Ethyl 2-(1H-indol-3-yl)-5-[1-(4-methoxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-4-nitro-3-(p-tol­yl)pyrrolidine-2-carboxyl­ate

Sruthi, G.T.; Gayathri, D.; Velmurugan, D.; Ravikumar, K.; Arumugam, N.

doi:10.1107/S1600536807014274

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Ethyl 2-(1H-indol-3-yl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitro-3-(p-tolyl)pyrrolidine-2-carboxylate

G. T. Sruthi, D. Gayathri, D. Velmurugan, K. Ravikumar and N. Arumugam

In the title molecule, C₃₉H₃₈N₄O₆, the pyrrolidine ring adopts a twist conformation. The crystal packing is stabilized by N—H

O and C—H

O intermolecular interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014274/ci2318sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014274/ci2318Isup2.hkl Contains datablock I

CCDC reference: 647145

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.147
Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.80 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.51 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C35
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C36
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.01
           From the CIF: _reflns_number_total               4167
           Count of symmetry unique reflns         4258
           Completeness (_total/calc)             97.86%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT792_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C24    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C25    = ...          S

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

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

Computing details top

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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Ethyl 2-(1H-indol-3-yl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]- 4-nitro-3-(p-tolyl)pyrrolidine-2-carboxylate top

Crystal data top

C₃₉H₃₈N₄O₆	F(000) = 1392
M_r = 658.73	D_x = 1.245 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2058 reflections
a = 11.2689 (8) Å	θ = 1.1–25.0°
b = 35.612 (2) Å	µ = 0.09 mm⁻¹
c = 8.8848 (6) Å	T = 293 K
β = 99.785 (1)°	Block, colourless
V = 3513.7 (4) Å³	0.27 × 0.24 × 0.23 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3771 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 28.0°, θ_min = 1.1°
ω scans	h = −14→14
20233 measured reflections	k = −46→46
4167 independent reflections	l = −11→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0919P)² + 0.4686P] where P = (F_o² + 2F_c²)/3
