Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide

The crystal structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide have been determined.

Key indicators

Structure: 3a

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.111
• Data-to-parameter ratio = 23.6

Structure: 3b

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.039
• wR factor = 0.115
• Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Datablock: 3a


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A      ..CL1      .       2.86 Ang.

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 3b


Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT220_ALERT_2_C NonSolvent   Resd 2  C   Ueq(max)/Ueq(min) Range        3.7 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        5.3 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 2  H   Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16A     --C19A     .        5.5 s.u.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8AB     ..CL1A     .       2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A     ..O5C      .       2.63 Ang.

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         20 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         20 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        38% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         21 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        399 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2010); cell refinement: APEX2 (Bruker, 2010); data reduction: APEX2 and SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-Chloro-4-ethoxy-3,5-dimethoxy-N-(3-oxocyclohex-1-en-1-yl)benzamide (3a)

Crystal data

C17H20ClNO5	F(000) = 744
Mr = 353.79	Dx = 1.413 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.654 (3) Å	Cell parameters from 5173 reflections
b = 8.9148 (17) Å	θ = 2.7–31.0°
c = 13.045 (2) Å	µ = 0.26 mm^−1
β = 102.581 (3)°	T = 150 K
V = 1663.2 (5) Å^3	Prism, yellow
Z = 4	0.34 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer	5291 independent reflections
Radiation source: sealed tube	4023 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm^-1	Rint = 0.041
φ and ω scans	θmax = 31.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −21→21
Tmin = 0.885, Tmax = 0.975	k = −12→12
21434 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: mixed
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 0.4383P] where P = (Fo^2 + 2Fc^2)/3
5291 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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

Refinement. Compound #4

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

	x	y	z	Uiso*/Ueq
Cl1	0.29234 (3)	0.32109 (4)	0.48615 (3)	0.02725 (10)
O1	0.18273 (7)	0.38773 (11)	0.64208 (7)	0.0241 (2)
O2	0.10261 (6)	0.65866 (12)	0.67309 (7)	0.0239 (2)
O3	0.10408 (7)	0.88836 (11)	0.54071 (9)	0.0302 (2)
O4	0.25869 (8)	0.47397 (12)	0.27145 (8)	0.0320 (3)
O5	0.38442 (7)	0.56929 (12)	−0.02661 (7)	0.0249 (2)
N1	0.33695 (8)	0.69571 (13)	0.31234 (8)	0.0191 (2)
H1A	0.3526 (12)	0.762 (2)	0.3588 (13)	0.026 (4)*
C1	0.23398 (9)	0.60558 (15)	0.42223 (10)	0.0193 (2)
C2	0.23353 (9)	0.48844 (14)	0.49310 (10)	0.0189 (2)
C3	0.18745 (9)	0.50552 (14)	0.57581 (10)	0.0186 (2)
C4	0.14420 (9)	0.64091 (15)	0.58915 (10)	0.0194 (2)
C5	0.14667 (9)	0.76025 (15)	0.51996 (10)	0.0204 (2)
C6	0.19046 (9)	0.74103 (15)	0.43585 (10)	0.0207 (3)
H6A	0.190600	0.820783	0.387583	0.025*
C7	0.25364 (12)	0.39211 (18)	0.73685 (12)	0.0323 (3)
H7A	0.247923	0.303626	0.779583	0.048*
H7B	0.246122	0.483071	0.776384	0.048*
H7C	0.315408	0.392639	0.719441	0.048*
C8	0.00347 (10)	0.62546 (17)	0.64724 (12)	0.0260 (3)
H8A	−0.006469	0.516730	0.633878	0.031*
H8B	−0.027186	0.680643	0.583095	0.031*
C9	−0.03754 (11)	0.6722 (2)	0.73783 (14)	0.0410 (4)
H9A	−0.104576	0.649464	0.722087	0.061*
H9B	−0.028357	0.780238	0.749697	0.061*
H9C	−0.006531	0.617541	0.801030	0.061*
C10	0.12623 (12)	1.02402 (17)	0.49314 (14)	0.0327 (3)
H10A	0.109255	1.110196	0.531760	0.049*
H10B	0.091199	1.028074	0.420061	0.049*
H10C	0.193419	1.026858	0.494974	0.049*
C11	0.27614 (9)	0.58307 (16)	0.32791 (10)	0.0213 (3)
C12	0.38339 (9)	0.70472 (14)	0.22986 (10)	0.0180 (2)
C13	0.36265 (9)	0.61821 (15)	0.14259 (10)	0.0204 (3)
H13A	0.315554	0.543565	0.137043	0.024*
C14	0.41092 (9)	0.63713 (15)	0.05714 (10)	0.0201 (2)
C15	0.49279 (10)	0.74267 (18)	0.07335 (11)	0.0262 (3)
H15A	0.499687	0.781566	0.004357	0.031*
H15B	0.550511	0.686924	0.104906	0.031*
C16	0.48180 (11)	0.87402 (17)	0.14418 (11)	0.0275 (3)
H16A	0.430304	0.939526	0.107746	0.033*
H16B	0.540060	0.934001	0.158934	0.033*
C17	0.46077 (10)	0.81930 (16)	0.24729 (11)	0.0234 (3)
H17A	0.518006	0.774546	0.291063	0.028*
H17B	0.442654	0.905888	0.286032	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.03470 (19)	0.02092 (16)	0.02974 (18)	0.00364 (13)	0.01494 (14)	−0.00058 (13)
O1	0.0298 (5)	0.0226 (5)	0.0213 (5)	−0.0047 (4)	0.0089 (4)	0.0046 (4)
O2	0.0204 (5)	0.0342 (5)	0.0200 (5)	−0.0020 (4)	0.0107 (4)	−0.0029 (4)
O3	0.0330 (6)	0.0225 (5)	0.0407 (6)	0.0067 (4)	0.0200 (5)	0.0031 (4)
O4	0.0448 (6)	0.0290 (5)	0.0281 (5)	−0.0144 (5)	0.0210 (5)	−0.0079 (4)
O5	0.0320 (5)	0.0273 (5)	0.0173 (4)	0.0001 (4)	0.0092 (4)	−0.0014 (4)
N1	0.0220 (5)	0.0222 (5)	0.0153 (5)	−0.0033 (4)	0.0087 (4)	−0.0023 (4)
C1	0.0192 (6)	0.0227 (6)	0.0177 (6)	−0.0027 (5)	0.0076 (4)	0.0000 (5)
C2	0.0194 (6)	0.0191 (6)	0.0202 (6)	−0.0008 (5)	0.0085 (4)	−0.0009 (5)
C3	0.0189 (6)	0.0203 (6)	0.0176 (6)	−0.0035 (5)	0.0065 (4)	0.0012 (5)
C4	0.0187 (6)	0.0239 (6)	0.0173 (6)	−0.0023 (5)	0.0075 (4)	−0.0007 (5)
C5	0.0181 (6)	0.0215 (6)	0.0227 (6)	0.0005 (5)	0.0071 (5)	0.0002 (5)
C6	0.0205 (6)	0.0222 (6)	0.0206 (6)	0.0003 (5)	0.0072 (5)	0.0039 (5)
C7	0.0401 (9)	0.0305 (8)	0.0242 (7)	−0.0003 (6)	0.0026 (6)	0.0077 (6)
C8	0.0210 (6)	0.0297 (7)	0.0301 (7)	−0.0005 (5)	0.0114 (5)	−0.0007 (6)
C9	0.0256 (8)	0.0645 (12)	0.0379 (9)	0.0013 (8)	0.0178 (7)	−0.0059 (8)
C10	0.0356 (8)	0.0216 (7)	0.0420 (9)	0.0061 (6)	0.0107 (7)	0.0059 (6)
C11	0.0230 (6)	0.0242 (6)	0.0190 (6)	−0.0021 (5)	0.0094 (5)	0.0011 (5)
C12	0.0183 (6)	0.0206 (6)	0.0165 (5)	0.0011 (4)	0.0065 (4)	0.0028 (4)
C13	0.0217 (6)	0.0245 (6)	0.0165 (6)	−0.0025 (5)	0.0072 (4)	0.0009 (5)
C14	0.0220 (6)	0.0229 (6)	0.0165 (6)	0.0032 (5)	0.0065 (4)	0.0027 (5)
C15	0.0258 (7)	0.0357 (8)	0.0202 (6)	−0.0046 (6)	0.0116 (5)	−0.0005 (6)
C16	0.0305 (7)	0.0290 (7)	0.0263 (7)	−0.0101 (6)	0.0132 (6)	−0.0001 (6)
C17	0.0240 (6)	0.0274 (7)	0.0208 (6)	−0.0066 (5)	0.0096 (5)	−0.0030 (5)

