2-Anilino-3-benzoyl-4-(2-chloro­phen­yl)-7,7-dimethyl-7,8-dihydro-4H-chromen-5(6H)-one

There are two independent mol­ecules in the asymmetric unit of the title compound, C₃₀H₂₆ClNO₃. Both mol­ecules are linked through C—H...O hydrogen bonds into centrosymmetric dimers, providing stabilization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.127
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.86 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C34    -   C60     ..       6.16 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C34

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-Anilino-3-benzoyl-4-(2-chlorophenyl)-7,7-dimethyl-7,8-dihydro- 4H-chromen-5(6H)-one

Crystal data

C30H26ClNO3	Z = 8
Mr = 483.97	F(000) = 2032
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4318 reflections
a = 19.982 (5) Å	θ = 2.2–20.9°
b = 13.768 (4) Å	µ = 0.18 mm^−1
c = 19.018 (5) Å	T = 293 K
β = 103.956 (3)°	Block, colourless
V = 5078 (2) Å^3	0.26 × 0.22 × 0.16 mm

Data collection

Bruck APEX-II CCD area-detector diffractometer	8974 independent reflections
Radiation source: fine-focus sealed tube	5707 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.954, Tmax = 0.971	k = −12→16
27044 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 1.1067P] where P = (Fo^2 + 2Fc^2)/3
8974 reflections	(Δ/σ)max < 0.001
635 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.33 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
Cl1	0.16108 (4)	0.48676 (5)	0.33783 (4)	0.0632 (2)
Cl2	0.26123 (4)	0.99927 (5)	0.34510 (4)	0.0704 (2)
O1	0.18566 (9)	0.28086 (13)	0.55956 (11)	0.0757 (6)
O2	−0.07317 (8)	0.49171 (12)	0.33570 (10)	0.0618 (5)
O3	0.11028 (8)	0.59057 (10)	0.46954 (8)	0.0491 (4)
O4	0.34680 (11)	0.79099 (14)	0.56146 (11)	0.0835 (7)
O5	0.49362 (10)	0.99592 (11)	0.32865 (10)	0.0628 (5)
O6	0.37832 (8)	1.09846 (10)	0.46665 (8)	0.0494 (4)
N1	0.00914 (9)	0.62913 (13)	0.39520 (10)	0.0453 (5)
H1	−0.0300	0.6117	0.3682	0.054*
N2	0.44114 (11)	1.13389 (13)	0.38790 (11)	0.0557 (5)
H2	0.4678	1.1158	0.3609	0.067*
C1	0.15463 (11)	0.52607 (17)	0.51283 (12)	0.0445 (6)
C2	0.21029 (12)	0.57921 (18)	0.56491 (13)	0.0573 (7)
H2A	0.1928	0.6017	0.6054	0.069*
H2B	0.2237	0.6357	0.5411	0.069*
C3	0.27344 (12)	0.51524 (18)	0.59327 (13)	0.0516 (6)
C4	0.24839 (14)	0.4188 (2)	0.61678 (14)	0.0710 (8)
H4A	0.2876	0.3754	0.6310	0.085*
H4B	0.2305	0.4301	0.6592	0.085*
C5	0.19326 (12)	0.36868 (19)	0.55975 (13)	0.0548 (6)
C6	0.14630 (11)	0.43024 (16)	0.50647 (11)	0.0410 (5)
C7	0.08938 (10)	0.38390 (15)	0.44984 (11)	0.0380 (5)
H7	0.0661	0.3382	0.4755	0.046*
C8	0.11686 (10)	0.32383 (16)	0.39484 (12)	0.0409 (5)
C9	0.14557 (11)	0.36239 (17)	0.34220 (13)	0.0489 (6)
C10	0.16461 (14)	0.3041 (2)	0.29016 (15)	0.0680 (8)
H10	0.1834	0.3319	0.2547	0.082*
C11	0.15533 (15)	0.2055 (2)	0.29186 (17)	0.0749 (8)
H11	0.1673	0.1663	0.2570	0.090*
