Dimethyl 4-(4-isopropyl­carbonyl­oxyphen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

In the mol­ecule of the title compound, C₂₁H₂₅NO₆, the substituted 1,4-dihydro­pyridine (1,4-DHP) ring has a flattened boat conformation. The carbonyl groups of the ester groups at positions 3 and 5 of the 1,4-DHP ring have cis configurations with respect to the double bonds in the 1,4-DHP ring. In the solid state, the mol­ecules are linked by inter­molecular N—H...O hydrogen bonds. Weak intra­molecular C—H...O inter­actions stabilize the mol­ecular structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.141
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C22

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C20A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C20B
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H16C   ..  H21F    ..       2.12 Ang.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H1     ..  H21A    ..       2.11 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.80 Deg.
              C20A -C19  -C20B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.90 Deg.
              C20A -C21  -C20B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.60 Deg.
              H21A -C21  -H21D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.30 Deg.
              H21B -C21  -H21F    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.70 Deg.
              C20B -C22  -C20A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.90 Deg.
              H22A -C22  -H22D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.20 Deg.
              H22C -C22  -H22E    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  15 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
  14 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Dimethyl 4-(4-isopropylcarbonyloxyphenyl)-2,6-dimethyl- 1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

C21H25NO6	Z = 2
Mr = 387.42	F(000) = 412
Triclinic, P1	Dx = 1.296 Mg m^−3
Hall symbol: -P 1	Melting point = 489–493 K
a = 8.4488 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5809 (5) Å	Cell parameters from 6302 reflections
c = 11.5520 (6) Å	θ = 4.7–56.0°
α = 103.020 (1)°	µ = 0.10 mm^−1
β = 95.971 (1)°	T = 273 K
γ = 95.506 (1)°	Block, brown