Geometric parameters (Å, º)

Cl1—C2	1.7352 (13)	C8—C9	1.497 (2)
O1—C3	1.3714 (15)	C8—H8A	0.9900
O1—C7	1.4317 (18)	C8—H8B	0.9900
O2—C4	1.3734 (14)	C9—H9A	0.9800
O2—C8	1.4486 (16)	C9—H9B	0.9800
O3—C5	1.3567 (16)	C9—H9C	0.9800
O3—C10	1.4285 (18)	C10—H10A	0.9800
O4—C11	1.2132 (17)	C10—H10B	0.9800
O5—C14	1.2350 (16)	C10—H10C	0.9800
N1—C11	1.3865 (17)	C12—C13	1.3536 (18)
N1—C12	1.3950 (15)	C12—C17	1.5061 (18)
N1—H1A	0.844 (18)	C13—C14	1.4543 (17)
C1—C6	1.3949 (18)	C13—H13A	0.9500
C1—C2	1.3956 (18)	C14—C15	1.5029 (19)
C1—C11	1.5056 (17)	C15—C16	1.522 (2)
C2—C3	1.4001 (16)	C15—H15A	0.9900
C3—C4	1.3917 (18)	C15—H15B	0.9900
C4—C5	1.4008 (19)	C16—C17	1.5241 (19)
C5—C6	1.3969 (17)	C16—H16A	0.9900
C6—H6A	0.9500	C16—H16B	0.9900
C7—H7A	0.9800	C17—H17A	0.9900
C7—H7B	0.9800	C17—H17B	0.9900
C7—H7C	0.9800
C3—O1—C7	113.37 (11)	C8—C9—H9C	109.5
C4—O2—C8	112.80 (10)	H9A—C9—H9C	109.5
C5—O3—C10	117.91 (11)	H9B—C9—H9C	109.5
C11—N1—C12	126.28 (11)	O3—C10—H10A	109.5
C11—N1—H1A	119.2 (12)	O3—C10—H10B	109.5
C12—N1—H1A	114.3 (12)	H10A—C10—H10B	109.5
C6—C1—C2	119.68 (11)	O3—C10—H10C	109.5
C6—C1—C11	119.99 (11)	H10A—C10—H10C	109.5
C2—C1—C11	120.24 (12)	H10B—C10—H10C	109.5
C1—C2—C3	120.11 (12)	O4—C11—N1	123.29 (11)
C1—C2—Cl1	122.32 (9)	O4—C11—C1	122.22 (12)
C3—C2—Cl1	117.53 (10)	N1—C11—C1	114.48 (11)
O1—C3—C4	119.88 (11)	C13—C12—N1	123.91 (12)
O1—C3—C2	120.10 (11)	C13—C12—C17	122.49 (11)
C4—C3—C2	119.99 (11)	N1—C12—C17	113.59 (11)
O2—C4—C3	119.54 (11)	C12—C13—C14	121.39 (12)
O2—C4—C5	120.30 (12)	C12—C13—H13A	119.3
C3—C4—C5	120.11 (11)	C14—C13—H13A	119.3
O3—C5—C6	124.74 (12)	O5—C14—C13	120.63 (12)
O3—C5—C4	115.67 (11)	O5—C14—C15	121.24 (11)
C6—C5—C4	119.59 (12)	C13—C14—C15	118.12 (11)
C1—C6—C5	120.47 (12)	C14—C15—C16	112.36 (11)
C1—C6—H6A	119.8	C14—C15—H15A	109.1
C5—C6—H6A	119.8	C16—C15—H15A	109.1
O1—C7—H7A	109.5	C14—C15—H15B	109.1
O1—C7—H7B	109.5	C16—C15—H15B	109.1
H7A—C7—H7B	109.5	H15A—C15—H15B	107.9
O1—C7—H7C	109.5	C15—C16—C17	110.98 (12)
H7A—C7—H7C	109.5	C15—C16—H16A	109.4
H7B—C7—H7C	109.5	C17—C16—H16A	109.4
O2—C8—C9	108.30 (12)	C15—C16—H16B	109.4
O2—C8—H8A	110.0	C17—C16—H16B	109.4
C9—C8—H8A	110.0	H16A—C16—H16B	108.0
O2—C8—H8B	110.0	C12—C17—C16	111.97 (11)
C9—C8—H8B	110.0	C12—C17—H17A	109.2
H8A—C8—H8B	108.4	C16—C17—H17A	109.2
C8—C9—H9A	109.5	C12—C17—H17B	109.2
C8—C9—H9B	109.5	C16—C17—H17B	109.2
H9A—C9—H9B	109.5	H17A—C17—H17B	107.9
C6—C1—C2—C3	1.71 (19)	C11—C1—C6—C5	176.51 (12)
C11—C1—C2—C3	−174.66 (12)	O3—C5—C6—C1	178.77 (13)
C6—C1—C2—Cl1	−175.87 (10)	C4—C5—C6—C1	−1.9 (2)
C11—C1—C2—Cl1	7.76 (18)	C4—O2—C8—C9	−170.82 (13)
C7—O1—C3—C4	−85.34 (15)	C12—N1—C11—O4	2.7 (2)
C7—O1—C3—C2	96.38 (15)	C12—N1—C11—C1	−178.18 (12)
C1—C2—C3—O1	176.51 (12)	C6—C1—C11—O4	−129.20 (15)
Cl1—C2—C3—O1	−5.80 (17)	C2—C1—C11—O4	47.2 (2)
C1—C2—C3—C4	−1.77 (19)	C6—C1—C11—N1	51.64 (17)
Cl1—C2—C3—C4	175.92 (10)	C2—C1—C11—N1	−132.00 (13)
C8—O2—C4—C3	−94.55 (14)	C11—N1—C12—C13	12.4 (2)
C8—O2—C4—C5	88.21 (15)	C11—N1—C12—C17	−166.70 (13)
O1—C3—C4—O2	4.46 (18)	N1—C12—C13—C14	177.36 (12)
C2—C3—C4—O2	−177.25 (11)	C17—C12—C13—C14	−3.6 (2)
O1—C3—C4—C5	−178.29 (12)	C12—C13—C14—O5	−171.94 (13)
C2—C3—C4—C5	−0.01 (19)	C12—C13—C14—C15	7.3 (2)
C10—O3—C5—C6	−18.0 (2)	O5—C14—C15—C16	146.86 (13)
C10—O3—C5—C4	162.68 (13)	C13—C14—C15—C16	−32.36 (18)
O2—C4—C5—O3	−1.55 (19)	C14—C15—C16—C17	52.88 (17)
C3—C4—C5—O3	−178.78 (12)	C13—C12—C17—C16	24.94 (19)
O2—C4—C5—C6	179.06 (12)	N1—C12—C17—C16	−155.90 (12)
C3—C4—C5—C6	1.8 (2)	C15—C16—C17—C12	−48.67 (17)
C2—C1—C6—C5	0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5^i	0.844 (18)	2.098 (18)	2.9410 (15)	177.1 (16)
C7—H7A···Cl1^ii	0.98	2.86	3.7022 (16)	145
C7—H7A···O4^ii	0.98	2.48	3.293 (2)	140
C9—H9A···O4^iii	0.98	2.53	3.470 (2)	161