C12	0.12867 (14)	0.1648 (2)	0.34445 (17)	0.0716 (8)
H12	0.1230	0.0979	0.3457	0.086*
C13	0.11020 (12)	0.22212 (18)	0.39545 (14)	0.0561 (6)
H13	0.0928	0.1931	0.4315	0.067*
C14	0.03558 (10)	0.45911 (15)	0.41478 (11)	0.0374 (5)
C15	−0.02856 (11)	0.43178 (16)	0.36739 (11)	0.0421 (5)
C16	−0.04389 (10)	0.32614 (16)	0.35319 (11)	0.0396 (5)
C17	−0.04122 (12)	0.28566 (18)	0.28733 (12)	0.0511 (6)
H17	−0.0300	0.3241	0.2516	0.061*
C18	−0.05526 (14)	0.18834 (19)	0.27467 (13)	0.0609 (7)
H18	−0.0528	0.1615	0.2305	0.073*
C19	−0.07280 (13)	0.13068 (19)	0.32590 (14)	0.0595 (7)
H19	−0.0822	0.0651	0.3167	0.071*
C20	−0.07637 (13)	0.17006 (19)	0.39072 (14)	0.0591 (7)
H20	−0.0886	0.1314	0.4257	0.071*
C21	−0.06176 (12)	0.26747 (18)	0.40450 (12)	0.0505 (6)
H21	−0.0640	0.2937	0.4489	0.061*
C22	0.05076 (11)	0.55663 (16)	0.42556 (11)	0.0393 (5)
C23	0.02076 (11)	0.73136 (15)	0.40147 (11)	0.0424 (5)
C24	−0.03522 (13)	0.78954 (18)	0.40307 (14)	0.0571 (7)
H24	−0.0781	0.7617	0.4008	0.069*
C25	−0.02730 (16)	0.88888 (19)	0.40812 (16)	0.0740 (8)
H25	−0.0650	0.9278	0.4094	0.089*
C26	0.03569 (17)	0.93104 (19)	0.41124 (15)	0.0719 (8)
H26	0.0409	0.9981	0.4155	0.086*
C27	0.09066 (14)	0.87363 (19)	0.40802 (13)	0.0593 (7)
H27	0.1331	0.9021	0.4090	0.071*
C28	0.08400 (12)	0.77376 (17)	0.40335 (12)	0.0490 (6)
H28	0.1218	0.7353	0.4015	0.059*
C29	0.32235 (15)	0.5651 (2)	0.65735 (15)	0.0795 (9)
H29A	0.3353	0.6275	0.6425	0.119*
H29B	0.3628	0.5259	0.6738	0.119*
H29C	0.2996	0.5732	0.6960	0.119*
C30	0.31091 (14)	0.4997 (2)	0.53385 (16)	0.0816 (9)
H30A	0.2797	0.4725	0.4921	0.122*
H30B	0.3488	0.4560	0.5506	0.122*
H30C	0.3280	0.5608	0.5212	0.122*
C31	0.36073 (11)	0.93959 (17)	0.50701 (11)	0.0432 (5)
C32	0.34230 (13)	0.8791 (2)	0.56289 (14)	0.0608 (7)
C33	0.32230 (18)	0.9316 (2)	0.62474 (16)	0.0851 (10)
H33A	0.2925	0.8894	0.6445	0.102*
H33B	0.3637	0.9429	0.6627	0.102*
C34	0.28592 (13)	1.02768 (19)	0.60494 (13)	0.0571 (7)
C35	0.33010 (13)	1.09086 (18)	0.56797 (13)	0.0573 (7)
H35A	0.3028	1.1454	0.5446	0.069*
H35B	0.3687	1.1165	0.6043	0.069*
C36	0.35672 (11)	1.03551 (17)	0.51290 (12)	0.0447 (5)
C37	0.41547 (11)	1.06284 (16)	0.42125 (12)	0.0436 (5)
C38	0.42576 (11)	0.96485 (15)	0.41206 (11)	0.0385 (5)
C39	0.38778 (11)	0.89118 (15)	0.44835 (11)	0.0403 (5)
H39	0.4223	0.8437	0.4725	0.048*
C40	0.33230 (11)	0.83403 (16)	0.39465 (13)	0.0458 (6)
C41	0.33817 (13)	0.73242 (18)	0.39197 (16)	0.0651 (7)
H41	0.3746	0.7020	0.4242	0.078*
C42	0.29244 (17)	0.6770 (2)	0.3439 (2)	0.0902 (11)
H42	0.2983	0.6100	0.3434	0.108*
C43	0.23822 (17)	0.7190 (2)	0.2966 (2)	0.0895 (10)
H43	0.2073	0.6808	0.2635	0.107*
C44	0.22907 (14)	0.8184 (2)	0.29774 (16)	0.0758 (8)
H44	0.1917	0.8475	0.2660	0.091*
C45	0.27630 (12)	0.87447 (18)	0.34677 (13)	0.0531 (6)
C46	0.46688 (11)	0.93616 (16)	0.36375 (12)	0.0427 (5)
C47	0.47926 (10)	0.83123 (15)	0.35072 (11)	0.0375 (5)
C48	0.50989 (11)	0.76785 (17)	0.40613 (13)	0.0474 (6)
