8)	0.0009 (7)
C6	0.060 (1)	0.0459 (8)	0.0490 (9)	0.0052 (7)	−0.0016 (7)	0.0035 (7)
C7	0.077 (1)	0.060 (1)	0.0525 (10)	−0.0084 (9)	−0.0051 (9)	0.0034 (8)
C8	0.097 (2)	0.076 (1)	0.056 (1)	−0.010 (1)	−0.017 (1)	−0.0029 (10)
C9	0.105 (2)	0.088 (2)	0.0468 (10)	0.010 (1)	−0.008 (1)	0.005 (1)
C10	0.101 (2)	0.091 (2)	0.060 (1)	0.001 (1)	0.006 (1)	0.027 (1)
C11	0.075 (1)	0.068 (1)	0.066 (1)	−0.007 (1)	−0.0018 (10)	0.0172 (10)

Geometric parameters (Å, º) top

O1—C3	1.235 (2)	C6—C7	1.395
O1—C3	1.254	C6—C11	1.395
N2—C3	1.330 (2)	C7—C8	1.388 (3)
N2—H2A	0.93 (2)	C7—H7	0.89 (2)
N2—H2B	0.88 (2)	C7—C8	1.395
N2—C3	1.349	C7—H7	0.96
N2—H2A	0.96	C8—C9	1.363 (4)
N2—H2B	0.96	C8—H8	0.89 (3)
C3—C4	1.482 (2)	C8—C9	1.395
C3—C4	1.478	C8—H8	0.96
C4—C5	1.316 (2)	C9—C10	1.365 (4)
C4—H4	0.98 (2)	C9—H9	1.03 (3)
C4—C5	1.519	C9—C10	1.395
C4—C5ⁱ	1.582	C9—H9	0.96
C4—H4	0.95	C10—C11	1.383 (3)
C5—C6	1.474 (2)	C10—H10	0.87 (3)
C5—H5	0.95 (2)	C10—C11	1.395
C5—C6	1.478	C10—H10	0.96
C5—H5	0.95	C11—H11	0.97 (3)
C6—C7	1.390 (3)	C11—H11	0.96
C6—C11	1.391 (3)

C3—N2—H2A	118 (1)	C5—C6—C7*	108.9
C3—N2—H2B	117 (1)	C5—C6—C11*	131.1
H2A—N2—H2B	120 (1)	C7—C6—C11*	120.0
C3—N2—H2*A	120	C6—C7—C8	120.3 (2)
C3—N2—H2*B	120	C6—C7—H7	117 (1)
H2A—N2—H2*B	120	C8—C7—H7	122 (1)
O1—C3—N2	122.1 (2)	C6—C7—C8*	120.0
O1—C3—C4	121.2 (1)	C6—C7—H7*	120
N2—C3—C4	116.7 (1)	C8—C7—H7*	120
O1—C3—N2*	114.9	C7—C8—C9	120.7 (2)
O1—C3—C4*	120.8	C7—C8—H8	116 (1)
N2—C3—C4*	123.0	C9—C8—H8	122 (1)
C3—C4—C5	121.3 (2)	C7—C8—C9*	120.0
C3—C4—H4	116 (1)	C7—C8—H8*	120
C5—C4—H4	122 (1)	C9—C8—H8*	120
C3—C4—C5*	119.3	C8—C9—C10	119.7 (2)
C3—C4—C5*ⁱ	113.6	C8—C9—H9	118 (1)
C3—C4—H4*	112	C10—C9—H9	121 (1)
C5—C4—C5*ⁱ	86.6	C8—C9—C10*	120.0
C5—C4—H4*	112	C8—C9—H9*	120
C5ⁱ—C4—H4*	112	C10—C9—H9*	120
C4—C5—C6	127.7 (2)	C9—C10—C11	120.7 (2)
C4—C5—H5	115 (1)	C9—C10—H10	123 (1)
C6—C5—H5	116 (1)	C11—C10—H10	116 (1)
C4—C5—C4*ⁱ	93.4	C9—C10—C11*	120.0
C4—C5—C6*	123.0	C9—C10—H10*	120
C4—C5—H5*	108	C11—C10—H10*	120
C4ⁱ—C5—C6*	115.8	C6—C11—C10	120.4 (2)
C4ⁱ—C5—H5*	108	C6—C11—H11	115 (1)
C6—C5—H5*	108	C10—C11—H11	123 (1)
C5—C6—C7	122.5 (2)	C6—C11—C10*	120.0
C5—C6—C11	119.3 (2)	C6—C11—H11*	120
C7—C6—C11	118.2 (2)	C10—C11—H11*	120

