3-(6-Benzoyl-5-chloro-2-oxo-2,3-di­hydro-1,3-benzoxazol-3-yl)­propanoic acid

The title compound, C₁₇H₁₂ClNO₅, consists of a main benzo­thia­zole group and its substituents which are one Cl atom, a benzoyl group and a propanoic acid group. There is a 0.779 (4)/0.221 (4) disorder in the terminal propanoic acid group. The crystal structure is stabilized by intermolecular O—H...O hydrogen-bond contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.085
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.724
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C4B
PLAT301_ALERT_3_C Main Residue  Disorder .........................      20.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1      =       3.42 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H12 Cl N O5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990) and WinGX publication routines (Farrugia, 1999).

3-(6-Benzoyl-5-chloro-2-oxo-2,3-dihydro-1,3-benzoxazol-3-yl)propanoic acid

Crystal data

C17H12ClNO5	F(000) = 1424
Mr = 345.73	Dx = 1.470 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6761 reflections
a = 26.015 (10) Å	θ = 1.7–28.1°
b = 6.252 (5) Å	µ = 0.27 mm^−1
c = 20.412 (4) Å	T = 293 K
β = 109.749 (16)°	Plate, colorless
V = 3125 (3) Å^3	0.60 × 0.44 × 0.13 mm
Z = 8

Data collection

Stoe IPDS-2 diffractometer	3791 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1700 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.033
Detector resolution: 6.67 pixels mm^-1	θmax = 28.1°, θmin = 1.7°
ω scans	h = −32→34
Absorption correction: integration (Stoe & Cie, 2002)	k = −8→8
Tmin = 0.854, Tmax = 0.965	l = −16→26
6761 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0486P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.72	(Δ/σ)max < 0.001
3791 reflections	Δρmax = 0.16 e Å^−3
243 parameters	Δρmin = −0.17 e Å^−3
10 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.03581 (2)	0.73522 (8)	0.01708 (2)	0.0843 (2)
O1	0.16767 (5)	1.1278 (2)	0.27569 (5)	0.0720 (4)
O2	0.23031 (6)	1.3865 (3)	0.28662 (7)	0.1030 (6)
O3A	0.25148 (11)	1.5366 (3)	0.04746 (14)	0.0809 (10)	0.779 (4)