V = 993.07 (8) Å^3	0.10 × 0.07 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω scans	h = −10→10
9621 measured reflections	k = −12→12
3487 independent reflections	l = −13→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.073P)^2 + 0.3133P] where P = (Fo^2 + 2Fc^2)/3
3487 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.25 e Å^−3
6 restraints	Δρmin = −0.25 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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)
O1	0.14404 (19)	0.77105 (18)	−0.10988 (15)	0.0793 (5)
O2	0.35980 (17)	0.66686 (14)	−0.13014 (12)	0.0629 (4)
O3	0.90726 (16)	0.90870 (16)	0.25243 (16)	0.0750 (5)
O4	0.80889 (15)	0.71504 (13)	0.13402 (13)	0.0590 (4)
N1	0.43659 (18)	1.01299 (14)	0.20388 (14)	0.0498 (4)
H1	0.4022	1.0765	0.2513	0.060*
C2	0.3372 (2)	0.94644 (17)	0.10167 (16)	0.0458 (4)
C3	0.36925 (19)	0.82796 (16)	0.04414 (15)	0.0421 (4)
C4	0.49947 (19)	0.76271 (15)	0.10192 (15)	0.0401 (4)
H4	0.5491	0.7099	0.0378	0.048*
C5	0.62807 (19)	0.86555 (16)	0.17905 (15)	0.0417 (4)
C6	0.5881 (2)	0.98287 (16)	0.23386 (16)	0.0450 (4)
C7	0.42341 (18)	0.67100 (15)	0.17155 (15)	0.0408 (4)
C8	0.4208 (2)	0.70763 (18)	0.29396 (17)	0.0523 (4)
H8	0.4693	0.7899	0.3366	0.063*
C9	0.3469 (3)	0.62361 (19)	0.35427 (18)	0.0584 (5)
H9	0.3469	0.6490	0.4368	0.070*
C10	0.2744 (2)	0.50364 (17)	0.29140 (18)	0.0515 (5)
C11	0.2732 (2)	0.46403 (17)	0.16999 (18)	0.0536 (5)
H11	0.2224	0.3822	0.1281	0.064*
C12	0.3486 (2)	0.54734 (16)	0.11067 (17)	0.0485 (4)
H12	0.3494	0.5203	0.0284	0.058*
C13	0.2054 (2)	1.0210 (2)	0.0668 (2)	0.0612 (5)
H13A	0.1228	1.0162	0.1173	0.092*
H13B	0.1613	0.9838	−0.0153	0.092*
H13C	0.2475	1.1107	0.0758	0.092*
C14	0.2769 (2)	0.75651 (18)	−0.07060 (16)	0.0492 (4)
C15	0.2833 (3)	0.5822 (2)	−0.24076 (19)	0.0703 (6)
H15A	0.3196	0.6130	−0.3067	0.105*
H15B	0.1692	0.5816	−0.2445	0.105*
H15C	0.3098	0.4951	−0.2452	0.105*
C16	0.6904 (3)	1.08884 (19)	0.3264 (2)	0.0613 (5)
H16A	0.6236	1.1479	0.3672	0.092*
H16B	0.7641	1.1356	0.2884	0.092*
H16C	0.7491	1.0512	0.3830	0.092*
C17	0.7936 (2)	0.83660 (18)	0.19505 (16)	0.0470 (4)
C18	0.9701 (2)	0.6807 (3)	0.1366 (2)	0.0725 (6)
H18A	1.0173	0.6930	0.2182	0.109*
H18B	1.0328	0.7355	0.0979	0.109*
H18C	0.9677	0.5909	0.0952	0.109*
O5	0.18894 (17)	0.42401 (13)	0.35286 (14)	0.0655 (4)
O6	0.36683 (18)	0.28097 (14)	0.33147 (16)	0.0707 (4)
