Racemic and chiral 1-[N-(chloro­acetyl)carbamoylamino]-2,3-dihydro-1H-inden-2-yl chloroacetate

In the racemic crystals of (1S,2R)- or (1R,2S)-1-[N-(chloro­acetyl)­carbamoyl­amino]-2,3-di­hydro-1H-inden-2-yl chloro­acetate, C₁₄H₁₄Cl₂N₂O₄, (I), the enantiomeric mol­ecules form a dimeric structure via the N—H...O cyclic hydrogen bond of the carbamoyl moieties. In the chiral crystals of (—)-(1S,2R)-1-[N-(chloro­acetyl)­carbamoyl­amino]-2,3-di­hydro-1H-inden-2-yl chloro­acetate, C₁₄H₁₄Cl₂N₂O₄, (II), the N—­H...O intermolecular hydrogen bond forms a zigzag chain around the twofold screw axis. The melting points and calculated densities of (I) and (II) are 446 and 396 K, and 1.481 and 1.445 Mg m⁻³, respectively.

Computing details

For both 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, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C14H14Cl2N2O4	Z = 2
Mr = 345.18	Dx = 1.481 Mg m^−3
Triclinic, P1	Melting point: 446 K
a = 10.017 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.575 (6) Å	Cell parameters from 25 reflections
c = 4.883 (3) Å	θ = 14.3–15.0°
α = 95.63 (3)°	µ = 0.44 mm^−1
β = 90.84 (4)°	T = 298 K
γ = 106.28 (3)°	Needle, colourless
V = 773.8 (6) Å^3	0.60 × 0.10 × 0.05 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −13→13
Tmin = 0.916, Tmax = 0.979	k = −22→22
3951 measured reflections	l = 0→6
3536 independent reflections	3 standard reflections every 150 reflections
2066 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0588P)^2 + 0.3077P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.141	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.51 e Å^−3
3536 reflections	Δρmin = −0.31 e Å^−3
208 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.1312 (1)	1.01781 (6)	0.7967 (2)	0.0790 (3)
Cl2	−0.3048 (1)	0.76653 (8)	−0.2329 (3)	0.1027 (4)
O3	0.4641 (2)	0.8967 (1)	−0.1426 (4)	0.0554 (5)
O4	0.1663 (2)	0.8741 (1)	0.4446 (5)	0.0622 (6)
O5	0.0457 (2)	0.7147 (1)	−0.1336 (4)	0.0477 (5)
O6	−0.1033 (3)	0.6845 (2)	−0.5006 (5)	0.0827 (8)
N7	0.2942 (3)	0.8019 (1)	0.0507 (5)	0.0466 (6)
N8	0.3531 (2)	0.9436 (1)	0.2149 (5)	0.0415 (5)
C9	0.1493 (3)	0.6902 (2)	−0.3007 (5)	0.0469 (7)
C10	0.1247 (3)	0.5944 (2)	−0.3285 (6)	0.0522 (7)
C11	0.2226 (3)	0.5799 (2)	−0.1167 (6)	0.0463 (7)
C12	0.2338 (4)	0.5042 (2)	−0.0318 (7)	0.0629 (9)
C13	0.3331 (5)	0.5055 (2)	0.1631 (9)	0.078 (1)
C14	0.4248 (4)	0.5806 (3)	0.2763 (8)	0.076 (1)