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱⁱ	0.93 (2)	2.02 (2)	2.943 (2)	172 (2)
N2—H2B···O1ⁱⁱⁱ	0.88 (2)	2.15 (2)	2.939 (2)	149 (2)
N2—H2A···O1ⁱⁱ	0.96	2.46	3.257	141
N2—H2B···O1ⁱⁱⁱ	0.96	2.13	3.025	155
N2—H2A···O1*ⁱⁱ	0.93 (2)	2.48	3.404	171
N2—H2B···O1*ⁱⁱⁱ	0.88 (2)	2.31	3.122	153
N2—H2A···O1*ⁱⁱ	0.96	2.94	3.809	151
N2—H2B···O1*ⁱⁱⁱ	0.96	2.10	3.049	168

Symmetry codes: (ii) −x+2, −y+1, −z+3; (iii) x, y−1, z.

(V) top

Crystal data top

C₁₈H₁₆Cl₂N₂O₂	Z = 2
M_r = 363.24	D_x = 1.432 Mg m⁻³
Triclinic, P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.733 (3) Å	Cell parameters from 25 reflections
b = 18.578 (9) Å	θ = 10.8–14.4°
c = 5.210 (3) Å	µ = 0.40 mm⁻¹
α = 91.86 (4)°	T = 298 K
β = 93.04 (4)°	Needle, colourless
γ = 93.21 (3)°	0.4 × 0.1 × 0.05 mm
V = 842.2 (7) Å³