C19	0.2437 (2)	0.31111 (18)	0.36385 (18)	0.0537 (5)
C20A	0.1248 (3)	0.2287 (2)	0.4131 (2)	0.0522 (8)	0.842 (7)
H20A	0.0379	0.1919	0.3475	0.063*	0.842 (7)
C20B	0.2041 (13)	0.2663 (9)	0.4790 (10)	0.061 (5)	0.158 (7)
H20B	0.2901	0.3034	0.5451	0.073*	0.158 (7)
C21	0.1959 (3)	0.1145 (2)	0.4454 (3)	0.0803 (7)
H21A	0.2419	0.0677	0.3784	0.121*	0.842 (7)
H21B	0.1134	0.0573	0.4655	0.121*	0.842 (7)
H21C	0.2777	0.1454	0.5128	0.121*	0.842 (7)
H21D	0.2952	0.0903	0.4190	0.121*	0.158 (7)
H21E	0.1094	0.0785	0.3822	0.121*	0.158 (7)
H21F	0.1780	0.0812	0.5143	0.121*	0.158 (7)
C22	0.0487 (4)	0.3085 (3)	0.5131 (3)	0.1017 (10)
H22A	0.0053	0.3795	0.4870	0.153*	0.842 (7)
H22B	0.1281	0.3426	0.5816	0.153*	0.842 (7)
H22C	−0.0358	0.2541	0.5343	0.153*	0.842 (7)
H22D	0.0553	0.4020	0.5283	0.153*	0.158 (7)
H22E	0.0262	0.2810	0.5841	0.153*	0.158 (7)
H22F	−0.0356	0.2698	0.4489	0.153*	0.158 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0584 (9)	0.0991 (12)	0.0714 (10)	0.0206 (8)	−0.0130 (7)	0.0065 (9)
O2	0.0652 (9)	0.0625 (8)	0.0541 (8)	0.0157 (7)	−0.0015 (6)	0.0004 (6)
O3	0.0406 (8)	0.0780 (10)	0.0949 (11)	0.0041 (7)	−0.0052 (7)	0.0046 (8)
O4	0.0403 (7)	0.0588 (8)	0.0784 (9)	0.0178 (6)	0.0096 (6)	0.0117 (7)
N1	0.0495 (8)	0.0431 (8)	0.0570 (9)	0.0160 (6)	0.0073 (7)	0.0076 (7)
C2	0.0407 (9)	0.0497 (10)	0.0523 (10)	0.0117 (7)	0.0096 (7)	0.0191 (8)
C3	0.0374 (8)	0.0455 (9)	0.0471 (9)	0.0074 (7)	0.0076 (7)	0.0163 (7)
C4	0.0373 (8)	0.0384 (8)	0.0459 (9)	0.0091 (6)	0.0075 (7)	0.0100 (7)
C5	0.0367 (8)	0.0421 (9)	0.0486 (9)	0.0054 (7)	0.0067 (7)	0.0148 (7)
C6	0.0433 (9)	0.0417 (9)	0.0522 (10)	0.0049 (7)	0.0069 (7)	0.0151 (7)
C7	0.0347 (8)	0.0384 (8)	0.0512 (9)	0.0105 (6)	0.0059 (7)	0.0121 (7)
C8	0.0593 (11)	0.0430 (9)	0.0538 (11)	0.0018 (8)	0.0122 (8)	0.0093 (8)
C9	0.0698 (13)	0.0547 (11)	0.0544 (11)	0.0096 (9)	0.0206 (9)	0.0145 (9)
C10	0.0492 (10)	0.0431 (9)	0.0724 (12)	0.0148 (8)	0.0224 (9)	0.0246 (9)
C11	0.0576 (11)	0.0356 (9)	0.0682 (12)	0.0050 (8)	0.0103 (9)	0.0130 (8)
C12	0.0554 (10)	0.0383 (9)	0.0526 (10)	0.0090 (7)	0.0078 (8)	0.0105 (7)
C13	0.0557 (11)	0.0629 (12)	0.0708 (13)	0.0253 (9)	0.0063 (9)	0.0211 (10)
C14	0.0470 (10)	0.0533 (10)	0.0505 (10)	0.0059 (8)	0.0057 (8)	0.0192 (8)
C15	0.0913 (16)	0.0564 (12)	0.0553 (12)	0.0034 (11)	−0.0040 (11)	0.0055 (9)