4167 reflections	(Δ/σ)_max = 0.001
446 parameters	Δρ_max = 0.36 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5607 (2)	0.09808 (7)	0.6239 (3)	0.0421 (5)
C2	0.4572 (2)	0.06998 (7)	0.6594 (3)	0.0411 (5)
H2	0.4963	0.0466	0.6989	0.049*
C3	0.4086 (2)	0.08909 (7)	0.7907 (3)	0.0448 (5)
H3	0.3204	0.0888	0.7724	0.054*
C4	0.4569 (2)	0.13011 (7)	0.7897 (3)	0.0442 (5)
H4	0.4051	0.1433	0.7064	0.053*
C5	0.5317 (2)	0.11692 (8)	0.4665 (3)	0.0463 (5)
H5A	0.5130	0.0977	0.3886	0.056*
H5B	0.4611	0.1327	0.4630	0.056*
C6	0.6350 (2)	0.14048 (8)	0.4320 (3)	0.0469 (5)
C7	0.6778 (3)	0.17310 (8)	0.5011 (4)	0.0572 (7)
H7	0.6454	0.1852	0.5774	0.069*
C8	0.7981 (3)	0.16114 (8)	0.3337 (3)	0.0518 (6)
C9	0.8889 (3)	0.16055 (11)	0.2442 (4)	0.0668 (9)
H9	0.9473	0.1792	0.2537	0.080*
C10	0.8897 (3)	0.13176 (13)	0.1425 (5)	0.0745 (10)
H10	0.9490	0.1311	0.0814	0.089*
C11	0.8035 (4)	0.10338 (11)	0.1284 (4)	0.0679 (9)
H11	0.8061	0.0842	0.0579	0.082*
C12	0.7145 (3)	0.10328 (9)	0.2173 (3)	0.0544 (7)
H12	0.6572	0.0842	0.2069	0.065*
C13	0.7111 (2)	0.13203 (7)	0.3231 (3)	0.0442 (5)
C14	0.6807 (2)	0.07714 (8)	0.6373 (3)	0.0480 (6)
C15	0.7958 (4)	0.03507 (15)	0.5185 (5)	0.0878 (13)
H15A	0.8545	0.0537	0.5005	0.105*
H15B	0.8253	0.0229	0.6153	0.105*
C16	0.7802 (6)	0.00776 (18)	0.3974 (8)	0.115 (2)
H16A	0.7280	−0.0119	0.4207	0.172*
H16B	0.8570	−0.0027	0.3873	0.172*
H16C	0.7452	0.0197	0.3033	0.172*
C17	0.3610 (2)	0.06007 (7)	0.5243 (3)	0.0436 (5)
C18	0.3767 (3)	0.02870 (8)	0.4378 (4)	0.0575 (7)
H18	0.4458	0.0142	0.4632	0.069*
C19	0.2910 (4)	0.01870 (11)	0.3141 (5)	0.0704 (9)
H19	0.3041	−0.0023	0.2571	0.084*
C20	0.1863 (3)	0.03908 (11)	0.2727 (4)	0.0691 (9)
C21	0.1706 (3)	0.07023 (12)	0.3596 (5)	0.0714 (9)
H21	0.1006	0.0844	0.3350	0.086*
C22	0.2566 (3)	0.08085 (10)	0.4824 (4)	0.0610 (8)
H22	0.2442	0.1022	0.5377	0.073*
C23	0.0926 (5)	0.02713 (19)	0.1372 (7)	0.1093 (18)
H23A	0.1304	0.0243	0.0488	0.164*
H23B	0.0309	0.0459	0.1175	0.164*
H23C	0.0576	0.0037	0.1597	0.164*
C24	0.4591 (3)	0.15366 (8)	0.9319 (3)	0.0488 (6)
H24	0.5110	0.1428	1.0210	0.059*
C25	0.3338 (3)	0.16696 (9)	0.9692 (4)	0.0572 (7)
H25	0.3288	0.1628	1.0770	0.069*
C26	0.2190 (3)	0.15520 (10)	0.8664 (4)	0.0596 (7)
C27	0.1818 (4)	0.17296 (12)	0.7266 (5)	0.0732 (9)
H27	0.2273	0.1926	0.6969	0.088*
C28	0.0773 (4)	0.16154 (15)	0.6312 (6)	0.0878 (13)
H28	0.0531	0.1737	0.5385	0.105*
C29	0.0102 (4)	0.13284 (16)	0.6715 (6)	0.0881 (13)
H29	−0.0592	0.1252	0.6064	0.106*