Data collection top

Rigaku AFC7R diffractometer	R_int = 0.029
θ–2θ scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: Ψ-scan (North et al., 1968)	h = 0→10
T_min = 0.868, T_max = 0.980	k = −22→22
3320 measured reflections	l = −6→6
2961 independent reflections	3 standard reflections every 150 reflections
1393 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.091	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.221	(Δ/σ)_max = 0.0001
S = 1.60	Δρ_max = 0.85 e Å⁻³
2961 reflections	Δρ_min = −0.39 e Å⁻³
217 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.2471 (3)	0.1787 (1)	−0.1216 (5)	0.0694 (8)
Cl51	0.9257 (3)	0.3186 (1)	0.7596 (6)	0.091 (1)
O2	0.8142 (5)	0.4996 (3)	0.6610 (9)	0.043 (1)
O52	0.1970 (5)	0.0077 (3)	0.686 (1)	0.046 (1)
N3	0.8547 (6)	0.5089 (4)	0.238 (1)	0.050 (2)
N53	0.1389 (7)	0.0325 (4)	0.275 (1)	0.062 (2)
C4	0.7678 (8)	0.5029 (4)	0.434 (1)	0.035 (2)
C5	0.5967 (7)	0.5025 (4)	0.368 (1)	0.033 (2)
C6	0.5013 (7)	0.4409 (4)	0.500 (1)	0.037 (2)
C7	0.4305 (7)	0.3791 (4)	0.335 (1)	0.038 (2)
C8	0.5020 (8)	0.3542 (4)	0.126 (2)	0.047 (2)
C9	0.4489 (8)	0.2927 (4)	−0.020 (2)	0.049 (2)
C10	0.3162 (9)	0.2564 (4)	0.057 (2)	0.046 (2)
C11	0.2410 (8)	0.2789 (4)	0.264 (2)	0.049 (2)
C12	0.2974 (8)	0.3401 (4)	0.402 (2)	0.047 (2)
C54	0.2360 (7)	0.0217 (4)	0.468 (1)	0.035 (2)
C55	0.4053 (7)	0.0294 (4)	0.409 (1)	0.038 (2)
C56	0.5191 (7)	0.0450 (4)	0.643 (1)	0.040 (2)
C57	0.6207 (7)	0.1132 (4)	0.660 (1)	0.039 (2)
C58	0.6154 (8)	0.1666 (4)	0.479 (2)	0.051 (2)
C59	0.7120 (9)	0.2294 (4)	0.509 (2)	0.055 (2)
C60	0.8118 (9)	0.2389 (4)	0.719 (2)	0.056 (2)
C61	0.8216 (9)	0.1869 (5)	0.899 (2)	0.059 (2)
C62	0.7265 (8)	0.1239 (4)	0.869 (2)	0.052 (2)
H3A	0.9672	0.5099	0.2671	0.0581*
H3B	0.8142	0.5120	0.0640	0.0581*
H5	0.5736	0.4997	0.1778	0.0366*
H6	0.5712	0.4209	0.6282	0.0422*
H8	0.5977	0.3793	0.0774	0.0496*
H9	0.5004	0.2758	−0.1680	0.0610*
H11	0.1495	0.2515	0.3071	0.0571*
H12	0.2450	0.3542	0.5576	0.0526*
H53A	0.0292	0.0292	0.2991	0.0655*
H53B	0.1734	0.0457	0.1093	0.0655*
H55	0.4233	0.0631	0.2763	0.0457*
H56	0.4634	0.0421	0.7990	0.0444*
H58	0.5451	0.1596	0.3291	0.0584*
H59	0.7049	0.2664	0.3874	0.0672*
H61	0.8982	0.1934	1.0404	0.0702*
H62	0.7328	0.0880	1.0032	0.0562*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.073 (2)	0.047 (1)	0.087 (2)	−0.006 (1)	0.007 (1)	−0.010 (1)
Cl51	0.065 (2)	0.059 (1)	0.144 (3)	−0.019 (1)	0.006 (2)	−0.008 (2)
O2	0.033 (3)	0.065 (3)	0.031 (3)	0.004 (2)	−0.002 (2)	0.005 (3)
O52	0.031 (3)	0.060 (3)	0.046 (3)	0.000 (2)	0.007 (2)	0.005 (3)
N3	0.027 (3)	0.090 (5)	0.034 (4)	0.007 (3)	0.007 (3)	0.000 (4)
N53	0.031 (3)	0.103 (6)	0.052 (5)	−0.008 (3)	0.002 (3)	0.030 (4)
C4	0.039 (4)	0.037 (4)	0.029 (4)	0.004 (3)	0.000 (4)	−0.001 (3)
C5	0.022 (3)	0.047 (4)	0.031 (4)	−0.002 (3)	0.000 (3)	0.005 (3)
C6	0.025 (3)	0.048 (4)	0.038 (4)	0.006 (3)	−0.001 (3)	0.010 (4)
C7	0.028 (4)	0.043 (4)	0.044 (5)	0.005 (3)	0.005 (4)	0.010 (4)
C8	0.043 (4)	0.053 (5)	0.044 (5)	−0.007 (4)	0.007 (4)	0.011 (4)
C9	0.039 (4)	0.053 (5)	0.058 (6)	0.014 (4)	0.012 (4)	0.007 (4)
C10	0.044 (4)	0.040 (4)	0.054 (6)	0.004 (3)	−0.004 (4)	−0.001 (4)
C11	0.043 (4)	0.059 (5)	0.045 (5)	−0.008 (4)	0.008 (4)	−0.003 (4)
C12	0.035 (4)	0.049 (5)	0.055 (5)	−0.006 (4)	0.009 (4)	0.007 (4)
C54	0.031 (4)	0.037 (4)	0.038 (5)	0.005 (3)	−0.001 (4)	0.004 (4)
C55	0.030 (4)	0.039 (4)	0.043 (5)	−0.004 (3)	0.001 (3)	0.010 (4)
C56	0.032 (4)	0.048 (4)	0.039 (5)	−0.001 (3)	0.003 (4)	0.006 (4)
C57	0.022 (3)	0.048 (4)	0.047 (5)	0.002 (3)	0.005 (3)	0.000 (4)
C58	0.044 (4)	0.054 (5)	0.053 (5)	−0.003 (4)	−0.001 (4)	0.001 (4)
C59	0.057 (5)	0.044 (5)	0.063 (6)	0.005 (4)	−0.001 (5)	0.004 (4)
C60	0.043 (5)	0.047 (5)	0.077 (7)	0.000 (4)	0.004 (5)	−0.007 (5)
C61	0.043 (4)	0.061 (5)	0.072 (7)	−0.005 (4)	−0.011 (4)	−0.002 (5)
C62	0.044 (4)	0.061 (5)	0.049 (5)	−0.009 (4)	−0.009 (4)	−0.002 (4)