H48	0.5220	0.7897	0.4538	0.057*
C49	0.52237 (14)	0.67245 (18)	0.39050 (16)	0.0625 (7)
H49	0.5434	0.6308	0.4278	0.075*
C50	0.50423 (16)	0.6387 (2)	0.32098 (17)	0.0712 (8)
H50	0.5120	0.5741	0.3110	0.085*
C51	0.47461 (15)	0.7005 (2)	0.26624 (15)	0.0685 (8)
H51	0.4622	0.6779	0.2188	0.082*
C52	0.46300 (13)	0.79621 (18)	0.28084 (13)	0.0540 (6)
H52	0.4439	0.8379	0.2428	0.065*
C53	0.43014 (13)	1.23568 (16)	0.39120 (12)	0.0452 (6)
C54	0.36506 (13)	1.27462 (18)	0.38047 (14)	0.0595 (7)
H54	0.3267	1.2341	0.3719	0.071*
C55	0.35698 (15)	1.3740 (2)	0.38245 (15)	0.0701 (8)
H55	0.3130	1.4002	0.3758	0.084*
C56	0.41274 (16)	1.4342 (2)	0.39405 (16)	0.0732 (8)
H56	0.4068	1.5011	0.3950	0.088*
C57	0.47767 (15)	1.39545 (18)	0.40426 (16)	0.0702 (8)
H57	0.5158	1.4363	0.4122	0.084*
C58	0.48664 (13)	1.29583 (17)	0.40275 (13)	0.0535 (6)
H58	0.5307	1.2697	0.4095	0.064*
C59	0.2758 (2)	1.0793 (2)	0.67220 (18)	0.1070 (13)
H59A	0.2456	1.0417	0.6938	0.160*
H59B	0.2559	1.1421	0.6591	0.160*
H59C	0.3196	1.0866	0.7063	0.160*
C60	0.21569 (15)	1.0131 (2)	0.5532 (2)	0.0930 (11)
H60A	0.2214	0.9839	0.5092	0.140*
H60B	0.1932	1.0748	0.5424	0.140*
H60C	0.1881	0.9714	0.5753	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0737 (4)	0.0486 (4)	0.0748 (5)	−0.0008 (3)	0.0326 (4)	0.0139 (3)
Cl2	0.0671 (4)	0.0594 (4)	0.0775 (5)	0.0156 (3)	0.0034 (4)	0.0039 (3)
O1	0.0676 (12)	0.0505 (12)	0.0920 (14)	−0.0047 (10)	−0.0140 (10)	0.0271 (10)
O2	0.0465 (9)	0.0481 (10)	0.0778 (12)	0.0065 (8)	−0.0106 (9)	0.0055 (9)
O3	0.0474 (9)	0.0361 (9)	0.0562 (10)	0.0057 (7)	−0.0027 (8)	−0.0033 (7)
O4	0.1155 (17)	0.0527 (12)	0.1050 (16)	0.0246 (12)	0.0711 (14)	0.0341 (11)
O5	0.0867 (13)	0.0393 (10)	0.0799 (12)	0.0013 (9)	0.0543 (11)	0.0071 (8)
O6	0.0685 (10)	0.0328 (8)	0.0561 (10)	−0.0031 (8)	0.0331 (8)	−0.0033 (7)
N1	0.0417 (10)	0.0368 (11)	0.0523 (11)	0.0061 (9)	0.0011 (9)	0.0015 (9)
N2	0.0742 (14)	0.0339 (11)	0.0736 (14)	−0.0046 (10)	0.0461 (12)	0.0001 (10)
C1	0.0389 (12)	0.0450 (14)	0.0471 (13)	0.0063 (11)	0.0055 (10)	0.0008 (11)
C2	0.0513 (14)	0.0541 (16)	0.0594 (15)	0.0000 (12)	−0.0006 (12)	−0.0075 (12)
C3	0.0416 (13)	0.0553 (16)	0.0523 (14)	0.0003 (12)	0.0003 (11)	0.0030 (12)
C4	0.0635 (17)	0.073 (2)	0.0623 (17)	−0.0043 (15)	−0.0120 (14)	0.0172 (15)
C5	0.0473 (14)	0.0529 (17)	0.0596 (16)	−0.0008 (13)	0.0037 (12)	0.0167 (13)
C6	0.0374 (12)	0.0411 (14)	0.0435 (13)	0.0008 (10)	0.0077 (10)	0.0046 (10)
C7	0.0369 (11)	0.0345 (12)	0.0424 (12)	0.0015 (10)	0.0092 (10)	0.0041 (10)
C8	0.0338 (11)	0.0381 (13)	0.0496 (13)	0.0041 (10)	0.0074 (10)	0.0055 (10)
C9	0.0463 (13)	0.0446 (14)	0.0571 (15)	0.0040 (11)	0.0152 (12)	0.0045 (12)
C10	0.0713 (18)	0.070 (2)	0.0722 (19)	0.0088 (16)	0.0360 (15)	0.0024 (15)
C11	0.079 (2)	0.065 (2)	0.090 (2)	0.0135 (16)	0.0389 (18)	−0.0131 (16)
C12	0.0709 (18)	0.0409 (16)	0.109 (2)	0.0081 (14)	0.0329 (17)	−0.0054 (16)
C13	0.0482 (14)	0.0471 (16)	0.0748 (18)	0.0060 (12)	0.0180 (13)	−0.0033 (13)