C30	0.0455 (4)	0.11496 (16)	0.8098 (6)	0.0856 (12)
H30	−0.0001	0.0953	0.8383	0.103*
C31	0.1492 (3)	0.12648 (13)	0.9063 (5)	0.0711 (9)
H31	0.1718	0.1145	0.9998	0.085*
C32	0.3792 (4)	0.20635 (9)	0.9437 (4)	0.0647 (8)
C33	0.5897 (3)	0.21341 (8)	0.8833 (4)	0.0606 (8)
C34	0.5759 (5)	0.24732 (13)	0.8060 (7)	0.0955 (15)
H34	0.4993	0.2568	0.7711	0.115*
C35	0.6751 (5)	0.26671 (13)	0.7813 (8)	0.1046 (18)
H35	0.6653	0.2894	0.7291	0.126*
C36	0.7915 (4)	0.25308 (12)	0.8329 (5)	0.0817 (11)
C37	0.8034 (4)	0.21860 (13)	0.9044 (6)	0.0866 (13)
H37	0.8795	0.2084	0.9357	0.104*
C38	0.7028 (4)	0.19914 (10)	0.9296 (5)	0.0773 (11)
H38	0.7119	0.1760	0.9789	0.093*
C39	1.0005 (5)	0.2577 (2)	0.8122 (8)	0.1116 (18)
H39A	1.0356	0.2533	0.9169	0.167*
H39B	1.0522	0.2738	0.7658	0.167*
H39C	0.9911	0.2342	0.7585	0.167*
N1	0.5742 (2)	0.12637 (6)	0.7444 (3)	0.0465 (5)
H1	0.6387	0.1384	0.7812	0.056*
N2	0.7755 (3)	0.18543 (7)	0.4419 (3)	0.0608 (6)
H2A	0.8161	0.2055	0.4694	0.073*
N3	0.4581 (3)	0.07141 (6)	0.9431 (3)	0.0527 (5)
N4	0.4852 (2)	0.19376 (7)	0.9102 (3)	0.0578 (6)
O1	0.7643 (2)	0.08165 (9)	0.7392 (4)	0.0707 (7)
O2	0.68003 (19)	0.05323 (6)	0.5243 (3)	0.0599 (5)
O3	0.5522 (3)	0.05385 (7)	0.9573 (4)	0.0714 (6)
O4	0.4039 (3)	0.07666 (10)	1.0473 (4)	0.0901 (9)
O5	0.3384 (3)	0.23761 (8)	0.9479 (5)	0.0920 (9)
O6	0.8856 (4)	0.27505 (10)	0.8052 (5)	0.1065 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0368 (11)	0.0387 (11)	0.0528 (13)	−0.0023 (9)	0.0129 (10)	0.0003 (10)
C2	0.0366 (11)	0.0358 (11)	0.0526 (13)	0.0001 (9)	0.0128 (10)	−0.0016 (10)
C3	0.0413 (12)	0.0432 (12)	0.0520 (13)	−0.0018 (10)	0.0137 (10)	−0.0043 (10)
C4	0.0445 (12)	0.0376 (11)	0.0513 (13)	0.0029 (9)	0.0103 (10)	−0.0004 (10)
C5	0.0408 (12)	0.0473 (13)	0.0516 (14)	−0.0001 (10)	0.0100 (10)	0.0026 (11)
C6	0.0471 (13)	0.0438 (13)	0.0505 (13)	−0.0012 (10)	0.0097 (11)	0.0053 (11)
C7	0.0687 (18)	0.0442 (14)	0.0602 (16)	−0.0051 (13)	0.0155 (14)	0.0026 (12)
C8	0.0507 (14)	0.0510 (14)	0.0513 (14)	−0.0074 (11)	0.0020 (11)	0.0115 (11)
C9	0.0495 (16)	0.083 (2)	0.069 (2)	−0.0145 (15)	0.0131 (14)	0.0167 (17)
C10	0.061 (2)	0.100 (3)	0.068 (2)	0.0071 (18)	0.0276 (17)	0.0118 (19)
C11	0.072 (2)	0.075 (2)	0.0591 (18)	0.0075 (17)	0.0180 (16)	−0.0044 (16)
C12	0.0583 (16)	0.0554 (16)	0.0485 (15)	−0.0034 (13)	0.0056 (12)	0.0013 (11)
C13	0.0401 (12)	0.0474 (13)	0.0438 (12)	−0.0028 (10)	0.0036 (9)	0.0087 (10)
C14	0.0400 (13)	0.0509 (13)	0.0559 (15)	0.0018 (10)	0.0163 (11)	0.0019 (11)
C15	0.078 (2)	0.105 (3)	0.085 (3)	0.041 (2)	0.028 (2)	−0.001 (2)