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

2-Chloro-N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-4-ethoxy-3,5-dimethoxybenzamide (3b)

Crystal data

C19H24ClNO5	F(000) = 1616
Mr = 381.84	Dx = 1.292 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6986 (13) Å	Cell parameters from 23388 reflections
b = 10.6309 (10) Å	θ = 2.4–31.0°
c = 25.131 (2) Å	µ = 0.22 mm^−1
β = 90.1851 (14)°	T = 150 K
V = 3926.9 (6) Å^3	Prism, colourless
Z = 8	0.48 × 0.44 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer	12630 independent reflections
Radiation source: sealed tube	10320 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm^-1	Rint = 0.026
φ and ω scans	θmax = 31.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −21→21
Tmin = 0.841, Tmax = 0.954	k = −15→15
67292 measured reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: mixed
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 1.0458P] where P = (Fo^2 + 2Fc^2)/3
12630 reflections	(Δ/σ)max = 0.006
584 parameters	Δρmax = 0.64 e Å^−3
399 restraints	Δρmin = −0.35 e Å^−3

Special details

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

Refinement. Compound #6

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1A	0.74167 (2)	1.06636 (3)	0.50622 (2)	0.03341 (7)
O1A	0.85300 (6)	0.92470 (9)	0.43031 (3)	0.03358 (19)
O2A	0.96808 (6)	0.73233 (10)	0.45218 (4)	0.0371 (2)
O3A	0.98422 (6)	0.64044 (10)	0.55396 (4)	0.0411 (2)
O4A	0.79762 (5)	0.97694 (9)	0.66166 (3)	0.03064 (18)
O5A	0.54514 (6)	1.01715 (10)	0.78213 (3)	0.0376 (2)
N1A	0.67015 (6)	0.94345 (9)	0.61067 (4)	0.02155 (17)
H1AA	0.6506 (11)	0.9153 (15)	0.5810 (7)	0.034 (4)*
C1A	0.81762 (7)	0.89610 (10)	0.57423 (4)	0.02277 (19)
C2A	0.81118 (7)	0.94022 (11)	0.52235 (4)	0.0245 (2)
C3A	0.86370 (7)	0.88575 (12)	0.48185 (4)	0.0272 (2)
C4A	0.92222 (7)	0.78611 (12)	0.49363 (5)	0.0293 (2)
C5A	0.92801 (7)	0.74122 (12)	0.54613 (5)	0.0293 (2)
C6A	0.87719 (7)	0.79758 (11)	0.58605 (4)	0.0263 (2)
H6AA	0.882994	0.768878	0.621695	0.032*
C7A	0.91558 (11)	1.01997 (17)	0.41412 (5)	0.0474 (4)
H7AA	0.903236	1.043380	0.377078	0.071*
H7AB	0.977879	0.987895	0.417198	0.071*
H7AC	0.908551	1.093994	0.436981	0.071*
C8A	1.06559 (9)	0.7271 (2)	0.45645 (6)	0.0624 (5)
H8AA	1.083977	0.647258	0.473668	0.075*
H8AB	1.087544	0.797509	0.478864	0.075*
C9A	1.10703 (11)	0.7356 (2)	0.40297 (7)	0.0628 (5)
H9AA	1.172751	0.721418	0.405797	0.094*
H9AB	1.095707	0.819284	0.388025	0.094*
H9AC	1.080069	0.671610	0.379685	0.094*
C10A	0.99347 (11)	0.59578 (18)	0.60744 (7)	0.0550 (4)
H10A	1.033598	0.522173	0.607983	0.082*
H10B	0.933524	0.572283	0.621209	0.082*
H10C	1.019610	0.662303	0.629735	0.082*
C11A	0.76218 (7)	0.94515 (10)	0.61997 (4)	0.02202 (19)
C12A	0.60074 (6)	0.97178 (10)	0.64589 (4)	0.02102 (18)
C13A	0.61233 (7)	0.98962 (10)	0.69867 (4)	0.02312 (19)
H13A	0.671961	0.987378	0.713341	0.028*
C14A	0.53549 (7)	1.01213 (11)	0.73334 (4)	0.0258 (2)
C15A	0.44417 (8)	1.03239 (13)	0.70805 (5)	0.0322 (2)
H15A	0.437492	1.122477	0.698850	0.039*
H15C	0.396169	1.011049	0.734077	0.039*
C16A	0.43022 (7)	0.95307 (15)	0.65763 (5)	0.0363 (3)
C17A	0.50923 (7)	0.98156 (14)	0.61962 (4)	0.0327 (3)
H17A	0.506711	0.922034	0.589352	0.039*
H17B	0.501634	1.067588	0.605191	0.039*
C18A	0.34099 (9)	0.9921 (3)	0.63114 (6)	0.0782 (8)
H18A	0.290687	0.979665	0.656099	0.117*
H18B	0.330783	0.940598	0.599323	0.117*
H18C	0.344203	1.080952	0.620991	0.117*
C19A	0.42926 (11)	0.81411 (18)	0.67166 (7)	0.0577 (5)
H19A	0.380973	0.797814	0.697561	0.087*
H19B	0.488156	0.790343	0.687029	0.087*
H19C	0.418020	0.764497	0.639432	0.087*
Cl1B	0.33068 (2)	0.36791 (3)	0.37042 (2)	0.03251 (7)
O1B	0.19443 (6)	0.32113 (8)	0.28774 (3)	0.03058 (17)
O2B	0.12498 (6)	0.49472 (9)	0.21650 (3)	0.03228 (18)
O3B	0.17637 (6)	0.73524 (8)	0.22015 (3)	0.03071 (18)
O4B	0.35516 (6)	0.74079 (10)	0.40209 (4)	0.0415 (2)
C1B	0.31411 (6)	0.60638 (10)	0.33084 (4)	0.02011 (18)
C2B	0.28768 (7)	0.48116 (10)	0.32756 (4)	0.02208 (19)
C3B	0.22268 (7)	0.44399 (10)	0.28987 (4)	0.02362 (19)