O4A	0.19806 (8)	1.8196 (4)	0.03518 (10)	0.0804 (8)	0.779 (4)
O5	0.05053 (6)	0.4145 (2)	0.17979 (10)	0.1160 (8)
N1A	0.18084 (11)	1.2392 (4)	0.17986 (13)	0.0565 (8)	0.779 (4)
C1	0.19599 (8)	1.2712 (3)	0.24987 (10)	0.0732 (7)
C2A	0.20998 (9)	1.3304 (3)	0.13703 (13)	0.0627 (8)	0.779 (4)
C3A	0.18490 (9)	1.5359 (4)	0.10333 (13)	0.0683 (9)	0.779 (4)
C4A	0.21501 (14)	1.6322 (6)	0.06003 (16)	0.0644 (11)	0.779 (4)
C5	0.13850 (6)	1.0935 (2)	0.15967 (8)	0.0546 (5)
C6	0.10822 (7)	1.0131 (3)	0.09615 (8)	0.0618 (6)
C7	0.07225 (6)	0.8507 (3)	0.09624 (8)	0.0575 (5)
C8	0.06678 (6)	0.7702 (2)	0.15659 (8)	0.0567 (5)
C9	0.09797 (7)	0.8571 (3)	0.22034 (9)	0.0646 (6)
C10	0.13266 (6)	1.0178 (3)	0.21982 (8)	0.0562 (5)
C11	0.03006 (7)	0.5844 (3)	0.15753 (9)	0.0684 (7)
C12	−0.02965 (7)	0.6178 (3)	0.13571 (8)	0.0592 (6)
C13	−0.06296 (8)	0.4505 (3)	0.14145 (9)	0.0754 (7)
C14	−0.11887 (9)	0.4800 (4)	0.12145 (11)	0.0851 (9)
C15	−0.14115 (8)	0.6711 (4)	0.09620 (10)	0.0859 (8)
C16	−0.10908 (8)	0.8381 (4)	0.09062 (9)	0.0786 (8)
C17	−0.05325 (7)	0.8120 (3)	0.11075 (8)	0.0660 (6)
C2B	0.1789 (4)	1.4548 (15)	0.1352 (5)	0.068 (3)*	0.221 (4)
C3B	0.2214 (4)	1.3844 (14)	0.1049 (5)	0.071 (3)*	0.221 (4)
C4B	0.2357 (7)	1.554 (2)	0.0598 (8)	0.061 (4)*	0.221 (4)
O4B	0.2684 (4)	1.4969 (15)	0.0327 (5)	0.092 (3)*	0.221 (4)
N1B	0.1678 (4)	1.2939 (15)	0.1798 (5)	0.053 (3)*	0.221 (4)
O3B	0.2031 (5)	1.705 (2)	0.0430 (6)	0.079 (4)*	0.221 (4)
H3B	0.18440	1.63700	0.13920	0.0820*	0.779 (4)
H4A	0.21620	1.86200	0.01180	0.1210*	0.779 (4)
H14	−0.14120	0.36800	0.12540	0.1020*
H15	−0.17880	0.68910	0.08250	0.1030*
H16	−0.12480	0.96900	0.07330	0.0940*
H17	−0.03140	0.92630	0.10740	0.0790*
H6	0.11160	1.06480	0.05510	0.0740*
H9	0.09510	0.80660	0.26180	0.0780*
H13	−0.04770	0.31880	0.15870	0.0910*
H2A	0.21000	1.22850	0.10120	0.0750*	0.779 (4)
H2B	0.24760	1.35630	0.16570	0.0750*	0.779 (4)
H3A	0.14740	1.50950	0.07420	0.0820*	0.779 (4)
H2B1	0.19120	1.58470	0.16180	0.0820*	0.221 (4)
H2B2	0.14530	1.48740	0.09750	0.0820*	0.221 (4)
H3B1	0.20840	1.25730	0.07700	0.0860*	0.221 (4)
H3B2	0.25440	1.34600	0.14260	0.0860*	0.221 (4)