C16	0.124 (4)	0.094 (4)	0.131 (5)	0.034 (3)	0.035 (4)	−0.025 (3)
C17	0.0408 (12)	0.0389 (12)	0.0532 (14)	−0.0060 (9)	0.0141 (10)	−0.0053 (10)
C18	0.0557 (16)	0.0475 (14)	0.0702 (18)	0.0003 (12)	0.0135 (13)	−0.0138 (13)
C19	0.081 (2)	0.0592 (18)	0.071 (2)	−0.0078 (17)	0.0129 (17)	−0.0224 (16)
C20	0.064 (2)	0.073 (2)	0.0674 (19)	−0.0174 (16)	0.0034 (15)	−0.0104 (16)
C21	0.0495 (17)	0.077 (2)	0.083 (2)	0.0050 (15)	−0.0022 (16)	−0.0092 (18)
C22	0.0519 (16)	0.0549 (16)	0.075 (2)	0.0055 (13)	0.0056 (14)	−0.0173 (14)
C23	0.101 (4)	0.121 (4)	0.093 (3)	−0.018 (3)	−0.019 (3)	−0.033 (3)
C24	0.0532 (14)	0.0437 (13)	0.0483 (13)	0.0076 (11)	0.0053 (11)	−0.0022 (11)
C25	0.0656 (18)	0.0569 (16)	0.0505 (15)	0.0136 (13)	0.0139 (13)	−0.0074 (12)
C26	0.0527 (15)	0.0657 (18)	0.0634 (17)	0.0172 (13)	0.0182 (13)	−0.0042 (14)
C27	0.067 (2)	0.072 (2)	0.079 (2)	0.0141 (17)	0.0102 (17)	0.0052 (18)
C28	0.071 (2)	0.106 (3)	0.081 (3)	0.025 (2)	−0.004 (2)	0.010 (2)
C29	0.061 (2)	0.112 (4)	0.089 (3)	0.006 (2)	0.005 (2)	−0.001 (3)
C30	0.0565 (19)	0.106 (3)	0.099 (3)	−0.002 (2)	0.027 (2)	0.003 (3)
C31	0.0571 (19)	0.093 (3)	0.068 (2)	0.0105 (17)	0.0244 (16)	0.0047 (18)
C32	0.078 (2)	0.0521 (16)	0.0630 (18)	0.0120 (15)	0.0103 (16)	−0.0079 (14)
C33	0.081 (2)	0.0403 (14)	0.0606 (17)	−0.0004 (13)	0.0109 (15)	−0.0088 (12)
C34	0.095 (3)	0.067 (2)	0.133 (4)	0.024 (2)	0.045 (3)	0.028 (3)
C35	0.121 (4)	0.062 (2)	0.143 (5)	0.015 (2)	0.057 (4)	0.034 (3)
C36	0.101 (3)	0.062 (2)	0.084 (3)	−0.014 (2)	0.021 (2)	−0.0041 (19)
C37	0.074 (2)	0.073 (2)	0.101 (3)	−0.0156 (19)	−0.019 (2)	0.004 (2)
C38	0.081 (2)	0.0535 (17)	0.086 (2)	−0.0122 (16)	−0.0182 (19)	0.0099 (17)
C39	0.085 (3)	0.119 (4)	0.125 (5)	−0.029 (3)	0.001 (3)	−0.013 (3)
N1	0.0437 (11)	0.0420 (11)	0.0553 (13)	−0.0055 (8)	0.0129 (10)	−0.0067 (9)
N2	0.0701 (16)	0.0450 (12)	0.0661 (15)	−0.0171 (11)	0.0086 (12)	0.0034 (11)
N3	0.0647 (15)	0.0394 (11)	0.0560 (13)	−0.0092 (10)	0.0165 (11)	−0.0017 (10)
N4	0.0670 (16)	0.0402 (11)	0.0657 (15)	0.0071 (10)	0.0099 (12)	−0.0078 (10)
O1	0.0427 (10)	0.1000 (19)	0.0674 (14)	0.0107 (11)	0.0035 (10)	−0.0089 (12)
O2	0.0529 (11)	0.0602 (12)	0.0685 (13)	0.0133 (9)	0.0161 (10)	−0.0060 (10)
O3	0.0772 (16)	0.0666 (14)	0.0655 (14)	0.0090 (12)	−0.0017 (12)	0.0010 (11)
O4	0.104 (2)	0.106 (2)	0.0697 (16)	0.0068 (17)	0.0420 (16)	0.0166 (15)
O5	0.108 (2)	0.0548 (13)	0.115 (2)	0.0287 (14)	0.0238 (18)	−0.0125 (14)
O6	0.114 (3)	0.082 (2)	0.130 (3)	−0.0224 (19)	0.041 (2)	0.002 (2)