C16	0.0615 (12)	0.0444 (10)	0.0720 (13)	0.0025 (8)	−0.0025 (10)	0.0081 (9)
C17	0.0399 (9)	0.0523 (10)	0.0524 (10)	0.0067 (8)	0.0085 (7)	0.0183 (8)
C18	0.0454 (11)	0.0880 (16)	0.0895 (16)	0.0306 (11)	0.0154 (10)	0.0202 (13)
O5	0.0659 (9)	0.0526 (8)	0.0963 (11)	0.0201 (7)	0.0414 (8)	0.0362 (7)
O6	0.0673 (9)	0.0541 (8)	0.1075 (12)	0.0211 (7)	0.0392 (9)	0.0358 (8)
C19	0.0557 (11)	0.0453 (10)	0.0659 (12)	0.0102 (8)	0.0190 (9)	0.0185 (9)
C20A	0.0512 (15)	0.0505 (13)	0.0547 (15)	−0.0037 (10)	0.0069 (11)	0.0164 (11)
C20B	0.062 (9)	0.054 (8)	0.064 (9)	−0.004 (6)	−0.005 (7)	0.018 (7)
C21	0.0895 (17)	0.0686 (14)	0.0971 (18)	0.0058 (12)	0.0247 (14)	0.0453 (13)
C22	0.134 (3)	0.0783 (17)	0.105 (2)	0.0077 (16)	0.072 (2)	0.0230 (15)

Geometric parameters (Å, º)

O1—C14	1.203 (2)	C13—H13C	0.9600
O2—C14	1.341 (2)	C15—H15A	0.9600
O2—C15	1.434 (2)	C15—H15B	0.9600
O3—C17	1.201 (2)	C15—H15C	0.9600
O4—C17	1.345 (2)	C16—H16A	0.9600
O4—C18	1.442 (2)	C16—H16B	0.9600
N1—C6	1.377 (2)	C16—H16C	0.9600
N1—C2	1.379 (2)	C18—H18A	0.9600
N1—H1	0.8600	C18—H18B	0.9600
C2—C3	1.347 (2)	C18—H18C	0.9600
C2—C13	1.498 (2)	O5—C19	1.349 (2)
C3—C14	1.469 (2)	O6—C19	1.190 (2)
C3—C4	1.528 (2)	C19—C20A	1.505 (3)
C4—C5	1.514 (2)	C19—C20B	1.566 (8)
C4—C7	1.530 (2)	C20A—C21	1.503 (3)
C4—H4	0.9800	C20A—C22	1.510 (3)
C5—C6	1.352 (2)	C20A—H20A	0.9800
C5—C17	1.462 (2)	C20B—C22	1.490 (8)
C6—C16	1.493 (3)	C20B—C21	1.558 (8)
C7—C8	1.383 (2)	C20B—H20B	0.9800
C7—C12	1.393 (2)	C21—H21A	0.9600
C8—C9	1.389 (3)	C21—H21B	0.9600
C8—H8	0.9300	C21—H21C	0.9600
C9—C10	1.363 (3)	C21—H21D	0.9600
C9—H9	0.9300	C21—H21E	0.9600
C10—C11	1.369 (3)	C21—H21F	0.9600
C10—O5	1.412 (2)	C22—H22A	0.9600
C11—C12	1.381 (3)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C12—H12	0.9300	C22—H22D	0.9600
C13—H13A	0.9600	C22—H22E	0.9600
C13—H13B	0.9600	C22—H22F	0.9600
C14—O2—C15	118.33 (16)	O6—C19—C20A	126.17 (18)
C17—O4—C18	115.80 (16)	O5—C19—C20A	111.25 (16)
C6—N1—C2	123.25 (14)	O6—C19—C20B	114.0 (4)
C6—N1—H1	118.4	O5—C19—C20B	114.5 (3)
C2—N1—H1	118.4	C20A—C19—C20B	35.8 (4)
C3—C2—N1	118.79 (15)	C21—C20A—C19	111.47 (19)
C3—C2—C13	127.85 (17)	C21—C20A—C22	113.4 (2)
N1—C2—C13	113.34 (16)	C19—C20A—C22	112.6 (2)
C2—C3—C14	121.69 (15)	C21—C20A—H20A	106.3
C2—C3—C4	119.48 (15)	C19—C20A—H20A	106.3
C14—C3—C4	118.77 (14)	C22—C20A—H20A	106.3