H4B	0.27210	1.59160	0.00680	0.1380*	0.221 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0938 (4)	0.0930 (4)	0.0664 (3)	−0.0277 (3)	0.0273 (2)	−0.0190 (2)
O1	0.0819 (8)	0.0786 (8)	0.0504 (6)	−0.0035 (7)	0.0156 (6)	−0.0010 (6)
O2	0.1017 (10)	0.1084 (11)	0.0788 (9)	−0.0306 (9)	0.0041 (8)	−0.0159 (8)
O3A	0.091 (2)	0.0730 (14)	0.0894 (16)	0.0191 (13)	0.0445 (14)	0.0158 (11)
O4A	0.0935 (13)	0.0686 (14)	0.0930 (13)	0.0171 (11)	0.0497 (10)	0.0227 (11)
O5	0.0988 (11)	0.0616 (8)	0.2000 (18)	0.0163 (8)	0.0669 (11)	0.0362 (10)
N1A	0.0534 (14)	0.0571 (15)	0.0571 (13)	0.0003 (13)	0.0162 (11)	0.0012 (11)
C1	0.0725 (11)	0.0757 (12)	0.0622 (11)	−0.0079 (11)	0.0108 (9)	−0.0041 (10)
C2A	0.0548 (13)	0.0579 (13)	0.0759 (16)	−0.0013 (11)	0.0226 (12)	0.0053 (11)
C3A	0.0665 (15)	0.0694 (15)	0.0720 (15)	0.0098 (12)	0.0275 (12)	0.0077 (12)
C4A	0.0563 (19)	0.074 (2)	0.0616 (18)	0.0108 (18)	0.0182 (15)	0.0081 (17)
C5	0.0544 (9)	0.0581 (9)	0.0518 (9)	−0.0021 (8)	0.0186 (7)	0.0029 (8)
C6	0.0685 (11)	0.0704 (11)	0.0495 (9)	−0.0090 (9)	0.0238 (8)	0.0020 (8)
C7	0.0588 (9)	0.0605 (9)	0.0552 (9)	−0.0021 (8)	0.0218 (8)	−0.0042 (8)
C8	0.0581 (9)	0.0543 (9)	0.0634 (10)	0.0057 (8)	0.0280 (8)	0.0060 (8)
C9	0.0782 (11)	0.0653 (10)	0.0566 (10)	0.0061 (9)	0.0310 (9)	0.0107 (8)
C10	0.0606 (10)	0.0581 (9)	0.0489 (9)	0.0047 (8)	0.0172 (8)	0.0010 (7)
C11	0.0790 (12)	0.0506 (10)	0.0849 (12)	0.0054 (9)	0.0400 (10)	0.0079 (9)
C12	0.0674 (10)	0.0570 (10)	0.0605 (9)	−0.0049 (9)	0.0312 (8)	−0.0012 (8)
C13	0.0919 (15)	0.0637 (11)	0.0805 (12)	−0.0116 (11)	0.0421 (11)	−0.0054 (9)
C14	0.0825 (15)	0.0935 (16)	0.0890 (14)	−0.0303 (13)	0.0419 (12)	−0.0190 (12)
C15	0.0682 (12)	0.1152 (17)	0.0745 (13)	−0.0094 (13)	0.0242 (10)	−0.0180 (13)
C16	0.0709 (13)	0.0933 (14)	0.0710 (12)	0.0054 (11)	0.0234 (10)	0.0026 (10)
C17	0.0651 (11)	0.0686 (11)	0.0691 (11)	0.0004 (9)	0.0288 (9)	0.0052 (8)

Geometric parameters (Å, º)

Cl1—C7	1.731 (2)	C8—C11	1.508 (3)
O1—C1	1.374 (3)	C8—C9	1.390 (3)
O1—C10	1.379 (2)	C9—C10	1.353 (3)
O2—C1	1.195 (3)	C11—C12	1.479 (3)
O3A—C4A	1.220 (5)	C12—C13	1.388 (3)
O3B—C4B	1.24 (2)	C12—C17	1.378 (3)
O4A—C4A	1.294 (5)	C13—C14	1.384 (3)
O4B—C4B	1.22 (2)	C14—C15	1.352 (4)