C4B	0.18562 (7)	0.53194 (11)	0.25503 (4)	0.0240 (2)
C5B	0.21397 (7)	0.65796 (10)	0.25735 (4)	0.02301 (19)
C6B	0.27647 (7)	0.69485 (10)	0.29595 (4)	0.02189 (18)
H6BA	0.293725	0.780733	0.298645	0.026*
C7B	0.23634 (11)	0.25212 (13)	0.24515 (7)	0.0436 (3)
H7BA	0.215324	0.164658	0.245936	0.065*
H7BB	0.302605	0.254294	0.249483	0.065*
H7BC	0.219649	0.290379	0.211010	0.065*
C8B	0.03306 (9)	0.47519 (14)	0.23569 (6)	0.0416 (3)
H8BA	0.034665	0.416637	0.266315	0.050*
H8BB	−0.003821	0.435696	0.207205	0.050*
C9B	−0.01135 (10)	0.59598 (18)	0.25249 (10)	0.0675 (6)
H9BA	−0.072982	0.578521	0.265278	0.101*
H9BB	−0.014447	0.653490	0.222061	0.101*
H9BC	0.024414	0.634758	0.281091	0.101*
C10B	0.20442 (9)	0.86380 (11)	0.22096 (5)	0.0310 (2)
H10D	0.173044	0.909934	0.192567	0.047*
H10E	0.270299	0.868615	0.215424	0.047*
H10F	0.189185	0.901108	0.255464	0.047*
C11B	0.37827 (7)	0.65588 (10)	0.37276 (4)	0.02269 (19)
O5B	0.5926 (5)	0.7923 (8)	0.5286 (3)	0.0383 (12)	0.551 (2)
N1B	0.4614 (6)	0.6071 (10)	0.3766 (4)	0.0274 (15)	0.551 (2)
H1BA	0.471 (3)	0.552 (4)	0.3576 (18)	0.026 (13)*	0.551 (2)
C12B	0.5307 (6)	0.6264 (11)	0.4131 (5)	0.0259 (10)	0.551 (2)
C13B	0.5224 (5)	0.7057 (8)	0.4537 (3)	0.0210 (9)	0.551 (2)
H13B	0.466093	0.746700	0.460177	0.025*	0.551 (2)
C14B	0.6004 (6)	0.7288 (8)	0.4881 (4)	0.0293 (11)	0.551 (2)
C15B	0.69268 (14)	0.6766 (2)	0.47298 (9)	0.0304 (5)	0.551 (2)
H15B	0.729500	0.665206	0.505684	0.036*	0.551 (2)
H15D	0.724367	0.738554	0.450190	0.036*	0.551 (2)
C16B	0.6870 (4)	0.5507 (7)	0.4434 (3)	0.0262 (9)	0.551 (2)
C17B	0.62225 (13)	0.5682 (2)	0.39563 (8)	0.0261 (4)	0.551 (2)
H17C	0.610886	0.485622	0.378636	0.031*	0.551 (2)
H17D	0.651346	0.623624	0.368993	0.031*	0.551 (2)
C18B	0.65099 (17)	0.4478 (2)	0.48043 (10)	0.0384 (5)	0.551 (2)
H18D	0.692949	0.437144	0.510480	0.058*	0.551 (2)
H18E	0.646148	0.368375	0.460797	0.058*	0.551 (2)
H18F	0.590875	0.471931	0.493723	0.058*	0.551 (2)
C19B	0.78134 (15)	0.5136 (3)	0.42324 (10)	0.0436 (7)	0.551 (2)
H19D	0.823551	0.507798	0.453410	0.065*	0.551 (2)
H19E	0.803155	0.577384	0.398177	0.065*	0.551 (2)
H19F	0.777791	0.431964	0.405263	0.065*	0.551 (2)
O5C	0.6059 (7)	0.7977 (10)	0.5201 (4)	0.0413 (15)	0.449 (2)
N1C	0.4643 (5)	0.5949 (11)	0.3708 (4)	0.0156 (9)	0.449 (2)
H1CA	0.476 (3)	0.549 (4)	0.3423 (18)	0.019 (12)*	0.449 (2)
C12C	0.5324 (8)	0.6138 (14)	0.4091 (6)	0.0262 (12)	0.449 (2)
C13C	0.5340 (6)	0.6981 (11)	0.4488 (4)	0.0268 (13)	0.449 (2)
H13C	0.485165	0.756476	0.450818	0.032*	0.449 (2)
C14C	0.6048 (7)	0.7067 (10)	0.4889 (5)	0.0310 (13)	0.449 (2)
C15C	0.67207 (18)	0.6008 (3)	0.49113 (11)	0.0341 (6)	0.449 (2)
H15E	0.649682	0.536354	0.516327	0.041*	0.449 (2)
H15F	0.730553	0.633284	0.505144	0.041*	0.449 (2)
C16C	0.6890 (6)	0.5385 (9)	0.4371 (4)	0.0293 (12)	0.449 (2)
C17C	0.59763 (16)	0.5023 (2)	0.41227 (10)	0.0244 (5)	0.449 (2)
H17E	0.607993	0.468961	0.376009	0.029*	0.449 (2)
H17F	0.569501	0.434700	0.433730	0.029*	0.449 (2)
C18C	0.7464 (2)	0.4183 (3)	0.44515 (14)	0.0434 (8)	0.449 (2)
H18G	0.806403	0.441080	0.459204	0.065*	0.449 (2)
H18H	0.753484	0.375020	0.410976	0.065*	0.449 (2)
H18I	0.715614	0.362431	0.470371	0.065*	0.449 (2)
C19C	0.74033 (19)	0.6285 (3)	0.39994 (12)	0.0373 (7)	0.449 (2)
H19G	0.706920	0.708007	0.397146	0.056*	0.449 (2)
H19H	0.745573	0.590307	0.364584	0.056*	0.449 (2)
H19I	0.801241	0.644531	0.414378	0.056*	0.449 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.03295 (13)	0.04046 (16)	0.02684 (13)	0.00661 (11)	0.00220 (10)	0.00619 (11)
O1A	0.0289 (4)	0.0525 (5)	0.0193 (4)	−0.0066 (4)	0.0016 (3)	−0.0010 (4)
O2A	0.0223 (4)	0.0560 (6)	0.0330 (4)	−0.0005 (4)	0.0088 (3)	−0.0150 (4)
O3A	0.0336 (4)	0.0458 (5)	0.0439 (5)	0.0154 (4)	0.0105 (4)	0.0032 (4)
O4A	0.0233 (3)	0.0448 (5)	0.0238 (4)	−0.0036 (3)	0.0004 (3)	−0.0060 (3)
O5A	0.0335 (4)	0.0616 (6)	0.0178 (4)	−0.0051 (4)	0.0043 (3)	0.0003 (4)
N1A	0.0193 (4)	0.0277 (4)	0.0176 (4)	−0.0009 (3)	0.0024 (3)	−0.0040 (3)
C1A	0.0181 (4)	0.0292 (5)	0.0211 (4)	−0.0022 (4)	0.0033 (3)	−0.0018 (4)
