Crystal structure of methyl 3′-benzamido-4′-(4-meth­oxy­phen­yl)-1′-methyl­spiro­[indeno­[1,2-b]quinoxaline-11,2′-pyrrolidine]-3′-carboxyl­ate

In the title compound, the mean plane through pyrrolidine ring is approximately orthogonal to the mean plane of the cyclo­pentane ring, making a dihedral angle of 88.78 (10)°. An intra­molecular N—H...N inter­action is observed. The crystal packing features C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.140
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...    -11.275 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.860 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)       0.02 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C16     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C26     (Centro SPGR)          R Verify
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        755 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          10 Note

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

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Methyl 3'-benzamido-4'-(4-methoxyphenyl)-1'-methylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-carboxylate

Crystal data

C35H30N4O3	Z = 2
Mr = 554.63	F(000) = 584
Triclinic, P1	Dx = 1.289 Mg m^−3
a = 10.1194 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8066 (4) Å	Cell parameters from 42296 reflections
c = 14.9948 (6) Å	θ = 2.1–30.6°
α = 110.57 (2)°	µ = 0.08 mm^−1
β = 97.10 (2)°	T = 293 K
γ = 106.17 (2)°	Block, colourless
V = 1429.1 (4) Å^3	0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4733 reflections with I > 2σ(I)
Radiation source: graphite	Rint = 0.034
Bruker axs kappa axes2 CCD Diffractometer scans	θmax = 30.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.719, Tmax = 0.746	k = −15→15
42242 measured reflections	l = −20→20
8042 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 0.3893P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.23 e Å^−3
8042 reflections	Δρmin = −0.20 e Å^−3
383 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0083 (13)

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.