C15	0.4174 (3)	0.6571 (2)	0.1914 (7)	0.0594 (8)
C16	0.3157 (3)	0.6556 (2)	−0.0063 (6)	0.0441 (6)
C17	0.2915 (3)	0.7286 (2)	−0.1413 (5)	0.0442 (6)
C18	0.3745 (3)	0.8790 (2)	0.0269 (5)	0.0387 (6)
C19	0.2519 (3)	0.9386 (2)	0.4008 (6)	0.0431 (6)
C20	0.2573 (4)	1.0246 (2)	0.5479 (7)	0.0580 (8)
C21	−0.0721 (4)	0.7148 (2)	−0.2672 (7)	0.0579 (8)
C22	−0.1534 (4)	0.7566 (3)	−0.0749 (9)	0.084 (1)
H7	0.235 (3)	0.801 (2)	0.154 (6)	0.0499 (1)*
H8	0.405 (3)	0.990 (2)	0.195 (6)	0.0516 (1)*
H9	0.1499	0.7108	−0.4778	0.0561*
H10A	0.0304	0.5656	−0.2971	0.0631*
H10B	0.1454	0.5743	−0.5106	0.0631*
H12	0.1711	0.4514	−0.1101	0.0769*
H13	0.3403	0.4538	0.2255	0.0945*
H14	0.4969	0.5804	0.4116	0.0910*
H15	0.4808	0.7096	0.2701	0.0734*
H17	0.3622	0.7451	−0.2711	0.0523*
H20A	0.3476	1.0496	0.6332	0.0712*
H20B	0.2421	1.0603	0.4137	0.0712*
H22A	−0.0960	0.8118	−0.0041	0.1013*
H22B	−0.1784	0.7242	0.0794	0.1013*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0800 (6)	0.0874 (6)	0.0719 (6)	0.0342 (5)	0.0158 (5)	−0.0135 (5)
Cl2	0.0599 (6)	0.1116 (9)	0.141 (1)	0.0236 (5)	−0.0187 (6)	0.0410 (8)
O3	0.053 (1)	0.0318 (9)	0.073 (1)	−0.0011 (8)	0.025 (1)	−0.0020 (9)
O4	0.069 (1)	0.039 (1)	0.071 (1)	0.0019 (10)	0.028 (1)	0.0015 (10)
O5	0.058 (1)	0.045 (1)	0.039 (1)	0.0157 (9)	−0.0066 (9)	−0.0010 (8)
O6	0.097 (2)	0.087 (2)	0.056 (1)	0.019 (1)	−0.029 (1)	−0.006 (1)
N7	0.058 (1)	0.028 (1)	0.045 (1)	−0.0016 (10)	0.017 (1)	−0.0017 (9)
N8	0.044 (1)	0.024 (1)	0.050 (1)	0.0001 (9)	0.006 (1)	0.0003 (9)
C9	0.066 (2)	0.034 (1)	0.034 (1)	0.004 (1)	0.008 (1)	0.000 (1)
C10	0.060 (2)	0.034 (1)	0.051 (2)	−0.003 (1)	0.012 (1)	−0.007 (1)
C11	0.057 (2)	0.030 (1)	0.047 (2)	0.006 (1)	0.019 (1)	−0.002 (1)
C12	0.084 (2)	0.033 (1)	0.069 (2)	0.013 (1)	0.023 (2)	−0.002 (1)
C13	0.105 (3)	0.056 (2)	0.087 (3)	0.041 (2)	0.017 (2)	0.014 (2)
C14	0.080 (2)	0.079 (3)	0.080 (3)	0.041 (2)	−0.001 (2)	0.005 (2)
C15	0.058 (2)	0.055 (2)	0.061 (2)	0.014 (1)	0.006 (2)	−0.005 (2)
C16	0.051 (2)	0.034 (1)	0.043 (1)	0.007 (1)	0.015 (1)	−0.003 (1)
C17	0.053 (2)	0.029 (1)	0.043 (1)	−0.001 (1)	0.015 (1)	−0.001 (1)
C18	0.037 (1)	0.028 (1)	0.046 (1)	0.0025 (10)	0.001 (1)	0.001 (1)
C19	0.048 (1)	0.035 (1)	0.044 (1)	0.009 (1)	0.002 (1)	0.003 (1)
C20	0.073 (2)	0.044 (2)	0.057 (2)	0.018 (1)	0.011 (2)	−0.003 (1)
C21	0.071 (2)	0.041 (2)	0.056 (2)	0.009 (1)	−0.016 (2)	0.007 (1)
C22	0.086 (3)	0.085 (3)	0.091 (3)	0.049 (2)	−0.031 (2)	−0.014 (2)