C14	0.0372 (12)	0.0357 (12)	0.0389 (12)	0.0029 (10)	0.0082 (9)	0.0001 (9)
C15	0.0408 (12)	0.0432 (13)	0.0415 (12)	0.0018 (11)	0.0081 (10)	0.0020 (10)
C16	0.0319 (11)	0.0432 (13)	0.0408 (12)	0.0009 (10)	0.0032 (9)	0.0024 (10)
C17	0.0628 (15)	0.0507 (16)	0.0396 (13)	−0.0048 (12)	0.0120 (11)	0.0030 (11)
C18	0.0795 (19)	0.0567 (17)	0.0445 (14)	−0.0030 (14)	0.0112 (13)	−0.0080 (13)
C19	0.0730 (17)	0.0417 (14)	0.0552 (16)	−0.0071 (13)	−0.0014 (13)	0.0009 (12)
C20	0.0667 (17)	0.0566 (17)	0.0527 (16)	−0.0126 (14)	0.0121 (13)	0.0111 (13)
C21	0.0524 (14)	0.0568 (16)	0.0430 (14)	−0.0019 (12)	0.0129 (11)	−0.0011 (12)
C22	0.0363 (12)	0.0421 (13)	0.0388 (12)	0.0041 (11)	0.0075 (10)	−0.0014 (10)
C23	0.0507 (14)	0.0367 (13)	0.0392 (13)	0.0058 (11)	0.0099 (10)	0.0047 (10)
C24	0.0572 (15)	0.0465 (15)	0.0714 (17)	0.0119 (13)	0.0228 (13)	0.0170 (12)
C25	0.083 (2)	0.0429 (16)	0.107 (2)	0.0206 (15)	0.0424 (18)	0.0183 (15)
C26	0.096 (2)	0.0347 (15)	0.088 (2)	0.0002 (16)	0.0279 (18)	0.0035 (14)
C27	0.0665 (17)	0.0520 (17)	0.0590 (16)	−0.0087 (14)	0.0145 (13)	0.0060 (13)
C28	0.0507 (14)	0.0478 (15)	0.0488 (14)	0.0042 (12)	0.0126 (11)	0.0021 (11)
C29	0.0669 (18)	0.080 (2)	0.0751 (19)	−0.0082 (16)	−0.0151 (15)	−0.0013 (16)
C30	0.0520 (16)	0.107 (3)	0.086 (2)	−0.0012 (16)	0.0181 (15)	−0.0032 (18)
C31	0.0457 (13)	0.0426 (14)	0.0454 (13)	0.0021 (11)	0.0186 (10)	0.0062 (10)
C32	0.0677 (17)	0.0554 (18)	0.0685 (18)	0.0160 (14)	0.0343 (14)	0.0217 (14)
C33	0.114 (3)	0.085 (2)	0.075 (2)	0.030 (2)	0.0583 (19)	0.0287 (17)
C34	0.0610 (16)	0.0594 (17)	0.0606 (16)	0.0091 (13)	0.0338 (13)	0.0041 (13)
C35	0.0632 (16)	0.0590 (16)	0.0570 (15)	−0.0009 (13)	0.0287 (13)	−0.0086 (12)
C36	0.0474 (13)	0.0444 (15)	0.0453 (13)	−0.0009 (11)	0.0172 (11)	−0.0003 (11)
C37	0.0496 (13)	0.0384 (13)	0.0474 (13)	−0.0021 (11)	0.0205 (11)	−0.0032 (11)
C38	0.0432 (12)	0.0309 (12)	0.0441 (13)	−0.0027 (10)	0.0154 (10)	−0.0008 (9)
C39	0.0416 (12)	0.0320 (12)	0.0497 (13)	0.0006 (10)	0.0160 (10)	0.0045 (10)
C40	0.0442 (13)	0.0372 (13)	0.0620 (15)	−0.0034 (11)	0.0243 (12)	0.0009 (11)
C41	0.0514 (15)	0.0441 (16)	0.103 (2)	−0.0104 (13)	0.0248 (15)	−0.0047 (14)
C42	0.066 (2)	0.0514 (19)	0.155 (3)	−0.0193 (17)	0.030 (2)	−0.026 (2)
C43	0.070 (2)	0.075 (2)	0.121 (3)	−0.0296 (19)	0.019 (2)	−0.038 (2)
C44	0.0530 (16)	0.087 (2)	0.085 (2)	−0.0111 (16)	0.0109 (15)	−0.0094 (17)
C45	0.0468 (14)	0.0504 (15)	0.0647 (16)	−0.0019 (12)	0.0184 (13)	−0.0028 (12)
C46	0.0465 (13)	0.0360 (13)	0.0475 (13)	0.0005 (11)	0.0153 (11)	0.0030 (10)
C47	0.0367 (12)	0.0360 (12)	0.0424 (13)	0.0006 (10)	0.0149 (10)	0.0009 (10)
C48	0.0451 (13)	0.0486 (15)	0.0472 (14)	0.0054 (11)	0.0088 (11)	0.0034 (11)
C49	0.0690 (17)	0.0479 (16)	0.0749 (19)	0.0202 (14)	0.0259 (14)	0.0191 (14)
C50	0.100 (2)	0.0428 (16)	0.085 (2)	0.0117 (15)	0.0507 (18)	−0.0038 (15)
C51	0.096 (2)	0.0563 (18)	0.0586 (17)	0.0004 (16)	0.0301 (16)	−0.0132 (14)