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

	x	y	z	Uiso*/Ueq
O3	0.90953 (13)	0.46770 (13)	0.11738 (9)	0.0534 (3)
C18	1.0071 (2)	0.4247 (3)	0.35278 (16)	0.0756 (7)
H1A	0.9742	0.3463	0.3705	0.113*
H1B	1.0612	0.5078	0.4107	0.113*
H1C	1.0657	0.4053	0.3077	0.113*
N1	0.65819 (15)	0.65584 (13)	0.34701 (9)	0.0400 (3)
N2	0.73382 (15)	0.62468 (15)	0.52637 (9)	0.0444 (3)
N3	0.72086 (13)	0.50088 (13)	0.17371 (9)	0.0352 (3)
H3	0.6741	0.5573	0.1898	0.042*
N4	0.44863 (14)	0.37083 (14)	0.20107 (9)	0.0401 (3)
O2	0.88730 (12)	0.44674 (13)	0.30692 (8)	0.0480 (3)
C8	0.63890 (16)	0.53406 (16)	0.35130 (10)	0.0350 (3)
C16	0.67525 (16)	0.37164 (15)	0.18823 (10)	0.0334 (3)
C29	0.60006 (17)	0.25131 (16)	−0.00058 (10)	0.0375 (3)
O1	0.81760 (14)	0.22640 (13)	0.19250 (10)	0.0585 (3)
C6	0.57491 (17)	0.29247 (16)	0.31890 (11)	0.0377 (3)
C7	0.58109 (16)	0.39113 (15)	0.26483 (10)	0.0344 (3)
C9	0.67140 (16)	0.51875 (17)	0.44116 (11)	0.0367 (3)
C5	0.62551 (17)	0.36968 (17)	0.42023 (11)	0.0384 (3)
C26	0.56904 (17)	0.24648 (16)	0.09437 (10)	0.0379 (3)
H15	0.5757	0.1587	0.0964	0.045*
C10	0.76469 (18)	0.75469 (17)	0.52334 (12)	0.0435 (4)
C17	0.80205 (17)	0.33770 (17)	0.22560 (11)	0.0396 (4)
C15	0.72413 (18)	0.77054 (17)	0.43540 (12)	0.0418 (4)
C19	0.83285 (17)	0.53765 (17)	0.13631 (11)	0.0395 (4)
C20	0.85645 (17)	0.66951 (17)	0.11898 (12)	0.0432 (4)
C30	0.67957 (18)	0.17659 (17)	−0.04772 (11)	0.0437 (4)
H21	0.7072	0.1167	−0.0238	0.052*
C14	0.7555 (2)	0.90641 (19)	0.43761 (14)	0.0551 (5)
H22	0.7261	0.9184	0.3809	0.066*
C1	0.5266 (2)	0.14754 (18)	0.28220 (13)	0.0506 (4)
H23	0.4945	0.0941	0.2148	0.061*
C32	0.6805 (2)	0.27734 (19)	−0.16772 (12)	0.0497 (4)
C27	0.42273 (18)	0.25135 (19)	0.10854 (12)	0.0477 (4)
H25A	0.3725	0.2637	0.0547	0.057*
H25B	0.3662	0.1646	0.1112	0.057*
C34	0.55824 (19)	0.33612 (18)	−0.04027 (12)	0.0469 (4)
H26	0.5017	0.3852	−0.0113	0.056*
C31	0.7190 (2)	0.18931 (19)	−0.13021 (12)	0.0504 (4)
H27	0.7724	0.1375	−0.1608	0.060*
C33	0.5985 (2)	0.3496 (2)	−0.12196 (12)	0.0523 (4)
H28	0.5698	0.4085	−0.1465	0.063*
C11	0.8396 (2)	0.8756 (2)	0.60964 (14)	0.0585 (5)
H29	0.8674	0.8665	0.6678	0.070*
C4	0.6250 (2)	0.30391 (19)	0.48471 (13)	0.0493 (4)
H30	0.6584	0.3566	0.5522	0.059*
C25	0.8142 (2)	0.77785 (19)	0.17246 (14)	0.0570 (5)
H31	0.7671	0.7694	0.2207	0.068*
C3	0.5742 (2)	0.1597 (2)	0.44692 (14)	0.0569 (5)
H32	0.5720	0.1137	0.4891	0.068*
C21	0.9233 (2)	0.6814 (2)	0.04555 (15)	0.0594 (5)
H33	0.9513	0.6086	0.0084	0.071*
C28	0.3265 (2)	0.3608 (2)	0.24324 (14)	0.0590 (5)
H34A	0.2988	0.2748	0.2528	0.088*
H34B	0.2492	0.3615	0.1995	0.088*
H34C	0.3506	0.4395	0.3053	0.088*
C23	0.9084 (2)	0.9101 (3)	0.08298 (19)	0.0767 (7)
H35	0.9273	0.9917	0.0714	0.092*
C12	0.8717 (2)	1.0055 (2)	0.60860 (16)	0.0670 (6)
H36	0.9227	1.0847	0.6659	0.080*
C13	0.8290 (2)	1.0212 (2)	0.52266 (16)	0.0657 (6)
H37	0.8507	1.1110	0.5232	0.079*
C2	0.5264 (2)	0.0822 (2)	0.34684 (14)	0.0596 (5)
H38	0.4934	−0.0156	0.3223	0.071*
C35	0.7294 (3)	0.2971 (3)	−0.25442 (15)	0.0755 (7)
H39A	0.6599	0.3178	−0.2908	0.113*
H39B	0.7413	0.2124	−0.2962	0.113*
H39C	0.8183	0.3738	−0.2315	0.113*
C24	0.8410 (3)	0.8988 (2)	0.15508 (17)	0.0717 (6)
H40	0.8134	0.9720	0.1921	0.086*