C5—C4—C3	110.06 (13)	C22—C20B—C21	111.4 (6)
C5—C4—C7	112.93 (13)	C22—C20B—C19	110.3 (6)
C3—C4—C7	109.58 (13)	C21—C20B—C19	105.4 (6)
C5—C4—H4	108.0	C22—C20B—H20B	109.9
C3—C4—H4	108.0	C21—C20B—H20B	109.9
C7—C4—H4	108.0	C19—C20B—H20B	109.9
C6—C5—C17	120.60 (16)	C20A—C21—C20B	35.9 (4)
C6—C5—C4	119.53 (14)	C20A—C21—H21A	109.5
C17—C5—C4	119.87 (14)	C20B—C21—H21A	122.9
C5—C6—N1	118.76 (15)	C20A—C21—H21B	109.5
C5—C6—C16	127.62 (16)	C20B—C21—H21B	123.4
N1—C6—C16	113.62 (15)	H21A—C21—H21B	109.5
C8—C7—C12	117.76 (16)	C20A—C21—H21C	109.5
C8—C7—C4	122.38 (15)	C20B—C21—H21C	73.6
C12—C7—C4	119.82 (15)	H21A—C21—H21C	109.5
C7—C8—C9	121.10 (17)	H21B—C21—H21C	109.5
C7—C8—H8	119.4	C20A—C21—H21D	120.7
C9—C8—H8	119.4	C20B—C21—H21D	109.5
C10—C9—C8	119.36 (18)	H21A—C21—H21D	36.6
C10—C9—H9	120.3	H21B—C21—H21D	125.8
C8—C9—H9	120.3	H21C—C21—H21D	73.0
C9—C10—C11	121.36 (17)	C20A—C21—H21E	73.7
C9—C10—O5	118.38 (18)	C20B—C21—H21E	109.5
C11—C10—O5	120.08 (17)	H21A—C21—H21E	72.9
C10—C11—C12	119.04 (17)	H21B—C21—H21E	65.2
C10—C11—H11	120.5	H21C—C21—H21E	174.6
C12—C11—H11	120.5	H21D—C21—H21E	109.5
C11—C12—C7	121.37 (17)	C20A—C21—H21F	125.5
C11—C12—H12	119.3	C20B—C21—H21F	109.5
C7—C12—H12	119.3	H21A—C21—H21F	123.7
C2—C13—H13A	109.5	H21B—C21—H21F	44.3
C2—C13—H13B	109.5	H21C—C21—H21F	65.2
H13A—C13—H13B	109.5	H21D—C21—H21F	109.5
C2—C13—H13C	109.5	H21E—C21—H21F	109.5
H13A—C13—H13C	109.5	C20B—C22—C20A	36.7 (5)
H13B—C13—H13C	109.5	C20B—C22—H22A	121.4
O1—C14—O2	121.92 (18)	C20A—C22—H22A	109.5
O1—C14—C3	127.19 (18)	C20B—C22—H22B	72.8
O2—C14—C3	110.88 (15)	C20A—C22—H22B	109.5
O2—C15—H15A	109.5	H22A—C22—H22B	109.5
O2—C15—H15B	109.5	C20B—C22—H22C	125.1
H15A—C15—H15B	109.5	C20A—C22—H22C	109.5
O2—C15—H15C	109.5	H22A—C22—H22C	109.5
H15A—C15—H15C	109.5	H22B—C22—H22C	109.5
H15B—C15—H15C	109.5	C20B—C22—H22D	109.5
C6—C16—H16A	109.5	C20A—C22—H22D	122.2
C6—C16—H16B	109.5	H22A—C22—H22D	35.9
H16A—C16—H16B	109.5	H22B—C22—H22D	73.6
C6—C16—H16C	109.5	H22C—C22—H22D	124.0
H16A—C16—H16C	109.5	C20B—C22—H22E	109.5
H16B—C16—H16C	109.5	C20A—C22—H22E	124.4
O3—C17—O4	121.37 (16)	H22A—C22—H22E	124.8
O3—C17—C5	126.99 (17)	H22B—C22—H22E	65.3
O4—C17—C5	111.63 (15)	H22C—C22—H22E	44.2
O4—C18—H18A	109.5	H22D—C22—H22E	109.5
O4—C18—H18B	109.5	C20B—C22—H22F	109.5
H18A—C18—H18B	109.5	C20A—C22—H22F	72.8