Geometric parameters (Å, º) top

C1—N1	1.459 (3)	C20—C23	1.521 (6)
C1—C14	1.531 (4)	C21—C22	1.383 (5)
C1—C5	1.536 (4)	C21—H21	0.93
C1—C2	1.608 (3)	C22—H22	0.93
C2—C17	1.516 (4)	C23—H23A	0.96
C2—C3	1.530 (3)	C23—H23B	0.96
C2—H2	0.98	C23—H23C	0.96
C3—N3	1.511 (4)	C24—N4	1.477 (4)
C3—C4	1.559 (4)	C24—C25	1.577 (4)
C3—H3	0.98	C24—H24	0.98
C4—N1	1.452 (3)	C25—C26	1.511 (5)
C4—C24	1.513 (4)	C25—C32	1.523 (5)
C4—H4	0.98	C25—H25	0.98
C5—C6	1.508 (4)	C26—C31	1.373 (6)
C5—H5A	0.97	C26—C27	1.394 (5)
C5—H5B	0.97	C27—C28	1.390 (6)
C6—C7	1.363 (4)	C27—H27	0.93
C6—C13	1.430 (4)	C28—C29	1.355 (8)
C7—N2	1.371 (4)	C28—H28	0.93
C7—H7	0.93	C29—C30	1.382 (7)
C8—N2	1.349 (4)	C29—H29	0.93
C8—C9	1.399 (5)	C30—C31	1.388 (6)
C8—C13	1.418 (4)	C30—H30	0.93
C9—C10	1.368 (6)	C31—H31	0.93
C9—H9	0.93	C32—O5	1.207 (4)
C10—C11	1.392 (6)	C32—N4	1.355 (5)
C10—H10	0.93	C33—C38	1.368 (6)
C11—C12	1.379 (5)	C33—C34	1.385 (5)
C11—H11	0.93	C33—N4	1.425 (5)
C12—C13	1.394 (4)	C34—C35	1.363 (8)
C12—H12	0.93	C34—H34	0.93
C14—O1	1.201 (4)	C35—C36	1.400 (7)
C14—O2	1.316 (4)	C35—H35	0.93
C15—C16	1.439 (8)	C36—O6	1.374 (5)
C15—O2	1.465 (4)	C36—C37	1.379 (6)
C15—H15A	0.97	C37—C38	1.379 (6)
C15—H15B	0.97	C37—H37	0.93
C16—H16A	0.96	C38—H38	0.93
C16—H16B	0.96	C39—O6	1.426 (8)
C16—H16C	0.96	C39—H39A	0.96
C17—C18	1.385 (4)	C39—H39B	0.96
C17—C22	1.386 (4)	C39—H39C	0.96
C18—C19	1.381 (5)	N1—H1	0.86
C18—H18	0.93	N2—H2A	0.86
C19—C20	1.381 (6)	N3—O4	1.207 (4)
C19—H19	0.93	N3—O3	1.220 (4)
C20—C21	1.380 (6)

