Diethyl 4-(3-chloro­phen­yl)-2,6-diphenyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

In the title compound, C₂₉H₂₆ClNO₄, the di­hydro­pyridine ring adopts a shallow boat conformation. The mean plane of the di­hydro­pyridine ring (all atoms) subtends dihedral angles of 66.54 (1), 73.71 (1) and 79.47 (1)° with the two phenyl rings and the chloro­phenyl ring, respectively. In the crystal, N—H...O hydrogen bonds link the mol­ecules into [001] chains.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.192
• Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT147_ALERT_1_C s.u. on Symmetry Constrained Cell Angle(s) .....     Please Check
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10      --C11      .        5.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C27      --C28      .        5.3 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C15 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C28 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C21 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C24 Check
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C24       -C29      .       1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00403 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.039 Report

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)      0.005 Ang.
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         51 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Diethyl 4-(3-chlorophenyl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

C29H26ClNO4	F(000) = 1024
Mr = 487.96	Dx = 1.254 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.519 (5) Å	Cell parameters from 6384 reflections
b = 22.059 (5) Å	θ = 1.9–28.4°
c = 11.246 (5) Å	µ = 0.18 mm^−1
β = 97.867 (5)°	T = 295 K
V = 2584.9 (18) Å^3	Block, yellow
Z = 4	0.20 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	3478 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28.4°, θmin = 1.9°
Tmin = 0.968, Tmax = 0.975	h = −14→13
24505 measured reflections	k = −29→22
6384 independent reflections	l = −10→14

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.192	w = 1/[σ^2(Fo^2) + (0.0826P)^2 + 0.5988P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
6384 reflections	Δρmax = 0.28 e Å^−3
318 parameters	Δρmin = −0.40 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. The H atoms were positioned geometrically (N—H = 0.86, C—H = 0.93–0.98 Å) and refined as riding atoms with U_iso(H) = 1.2U_eq(carrier) or 1.5U_eq(methyl carrier).