C2A	0.0195 (4)	0.0320 (5)	0.0220 (5)	−0.0011 (4)	0.0017 (3)	0.0000 (4)
C3A	0.0208 (4)	0.0409 (6)	0.0200 (5)	−0.0046 (4)	0.0029 (4)	−0.0032 (4)
C4A	0.0189 (4)	0.0416 (6)	0.0274 (5)	−0.0031 (4)	0.0070 (4)	−0.0080 (5)
C5A	0.0200 (4)	0.0353 (6)	0.0326 (6)	0.0019 (4)	0.0053 (4)	−0.0016 (5)
C6A	0.0196 (4)	0.0340 (6)	0.0252 (5)	0.0002 (4)	0.0042 (4)	0.0016 (4)
C7A	0.0488 (8)	0.0673 (10)	0.0262 (6)	−0.0183 (7)	0.0043 (5)	0.0060 (6)
C8A	0.0219 (6)	0.1254 (17)	0.0400 (8)	0.0095 (8)	0.0090 (5)	−0.0176 (9)
C9A	0.0377 (7)	0.0939 (14)	0.0570 (10)	−0.0074 (8)	0.0225 (7)	−0.0248 (10)
C10A	0.0494 (8)	0.0604 (10)	0.0552 (9)	0.0266 (8)	0.0120 (7)	0.0177 (8)
C11A	0.0197 (4)	0.0250 (5)	0.0213 (4)	−0.0013 (3)	0.0031 (3)	−0.0002 (4)
C12A	0.0201 (4)	0.0228 (5)	0.0202 (4)	0.0008 (3)	0.0031 (3)	−0.0002 (4)
C13A	0.0214 (4)	0.0287 (5)	0.0193 (4)	−0.0013 (4)	0.0018 (3)	0.0004 (4)
C14A	0.0266 (5)	0.0311 (5)	0.0199 (5)	−0.0002 (4)	0.0039 (4)	0.0008 (4)
C15A	0.0273 (5)	0.0462 (7)	0.0232 (5)	0.0103 (5)	0.0048 (4)	−0.0002 (5)
C16A	0.0187 (4)	0.0670 (9)	0.0232 (5)	0.0029 (5)	0.0020 (4)	−0.0056 (5)
C17A	0.0219 (5)	0.0560 (8)	0.0201 (5)	0.0068 (5)	0.0006 (4)	−0.0016 (5)
C18A	0.0225 (6)	0.180 (2)	0.0325 (7)	0.0184 (10)	−0.0011 (5)	−0.0117 (11)
C19A	0.0454 (8)	0.0640 (11)	0.0639 (10)	−0.0278 (7)	0.0217 (7)	−0.0218 (8)
Cl1B	0.03134 (13)	0.03067 (14)	0.03546 (15)	−0.00338 (10)	−0.00739 (11)	0.01257 (11)
O1B	0.0322 (4)	0.0260 (4)	0.0335 (4)	−0.0104 (3)	−0.0015 (3)	0.0034 (3)
O2B	0.0319 (4)	0.0379 (5)	0.0270 (4)	−0.0106 (3)	−0.0110 (3)	0.0017 (3)
O3B	0.0340 (4)	0.0294 (4)	0.0287 (4)	−0.0042 (3)	−0.0122 (3)	0.0075 (3)
O4B	0.0345 (4)	0.0486 (6)	0.0412 (5)	0.0168 (4)	−0.0129 (4)	−0.0232 (4)
C1B	0.0169 (4)	0.0262 (5)	0.0172 (4)	0.0002 (3)	0.0008 (3)	−0.0015 (4)
C2B	0.0195 (4)	0.0258 (5)	0.0209 (4)	−0.0007 (3)	0.0004 (3)	0.0043 (4)
C3B	0.0222 (4)	0.0248 (5)	0.0239 (5)	−0.0057 (4)	0.0008 (4)	0.0015 (4)
C4B	0.0214 (4)	0.0296 (5)	0.0209 (5)	−0.0053 (4)	−0.0030 (3)	0.0004 (4)
C5B	0.0223 (4)	0.0262 (5)	0.0205 (4)	−0.0012 (4)	−0.0023 (3)	0.0029 (4)
C6B	0.0211 (4)	0.0229 (5)	0.0217 (4)	−0.0012 (3)	−0.0013 (3)	−0.0001 (4)
C7B	0.0510 (8)	0.0262 (6)	0.0538 (9)	−0.0048 (5)	0.0071 (6)	−0.0044 (6)
C8B	0.0284 (6)	0.0426 (7)	0.0536 (8)	−0.0126 (5)	−0.0136 (5)	0.0074 (6)
C9B	0.0263 (6)	0.0535 (10)	0.1226 (18)	−0.0024 (6)	−0.0072 (8)	0.0030 (11)
C10B	0.0358 (6)	0.0266 (5)	0.0306 (6)	0.0012 (4)	−0.0068 (4)	0.0051 (4)
C11B	0.0206 (4)	0.0276 (5)	0.0199 (4)	0.0015 (4)	−0.0020 (3)	−0.0019 (4)
O5B	0.044 (3)	0.0460 (17)	0.025 (2)	0.0018 (18)	−0.0094 (18)	−0.0140 (14)
N1B	0.0313 (19)	0.034 (2)	0.0166 (19)	0.0050 (12)	0.0028 (10)	−0.0165 (13)
C12B	0.0168 (14)	0.039 (3)	0.022 (2)	0.0082 (14)	−0.0033 (13)	−0.0089 (15)
C13B	0.0186 (16)	0.0277 (16)	0.0168 (14)	0.0033 (13)	−0.0052 (14)	−0.0116 (11)
C14B	0.0250 (14)	0.036 (2)	0.0273 (17)	0.0022 (14)	−0.0035 (11)	−0.0064 (16)
C15B	0.0246 (9)	0.0413 (12)	0.0254 (9)	−0.0051 (8)	−0.0078 (7)	−0.0024 (9)
C16B	0.0154 (13)	0.0386 (19)	0.0245 (18)	0.0026 (12)	−0.0049 (11)	0.0001 (14)
C17B	0.0198 (8)	0.0370 (11)	0.0216 (9)	0.0018 (7)	−0.0014 (7)	−0.0058 (8)
C18B	0.0415 (12)	0.0370 (12)	0.0367 (12)	0.0060 (9)	0.0004 (9)	0.0069 (9)
C19B	0.0224 (9)	0.0731 (19)	0.0351 (12)	0.0124 (10)	−0.0029 (8)	−0.0055 (12)
O5C	0.039 (2)	0.059 (2)	0.026 (3)	−0.0141 (15)	0.0007 (16)	−0.0192 (19)
N1C	0.0102 (13)	0.025 (2)	0.012 (2)	0.0063 (12)	−0.0053 (14)	−0.0123 (18)
C12C	0.028 (2)	0.035 (2)	0.0154 (18)	0.0042 (16)	−0.0047 (15)	−0.0139 (15)
C13C	0.024 (2)	0.029 (2)	0.028 (2)	0.0077 (15)	0.0039 (15)	−0.0020 (16)
C14C	0.034 (2)	0.039 (3)	0.0197 (18)	−0.0018 (18)	−0.0065 (15)	−0.009 (2)
C15C	0.0299 (12)	0.0471 (16)	0.0252 (12)	0.0027 (11)	−0.0088 (9)	−0.0059 (11)
C16C	0.029 (2)	0.035 (2)	0.024 (2)	0.0004 (15)	−0.0035 (15)	−0.0040 (16)
C17C	0.0234 (10)	0.0253 (11)	0.0246 (11)	0.0024 (9)	−0.0036 (8)	−0.0028 (9)
C18C	0.0343 (14)	0.0524 (18)	0.0434 (17)	0.0172 (13)	−0.0090 (12)	−0.0012 (14)
C19C	0.0297 (12)	0.0467 (16)	0.0356 (14)	−0.0080 (11)	0.0034 (10)	−0.0072 (12)