N1—C1—C14	107.4 (2)	C20—C21—H21	119.3
N1—C1—C5	110.2 (2)	C22—C21—H21	119.3
C14—C1—C5	109.4 (2)	C21—C22—C17	121.0 (3)
N1—C1—C2	105.9 (2)	C21—C22—H22	119.5
C14—C1—C2	110.0 (2)	C17—C22—H22	119.5
C5—C1—C2	113.7 (2)	C20—C23—H23A	109.5
C17—C2—C3	114.0 (2)	C20—C23—H23B	109.5
C17—C2—C1	115.8 (2)	H23A—C23—H23B	109.5
C3—C2—C1	103.78 (19)	C20—C23—H23C	109.5
C17—C2—H2	107.6	H23A—C23—H23C	109.5
C3—C2—H2	107.6	H23B—C23—H23C	109.5
C1—C2—H2	107.6	N4—C24—C4	113.7 (2)
N3—C3—C2	111.9 (2)	N4—C24—C25	86.7 (2)
N3—C3—C4	108.6 (2)	C4—C24—C25	117.0 (2)
C2—C3—C4	104.0 (2)	N4—C24—H24	112.3
N3—C3—H3	110.7	C4—C24—H24	112.3
C2—C3—H3	110.7	C25—C24—H24	112.3
C4—C3—H3	110.7	C26—C25—C32	116.1 (3)
N1—C4—C24	113.3 (2)	C26—C25—C24	119.7 (2)
N1—C4—C3	104.5 (2)	C32—C25—C24	84.8 (2)
C24—C4—C3	118.1 (2)	C26—C25—H25	111.2
N1—C4—H4	106.8	C32—C25—H25	111.2
C24—C4—H4	106.8	C24—C25—H25	111.2
C3—C4—H4	106.8	C31—C26—C27	118.0 (4)
C6—C5—C1	112.1 (2)	C31—C26—C25	121.3 (3)
C6—C5—H5A	109.2	C27—C26—C25	120.6 (3)
C1—C5—H5A	109.2	C28—C27—C26	120.4 (4)
C6—C5—H5B	109.2	C28—C27—H27	119.8
C1—C5—H5B	109.2	C26—C27—H27	119.8
H5A—C5—H5B	107.9	C29—C28—C27	120.9 (4)
C7—C6—C13	106.1 (3)	C29—C28—H28	119.6
C7—C6—C5	127.5 (3)	C27—C28—H28	119.6
C13—C6—C5	126.4 (2)	C28—C29—C30	119.5 (4)
C6—C7—N2	110.3 (3)	C28—C29—H29	120.2
C6—C7—H7	124.9	C30—C29—H29	120.2
N2—C7—H7	124.9	C29—C30—C31	119.9 (4)
N2—C8—C9	131.2 (3)	C29—C30—H30	120.1
N2—C8—C13	107.7 (3)	C31—C30—H30	120.1
C9—C8—C13	121.0 (3)	C26—C31—C30	121.3 (4)
C10—C9—C8	118.3 (3)	C26—C31—H31	119.3
C10—C9—H9	120.8	C30—C31—H31	119.3
C8—C9—H9	120.8	O5—C32—N4	131.8 (4)
C9—C10—C11	121.4 (3)	O5—C32—C25	134.8 (4)
C9—C10—H10	119.3	N4—C32—C25	93.4 (2)
C11—C10—H10	119.3	C38—C33—C34	119.6 (4)
C12—C11—C10	121.0 (3)	C38—C33—N4	121.4 (3)
C12—C11—H11	119.5	C34—C33—N4	119.0 (4)
C10—C11—H11	119.5	C35—C34—C33	119.7 (4)
C11—C12—C13	119.3 (3)	C35—C34—H34	120.1
C11—C12—H12	120.3	C33—C34—H34	120.1
C13—C12—H12	120.3	C34—C35—C36	121.3 (4)
C12—C13—C8	119.0 (3)	C34—C35—H35	119.4
C12—C13—C6	134.3 (3)	C36—C35—H35	119.4
C8—C13—C6	106.7 (2)	O6—C36—C37	124.9 (5)
O1—C14—O2	124.3 (3)	O6—C36—C35	116.9 (4)
O1—C14—C1	124.2 (3)	C37—C36—C35	118.2 (4)
O2—C14—C1	111.5 (2)	C38—C37—C36	120.3 (4)
C16—C15—O2	109.1 (4)	C38—C37—H37	119.9
C16—C15—H15A	109.9	C36—C37—H37	119.9
O2—C15—H15A	109.9	C33—C38—C37	120.9 (4)
C16—C15—H15B	109.9	C33—C38—H38	119.6
O2—C15—H15B	109.9	C37—C38—H38	119.6
H15A—C15—H15B	108.3	O6—C39—H39A	109.5
C15—C16—H16A	109.5	O6—C39—H39B	109.5
C15—C16—H16B	109.5	H39A—C39—H39B	109.5
H16A—C16—H16B	109.5	O6—C39—H39C	109.5
C15—C16—H16C	109.5	H39A—C39—H39C	109.5
H16A—C16—H16C	109.5	H39B—C39—H39C	109.5
H16B—C16—H16C	109.5	C4—N1—C1	106.3 (2)
C18—C17—C22	117.6 (3)	C4—N1—H1	126.9
C18—C17—C2	119.1 (2)	C1—N1—H1	126.9
C22—C17—C2	123.3 (2)	C8—N2—C7	109.2 (3)
C19—C18—C17	120.8 (3)	C8—N2—H2A	125.4
C19—C18—H18	119.6	C7—N2—H2A	125.4
C17—C18—H18	119.6	O4—N3—O3	123.0 (3)
C20—C19—C18	121.8 (3)	O4—N3—C3	117.7 (3)
C20—C19—H19	119.1	O3—N3—C3	119.2 (3)
C18—C19—H19	119.1	C32—N4—C33	131.2 (3)
C21—C20—C19	117.3 (3)	C32—N4—C24	95.1 (3)
C21—C20—C23	122.0 (4)	C33—N4—C24	133.3 (2)
C19—C20—C23	120.7 (4)	C14—O2—C15	115.0 (3)
C20—C21—C22	121.4 (3)	C36—O6—C39	117.9 (4)