C22	0.9479 (2)	0.8018 (3)	0.02791 (18)	0.0749 (7)
H41	0.9919	0.8095	−0.0218	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0527 (8)	0.0584 (8)	0.0618 (8)	0.0254 (6)	0.0289 (6)	0.0291 (6)
C18	0.0498 (12)	0.1065 (19)	0.0677 (13)	0.0350 (12)	−0.0025 (10)	0.0316 (13)
N1	0.0486 (8)	0.0388 (7)	0.0373 (7)	0.0205 (6)	0.0142 (6)	0.0153 (6)
N2	0.0497 (8)	0.0463 (8)	0.0329 (7)	0.0160 (7)	0.0073 (6)	0.0124 (6)
N3	0.0395 (7)	0.0338 (7)	0.0356 (6)	0.0132 (6)	0.0134 (6)	0.0162 (5)
N4	0.0363 (7)	0.0493 (8)	0.0347 (7)	0.0142 (6)	0.0091 (6)	0.0175 (6)
O2	0.0397 (6)	0.0585 (7)	0.0406 (6)	0.0190 (6)	0.0023 (5)	0.0152 (6)
C8	0.0366 (8)	0.0386 (8)	0.0334 (7)	0.0155 (7)	0.0116 (6)	0.0159 (6)
C16	0.0383 (8)	0.0319 (7)	0.0309 (7)	0.0123 (6)	0.0096 (6)	0.0134 (6)
C29	0.0411 (9)	0.0349 (8)	0.0290 (7)	0.0101 (7)	0.0036 (6)	0.0085 (6)
O1	0.0659 (9)	0.0504 (8)	0.0650 (8)	0.0323 (7)	0.0122 (7)	0.0217 (6)
C6	0.0389 (8)	0.0398 (8)	0.0361 (8)	0.0115 (7)	0.0098 (7)	0.0189 (7)
C7	0.0386 (8)	0.0341 (8)	0.0295 (7)	0.0100 (7)	0.0078 (6)	0.0137 (6)
C9	0.0376 (8)	0.0428 (9)	0.0319 (7)	0.0159 (7)	0.0100 (6)	0.0158 (7)
C5	0.0388 (9)	0.0436 (9)	0.0366 (8)	0.0144 (7)	0.0110 (7)	0.0199 (7)
C26	0.0438 (9)	0.0344 (8)	0.0313 (7)	0.0101 (7)	0.0065 (7)	0.0122 (6)
C10	0.0443 (9)	0.0426 (9)	0.0386 (8)	0.0153 (8)	0.0113 (7)	0.0103 (7)
C17	0.0418 (9)	0.0435 (9)	0.0375 (8)	0.0170 (8)	0.0110 (7)	0.0187 (7)
C15	0.0456 (9)	0.0380 (9)	0.0424 (9)	0.0185 (7)	0.0159 (7)	0.0122 (7)
C19	0.0399 (9)	0.0427 (9)	0.0336 (8)	0.0104 (7)	0.0107 (7)	0.0154 (7)
C20	0.0378 (9)	0.0448 (9)	0.0430 (9)	0.0050 (7)	0.0060 (7)	0.0216 (8)
C30	0.0524 (10)	0.0393 (9)	0.0354 (8)	0.0184 (8)	0.0067 (7)	0.0098 (7)
C14	0.0693 (13)	0.0434 (10)	0.0568 (11)	0.0258 (9)	0.0209 (10)	0.0185 (9)
C1	0.0618 (12)	0.0389 (9)	0.0424 (9)	0.0063 (8)	0.0066 (8)	0.0173 (8)
C32	0.0536 (11)	0.0528 (10)	0.0340 (8)	0.0106 (9)	0.0091 (8)	0.0144 (8)
C27	0.0408 (9)	0.0546 (10)	0.0367 (8)	0.0071 (8)	0.0062 (7)	0.0144 (8)
C34	0.0536 (11)	0.0544 (10)	0.0393 (9)	0.0273 (9)	0.0119 (8)	0.0198 (8)
C31	0.0548 (11)	0.0534 (10)	0.0367 (9)	0.0214 (9)	0.0133 (8)	0.0084 (8)
C33	0.0632 (12)	0.0584 (11)	0.0416 (9)	0.0249 (10)	0.0084 (8)	0.0258 (8)
C11	0.0606 (12)	0.0542 (11)	0.0445 (10)	0.0162 (10)	0.0073 (9)	0.0066 (9)
C4	0.0564 (11)	0.0565 (11)	0.0405 (9)	0.0173 (9)	0.0104 (8)	0.0282 (8)
C25	0.0723 (13)	0.0439 (10)	0.0518 (10)	0.0129 (9)	0.0156 (10)	0.0215 (9)
C3	0.0661 (12)	0.0561 (11)	0.0572 (11)	0.0153 (10)	0.0129 (10)	0.0383 (10)
C21	0.0503 (11)	0.0746 (13)	0.0676 (12)	0.0185 (10)	0.0235 (10)	0.0445 (11)
C28	0.0435 (10)	0.0802 (14)	0.0545 (11)	0.0221 (10)	0.0193 (9)	0.0257 (10)
C23	0.0649 (14)	0.0693 (15)	0.1019 (18)	0.0036 (12)	0.0038 (13)	0.0620 (14)
C12	0.0666 (14)	0.0476 (11)	0.0629 (13)	0.0151 (10)	0.0100 (11)	0.0009 (10)
C13	0.0742 (14)	0.0390 (10)	0.0765 (14)	0.0203 (10)	0.0232 (12)	0.0127 (10)
C2	0.0725 (14)	0.0425 (10)	0.0594 (12)	0.0079 (9)	0.0078 (10)	0.0280 (9)
C35	0.0943 (18)	0.0819 (15)	0.0520 (12)	0.0213 (13)	0.0321 (12)	0.0311 (11)
C24	0.0872 (16)	0.0458 (11)	0.0793 (15)	0.0158 (11)	0.0111 (13)	0.0309 (11)
C22	0.0581 (13)	0.0978 (18)	0.0932 (17)	0.0169 (13)	0.0233 (12)	0.0727 (16)