C52	0.0687 (16)	0.0513 (16)	0.0428 (14)	0.0119 (13)	0.0147 (12)	0.0036 (11)
C53	0.0636 (15)	0.0316 (13)	0.0466 (13)	−0.0004 (11)	0.0256 (12)	0.0021 (10)
C54	0.0583 (16)	0.0473 (16)	0.0753 (18)	−0.0022 (13)	0.0206 (14)	0.0053 (13)
C55	0.0661 (18)	0.0563 (18)	0.091 (2)	0.0155 (15)	0.0257 (16)	0.0102 (15)
C56	0.091 (2)	0.0352 (15)	0.099 (2)	0.0119 (16)	0.0349 (18)	0.0062 (14)
C57	0.077 (2)	0.0391 (15)	0.095 (2)	−0.0107 (14)	0.0227 (16)	0.0020 (14)
C58	0.0559 (15)	0.0382 (14)	0.0706 (17)	0.0009 (12)	0.0233 (13)	0.0052 (12)
C59	0.164 (4)	0.097 (3)	0.089 (2)	0.030 (2)	0.086 (2)	0.0105 (19)
C60	0.0580 (18)	0.086 (2)	0.143 (3)	−0.0003 (17)	0.040 (2)	0.009 (2)

Geometric parameters (Å, º)

Cl1—C9	1.746 (2)	C27—H27	0.9300
Cl2—C45	1.743 (3)	C28—H28	0.9300
O1—C5	1.219 (3)	C29—H29A	0.9600
O2—C15	1.257 (3)	C29—H29B	0.9600
O3—C22	1.361 (2)	C29—H29C	0.9600
O3—C1	1.378 (3)	C30—H30A	0.9600
O4—C32	1.217 (3)	C30—H30B	0.9600
O5—C46	1.257 (2)	C30—H30C	0.9600
O6—C37	1.359 (2)	C31—C36	1.329 (3)
O6—C36	1.376 (3)	C31—C32	1.465 (3)
N1—C22	1.338 (3)	C31—C39	1.507 (3)
N1—C23	1.427 (3)	C32—C33	1.514 (4)
N1—H1	0.8600	C33—C34	1.513 (4)
N2—C37	1.334 (3)	C33—H33A	0.9700
N2—C53	1.422 (3)	C33—H33B	0.9700
N2—H2	0.8600	C34—C59	1.519 (4)
C1—C6	1.332 (3)	C34—C60	1.520 (4)
C1—C2	1.491 (3)	C34—C35	1.526 (3)
C2—C3	1.527 (3)	C35—C36	1.493 (3)
C2—H2A	0.9700	C35—H35A	0.9700
C2—H2B	0.9700	C35—H35B	0.9700
C3—C30	1.514 (4)	C37—C38	1.382 (3)
C3—C4	1.523 (3)	C38—C46	1.428 (3)
C3—C29	1.529 (3)	C38—C39	1.528 (3)
C4—C5	1.513 (3)	C39—C40	1.531 (3)
C4—H4A	0.9700	C39—H39	0.9800
C4—H4B	0.9700	C40—C45	1.378 (3)
C5—C6	1.472 (3)	C40—C41	1.406 (3)
C6—C7	1.507 (3)	C41—C42	1.361 (4)
C7—C14	1.525 (3)	C41—H41	0.9300
C7—C8	1.535 (3)	C42—C43	1.359 (4)
C7—H7	0.9800	C42—H42	0.9300
C8—C9	1.375 (3)	C43—C44	1.382 (4)
C8—C13	1.407 (3)	C43—H43	0.9300
C9—C10	1.396 (3)	C44—C45	1.390 (4)
C10—C11	1.371 (4)	C44—H44	0.9300
C10—H10	0.9300	C46—C47	1.496 (3)
C11—C12	1.362 (4)	C47—C52	1.377 (3)
C11—H11	0.9300	C47—C48	1.391 (3)
C12—C13	1.368 (4)	C48—C49	1.383 (3)
C12—H12	0.9300	C48—H48	0.9300
C13—H13	0.9300	C49—C50	1.365 (4)
C14—C22	1.381 (3)	C49—H49	0.9300
C14—C15	1.428 (3)	C50—C51	1.364 (4)
C15—C16	1.497 (3)	C50—H50	0.9300
C16—C21	1.378 (3)	C51—C52	1.378 (3)
C16—C17	1.384 (3)	C51—H51	0.9300
C17—C18	1.378 (3)	C52—H52	0.9300
C17—H17	0.9300	C53—C58	1.374 (3)
C18—C19	1.366 (3)	C53—C54	1.376 (3)
C18—H18	0.9300	C54—C55	1.380 (3)
C19—C20	1.364 (3)	C54—H54	0.9300
C19—H19	0.9300	C55—C56	1.363 (4)
C20—C21	1.384 (3)	C55—H55	0.9300
C20—H20	0.9300	C56—C57	1.373 (4)
C21—H21	0.9300	C56—H56	0.9300
C23—C24	1.382 (3)	C57—C58	1.384 (3)
C23—C28	1.384 (3)	C57—H57	0.9300
C24—C25	1.378 (3)	C58—H58	0.9300
C24—H24	0.9300	C59—H59A	0.9600
C25—C26	1.374 (4)	C59—H59B	0.9600
C25—H25	0.9300	C59—H59C	0.9600
C26—C27	1.367 (4)	C60—H60A	0.9600
C26—H26	0.9300	C60—H60B	0.9600
C27—C28	1.382 (3)	C60—H60C	0.9600