N1—C1—C2—C17	133.3 (2)	N4—C24—C25—C26	116.5 (3)
C14—C1—C2—C17	−111.0 (2)	C4—C24—C25—C26	1.5 (4)
C5—C1—C2—C17	12.1 (3)	N4—C24—C25—C32	−0.7 (2)
N1—C1—C2—C3	7.6 (3)	C4—C24—C25—C32	−115.7 (3)
C14—C1—C2—C3	123.4 (2)	C32—C25—C26—C31	−159.2 (3)
C5—C1—C2—C3	−113.6 (2)	C24—C25—C26—C31	101.3 (4)
C17—C2—C3—N3	131.9 (2)	C32—C25—C26—C27	21.8 (4)
C1—C2—C3—N3	−101.3 (2)	C24—C25—C26—C27	−77.6 (4)
C17—C2—C3—C4	−111.1 (2)	C31—C26—C27—C28	−0.2 (5)
C1—C2—C3—C4	15.7 (3)	C25—C26—C27—C28	178.8 (4)
N3—C3—C4—N1	84.7 (3)	C26—C27—C28—C29	−0.5 (7)
C2—C3—C4—N1	−34.6 (3)	C27—C28—C29—C30	0.7 (8)
N3—C3—C4—C24	−42.2 (3)	C28—C29—C30—C31	0.0 (7)
C2—C3—C4—C24	−161.5 (2)	C27—C26—C31—C30	0.9 (5)
N1—C1—C5—C6	66.0 (3)	C25—C26—C31—C30	−178.1 (3)
C14—C1—C5—C6	−51.8 (3)	C29—C30—C31—C26	−0.8 (6)
C2—C1—C5—C6	−175.2 (2)	C26—C25—C32—O5	59.0 (6)
C1—C5—C6—C7	−68.4 (4)	C24—C25—C32—O5	179.6 (5)
C1—C5—C6—C13	108.9 (3)	C26—C25—C32—N4	−119.8 (3)
C13—C6—C7—N2	0.0 (3)	C24—C25—C32—N4	0.8 (3)
C5—C6—C7—N2	177.8 (3)	C38—C33—C34—C35	−2.1 (8)
N2—C8—C9—C10	179.6 (3)	N4—C33—C34—C35	179.1 (5)
C13—C8—C9—C10	2.0 (5)	C33—C34—C35—C36	−0.2 (9)
C8—C9—C10—C11	−0.7 (6)	C34—C35—C36—O6	−178.7 (5)
C9—C10—C11—C12	−0.3 (6)	C34—C35—C36—C37	2.6 (9)
C10—C11—C12—C13	−0.1 (5)	O6—C36—C37—C38	178.6 (5)
C11—C12—C13—C8	1.5 (4)	C35—C36—C37—C38	−2.8 (8)
C11—C12—C13—C6	−179.3 (3)	C34—C33—C38—C37	1.9 (7)
N2—C8—C13—C12	179.5 (3)	N4—C33—C38—C37	−179.3 (4)
C9—C8—C13—C12	−2.4 (4)	C36—C37—C38—C33	0.6 (7)
N2—C8—C13—C6	0.0 (3)	C24—C4—N1—C1	170.4 (2)
C9—C8—C13—C6	178.1 (3)	C3—C4—N1—C1	40.6 (3)
C7—C6—C13—C12	−179.4 (3)	C14—C1—N1—C4	−147.6 (2)