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

	x	y	z	Uiso*/Ueq
C1	0.3290 (2)	0.12025 (10)	0.47589 (19)	0.0522 (5)
H1	0.364970	0.156592	0.455041	0.063*
C2	0.4059 (2)	0.07648 (12)	0.5367 (2)	0.0707 (7)
H2	0.493445	0.083358	0.556614	0.085*
C3	0.3535 (3)	0.02293 (13)	0.5679 (2)	0.0757 (8)
H3	0.405875	−0.006916	0.607098	0.091*
C4	0.2245 (3)	0.01329 (11)	0.5414 (2)	0.0722 (7)
H4	0.188850	−0.022728	0.564405	0.087*
C5	0.1469 (2)	0.05674 (10)	0.4807 (2)	0.0582 (6)
H5	0.059071	0.049997	0.463143	0.070*
C6	0.19914 (19)	0.11043 (9)	0.44583 (17)	0.0428 (5)
C7	0.11605 (18)	0.15741 (9)	0.37990 (17)	0.0420 (5)
C8	0.0443 (2)	0.15097 (9)	0.27198 (18)	0.0463 (5)
C9	0.0366 (2)	0.09426 (11)	0.2012 (2)	0.0582 (6)
C10	0.1382 (3)	0.00161 (12)	0.1628 (3)	0.0837 (9)
H10A	0.114087	0.004609	0.076599	0.100*
H10B	0.075277	−0.023292	0.195352	0.100*
C11	0.2675 (4)	−0.02572 (15)	0.1905 (4)	0.1229 (14)
H11A	0.327992	−0.002317	0.152983	0.184*
H11B	0.265646	−0.066509	0.160525	0.184*
H11C	0.292792	−0.026027	0.275777	0.184*
C12	−0.0380 (2)	0.20264 (10)	0.21539 (18)	0.0519 (5)
H12	−0.122409	0.185946	0.184374	0.062*
C13	0.0185 (3)	0.22981 (12)	0.1105 (2)	0.0680 (7)
C14	−0.0232 (3)	0.21119 (17)	−0.0070 (2)	0.1011 (12)
H14	−0.085904	0.181396	−0.021709	0.121*
C15	0.0287 (5)	0.2370 (3)	−0.1013 (3)	0.145 (2)
H15	0.000901	0.223983	−0.179177	0.173*
C16	0.1202 (6)	0.2813 (2)	−0.0823 (5)	0.144 (3)
H16	0.153730	0.298948	−0.146468	0.173*
C17	0.1613 (4)	0.29910 (15)	0.0329 (4)	0.1202 (16)
C18	0.1107 (3)	0.27333 (12)	0.1287 (3)	0.0807 (8)
H18	0.140264	0.285992	0.206414	0.097*
C19	−0.05774 (18)	0.25090 (9)	0.30708 (16)	0.0436 (5)
C20	−0.1629 (2)	0.29297 (10)	0.26751 (18)	0.0472 (5)
C21	−0.2648 (3)	0.38644 (12)	0.3016 (2)	0.0739 (8)
H21A	−0.344665	0.368346	0.317869	0.089*
H21B	−0.273729	0.397671	0.217502	0.089*
C22	−0.2347 (5)	0.43973 (18)	0.3772 (4)	0.155 (2)
H22A	−0.239300	0.429377	0.459385	0.232*
H22B	−0.295244	0.471344	0.352380	0.232*
H22C	−0.149612	0.453524	0.369464	0.232*
C23	0.02010 (18)	0.25477 (8)	0.41280 (17)	0.0406 (4)
C24	0.0185 (2)	0.30256 (9)	0.50681 (18)	0.0441 (5)
C25	−0.0794 (3)	0.30666 (11)	0.5760 (2)	0.0629 (6)
H25	−0.146413	0.278868	0.564751	0.075*
C26	−0.0796 (3)	0.35092 (14)	0.6608 (2)	0.0842 (9)
H26	−0.147338	0.353369	0.705811	0.101*
C27	0.0169 (4)	0.39077 (16)	0.6798 (3)	0.0992 (11)
H27	0.014864	0.421235	0.736649	0.119*
C28	0.1178 (4)	0.38710 (14)	0.6167 (4)	0.1079 (12)
H28	0.186047	0.414051	0.631768	0.129*
C29	0.1177 (3)	0.34263 (12)	0.5293 (3)	0.0770 (8)
H29	0.186363	0.340110	0.485386	0.092*
N1	0.11284 (16)	0.21111 (7)	0.44327 (14)	0.0462 (4)
H1A	0.170700	0.217468	0.503767	0.055*
O1	0.14323 (16)	0.06147 (7)	0.21670 (14)	0.0619 (4)
O2	−0.0565 (2)	0.07963 (10)	0.1336 (2)	0.1071 (8)