Geometric parameters (Å, º) top

Cl1—C10	1.750 (7)	C9—H9	0.97
Cl51—C60	1.737 (8)	C10—C11	1.361 (11)
O2—C4	1.236 (9)	C11—C12	1.378 (11)
O52—C54	1.230 (9)	C11—H11	0.96
N3—C4	1.305 (9)	C12—H12	0.99
N3—H3A	0.99	C54—C55	1.527 (9)
N3—H3B	0.96	C55—C56	1.541 (9)
N53—C54	1.309 (9)	C55—C56ⁱⁱ	1.587 (10)
N53—H53A	0.97	C55—H55	0.96
N53—H53B	0.97	C56—C57	1.502 (10)
C4—C5	1.515 (9)	C56—H56	0.97
C5—C6	1.574 (9)	C57—C58	1.393 (11)
C5—C6ⁱ	1.560 (10)	C57—C62	1.393 (10)
C5—H5	1.00	C58—C59	1.401 (11)
C6—C7	1.496 (9)	C58—H58	0.97
C6—H6	0.98	C59—C60	1.364 (12)
C7—C8	1.364 (11)	C59—H59	0.95
C7—C12	1.402 (10)	C60—C61	1.369 (13)
C8—C9	1.394 (11)	C61—C62	1.397 (11)
C8—H8	0.98	C61—H61	0.97
C9—C10	1.390 (11)	C62—H62	0.98

C4—N3—H3A	120	C7—C12—C11	121.5 (7)
C4—N3—H3B	123	C7—C12—H12	120
H3A—N3—H3B	117	C11—C12—H12	118
C54—N53—H53A	120	O52—C54—N53	123.7 (6)
C54—N53—H53B	122	O52—C54—C55	121.1 (6)
H53A—N53—H53B	118	N53—C54—C55	115.2 (6)
O2—C4—N3	125.5 (6)	C54—C55—C56	115.7 (6)
O2—C4—C5	119.3 (6)	C54—C55—C56ⁱⁱ	114.2 (5)
N3—C4—C5	115.2 (6)	C54—C55—H55	112
C4—C5—C6	113.5 (5)	C56—C55—C56ⁱⁱ	89.5 (5)
C4—C5—C6ⁱ	119.7 (5)	C56—C55—H55	111
C4—C5—H5	112	C56ⁱⁱ—C55—H55	113
C6—C5—C6ⁱ	89.0 (5)	C55—C56—C55ⁱⁱ	90.5 (5)
C6—C5—H5	110	C55—C56—C57	120.0 (6)
C6ⁱ—C5—H5	111	C55—C56—H56	109
C5—C6—C5ⁱ	91.0 (5)	C55ⁱⁱ—C56—C57	118.6 (5)
C5—C6—C7	118.5 (6)	C55ⁱⁱ—C56—H56	109
C5—C6—H6	107	C57—C56—H56	109
C5ⁱ—C6—C7	122.5 (5)	C56—C57—C58	123.9 (6)
C5ⁱ—C6—H6	110	C56—C57—C62	118.3 (7)
C7—C6—H6	107	C58—C57—C62	117.8 (6)
C6—C7—C8	120.8 (6)	C57—C58—C59	120.8 (7)
C6—C7—C12	121.7 (7)	C57—C58—H58	119
C8—C7—C12	117.3 (6)	C59—C58—H58	120
C7—C8—C9	123.1 (7)	C58—C59—C60	119.9 (8)
C7—C8—H8	119	C58—C59—H59	120
C9—C8—H8	118	C60—C59—H59	120
C8—C9—C10	116.9 (7)	Cl51—C60—C59	119.2 (7)
C8—C9—H9	122	Cl51—C60—C61	120.0 (7)
C10—C9—H9	121	C59—C60—C61	120.8 (7)
Cl1—C10—C9	118.0 (6)	C60—C61—C62	119.7 (8)
Cl1—C10—C11	119.8 (6)	C60—C61—H61	119
C9—C10—C11	122.2 (7)	C62—C61—H61	121
C10—C11—C12	119.0 (7)	C57—C62—C61	121.0 (7)
C10—C11—H11	118	C57—C62—H62	121
C12—C11—H11	123	C61—C62—H62	118

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱⁱⁱ	0.99	1.94	2.925 (7)	173
N3—H3B···O2^iv	0.96	2.11	3.007 (8)	156
N53—H53A···O52^v	0.97	2.06	3.005 (7)	164
N53—H53B···O52^iv	0.97	2.32	3.163 (9)	146

Symmetry codes: (iii) −x+2, −y+1, −z+1; (iv) x, y, z−1; (v) −x, −y, −z+1.

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Crystal-to-crystal photodimerization of ­trans-­cinnamamides

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Crystal-to-crystal photodimerization of trans-cinnamamides