Geometric parameters (Å, º)

Cl1—C20	1.754 (4)	C11—C12	1.392 (4)
Cl2—C22	1.747 (5)	C11—C16	1.391 (3)
O3—C18	1.224 (3)	C12—C13	1.360 (6)
O4—C19	1.208 (3)	C12—H12	0.962
O5—C9	1.450 (4)	C13—C14	1.381 (5)
O5—C21	1.341 (4)	C13—H13	0.959
O6—C21	1.199 (4)	C14—C15	1.393 (6)
N7—C17	1.454 (3)	C14—H14	0.972
N7—C18	1.323 (3)	C15—C16	1.386 (4)
N7—H7	0.79 (3)	C15—H15	0.962
N8—C18	1.406 (3)	C16—C17	1.507 (4)
N8—C19	1.361 (4)	C17—H17	0.957
N8—H8	0.81 (3)	C19—C20	1.519 (4)
C9—C10	1.529 (4)	C20—H20A	0.953
C9—C17	1.550 (4)	C20—H20B	0.963
C9—H9	0.960	C21—C22	1.495 (6)
C10—C11	1.497 (4)	C22—H22A	0.961
C10—H10A	0.953	C22—H22B	0.963
C10—H10B	0.965
C9—O5—C21	116.2 (2)	C14—C15—H15	120.6
C17—N7—C18	123.7 (2)	C16—C15—H15	121.1
C17—N7—H7	122 (2)	C11—C16—C15	121.0 (3)
C18—N7—H7	113 (2)	C11—C16—C17	110.5 (2)
C18—N8—C19	128.5 (2)	C15—C16—C17	128.4 (2)
C18—N8—H8	113 (2)	N7—C17—C9	113.0 (2)
C19—N8—H8	119 (2)	N7—C17—C16	113.9 (2)
O5—C9—C10	111.2 (2)	N7—C17—H17	108.6
O5—C9—C17	106.8 (2)	C9—C17—C16	104.0 (2)
O5—C9—H9	110.2	C9—C17—H17	108.8
C10—C9—C17	106.0 (2)	C16—C17—H17	108.4
C10—C9—H9	111.3	O3—C18—N7	124.7 (2)
C17—C9—H9	111.2	O3—C18—N8	119.4 (2)
C9—C10—C11	104.8 (2)	N7—C18—N8	115.8 (2)
C9—C10—H10A	111.4	O4—C19—N8	124.8 (3)
C9—C10—H10B	110.8	O4—C19—C20	123.2 (3)
C11—C10—H10A	111.4	N8—C19—C20	112.0 (2)
C11—C10—H10B	110.5	Cl1—C20—C19	112.1 (2)
H10A—C10—H10B	107.9	Cl1—C20—H20A	109.6
C10—C11—C12	129.4 (2)	Cl1—C20—H20B	109.1
C10—C11—C16	111.1 (2)	C19—C20—H20A	109.1
C12—C11—C16	119.4 (3)	C19—C20—H20B	108.7
C11—C12—C13	119.6 (3)	H20A—C20—H20B	108.1
C11—C12—H12	119.9	O5—C21—O6	123.7 (3)
C13—C12—H12	120.5	O5—C21—C22	108.4 (3)
C12—C13—C14	121.3 (4)	O6—C21—C22	127.9 (4)
C12—C13—H13	120.1	Cl2—C22—C21	112.6 (3)
C14—C13—H13	118.5	Cl2—C22—H22A	109.1
C13—C14—C15	120.2 (4)	Cl2—C22—H22B	108.9
C13—C14—H14	120.3	C21—C22—H22A	109.3
C15—C14—H14	119.5	C21—C22—H22B	109.3
C14—C15—C16	118.4 (3)	H22A—C22—H22B	107.4
C9—O5—C21—C22	−169.5 (2)	C17—N7—C18—N8	173.7 (3)
C9—C17—N7—C18	−115.3 (3)	C17—C9—O5—C21	157.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O4	0.79 (3)	2.02 (3)	2.694 (3)	143 (3)
N8—H8···O3^i	0.81 (3)	2.01 (3)	2.823 (3)	179 (3)

Symmetry code: (i) −x+1, −y+2, −z.