O3	−0.24413 (15)	0.28243 (7)	0.18351 (14)	0.0628 (4)
O4	−0.16058 (17)	0.34422 (8)	0.32941 (14)	0.0711 (5)
Cl1	0.28030 (17)	0.35347 (5)	0.05870 (16)	0.1984 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0512 (13)	0.0519 (13)	0.0526 (13)	0.0048 (10)	0.0046 (10)	0.0055 (10)
C2	0.0581 (15)	0.0794 (18)	0.0730 (17)	0.0181 (13)	0.0034 (12)	0.0111 (14)
C3	0.092 (2)	0.0653 (17)	0.0690 (17)	0.0340 (15)	0.0064 (15)	0.0140 (13)
C4	0.102 (2)	0.0452 (14)	0.0692 (17)	0.0037 (14)	0.0108 (15)	0.0105 (12)
C5	0.0644 (14)	0.0484 (13)	0.0596 (14)	−0.0065 (11)	0.0007 (11)	0.0016 (11)
C6	0.0506 (12)	0.0378 (11)	0.0388 (11)	0.0021 (9)	0.0020 (9)	−0.0025 (8)
C7	0.0449 (11)	0.0408 (11)	0.0385 (11)	0.0007 (8)	−0.0001 (8)	−0.0020 (9)
C8	0.0507 (12)	0.0455 (12)	0.0403 (11)	0.0044 (9)	−0.0022 (9)	−0.0040 (9)
C9	0.0644 (15)	0.0546 (14)	0.0524 (13)	0.0029 (12)	−0.0039 (11)	−0.0124 (11)
C10	0.104 (2)	0.0551 (15)	0.092 (2)	0.0035 (15)	0.0138 (17)	−0.0272 (15)
C11	0.159 (4)	0.082 (2)	0.128 (3)	0.041 (2)	0.021 (3)	−0.018 (2)
C12	0.0555 (13)	0.0601 (13)	0.0364 (11)	0.0111 (10)	−0.0068 (9)	−0.0072 (10)
C13	0.0911 (18)	0.0708 (15)	0.0426 (13)	0.0412 (11)	0.0110 (12)	0.0098 (12)
C14	0.118 (3)	0.143 (3)	0.0401 (15)	0.069 (2)	0.0038 (15)	−0.0026 (17)
C15	0.185 (5)	0.209 (6)	0.0444 (18)	0.129 (4)	0.033 (3)	0.029 (3)
C16	0.199 (5)	0.150 (4)	0.106 (4)	0.124 (4)	0.101 (4)	0.076 (3)
C17	0.168 (4)	0.078 (2)	0.138 (3)	0.066 (2)	0.104 (3)	0.053 (2)
C18	0.111 (2)	0.0641 (16)	0.0769 (18)	0.0324 (12)	0.0474 (17)	0.0209 (14)
C19	0.0483 (11)	0.0482 (12)	0.0327 (10)	0.0067 (9)	−0.0002 (8)	−0.0019 (9)
C20	0.0525 (12)	0.0559 (13)	0.0328 (10)	0.0070 (10)	0.0050 (9)	0.0042 (10)
C21	0.0843 (19)	0.0685 (16)	0.0691 (16)	0.0350 (14)	0.0107 (14)	0.0115 (14)
C22	0.221 (5)	0.117 (3)	0.110 (3)	0.104 (3)	−0.036 (3)	−0.041 (2)
C23	0.0440 (11)	0.0396 (10)	0.0373 (10)	0.0006 (8)	0.0022 (8)	−0.0002 (8)
C24	0.0490 (12)	0.0406 (11)	0.0389 (11)	0.0031 (9)	−0.0072 (9)	−0.0024 (9)
C25	0.0761 (17)	0.0670 (15)	0.0465 (13)	−0.0036 (12)	0.0120 (12)	−0.0082 (11)
C26	0.113 (2)	0.094 (2)	0.0462 (15)	0.024 (2)	0.0122 (15)	−0.0156 (15)
C27	0.120 (3)	0.084 (2)	0.083 (2)	0.030 (2)	−0.025 (2)	−0.0421 (18)
C28	0.097 (2)	0.0656 (19)	0.149 (3)	−0.0134 (17)	−0.027 (2)	−0.042 (2)
C29	0.0648 (16)	0.0627 (16)	0.103 (2)	−0.0076 (13)	0.0079 (15)	−0.0216 (15)
N1	0.0510 (10)	0.0421 (9)	0.0407 (9)	0.0060 (8)	−0.0105 (7)	−0.0062 (7)
O1	0.0737 (11)	0.0501 (9)	0.0595 (10)	0.0076 (8)	0.0005 (8)	−0.0173 (7)
O2	0.0845 (14)	0.0985 (15)	0.1233 (17)	0.0145 (12)	−0.0388 (13)	−0.0616 (14)
O3	0.0619 (10)	0.0706 (11)	0.0497 (9)	0.0097 (8)	−0.0143 (8)	0.0042 (8)
O4	0.0870 (12)	0.0666 (11)	0.0532 (10)	0.0368 (9)	−0.0139 (8)	−0.0104 (8)
Cl1	0.2676 (17)	0.0805 (7)	0.2945 (19)	0.0159 (8)	0.2084 (16)	0.0452 (8)