Geometric parameters (Å, º)

Cl1A—C2A	1.7331 (12)	C3B—C4B	1.3908 (15)
O1A—C3A	1.3684 (14)	C4B—C5B	1.4042 (15)
O1A—C7A	1.4281 (17)	C5B—C6B	1.3903 (14)
O2A—C4A	1.3678 (13)	C6B—H6BA	0.9500
O2A—C8A	1.4381 (16)	C7B—H7BA	0.9800
O3A—C5A	1.3667 (15)	C7B—H7BB	0.9800
O3A—C10A	1.4313 (19)	C7B—H7BC	0.9800
O4A—C11A	1.2163 (13)	C8B—C9B	1.502 (2)
O5A—C14A	1.2349 (13)	C8B—H8BA	0.9900
N1A—C11A	1.3722 (13)	C8B—H8BB	0.9900
N1A—C12A	1.3859 (12)	C9B—H9BA	0.9800
N1A—H1AA	0.853 (16)	C9B—H9BB	0.9800
C1A—C2A	1.3885 (15)	C9B—H9BC	0.9800
C1A—C6A	1.3964 (15)	C10B—H10D	0.9800
C1A—C11A	1.5047 (14)	C10B—H10E	0.9800
C2A—C3A	1.4044 (15)	C10B—H10F	0.9800
C3A—C4A	1.3956 (17)	C11B—N1B	1.330 (8)
C4A—C5A	1.4053 (17)	C11B—N1C	1.421 (8)
C5A—C6A	1.3886 (15)	O5B—C14B	1.229 (8)
C6A—H6AA	0.9500	N1B—C12B	1.384 (8)
C7A—H7AA	0.9800	N1B—H1BA	0.77 (5)
C7A—H7AB	0.9800	C12B—C13B	1.330 (7)
C7A—H7AC	0.9800	C12B—C17B	1.545 (8)
C8A—C9A	1.480 (2)	C13B—C14B	1.455 (7)
C8A—H8AA	0.9900	C13B—H13B	0.9500
C8A—H8AB	0.9900	C14B—C15B	1.515 (8)
C9A—H9AA	0.9800	C15B—C16B	1.535 (7)
C9A—H9AB	0.9800	C15B—H15B	0.9900
C9A—H9AC	0.9800	C15B—H15D	0.9900
C10A—H10A	0.9800	C16B—C19B	1.530 (7)
C10A—H10B	0.9800	C16B—C18B	1.532 (8)
C10A—H10C	0.9800	C16B—C17B	1.540 (6)
C12A—C13A	1.3501 (14)	C17B—H17C	0.9900
C12A—C17A	1.5001 (15)	C17B—H17D	0.9900
C13A—C14A	1.4486 (14)	C18B—H18D	0.9800
C13A—H13A	0.9500	C18B—H18E	0.9800
C14A—C15A	1.4989 (16)	C18B—H18F	0.9800
C15A—C16A	1.5351 (18)	C19B—H19D	0.9800
C15A—H15A	0.9900	C19B—H19E	0.9800
C15A—H15C	0.9900	C19B—H19F	0.9800
C16A—C19A	1.519 (2)	O5C—C14C	1.244 (9)
C16A—C18A	1.5263 (19)	N1C—C12C	1.401 (9)
C16A—C17A	1.5364 (16)	N1C—H1CA	0.88 (5)
C17A—H17A	0.9900	C12C—C13C	1.342 (9)
C17A—H17B	0.9900	C12C—C17C	1.527 (10)
C18A—H18A	0.9800	C13C—C14C	1.450 (9)
C18A—H18B	0.9800	C13C—H13C	0.9500
C18A—H18C	0.9800	C14C—C15C	1.499 (8)
C19A—H19A	0.9800	C15C—C16C	1.532 (9)
C19A—H19B	0.9800	C15C—H15E	0.9900
C19A—H19C	0.9800	C15C—H15F	0.9900
Cl1B—C2B	1.7334 (11)	C16C—C17C	1.528 (9)
O1B—C3B	1.3715 (13)	C16C—C19C	1.537 (10)
O1B—C7B	1.4379 (17)	C16C—C18C	1.545 (9)
O2B—C4B	1.3724 (12)	C17C—H17E	0.9900
O2B—C8B	1.4510 (16)	C17C—H17F	0.9900
O3B—C5B	1.3605 (13)	C18C—H18G	0.9800
O3B—C10B	1.4277 (14)	C18C—H18H	0.9800
O4B—C11B	1.2147 (13)	C18C—H18I	0.9800
C1B—C2B	1.3891 (15)	C19C—H19G	0.9800
C1B—C6B	1.3986 (14)	C19C—H19H	0.9800
C1B—C11B	1.5065 (14)	C19C—H19I	0.9800
C2B—C3B	1.4000 (14)
C3A—O1A—C7A	114.34 (10)	O1B—C7B—H7BB	109.5
C4A—O2A—C8A	116.92 (10)	H7BA—C7B—H7BB	109.5
C5A—O3A—C10A	116.80 (10)	O1B—C7B—H7BC	109.5
C11A—N1A—C12A	127.99 (9)	H7BA—C7B—H7BC	109.5
C11A—N1A—H1AA	118.9 (11)	H7BB—C7B—H7BC	109.5
C12A—N1A—H1AA	112.8 (11)	O2B—C8B—C9B	112.15 (12)
C2A—C1A—C6A	119.60 (10)	O2B—C8B—H8BA	109.2
C2A—C1A—C11A	124.39 (10)	C9B—C8B—H8BA	109.2
C6A—C1A—C11A	115.99 (9)	O2B—C8B—H8BB	109.2
C1A—C2A—C3A	120.34 (10)	C9B—C8B—H8BB	109.2
C1A—C2A—Cl1A	121.28 (8)	H8BA—C8B—H8BB	107.9
C3A—C2A—Cl1A	118.34 (9)	C8B—C9B—H9BA	109.5
O1A—C3A—C4A	119.96 (10)	C8B—C9B—H9BB	109.5
O1A—C3A—C2A	119.96 (11)	H9BA—C9B—H9BB	109.5
C4A—C3A—C2A	119.94 (10)	C8B—C9B—H9BC	109.5
O2A—C4A—C3A	117.42 (11)	H9BA—C9B—H9BC	109.5
O2A—C4A—C5A	122.99 (11)	H9BB—C9B—H9BC	109.5
C3A—C4A—C5A	119.50 (10)	O3B—C10B—H10D	109.5
O3A—C5A—C6A	124.09 (11)	O3B—C10B—H10E	109.5
O3A—C5A—C4A	115.87 (10)	H10D—C10B—H10E	109.5
C6A—C5A—C4A	120.03 (11)	O3B—C10B—H10F	109.5
C5A—C6A—C1A	120.56 (11)	H10D—C10B—H10F	109.5
C5A—C6A—H6AA	119.7	H10E—C10B—H10F	109.5
C1A—C6A—H6AA	119.7	O4B—C11B—N1B	120.3 (4)
O1A—C7A—H7AA	109.5	O4B—C11B—N1C	127.6 (4)
O1A—C7A—H7AB	109.5	O4B—C11B—C1B	120.55 (9)
H7AA—C7A—H7AB	109.5	N1B—C11B—C1B	119.1 (4)
O1A—C7A—H7AC	109.5	N1C—C11B—C1B	111.8 (4)
H7AA—C7A—H7AC	109.5	C11B—N1B—C12B	131.6 (8)
H7AB—C7A—H7AC	109.5	C11B—N1B—H1BA	115 (4)
O2A—C8A—C9A	110.05 (14)	C12B—N1B—H1BA	112 (4)
O2A—C8A—H8AA	109.7	C13B—C12B—N1B	122.2 (7)