(II)

Crystal data

C14H14Cl2N2O4	Dx = 1.445 Mg m^−3
Mr = 345.18	Melting point: 392 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.409 (2) Å	Cell parameters from 22 reflections
b = 4.595 (2) Å	θ = 10.4–14.5°
c = 15.667 (1) Å	µ = 0.43 mm^−1
β = 105.079 (9)°	T = 298 K
V = 793.1 (3) Å^3	Needle, colourless
Z = 2	0.70 × 0.02 × 0.01 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = 0→15
Tmin = 0.956, Tmax = 0.991	k = −6→0
2130 measured reflections	l = −20→20
2031 independent reflections	3 standard reflections every 150 reflections
831 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + ] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.057	(Δ/σ)max = 0.001
wR(F^2) = 0.126	Δρmax = 0.24 e Å^−3
S = 0.97	Δρmin = −0.24 e Å^−3
2031 reflections	Absolute structure: Flack (1983)
208 parameters	Absolute structure parameter: 0.2 (2)
H atoms treated by a mixture of independent and constrained refinement

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.8787 (1)	−0.2517 (5)	−0.0263 (1)	0.0793 (7)
Cl2	1.2476 (2)	0.8432 (8)	0.2536 (1)	0.129 (1)
O3	0.5315 (4)	0.601 (1)	0.0979 (2)	0.079 (2)
O4	0.8493 (4)	0.142 (1)	0.1132 (3)	0.067 (2)
O5	0.9233 (4)	0.701 (1)	0.2743 (2)	0.066 (1)
O6	1.0494 (4)	1.067 (1)	0.3267 (4)	0.086 (2)
N7	0.7191 (4)	0.507 (1)	0.1864 (3)	0.051 (2)
N8	0.6554 (4)	0.294 (2)	0.0483 (3)	0.055 (2)
C9	0.8306 (5)	0.821 (2)	0.3107 (4)	0.059 (2)
C10	0.8519 (6)	0.733 (3)	0.4082 (4)	0.095 (3)
C11	0.7438 (6)	0.546 (2)	0.4114 (4)	0.064 (2)
C12	0.7188 (7)	0.411 (2)	0.4832 (4)	0.086 (3)
C13	0.6164 (8)	0.244 (3)	0.4725 (5)	0.099 (3)
C14	0.5370 (6)	0.225 (3)	0.3902 (6)	0.103 (3)
C15	0.5595 (7)	0.362 (2)	0.3181 (4)	0.080 (3)
C16	0.6638 (6)	0.522 (2)	0.3286 (4)	0.060 (2)
C17	0.7075 (5)	0.688 (2)	0.2590 (4)	0.054 (2)
C18	0.6303 (6)	0.476 (2)	0.1124 (4)	0.052 (2)
C19	0.7592 (6)	0.139 (2)	0.0516 (4)	0.053 (2)
C20	0.7527 (6)	−0.030 (2)	−0.0331 (4)	0.068 (2)
C21	1.0263 (6)	0.853 (2)	0.2851 (5)	0.063 (2)
C22	1.1012 (6)	0.711 (3)	0.2308 (5)	0.101 (3)