C22—O3—C1	119.11 (17)	H30A—C30—H30B	109.5
C37—O6—C36	118.84 (17)	C3—C30—H30C	109.5
C22—N1—C23	128.92 (19)	H30A—C30—H30C	109.5
C22—N1—H1	115.5	H30B—C30—H30C	109.5
C23—N1—H1	115.5	C36—C31—C32	118.2 (2)
C37—N2—C53	128.33 (19)	C36—C31—C39	122.77 (19)
C37—N2—H2	115.8	C32—C31—C39	118.9 (2)
C53—N2—H2	115.8	O4—C32—C31	121.2 (2)
C6—C1—O3	122.4 (2)	O4—C32—C33	121.8 (2)
C6—C1—C2	127.1 (2)	C31—C32—C33	116.9 (2)
O3—C1—C2	110.48 (19)	C34—C33—C32	115.1 (2)
C1—C2—C3	111.9 (2)	C34—C33—H33A	108.5
C1—C2—H2A	109.2	C32—C33—H33A	108.5
C3—C2—H2A	109.2	C34—C33—H33B	108.5
C1—C2—H2B	109.2	C32—C33—H33B	108.5
C3—C2—H2B	109.2	H33A—C33—H33B	107.5
H2A—C2—H2B	107.9	C33—C34—C59	110.7 (2)
C30—C3—C4	110.6 (2)	C33—C34—C60	111.0 (3)
C30—C3—C2	109.5 (2)	C59—C34—C60	108.5 (2)
C4—C3—C2	107.7 (2)	C33—C34—C35	108.4 (2)
C30—C3—C29	108.8 (2)	C59—C34—C35	109.3 (2)
C4—C3—C29	110.5 (2)	C60—C34—C35	108.9 (2)
C2—C3—C29	109.7 (2)	C36—C35—C34	112.1 (2)
C5—C4—C3	114.9 (2)	C36—C35—H35A	109.2
C5—C4—H4A	108.5	C34—C35—H35A	109.2
C3—C4—H4A	108.5	C36—C35—H35B	109.2
C5—C4—H4B	108.5	C34—C35—H35B	109.2
C3—C4—H4B	108.5	H35A—C35—H35B	107.9
H4A—C4—H4B	107.5	C31—C36—O6	122.49 (19)
O1—C5—C6	120.7 (2)	C31—C36—C35	127.2 (2)
O1—C5—C4	121.6 (2)	O6—C36—C35	110.28 (19)
C6—C5—C4	117.6 (2)	N2—C37—O6	111.66 (19)
C1—C6—C5	117.6 (2)	N2—C37—C38	124.7 (2)
C1—C6—C7	122.73 (19)	O6—C37—C38	123.61 (19)
C5—C6—C7	119.6 (2)	C37—C38—C46	118.54 (19)
C6—C7—C14	110.85 (17)	C37—C38—C39	119.05 (18)
C6—C7—C8	112.51 (17)	C46—C38—C39	122.18 (18)
C14—C7—C8	113.46 (17)	C31—C39—C38	110.28 (17)
C6—C7—H7	106.5	C31—C39—C40	112.94 (17)
C14—C7—H7	106.5	C38—C39—C40	113.48 (17)
C8—C7—H7	106.5	C31—C39—H39	106.5
C9—C8—C13	116.6 (2)	C38—C39—H39	106.5
C9—C8—C7	124.7 (2)	C40—C39—H39	106.5
C13—C8—C7	118.71 (19)	C45—C40—C41	116.1 (2)
C8—C9—C10	121.8 (2)	C45—C40—C39	125.1 (2)
C8—C9—Cl1	121.57 (18)	C41—C40—C39	118.8 (2)
C10—C9—Cl1	116.61 (19)	C42—C41—C40	122.3 (3)
C11—C10—C9	119.4 (3)	C42—C41—H41	118.9
C11—C10—H10	120.3	C40—C41—H41	118.9
C9—C10—H10	120.3	C43—C42—C41	120.4 (3)
C12—C11—C10	120.2 (3)	C43—C42—H42	119.8
C12—C11—H11	119.9	C41—C42—H42	119.8
C10—C11—H11	119.9	C42—C43—C44	119.9 (3)
C11—C12—C13	120.2 (3)	C42—C43—H43	120.1
C11—C12—H12	119.9	C44—C43—H43	120.1
C13—C12—H12	119.9	C43—C44—C45	119.3 (3)
C12—C13—C8	121.7 (2)	C43—C44—H44	120.3
C12—C13—H13	119.1	C45—C44—H44	120.3
C8—C13—H13	119.1	C40—C45—C44	122.0 (3)
C22—C14—C15	118.79 (19)	C40—C45—Cl2	121.29 (19)
C22—C14—C7	119.26 (18)	C44—C45—Cl2	116.7 (2)
C15—C14—C7	121.84 (19)	O5—C46—C38	123.0 (2)
O2—C15—C14	123.7 (2)	O5—C46—C47	115.81 (19)
O2—C15—C16	117.43 (19)	C38—C46—C47	121.16 (19)
C14—C15—C16	118.89 (19)	C52—C47—C48	118.0 (2)
C21—C16—C17	118.5 (2)	C52—C47—C46	119.20 (19)
C21—C16—C15	121.2 (2)	C48—C47—C46	122.7 (2)
C17—C16—C15	120.24 (19)	C49—C48—C47	120.1 (2)
C18—C17—C16	119.9 (2)	C49—C48—H48	119.9
C18—C17—H17	120.0	C47—C48—H48	119.9