C9A—C8A—H8AA	109.7	C13B—C12B—C17B	123.6 (6)
O2A—C8A—H8AB	109.7	N1B—C12B—C17B	113.1 (6)
C9A—C8A—H8AB	109.7	C12B—C13B—C14B	119.3 (6)
H8AA—C8A—H8AB	108.2	C12B—C13B—H13B	120.4
C8A—C9A—H9AA	109.5	C14B—C13B—H13B	120.4
C8A—C9A—H9AB	109.5	O5B—C14B—C13B	120.7 (7)
H9AA—C9A—H9AB	109.5	O5B—C14B—C15B	119.7 (7)
C8A—C9A—H9AC	109.5	C13B—C14B—C15B	119.6 (6)
H9AA—C9A—H9AC	109.5	C14B—C15B—C16B	113.2 (4)
H9AB—C9A—H9AC	109.5	C14B—C15B—H15B	108.9
O3A—C10A—H10A	109.5	C16B—C15B—H15B	108.9
O3A—C10A—H10B	109.5	C14B—C15B—H15D	108.9
H10A—C10A—H10B	109.5	C16B—C15B—H15D	108.9
O3A—C10A—H10C	109.5	H15B—C15B—H15D	107.8
H10A—C10A—H10C	109.5	C19B—C16B—C18B	109.4 (4)
H10B—C10A—H10C	109.5	C19B—C16B—C15B	109.7 (4)
O4A—C11A—N1A	124.73 (9)	C18B—C16B—C15B	110.3 (4)
O4A—C11A—C1A	121.52 (9)	C19B—C16B—C17B	109.4 (4)
N1A—C11A—C1A	113.66 (9)	C18B—C16B—C17B	110.3 (4)
C13A—C12A—N1A	124.56 (9)	C15B—C16B—C17B	107.8 (4)
C13A—C12A—C17A	122.20 (9)	C16B—C17B—C12B	111.3 (4)
N1A—C12A—C17A	113.25 (9)	C16B—C17B—H17C	109.4
C12A—C13A—C14A	121.19 (10)	C12B—C17B—H17C	109.4
C12A—C13A—H13A	119.4	C16B—C17B—H17D	109.4
C14A—C13A—H13A	119.4	C12B—C17B—H17D	109.4
O5A—C14A—C13A	121.13 (10)	H17C—C17B—H17D	108.0
O5A—C14A—C15A	120.98 (10)	C16B—C18B—H18D	109.5
C13A—C14A—C15A	117.88 (9)	C16B—C18B—H18E	109.5
C14A—C15A—C16A	112.84 (9)	H18D—C18B—H18E	109.5
C14A—C15A—H15A	109.0	C16B—C18B—H18F	109.5
C16A—C15A—H15A	109.0	H18D—C18B—H18F	109.5
C14A—C15A—H15C	109.0	H18E—C18B—H18F	109.5
C16A—C15A—H15C	109.0	C16B—C19B—H19D	109.5
H15A—C15A—H15C	107.8	C16B—C19B—H19E	109.5
C19A—C16A—C18A	110.90 (16)	H19D—C19B—H19E	109.5
C19A—C16A—C15A	110.13 (12)	C16B—C19B—H19F	109.5
C18A—C16A—C15A	108.85 (12)	H19D—C19B—H19F	109.5
C19A—C16A—C17A	110.10 (11)	H19E—C19B—H19F	109.5
C18A—C16A—C17A	108.99 (12)	C12C—N1C—C11B	123.0 (9)
C15A—C16A—C17A	107.80 (11)	C12C—N1C—H1CA	119 (3)
C12A—C17A—C16A	113.03 (9)	C11B—N1C—H1CA	117 (3)
C12A—C17A—H17A	109.0	C13C—C12C—N1C	128.2 (9)
C16A—C17A—H17A	109.0	C13C—C12C—C17C	118.0 (8)
C12A—C17A—H17B	109.0	N1C—C12C—C17C	111.9 (7)
C16A—C17A—H17B	109.0	C12C—C13C—C14C	124.8 (8)
H17A—C17A—H17B	107.8	C12C—C13C—H13C	117.6
C16A—C18A—H18A	109.5	C14C—C13C—H13C	117.6
C16A—C18A—H18B	109.5	O5C—C14C—C13C	119.6 (9)
H18A—C18A—H18B	109.5	O5C—C14C—C15C	123.6 (8)
C16A—C18A—H18C	109.5	C13C—C14C—C15C	116.8 (7)
H18A—C18A—H18C	109.5	C14C—C15C—C16C	113.6 (5)
H18B—C18A—H18C	109.5	C14C—C15C—H15E	108.8
C16A—C19A—H19A	109.5	C16C—C15C—H15E	108.8
C16A—C19A—H19B	109.5	C14C—C15C—H15F	108.8
H19A—C19A—H19B	109.5	C16C—C15C—H15F	108.8
C16A—C19A—H19C	109.5	H15E—C15C—H15F	107.7
H19A—C19A—H19C	109.5	C17C—C16C—C15C	109.0 (6)
H19B—C19A—H19C	109.5	C17C—C16C—C19C	110.0 (6)
C3B—O1B—C7B	112.62 (9)	C15C—C16C—C19C	110.6 (6)
C4B—O2B—C8B	114.21 (10)	C17C—C16C—C18C	108.9 (6)
C5B—O3B—C10B	116.84 (9)	C15C—C16C—C18C	109.4 (6)
C2B—C1B—C6B	119.81 (9)	C19C—C16C—C18C	109.0 (6)
C2B—C1B—C11B	123.40 (9)	C12C—C17C—C16C	112.2 (6)
C6B—C1B—C11B	116.68 (9)	C12C—C17C—H17E	109.2
C1B—C2B—C3B	120.05 (9)	C16C—C17C—H17E	109.2
C1B—C2B—Cl1B	121.83 (8)	C12C—C17C—H17F	109.2
C3B—C2B—Cl1B	118.10 (8)	C16C—C17C—H17F	109.2
O1B—C3B—C4B	119.85 (9)	H17E—C17C—H17F	107.9
O1B—C3B—C2B	120.07 (10)	C16C—C18C—H18G	109.5
C4B—C3B—C2B	120.08 (10)	C16C—C18C—H18H	109.5
O2B—C4B—C3B	120.17 (10)	H18G—C18C—H18H	109.5
O2B—C4B—C5B	119.75 (10)	C16C—C18C—H18I	109.5
C3B—C4B—C5B	119.98 (9)	H18G—C18C—H18I	109.5
O3B—C5B—C6B	125.11 (10)	H18H—C18C—H18I	109.5
O3B—C5B—C4B	115.33 (9)	C16C—C19C—H19G	109.5
C6B—C5B—C4B	119.56 (10)	C16C—C19C—H19H	109.5
C5B—C6B—C1B	120.46 (10)	H19G—C19C—H19H	109.5
C5B—C6B—H6BA	119.8	C16C—C19C—H19I	109.5
C1B—C6B—H6BA	119.8	H19G—C19C—H19I	109.5
O1B—C7B—H7BA	109.5	H19H—C19C—H19I	109.5
C6A—C1A—C2A—C3A	0.43 (16)	C8B—O2B—C4B—C3B	79.16 (14)
C11A—C1A—C2A—C3A	−177.91 (10)	C8B—O2B—C4B—C5B	−104.32 (12)
C6A—C1A—C2A—Cl1A	−177.38 (8)	O1B—C3B—C4B—O2B	−3.90 (16)
C11A—C1A—C2A—Cl1A	4.27 (15)	C2B—C3B—C4B—O2B	177.06 (9)