O5—C11	1.206 (3)	C15—C16	1.365 (4)
O4A—H4A	0.8203	C16—C17	1.379 (3)
O4B—H4B	0.8208	C2A—H2A	0.9701
N1A—C2A	1.453 (4)	C2A—H2B	0.9693
N1A—C1	1.363 (3)	C2B—H2B1	0.9692
N1A—C5	1.381 (3)	C2B—H2B2	0.9712
N1B—C1	1.377 (10)	C3A—H3A	0.9698
N1B—C5	1.452 (10)	C3A—H3B	0.9707
N1B—C2B	1.450 (14)	C3B—H3B1	0.9695
C2A—C3A	1.499 (3)	C3B—H3B2	0.9697
C2B—C3B	1.504 (15)	C6—H6	0.9296
C3A—C4A	1.492 (5)	C9—H9	0.9296
C3B—C4B	1.530 (18)	C13—H13	0.9301
C5—C6	1.365 (2)	C14—H14	0.9306
C5—C10	1.371 (2)	C15—H15	0.9301
C6—C7	1.381 (3)	C16—H16	0.9297
C7—C8	1.382 (2)	C17—H17	0.9299
Cl1···C12	3.477 (3)	C15···C4B^x	3.589 (16)
Cl1···C17	3.500 (3)	C16···O4B^xi	3.162 (11)
Cl1···Cl1^i	3.425 (3)	C17···Cl1	3.500 (3)
Cl1···H3A^ii	3.0807	C17···C7	3.385 (4)
O2···C2A^iii	3.303 (4)	C1···H3B2	3.0936
O2···C3A^iv	3.372 (4)	C2A···H6	3.0351
O2···C4A^iv	3.368 (4)	C3B···H15^vii	3.0402
O2···C1^iii	3.314 (4)	C4A···H4A^v	2.6696
O2···N1A^iii	3.099 (4)	C4B···H4B^v	2.5714
O3A···O4A^v	2.622 (4)	C5···H3B1	3.0458
O3A···C4A^v	3.340 (5)	C6···H3B^ii	3.0086
O3B···O4B^v	2.681 (16)	C6···H2A	2.9412
O3B···C4B^v	3.39 (2)	C7···H2B2^ii	2.9560
O4A···O3A^v	2.622 (4)	C7···H3A^ii	3.0281
O4A···C6^vi	3.231 (4)	C7···H17	2.8216
O4B···C16^vii	3.162 (11)	C7···H3B^ii	3.0557
O4B···C4B^v	3.365 (17)	C8···H17	2.5983
O4B···C15^vii	3.050 (11)	C14···H9^xii	3.0389
O4B···O3B^v	2.681 (16)	C15···H9^xii	2.8649
O5···N1B^ii	3.143 (11)	C16···H6^x	3.0147
O5···C10^ii	3.194 (3)	C16···H9^xii	2.9164
O5···C5^ii	3.173 (3)	H2B1···O3B	2.6550
O1···H3B2^iv	2.7768	H2B1···O2^iii	2.7176
O1···H2B^iv	2.7183	H2B1···O2	2.7037
O1···H14^viii	2.7830	H2B2···C7^vi	2.9560
O2···H2B1^iv	2.7176	H2B2···O3B	2.5455
O2···H2B	2.6609	H2A···O3A	2.6226
O2···H2B1	2.7037	H2A···O4A^ii	2.8575
O2···H3B^iv	2.7164	H2A···C6	2.9412
O3A···H15^vii	2.7649	H2B···O1^iii	2.7183
O3A···H4A^v	1.8054	H2B···O2	2.6609
O3A···H2A	2.6226	H2B···O3A	2.6964
O3A···H2B	2.6964	H3B1···C5	3.0458
O3B···H2B2	2.5455	H3A···C7^vi	3.0281
O3B···H2B1	2.6550	H3A···Cl1^vi	3.0807
O3B···H4B^v	1.8735	H3B···C6^vi	3.0086
O4A···H6^vi	2.8623	H3B···C7^vi	3.0557
O4A···H2A^vi	2.8575	H3B···O2^iii	2.7164
O4A···H16^ix	2.7258	H3B2···C1	3.0936
O4B···H4B^v	2.7937	H3B2···O1^iii	2.7768