C16—C17—H17	120.0	C50—C49—C48	120.8 (2)
C19—C18—C17	121.1 (2)	C50—C49—H49	119.6
C19—C18—H18	119.4	C48—C49—H49	119.6
C17—C18—H18	119.4	C49—C50—C51	119.5 (3)
C20—C19—C18	119.4 (2)	C49—C50—H50	120.3
C20—C19—H19	120.3	C51—C50—H50	120.3
C18—C19—H19	120.3	C50—C51—C52	120.4 (3)
C19—C20—C21	120.1 (2)	C50—C51—H51	119.8
C19—C20—H20	119.9	C52—C51—H51	119.8
C21—C20—H20	119.9	C47—C52—C51	121.2 (2)
C16—C21—C20	120.8 (2)	C47—C52—H52	119.4
C16—C21—H21	119.6	C51—C52—H52	119.4
C20—C21—H21	119.6	C58—C53—C54	120.0 (2)
N1—C22—O3	111.66 (18)	C58—C53—N2	118.1 (2)
N1—C22—C14	124.74 (19)	C54—C53—N2	121.9 (2)
O3—C22—C14	123.59 (18)	C53—C54—C55	119.7 (2)
C24—C23—C28	119.6 (2)	C53—C54—H54	120.2
C24—C23—N1	117.2 (2)	C55—C54—H54	120.2
C28—C23—N1	123.2 (2)	C56—C55—C54	120.7 (3)
C25—C24—C23	119.8 (2)	C56—C55—H55	119.6
C25—C24—H24	120.1	C54—C55—H55	119.6
C23—C24—H24	120.1	C55—C56—C57	119.6 (3)
C24—C25—C26	120.7 (3)	C55—C56—H56	120.2
C24—C25—H25	119.6	C57—C56—H56	120.2
C26—C25—H25	119.6	C56—C57—C58	120.3 (3)
C27—C26—C25	119.4 (2)	C56—C57—H57	119.8
C27—C26—H26	120.3	C58—C57—H57	119.8
C25—C26—H26	120.3	C53—C58—C57	119.7 (2)
C26—C27—C28	120.8 (3)	C53—C58—H58	120.2
C26—C27—H27	119.6	C57—C58—H58	120.2
C28—C27—H27	119.6	C34—C59—H59A	109.5
C27—C28—C23	119.6 (2)	C34—C59—H59B	109.5
C27—C28—H28	120.2	H59A—C59—H59B	109.5
C23—C28—H28	120.2	C34—C59—H59C	109.5
C3—C29—H29A	109.5	H59A—C59—H59C	109.5
C3—C29—H29B	109.5	H59B—C59—H59C	109.5
H29A—C29—H29B	109.5	C34—C60—H60A	109.5
C3—C29—H29C	109.5	C34—C60—H60B	109.5
H29A—C29—H29C	109.5	H60A—C60—H60B	109.5
H29B—C29—H29C	109.5	C34—C60—H60C	109.5
C3—C30—H30A	109.5	H60A—C60—H60C	109.5
C3—C30—H30B	109.5	H60B—C60—H60C	109.5
C22—O3—C1—C6	9.2 (3)	C36—C31—C32—O4	−177.9 (3)
C22—O3—C1—C2	−170.82 (19)	C39—C31—C32—O4	−1.9 (4)
C6—C1—C2—C3	21.3 (3)	C36—C31—C32—C33	−2.0 (4)
O3—C1—C2—C3	−158.70 (19)	C39—C31—C32—C33	174.0 (2)
C1—C2—C3—C30	72.4 (3)	O4—C32—C33—C34	−151.4 (3)
C1—C2—C3—C4	−48.0 (3)	C31—C32—C33—C34	32.7 (4)
C1—C2—C3—C29	−168.3 (2)	C32—C33—C34—C59	−173.4 (3)
C30—C3—C4—C5	−66.2 (3)	C32—C33—C34—C60	66.1 (3)
C2—C3—C4—C5	53.4 (3)	C32—C33—C34—C35	−53.5 (4)
C29—C3—C4—C5	173.2 (2)	C33—C34—C35—C36	45.0 (3)
C3—C4—C5—O1	153.7 (3)	C59—C34—C35—C36	165.7 (2)
C3—C4—C5—C6	−29.6 (3)	C60—C34—C35—C36	−75.9 (3)
O3—C1—C6—C5	−174.8 (2)	C32—C31—C36—O6	174.5 (2)
C2—C1—C6—C5	5.3 (4)	C39—C31—C36—O6	−1.4 (3)
O3—C1—C6—C7	2.3 (3)	C32—C31—C36—C35	−5.0 (4)
C2—C1—C6—C7	−177.7 (2)	C39—C31—C36—C35	179.2 (2)
O1—C5—C6—C1	175.5 (2)	C37—O6—C36—C31	−11.3 (3)
C4—C5—C6—C1	−1.2 (3)	C37—O6—C36—C35	168.24 (19)
O1—C5—C6—C7	−1.6 (4)	C34—C35—C36—C31	−18.1 (4)
C4—C5—C6—C7	−178.4 (2)	C34—C35—C36—O6	162.4 (2)
C1—C6—C7—C14	−13.0 (3)	C53—N2—C37—O6	−4.5 (3)
C5—C6—C7—C14	163.98 (19)	C53—N2—C37—C38	176.3 (2)
C1—C6—C7—C8	115.2 (2)	C36—O6—C37—N2	−170.73 (19)
C5—C6—C7—C8	−67.8 (3)	C36—O6—C37—C38	8.4 (3)
C6—C7—C8—C9	−71.9 (3)	N2—C37—C38—C46	0.2 (3)
C14—C7—C8—C9	55.0 (3)	O6—C37—C38—C46	−178.9 (2)