Geometric parameters (Å, º)

C1—C6	1.379 (3)	C15—C16	1.369 (7)
C1—C2	1.380 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.366 (7)
C2—C3	1.369 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.387 (4)
C3—C4	1.366 (4)	C17—Cl1	1.729 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.378 (3)	C19—C23	1.351 (3)
C4—H4	0.9300	C19—C20	1.465 (3)
C5—C6	1.385 (3)	C20—O3	1.207 (2)
C5—H5	0.9300	C20—O4	1.326 (3)
C6—C7	1.487 (3)	C21—O4	1.440 (3)
C7—C8	1.346 (3)	C21—C22	1.460 (5)
C7—N1	1.385 (2)	C21—H21A	0.9700
C8—C9	1.479 (3)	C21—H21B	0.9700
C8—C12	1.518 (3)	C22—H22A	0.9600
C9—O2	1.199 (3)	C22—H22B	0.9600
C9—O1	1.326 (3)	C22—H22C	0.9600
C10—O1	1.451 (3)	C23—N1	1.380 (2)
C10—C11	1.481 (4)	C23—C24	1.495 (3)
C10—H10A	0.9700	C24—C29	1.365 (3)
C10—H10B	0.9700	C24—C25	1.375 (3)
C11—H11A	0.9600	C25—C26	1.366 (4)
C11—H11B	0.9600	C25—H25	0.9300
C11—H11C	0.9600	C26—C27	1.338 (5)
C12—C13	1.516 (3)	C26—H26	0.9300
C12—C19	1.516 (3)	C27—C28	1.357 (5)
C12—H12	0.9800	C27—H27	0.9300
C13—C18	1.360 (4)	C28—C29	1.389 (4)
C13—C14	1.395 (4)	C28—H28	0.9300
C14—C15	1.380 (6)	C29—H29	0.9300
C14—H14	0.9300	N1—H1A	0.8600
C6—C1—C2	120.4 (2)	C17—C16—C15	118.5 (4)
C6—C1—H1	119.8	C17—C16—H16	120.8
C2—C1—H1	119.8	C15—C16—H16	120.8
C3—C2—C1	120.1 (3)	C16—C17—C18	120.9 (5)
C3—C2—H2	119.9	C16—C17—Cl1	119.1 (3)
C1—C2—H2	119.9	C18—C17—Cl1	120.0 (4)
C4—C3—C2	120.1 (2)	C13—C18—C17	120.9 (4)
C4—C3—H3	120.0	C13—C18—H18	119.5
C2—C3—H3	120.0	C17—C18—H18	119.5
C3—C4—C5	120.2 (2)	C23—C19—C20	124.64 (18)
C3—C4—H4	119.9	C23—C19—C12	121.34 (18)
C5—C4—H4	119.9	C20—C19—C12	113.96 (16)
C4—C5—C6	120.3 (2)	O3—C20—O4	122.37 (19)
C4—C5—H5	119.8	O3—C20—C19	122.7 (2)
C6—C5—H5	119.8	O4—C20—C19	114.95 (18)
C1—C6—C5	118.9 (2)	O4—C21—C22	107.3 (2)
C1—C6—C7	120.52 (18)	O4—C21—H21A	110.3
C5—C6—C7	120.57 (19)	C22—C21—H21A	110.3
C8—C7—N1	120.27 (17)	O4—C21—H21B	110.3
C8—C7—C6	126.50 (18)	C22—C21—H21B	110.3
N1—C7—C6	113.18 (16)	H21A—C21—H21B	108.5
C7—C8—C9	123.88 (19)	C21—C22—H22A	109.5
C7—C8—C12	121.08 (18)	C21—C22—H22B	109.5
C9—C8—C12	115.03 (17)	H22A—C22—H22B	109.5
O2—C9—O1	122.6 (2)	C21—C22—H22C	109.5
O2—C9—C8	123.3 (2)	H22A—C22—H22C	109.5
O1—C9—C8	114.02 (19)	H22B—C22—H22C	109.5
O1—C10—C11	107.6 (2)	C19—C23—N1	119.80 (17)
O1—C10—H10A	110.2	C19—C23—C24	127.08 (17)
C11—C10—H10A	110.2	N1—C23—C24	113.12 (16)
O1—C10—H10B	110.2	C29—C24—C25	117.7 (2)
C11—C10—H10B	110.2	C29—C24—C23	120.3 (2)
H10A—C10—H10B	108.5	C25—C24—C23	121.89 (19)
C10—C11—H11A	109.5	C26—C25—C24	121.0 (3)
C10—C11—H11B	109.5	C26—C25—H25	119.5
H11A—C11—H11B	109.5	C24—C25—H25	119.5