C5—C6—C13—C12	2.8 (5)	C5—C1—N1—C4	93.4 (2)
C7—C6—C13—C8	0.0 (3)	C2—C1—N1—C4	−30.0 (3)
C5—C6—C13—C8	−177.8 (3)	C9—C8—N2—C7	−177.8 (3)
N1—C1—C14—O1	6.5 (4)	C13—C8—N2—C7	0.0 (3)
C5—C1—C14—O1	126.1 (3)	C6—C7—N2—C8	0.0 (4)
C2—C1—C14—O1	−108.4 (3)	C2—C3—N3—O4	−160.4 (3)
N1—C1—C14—O2	−174.4 (2)	C4—C3—N3—O4	85.4 (3)
C5—C1—C14—O2	−54.8 (3)	C2—C3—N3—O3	22.4 (3)
C2—C1—C14—O2	70.7 (3)	C4—C3—N3—O3	−91.9 (3)
C3—C2—C17—C18	−148.5 (3)	O5—C32—N4—C33	7.2 (7)
C1—C2—C17—C18	91.2 (3)	C25—C32—N4—C33	−173.9 (3)
C3—C2—C17—C22	31.3 (4)	O5—C32—N4—C24	−179.7 (5)
C1—C2—C17—C22	−89.0 (3)	C25—C32—N4—C24	−0.8 (3)
C22—C17—C18—C19	0.1 (5)	C38—C33—N4—C32	144.6 (4)
C2—C17—C18—C19	179.9 (3)	C34—C33—N4—C32	−36.6 (6)
C17—C18—C19—C20	−0.7 (6)	C38—C33—N4—C24	−25.9 (6)
C18—C19—C20—C21	0.4 (6)	C34—C33—N4—C24	152.9 (4)
C18—C19—C20—C23	−179.2 (5)	C4—C24—N4—C32	118.9 (3)
C19—C20—C21—C22	0.5 (6)	C25—C24—N4—C32	0.8 (3)
C23—C20—C21—C22	−179.9 (5)	C4—C24—N4—C33	−68.2 (4)
C20—C21—C22—C17	−1.2 (6)	C25—C24—N4—C33	173.6 (3)
C18—C17—C22—C21	0.9 (5)	O1—C14—O2—C15	−7.5 (5)
C2—C17—C22—C21	−178.9 (3)	C1—C14—O2—C15	173.4 (3)
N1—C4—C24—N4	67.8 (3)	C16—C15—O2—C14	175.7 (4)
C3—C4—C24—N4	−169.6 (2)	C37—C36—O6—C39	17.7 (7)
N1—C4—C24—C25	166.6 (2)	C35—C36—O6—C39	−161.0 (5)
C3—C4—C24—C25	−70.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3	0.98	2.29	2.742 (4)	107
N2—H2A···O5ⁱ	0.86	2.05	2.829 (4)	149
C12—H12···O3ⁱⁱ	0.93	2.57	3.216 (4)	127
C16—H16A···O3ⁱⁱⁱ	0.96	2.55	3.488 (7)	167

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

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