O4B···H16^vii	2.6231	H4A···O3A^v	1.8054
O4B···H15^vii	2.3832	H4A···C4A^v	2.6696
O5···H13	2.5160	H4A···H4A^v	2.4204
N1A···O2^iv	3.099 (4)	H4B···O3B^v	1.8735
N1B···O5^vi	3.143 (11)	H4B···O4B^v	2.7937
C1···O2^iv	3.314 (4)	H4B···H4B^v	2.2597
C2A···O2^iv	3.303 (4)	H4B···C4B^v	2.5714
C3A···C6^vi	3.564 (4)	H6···C2A	3.0351
C3A···O2^iii	3.372 (4)	H6···O4A^ii	2.8623
C3A···C7^vi	3.492 (4)	H6···C16^x	3.0147
C4A···O2^iii	3.368 (4)	H9···C16^xii	2.9164
C4A···O3A^v	3.340 (5)	H9···C14^xii	3.0389
C4B···O4B^v	3.365 (17)	H9···C15^xii	2.8649
C4B···C15^x	3.589 (16)	H13···O5	2.5160
C4B···O3B^v	3.39 (2)	H14···O1^xiii	2.7830
C5···O5^vi	3.173 (3)	H15···O3A^xi	2.7649
C6···C3A^ii	3.564 (4)	H15···O4B^xi	2.3832
C6···O4A^ii	3.231 (4)	H15···C3B^xi	3.0402
C7···C3A^ii	3.492 (4)	H16···O4B^xi	2.6231
C7···C17	3.385 (4)	H16···O4A^ix	2.7258
C10···O5^vi	3.194 (3)	H17···C8	2.5983
C12···Cl1	3.477 (3)	H17···C7	2.8216
C15···O4B^xi	3.050 (11)
C1—O1—C10	107.35 (13)	C11—C12—C17	121.81 (17)
C4A—O4A—H4A	109.51	C13—C12—C17	118.83 (18)
C4B—O4B—H4B	109.51	C11—C12—C13	119.36 (17)
C1—N1A—C5	109.2 (2)	C12—C13—C14	119.90 (19)
C1—N1A—C2A	123.3 (2)	C13—C14—C15	120.2 (2)
C2A—N1A—C5	127.2 (2)	C14—C15—C16	120.8 (2)
C1—N1B—C2B	125.1 (8)	C15—C16—C17	119.8 (2)
C1—N1B—C5	104.5 (6)	C12—C17—C16	120.48 (19)
C2B—N1B—C5	128.2 (8)	N1A—C2A—H2A	109.22
O1—C1—N1A	107.70 (18)	N1A—C2A—H2B	109.14
O2—C1—N1A	129.6 (2)	C3A—C2A—H2B	109.15
O2—C1—N1B	127.8 (4)	H2A—C2A—H2B	107.89
O1—C1—O2	122.47 (17)	C3A—C2A—H2A	109.15
O1—C1—N1B	107.4 (5)	C3B—C2B—H2B1	109.04
N1A—C2A—C3A	112.2 (2)	H2B1—C2B—H2B2	107.84
N1B—C2B—C3B	112.7 (8)	N1B—C2B—H2B2	109.04
C2A—C3A—C4A	112.6 (2)	C3B—C2B—H2B2	109.00
C2B—C3B—C4B	114.0 (9)	N1B—C2B—H2B1	109.13
O4A—C4A—C3A	114.9 (3)	C4A—C3A—H3B	109.13
O3A—C4A—O4A	123.2 (3)	C2A—C3A—H3A	109.10
O3A—C4A—C3A	121.9 (3)	C2A—C3A—H3B	109.07
O4B—C4B—C3B	114.9 (11)	C4A—C3A—H3A	109.04
O3B—C4B—O4B	128.2 (15)	H3A—C3A—H3B	107.83
O3B—C4B—C3B	114.3 (15)	C2B—C3B—H3B1	108.81
N1A—C5—C10	106.20 (16)	C2B—C3B—H3B2	108.84
C6—C5—C10	121.35 (15)	C4B—C3B—H3B2	108.60
N1B—C5—C10	104.5 (4)	H3B1—C3B—H3B2	107.62
N1A—C5—C6	132.26 (18)	C4B—C3B—H3B1	108.78