H7	0.789 (5)	0.36 (2)	0.182 (4)	0.0786 (3)*
H8	0.594 (5)	0.28 (2)	0.007 (4)	0.0791 (3)*
H9	0.8287	1.0404	0.3053	0.0709*
H10A	0.8558	0.9148	0.4443	0.1125*
H10B	0.9250	0.6392	0.4274	0.1125*
H12	0.7727	0.4470	0.5403	0.1036*
H13	0.6003	0.1588	0.5214	0.1167*
H14	0.4645	0.1300	0.3831	0.1216*
H15	0.5035	0.3593	0.2615	0.0961*
H17	0.6524	0.8565	0.2368	0.0661*
H20A	0.6821	−0.1339	−0.0453	0.0816*
H20B	0.7470	0.1198	−0.0798	0.0816*
H22A	1.0628	0.7583	0.1699	0.1218*
H22B	1.1042	0.5222	0.2422	0.1218*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.066 (1)	0.089 (2)	0.084 (1)	−0.002 (1)	0.0206 (9)	−0.015 (1)
Cl2	0.062 (1)	0.229 (4)	0.094 (1)	−0.029 (2)	0.0181 (10)	−0.025 (2)
O3	0.045 (2)	0.136 (6)	0.046 (2)	0.020 (3)	−0.003 (2)	0.002 (3)
O4	0.050 (2)	0.098 (5)	0.046 (2)	0.008 (3)	−0.003 (2)	−0.005 (3)
O5	0.047 (2)	0.080 (4)	0.061 (3)	−0.001 (3)	0.000 (2)	−0.013 (3)
O6	0.074 (3)	0.086 (5)	0.094 (4)	−0.026 (3)	0.013 (3)	−0.033 (4)
N7	0.043 (3)	0.068 (4)	0.034 (3)	0.003 (3)	−0.004 (2)	−0.013 (3)
N8	0.033 (3)	0.091 (6)	0.034 (3)	0.000 (4)	−0.002 (2)	−0.004 (4)
C9	0.051 (4)	0.069 (7)	0.051 (4)	0.003 (4)	0.001 (3)	0.001 (4)
C10	0.072 (4)	0.155 (9)	0.049 (4)	−0.029 (7)	0.001 (3)	0.002 (6)
C11	0.061 (4)	0.084 (6)	0.041 (4)	0.011 (5)	0.006 (3)	0.003 (4)
C12	0.086 (5)	0.133 (9)	0.040 (4)	−0.002 (6)	0.015 (4)	0.001 (5)
C13	0.107 (6)	0.126 (8)	0.072 (5)	−0.017 (8)	0.040 (5)	−0.009 (7)
C14	0.082 (5)	0.151 (10)	0.086 (6)	−0.033 (8)	0.041 (5)	−0.032 (8)
C15	0.073 (5)	0.110 (8)	0.062 (5)	−0.013 (6)	0.025 (4)	−0.028 (5)
C16	0.051 (4)	0.074 (6)	0.054 (4)	0.007 (4)	0.014 (3)	−0.014 (4)
C17	0.047 (3)	0.062 (6)	0.045 (4)	0.008 (4)	0.000 (3)	−0.003 (4)
C18	0.049 (4)	0.070 (6)	0.033 (3)	−0.008 (4)	0.004 (3)	0.005 (4)
C19	0.046 (4)	0.072 (6)	0.041 (4)	−0.017 (4)	0.008 (3)	−0.002 (4)
C20	0.066 (4)	0.087 (7)	0.048 (4)	−0.003 (5)	0.007 (3)	0.002 (5)
C21	0.053 (4)	0.070 (7)	0.056 (4)	−0.013 (5)	−0.003 (4)	−0.006 (5)
C22	0.061 (4)	0.150 (10)	0.094 (5)	−0.026 (7)	0.024 (4)	−0.048 (7)

Geometric parameters (Å, º)