C10—C11—H11C	109.5	C27—C26—C25	120.5 (3)
H11A—C11—H11C	109.5	C27—C26—H26	119.8
H11B—C11—H11C	109.5	C25—C26—H26	119.8
C13—C12—C19	110.89 (19)	C26—C27—C28	120.5 (3)
C13—C12—C8	111.17 (18)	C26—C27—H27	119.7
C19—C12—C8	111.44 (16)	C28—C27—H27	119.7
C13—C12—H12	107.7	C27—C28—C29	119.2 (3)
C19—C12—H12	107.7	C27—C28—H28	120.4
C8—C12—H12	107.7	C29—C28—H28	120.4
C18—C13—C14	118.4 (3)	C24—C29—C28	120.9 (3)
C18—C13—C12	120.7 (2)	C24—C29—H29	119.5
C14—C13—C12	121.0 (3)	C28—C29—H29	119.5
C15—C14—C13	120.0 (4)	C23—N1—C7	122.35 (16)
C15—C14—H14	120.0	C23—N1—H1A	118.8
C13—C14—H14	120.0	C7—N1—H1A	118.8
C16—C15—C14	121.2 (5)	C9—O1—C10	117.38 (19)
C16—C15—H15	119.4	C20—O4—C21	118.62 (19)
C14—C15—H15	119.4
C6—C1—C2—C3	−0.1 (4)	C16—C17—C18—C13	−0.2 (5)
C1—C2—C3—C4	−1.6 (4)	Cl1—C17—C18—C13	−179.0 (2)
C2—C3—C4—C5	1.6 (4)	C13—C12—C19—C23	−106.0 (2)
C3—C4—C5—C6	0.2 (4)	C8—C12—C19—C23	18.4 (3)
C2—C1—C6—C5	1.8 (3)	C13—C12—C19—C20	71.5 (2)
C2—C1—C6—C7	−179.8 (2)	C8—C12—C19—C20	−164.12 (18)
C4—C5—C6—C1	−1.9 (3)	C23—C19—C20—O3	−166.5 (2)
C4—C5—C6—C7	179.7 (2)	C12—C19—C20—O3	16.2 (3)
C1—C6—C7—C8	120.3 (2)	C23—C19—C20—O4	14.9 (3)
C5—C6—C7—C8	−61.3 (3)	C12—C19—C20—O4	−162.47 (18)
C1—C6—C7—N1	−62.4 (2)	C20—C19—C23—N1	177.24 (18)
C5—C6—C7—N1	116.0 (2)	C12—C19—C23—N1	−5.6 (3)
N1—C7—C8—C9	−176.6 (2)	C20—C19—C23—C24	−2.3 (3)
C6—C7—C8—C9	0.5 (3)	C12—C19—C23—C24	174.84 (19)
N1—C7—C8—C12	2.0 (3)	C19—C23—C24—C29	−111.8 (3)
C6—C7—C8—C12	179.1 (2)	N1—C23—C24—C29	68.6 (3)
C7—C8—C9—O2	150.2 (3)	C19—C23—C24—C25	70.4 (3)
C12—C8—C9—O2	−28.4 (4)	N1—C23—C24—C25	−109.2 (2)
C7—C8—C9—O1	−31.4 (3)	C29—C24—C25—C26	2.6 (4)
C12—C8—C9—O1	150.0 (2)	C23—C24—C25—C26	−179.5 (2)
C7—C8—C12—C13	107.7 (2)	C24—C25—C26—C27	−1.1 (4)
C9—C8—C12—C13	−73.6 (3)	C25—C26—C27—C28	−1.3 (5)
C7—C8—C12—C19	−16.6 (3)	C26—C27—C28—C29	2.1 (5)
C9—C8—C12—C19	162.14 (18)	C25—C24—C29—C28	−1.8 (4)
C19—C12—C13—C18	39.7 (3)	C23—C24—C29—C28	−179.7 (3)
C8—C12—C13—C18	−84.9 (3)	C27—C28—C29—C24	−0.4 (5)
C19—C12—C13—C14	−139.9 (2)	C19—C23—N1—C7	−11.5 (3)
C8—C12—C13—C14	95.6 (3)	C24—C23—N1—C7	168.13 (17)
C18—C13—C14—C15	−0.2 (4)	C8—C7—N1—C23	13.4 (3)
C12—C13—C14—C15	179.3 (3)	C6—C7—N1—C23	−164.10 (17)
C13—C14—C15—C16	−0.6 (6)	O2—C9—O1—C10	−9.3 (4)
C14—C15—C16—C17	1.0 (7)	C8—C9—O1—C10	172.2 (2)
C15—C16—C17—C18	−0.6 (6)	C11—C10—O1—C9	179.2 (3)
C15—C16—C17—Cl1	178.1 (3)	O3—C20—O4—C21	5.3 (3)
C14—C13—C18—C17	0.7 (4)	C19—C20—O4—C21	−176.1 (2)
C12—C13—C18—C17	−178.9 (2)	C22—C21—O4—C20	−176.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.86	2.10	2.910 (2)	158

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