N1B—C5—C6	131.7 (4)	C7—C6—H6	121.82
C5—C6—C7	116.30 (15)	C5—C6—H6	121.87
Cl1—C7—C8	119.43 (13)	C8—C9—H9	121.22
C6—C7—C8	122.88 (15)	C10—C9—H9	121.22
Cl1—C7—C6	117.58 (12)	C12—C13—H13	120.01
C9—C8—C11	117.44 (14)	C14—C13—H13	120.09
C7—C8—C11	123.25 (14)	C13—C14—H14	119.92
C7—C8—C9	119.25 (15)	C15—C14—H14	119.89
C8—C9—C10	117.56 (16)	C16—C15—H15	119.58
O1—C10—C9	128.31 (15)	C14—C15—H15	119.60
O1—C10—C5	109.05 (14)	C17—C16—H16	120.08
C5—C10—C9	122.64 (15)	C15—C16—H16	120.15
O5—C11—C12	121.53 (18)	C12—C17—H17	119.81
C8—C11—C12	119.52 (16)	C16—C17—H17	119.71
O5—C11—C8	118.83 (17)
C10—O1—C1—O2	−178.5 (2)	Cl1—C7—C8—C11	−0.2 (2)
C10—O1—C1—N1A	−3.7 (2)	Cl1—C7—C8—C9	177.12 (13)
C1—O1—C10—C5	−0.78 (19)	C6—C7—C8—C9	1.0 (3)
C1—O1—C10—C9	177.94 (19)	C6—C7—C8—C11	−176.30 (17)
C2A—N1A—C1—O2	7.1 (4)	C9—C8—C11—O5	−69.3 (2)
C5—N1A—C1—O2	−178.9 (2)	C7—C8—C9—C10	−0.2 (3)
C5—N1A—C1—O1	6.8 (3)	C11—C8—C9—C10	177.26 (16)
C5—N1A—C2A—C3A	91.6 (3)	C7—C8—C11—O5	108.0 (2)
C1—N1A—C5—C6	177.86 (19)	C7—C8—C11—C12	−76.0 (2)
C1—N1A—C2A—C3A	−95.6 (3)	C9—C8—C11—C12	106.63 (18)
C2A—N1A—C1—O1	−167.1 (2)	C8—C9—C10—O1	−179.64 (16)
C2A—N1A—C5—C10	166.5 (2)	C8—C9—C10—C5	−1.1 (3)
C2A—N1A—C5—C6	−8.5 (4)	C8—C11—C12—C17	3.6 (2)
C1—N1A—C5—C10	−7.2 (2)	C8—C11—C12—C13	−175.32 (15)
N1A—C2A—C3A—C4A	179.2 (2)	O5—C11—C12—C13	0.5 (3)
C2A—C3A—C4A—O3A	8.6 (4)	O5—C11—C12—C17	179.48 (18)
C2A—C3A—C4A—O4A	−173.8 (2)	C11—C12—C13—C14	179.76 (17)
N1A—C5—C6—C7	173.5 (2)	C13—C12—C17—C16	−1.2 (2)
C6—C5—C10—C9	1.7 (3)	C17—C12—C13—C14	0.8 (3)
N1A—C5—C10—O1	4.9 (2)	C11—C12—C17—C16	179.82 (16)
N1A—C5—C10—C9	−173.9 (2)	C12—C13—C14—C15	0.1 (3)
C10—C5—C6—C7	−0.8 (3)	C13—C14—C15—C16	−0.6 (3)
C6—C5—C10—O1	−179.54 (15)	C14—C15—C16—C17	0.2 (3)
C5—C6—C7—Cl1	−176.66 (13)	C15—C16—C17—C12	0.8 (3)
C5—C6—C7—C8	−0.5 (3)

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x+1/2, −y+7/2, −z; (vi) x, y+1, z; (vii) x+1/2, y+1/2, z; (viii) −x, y+1, −z+1/2; (ix) −x, −y+3, −z; (x) −x, −y+2, −z; (xi) x−1/2, y−1/2, z; (xii) −x, y, −z+1/2; (xiii) −x, y−1, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H4A···O3A^v	0.82	1.81	2.622 (4)	173

Symmetry code: (v) −x+1/2, −y+7/2, −z.