C6—C7—C8—C13	110.8 (2)	N2—C37—C38—C39	−174.4 (2)
C14—C7—C8—C13	−122.3 (2)	O6—C37—C38—C39	6.6 (3)
C13—C8—C9—C10	2.5 (3)	C36—C31—C39—C38	14.8 (3)
C7—C8—C9—C10	−174.8 (2)	C32—C31—C39—C38	−161.0 (2)
C13—C8—C9—Cl1	−176.65 (17)	C36—C31—C39—C40	−113.4 (2)
C7—C8—C9—Cl1	6.0 (3)	C32—C31—C39—C40	70.8 (3)
C8—C9—C10—C11	−0.8 (4)	C37—C38—C39—C31	−16.9 (3)
Cl1—C9—C10—C11	178.4 (2)	C46—C38—C39—C31	168.71 (19)
C9—C10—C11—C12	−0.9 (4)	C37—C38—C39—C40	110.9 (2)
C10—C11—C12—C13	0.8 (5)	C46—C38—C39—C40	−63.4 (3)
C11—C12—C13—C8	1.1 (4)	C31—C39—C40—C45	67.2 (3)
C9—C8—C13—C12	−2.6 (3)	C38—C39—C40—C45	−59.3 (3)
C7—C8—C13—C12	174.9 (2)	C31—C39—C40—C41	−113.9 (2)
C6—C7—C14—C22	13.5 (3)	C38—C39—C40—C41	119.6 (2)
C8—C7—C14—C22	−114.2 (2)	C45—C40—C41—C42	1.6 (4)
C6—C7—C14—C15	−170.45 (18)	C39—C40—C41—C42	−177.5 (2)
C8—C7—C14—C15	61.8 (3)	C40—C41—C42—C43	−0.7 (5)
C22—C14—C15—O2	−1.6 (3)	C41—C42—C43—C44	−0.6 (5)
C7—C14—C15—O2	−177.6 (2)	C42—C43—C44—C45	1.0 (5)
C22—C14—C15—C16	177.49 (19)	C41—C40—C45—C44	−1.2 (4)
C7—C14—C15—C16	1.4 (3)	C39—C40—C45—C44	177.8 (2)
O2—C15—C16—C21	−106.1 (2)	C41—C40—C45—Cl2	178.65 (18)
C14—C15—C16—C21	74.8 (3)	C39—C40—C45—Cl2	−2.4 (3)
O2—C15—C16—C17	73.0 (3)	C43—C44—C45—C40	−0.1 (4)
C14—C15—C16—C17	−106.1 (2)	C43—C44—C45—Cl2	−179.9 (2)
C21—C16—C17—C18	−1.0 (3)	C37—C38—C46—O5	−0.7 (3)
C15—C16—C17—C18	179.9 (2)	C39—C38—C46—O5	173.7 (2)
C16—C17—C18—C19	0.9 (4)	C37—C38—C46—C47	−179.2 (2)
C17—C18—C19—C20	−0.1 (4)	C39—C38—C46—C47	−4.8 (3)
C18—C19—C20—C21	−0.5 (4)	O5—C46—C47—C52	−53.8 (3)
C17—C16—C21—C20	0.3 (3)	C38—C46—C47—C52	124.9 (2)
C15—C16—C21—C20	179.5 (2)	O5—C46—C47—C48	122.9 (2)
C19—C20—C21—C16	0.4 (4)	C38—C46—C47—C48	−58.4 (3)
C23—N1—C22—O3	2.4 (3)	C52—C47—C48—C49	−0.8 (3)
C23—N1—C22—C14	−178.3 (2)	C46—C47—C48—C49	−177.6 (2)
C1—O3—C22—N1	171.06 (18)	C47—C48—C49—C50	−0.8 (4)
C1—O3—C22—C14	−8.3 (3)	C48—C49—C50—C51	1.2 (4)
C15—C14—C22—N1	0.7 (3)	C49—C50—C51—C52	0.0 (4)
C7—C14—C22—N1	176.91 (19)	C48—C47—C52—C51	2.0 (3)
C15—C14—C22—O3	179.97 (19)	C46—C47—C52—C51	178.9 (2)
C7—C14—C22—O3	−3.9 (3)	C50—C51—C52—C47	−1.6 (4)
C22—N1—C23—C24	−143.7 (2)	C37—N2—C53—C58	132.7 (3)
C22—N1—C23—C28	38.6 (3)	C37—N2—C53—C54	−49.9 (4)
C28—C23—C24—C25	−1.4 (4)	C58—C53—C54—C55	−1.0 (4)
N1—C23—C24—C25	−179.2 (2)	N2—C53—C54—C55	−178.4 (2)
C23—C24—C25—C26	0.3 (4)	C53—C54—C55—C56	0.8 (4)
C24—C25—C26—C27	1.1 (5)	C54—C55—C56—C57	−0.3 (5)
C25—C26—C27—C28	−1.5 (4)	C55—C56—C57—C58	0.1 (5)
C26—C27—C28—C23	0.4 (4)	C54—C53—C58—C57	0.7 (4)
C24—C23—C28—C27	1.1 (3)	N2—C53—C58—C57	178.2 (2)
N1—C23—C28—C27	178.7 (2)	C56—C57—C58—C53	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3^i	0.93	2.55	3.409 (3)	154
C24—H24···O1^i	0.93	2.51	3.393 (3)	158
N1—H1···O2	0.86	1.90	2.582 (2)	136
N2—H2···O5	0.86	1.88	2.559 (2)	135
C28—H28···O3	0.93	2.42	2.811 (3)	106
C58—H58···O4^ii	0.93	2.52	3.446 (3)	175

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