Cl1—C20	1.741 (8)	C11—C12	1.38 (1)
Cl2—C22	1.726 (8)	C11—C16	1.383 (8)
O3—C18	1.231 (8)	C12—C13	1.37 (1)
O4—C19	1.214 (6)	C12—H12	0.959
O5—C9	1.435 (8)	C13—C14	1.37 (1)
O5—C21	1.339 (9)	C13—H13	0.920
O6—C21	1.17 (1)	C14—C15	1.37 (1)
N7—C17	1.441 (9)	C14—H14	0.917
N7—C18	1.333 (7)	C15—C16	1.37 (1)
N7—H7	1.05 (7)	C15—H15	0.949
N8—C18	1.394 (10)	C16—C17	1.52 (1)
N8—C19	1.371 (9)	C17—H17	1.002
N8—H8	0.82 (5)	C19—C20	1.522 (10)
C9—C10	1.537 (9)	C20—H20A	0.912
C9—C17	1.552 (8)	C20—H20B	0.996
C9—H9	1.013	C21—C22	1.50 (1)
C10—C11	1.51 (1)	C22—H22A	0.966
C10—H10A	1.005	C22—H22B	0.883
C10—H10B	0.917
C9—O5—C21	117.6 (6)	C14—C15—H15	122.6
C17—N7—C18	122.9 (6)	C16—C15—H15	118.1
C17—N7—H7	130 (3)	C11—C16—C15	119.8 (7)
C18—N7—H7	107 (3)	C11—C16—C17	111.9 (6)
C18—N8—C19	128.6 (5)	C15—C16—C17	128.3 (5)
C18—N8—H8	109 (5)	N7—C17—C9	112.5 (5)
C19—N8—H8	123 (5)	N7—C17—C16	113.1 (6)
O5—C9—C10	110.6 (5)	N7—C17—H17	110.5
O5—C9—C17	107.6 (5)	C9—C17—C16	104.1 (5)
O5—C9—H9	110.5	C9—C17—H17	106.2
C10—C9—C17	107.7 (6)	C16—C17—H17	110.1
C10—C9—H9	109.9	O3—C18—N7	124.2 (6)
C17—C9—H9	110.6	O3—C18—N8	119.8 (5)
C9—C10—C11	105.2 (5)	N7—C18—N8	116.0 (6)
C9—C10—H10A	108.2	O4—C19—N8	124.6 (6)
C9—C10—H10B	110.1	O4—C19—C20	122.6 (6)
C11—C10—H10A	111.7	N8—C19—C20	112.8 (5)
C11—C10—H10B	113.8	Cl1—C20—C19	113.2 (4)
H10A—C10—H10B	107.6	Cl1—C20—H20A	112.3
C10—C11—C12	128.8 (5)	Cl1—C20—H20B	110.2
C10—C11—C16	111.1 (6)	C19—C20—H20A	106.8
C12—C11—C16	120.1 (7)	C19—C20—H20B	105.4
C11—C12—C13	120.2 (6)	H20A—C20—H20B	108.7
C11—C12—H12	117.6	O5—C21—O6	124.8 (7)
C13—C12—H12	122.1	O5—C21—C22	108.1 (7)
C12—C13—C14	119.0 (9)	O6—C21—C22	127.0 (8)
C12—C13—H13	118.9	Cl2—C22—C21	113.1 (7)
C14—C13—H13	122.0	Cl2—C22—H22A	106.8
C13—C14—C15	121.7 (9)	Cl2—C22—H22B	108.6
C13—C14—H14	119.9	C21—C22—H22A	106.4
C15—C14—H14	118.3	C21—C22—H22B	108.1
C14—C15—C16	119.2 (6)	H22A—C22—H22B	113.9
C9—O5—C21—C22	−171.7 (6)	C17—N7—C18—N8	180.0 (7)
C9—C17—N7—C18	−149.4 (7)	C17—C9—O5—C21	156.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O4	1.05 (7)	1.75 (7)	2.688 (8)	146 (4)
N8—H8···O3^i	0.82 (5)	2.05 (6)	2.837 (6)	159 (8)

Symmetry code: (i) −x+1, y−1/2, −z.