C7A—O1A—C3A—C4A	−89.70 (15)	O1B—C3B—C4B—C5B	179.58 (9)
C7A—O1A—C3A—C2A	94.67 (14)	C2B—C3B—C4B—C5B	0.54 (16)
C1A—C2A—C3A—O1A	176.11 (10)	C10B—O3B—C5B—C6B	0.54 (16)
Cl1A—C2A—C3A—O1A	−6.00 (14)	C10B—O3B—C5B—C4B	−179.34 (10)
C1A—C2A—C3A—C4A	0.48 (16)	O2B—C4B—C5B—O3B	0.86 (15)
Cl1A—C2A—C3A—C4A	178.36 (9)	C3B—C4B—C5B—O3B	177.39 (10)
C8A—O2A—C4A—C3A	124.66 (15)	O2B—C4B—C5B—C6B	−179.03 (10)
C8A—O2A—C4A—C5A	−58.83 (18)	C3B—C4B—C5B—C6B	−2.50 (16)
O1A—C3A—C4A—O2A	0.97 (16)	O3B—C5B—C6B—C1B	−177.06 (10)
C2A—C3A—C4A—O2A	176.61 (10)	C4B—C5B—C6B—C1B	2.82 (15)
O1A—C3A—C4A—C5A	−175.67 (10)	C2B—C1B—C6B—C5B	−1.17 (15)
C2A—C3A—C4A—C5A	−0.03 (17)	C11B—C1B—C6B—C5B	−177.57 (9)
C10A—O3A—C5A—C6A	−3.11 (19)	C4B—O2B—C8B—C9B	67.92 (16)
C10A—O3A—C5A—C4A	178.00 (13)	C2B—C1B—C11B—O4B	−122.81 (13)
O2A—C4A—C5A—O3A	1.15 (17)	C6B—C1B—C11B—O4B	53.44 (14)
C3A—C4A—C5A—O3A	177.60 (10)	C2B—C1B—C11B—N1B	58.5 (6)
O2A—C4A—C5A—C6A	−177.78 (10)	C6B—C1B—C11B—N1B	−125.2 (6)
C3A—C4A—C5A—C6A	−1.34 (17)	C2B—C1B—C11B—N1C	59.4 (5)
O3A—C5A—C6A—C1A	−176.57 (11)	C6B—C1B—C11B—N1C	−124.3 (5)
C4A—C5A—C6A—C1A	2.27 (17)	O4B—C11B—N1B—C12B	7.2 (16)
C2A—C1A—C6A—C5A	−1.81 (16)	C1B—C11B—N1B—C12B	−174.2 (11)
C11A—C1A—C6A—C5A	176.67 (10)	C11B—N1B—C12B—C13B	0 (2)
C4A—O2A—C8A—C9A	−148.77 (16)	C11B—N1B—C12B—C17B	−169.0 (10)
C12A—N1A—C11A—O4A	−2.59 (18)	N1B—C12B—C13B—C14B	−175.2 (12)
C12A—N1A—C11A—C1A	174.03 (10)	C17B—C12B—C13B—C14B	−7.6 (18)
C2A—C1A—C11A—O4A	−129.47 (12)	C12B—C13B—C14B—O5B	−173.3 (12)
C6A—C1A—C11A—O4A	52.13 (15)	C12B—C13B—C14B—C15B	8.2 (15)
C2A—C1A—C11A—N1A	53.79 (14)	O5B—C14B—C15B—C16B	148.7 (9)
C6A—C1A—C11A—N1A	−124.61 (10)	C13B—C14B—C15B—C16B	−32.8 (11)
C11A—N1A—C12A—C13A	−9.78 (18)	C14B—C15B—C16B—C19B	172.5 (5)
C11A—N1A—C12A—C17A	170.04 (11)	C14B—C15B—C16B—C18B	−66.9 (6)
N1A—C12A—C13A—C14A	−176.55 (10)	C14B—C15B—C16B—C17B	53.5 (7)
C17A—C12A—C13A—C14A	3.65 (17)	C19B—C16B—C17B—C12B	−170.7 (7)
C12A—C13A—C14A—O5A	173.40 (12)	C18B—C16B—C17B—C12B	68.9 (7)
C12A—C13A—C14A—C15A	−8.11 (17)	C15B—C16B—C17B—C12B	−51.5 (7)
O5A—C14A—C15A—C16A	−146.37 (12)	C13B—C12B—C17B—C16B	31.0 (15)
C13A—C14A—C15A—C16A	35.13 (16)	N1B—C12B—C17B—C16B	−160.4 (9)
C14A—C15A—C16A—C19A	65.22 (14)	O4B—C11B—N1C—C12C	9.7 (15)
C14A—C15A—C16A—C18A	−173.01 (13)	C1B—C11B—N1C—C12C	−172.7 (11)
C14A—C15A—C16A—C17A	−54.92 (14)	C11B—N1C—C12C—C13C	−8 (3)
C13A—C12A—C17A—C16A	−26.27 (17)	C11B—N1C—C12C—C17C	155.4 (10)
N1A—C12A—C17A—C16A	153.90 (11)	N1C—C12C—C13C—C14C	176.1 (15)
C19A—C16A—C17A—C12A	−70.04 (15)	C17C—C12C—C13C—C14C	13 (2)
C18A—C16A—C17A—C12A	168.10 (14)	C12C—C13C—C14C—O5C	171.1 (16)
C15A—C16A—C17A—C12A	50.11 (15)	C12C—C13C—C14C—C15C	−11 (2)
C6B—C1B—C2B—C3B	−0.81 (14)	O5C—C14C—C15C—C16C	−151.4 (13)
C11B—C1B—C2B—C3B	175.34 (9)	C13C—C14C—C15C—C16C	30.3 (14)
C6B—C1B—C2B—Cl1B	−178.96 (8)	C14C—C15C—C16C—C17C	−51.9 (9)
C11B—C1B—C2B—Cl1B	−2.82 (14)	C14C—C15C—C16C—C19C	69.1 (9)
C7B—O1B—C3B—C4B	79.27 (13)	C14C—C15C—C16C—C18C	−170.8 (7)
C7B—O1B—C3B—C2B	−101.69 (13)	C13C—C12C—C17C—C16C	−35.8 (17)
C1B—C2B—C3B—O1B	−177.93 (9)	N1C—C12C—C17C—C16C	158.7 (11)
Cl1B—C2B—C3B—O1B	0.30 (14)	C15C—C16C—C17C—C12C	53.9 (10)
C1B—C2B—C3B—C4B	1.12 (15)	C19C—C16C—C17C—C12C	−67.5 (9)
Cl1B—C2B—C3B—C4B	179.34 (8)	C18C—C16C—C17C—C12C	173.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O5B	0.853 (16)	2.040 (18)	2.849 (8)	158.1 (15)
N1A—H1AA···O5C	0.853 (16)	2.081 (19)	2.909 (9)	163.5 (15)
C7A—H7AA···O2B^i	0.98	2.44	3.3451 (17)	153
C8A—H8AB···Cl1A^ii	0.99	2.92	3.703 (2)	137
C17A—H17A···O5B	0.99	2.42	3.285 (7)	146
C17A—H17A···O5C	0.99	2.63	3.481 (8)	144
C10B—H10F···O4A^iii	0.98	2.46	3.4013 (15)	161
N1B—H1BA···O5A^iv	0.77 (5)	2.31 (5)	2.985 (10)	147 (5)
N1C—H1CA···O5A^iv	0.88 (5)	1.96 (4)	2.795 (12)	159 (4)
C17C—H17E···O5A^iv	0.99	2.54	3.364 (3)	141

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