O4—C18—H18C	109.5	H22A—C22—H22F	73.6
H18A—C18—H18C	109.5	H22B—C22—H22F	174.8
H18B—C18—H18C	109.5	H22C—C22—H22F	65.3
C19—O5—C10	118.47 (14)	H22D—C22—H22F	109.5
O6—C19—O5	122.45 (17)	H22E—C22—H22F	109.5
C6—N1—C2—C3	17.5 (3)	C2—C3—C14—O1	−22.0 (3)
C6—N1—C2—C13	−160.90 (17)	C4—C3—C14—O1	155.0 (2)
N1—C2—C3—C14	−174.74 (15)	C2—C3—C14—O2	158.77 (16)
C13—C2—C3—C14	3.4 (3)	C4—C3—C14—O2	−24.2 (2)
N1—C2—C3—C4	8.2 (2)	C18—O4—C17—O3	−3.5 (3)
C13—C2—C3—C4	−173.66 (17)	C18—O4—C17—C5	175.36 (16)
C2—C3—C4—C5	−30.3 (2)	C6—C5—C17—O3	−1.6 (3)
C14—C3—C4—C5	152.55 (15)	C4—C5—C17—O3	179.31 (18)
C2—C3—C4—C7	94.45 (18)	C6—C5—C17—O4	179.64 (15)
C14—C3—C4—C7	−82.69 (18)	C4—C5—C17—O4	0.5 (2)
C3—C4—C5—C6	31.0 (2)	C9—C10—O5—C19	−114.7 (2)
C7—C4—C5—C6	−91.79 (18)	C11—C10—O5—C19	70.1 (2)
C3—C4—C5—C17	−149.87 (15)	C10—O5—C19—O6	5.5 (3)
C7—C4—C5—C17	87.32 (18)	C10—O5—C19—C20A	−170.61 (19)
C17—C5—C6—N1	171.22 (15)	C10—O5—C19—C20B	150.6 (5)
C4—C5—C6—N1	−9.7 (2)	O6—C19—C20A—C21	13.8 (4)
C17—C5—C6—C16	−8.7 (3)	O5—C19—C20A—C21	−170.2 (2)
C4—C5—C6—C16	170.40 (17)	C20B—C19—C20A—C21	−67.5 (5)
C2—N1—C6—C5	−16.8 (3)	O6—C19—C20A—C22	142.6 (3)
C2—N1—C6—C16	163.12 (17)	O5—C19—C20A—C22	−41.4 (3)
C5—C4—C7—C8	25.2 (2)	C20B—C19—C20A—C22	61.3 (5)
C3—C4—C7—C8	−97.93 (18)	O6—C19—C20B—C22	179.8 (5)
C5—C4—C7—C12	−157.13 (15)	O5—C19—C20B—C22	31.7 (9)
C3—C4—C7—C12	79.79 (18)	C20A—C19—C20B—C22	−61.1 (7)
C12—C7—C8—C9	0.4 (3)	O6—C19—C20B—C21	−59.8 (8)
C4—C7—C8—C9	178.18 (16)	O5—C19—C20B—C21	152.1 (4)
C7—C8—C9—C10	−0.7 (3)	C20A—C19—C20B—C21	59.3 (6)
C8—C9—C10—C11	0.2 (3)	C19—C20A—C21—C20B	67.7 (5)
C8—C9—C10—O5	−174.96 (17)	C22—C20A—C21—C20B	−60.6 (5)
C9—C10—C11—C12	0.6 (3)	C22—C20B—C21—C20A	60.5 (7)
O5—C10—C11—C12	175.68 (16)	C19—C20B—C21—C20A	−59.2 (6)
C10—C11—C12—C7	−0.9 (3)	C21—C20B—C22—C20A	−58.2 (6)
C8—C7—C12—C11	0.4 (3)	C19—C20B—C22—C20A	58.6 (6)
C4—C7—C12—C11	−177.42 (15)	C21—C20A—C22—C20B	63.4 (5)
C15—O2—C14—O1	−3.2 (3)	C19—C20A—C22—C20B	−64.4 (5)
C15—O2—C14—C3	176.03 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^i	0.86	2.22	3.030 (2)	158
C4—H4···O2	0.98	2.31	2.738 (2)	105
C4—H4···O4	0.98	2.35	2.7132 (19)	101
C13—H13B···O1	0.96	2.25	2.917 (3)	126
C15—H15B···O1	0.96	2.29	2.669 (3)	103
C16—H16C···O3	0.96	2.47	2.826 (3)	102
C22—H22A···O5	0.96	2.39	2.743 (3)	101

Symmetry code: (i) x, y+1, z.