Geometric parameters (Å, º)

O3—C19	1.2184 (19)	C30—H21	0.9300
C18—O2	1.438 (2)	C14—C13	1.363 (3)
C18—H1A	0.9600	C14—H22	0.9300
C18—H1B	0.9600	C1—C2	1.385 (2)
C18—H1C	0.9600	C1—H23	0.9300
N1—C8	1.3013 (19)	C32—C33	1.376 (3)
N1—C15	1.380 (2)	C32—C31	1.379 (3)
N2—C9	1.3085 (19)	C32—C35	1.509 (2)
N2—C10	1.370 (2)	C27—H25A	0.9700
N3—C19	1.3490 (19)	C27—H25B	0.9700
N3—C16	1.4458 (18)	C34—C33	1.380 (2)
N3—H3	0.8600	C34—H26	0.9300
N4—C28	1.451 (2)	C31—H27	0.9300
N4—C27	1.457 (2)	C33—H28	0.9300
N4—C7	1.460 (2)	C11—C12	1.356 (3)
O2—C17	1.3356 (19)	C11—H29	0.9300
C8—C9	1.424 (2)	C4—C3	1.370 (3)
C8—C7	1.520 (2)	C4—H30	0.9300
C16—C17	1.524 (2)	C25—C24	1.381 (3)
C16—C26	1.563 (2)	C25—H31	0.9300
C16—C7	1.576 (2)	C3—C2	1.378 (3)
C29—C30	1.379 (2)	C3—H32	0.9300
C29—C34	1.382 (2)	C21—C22	1.379 (3)
C29—C26	1.510 (2)	C21—H33	0.9300
O1—C17	1.1929 (19)	C28—H34A	0.9600
C6—C1	1.377 (2)	C28—H34B	0.9600
C6—C5	1.395 (2)	C28—H34C	0.9600
C6—C7	1.543 (2)	C23—C22	1.370 (3)
C9—C5	1.450 (2)	C23—C24	1.370 (3)
C5—C4	1.386 (2)	C23—H35	0.9300
C26—C27	1.534 (2)	C12—C13	1.390 (3)
C26—H15	0.9800	C12—H36	0.9300
C10—C11	1.405 (2)	C13—H37	0.9300
C10—C15	1.414 (2)	C2—H38	0.9300
C15—C14	1.401 (2)	C35—H39A	0.9600
C19—C20	1.497 (2)	C35—H39B	0.9600
C20—C25	1.379 (3)	C35—H39C	0.9600
C20—C21	1.386 (2)	C24—H40	0.9300
C30—C31	1.385 (2)	C22—H41	0.9300
O2—C18—H1A	109.5	C15—C14—H22	119.9
O2—C18—H1B	109.5	C6—C1—C2	119.23 (16)
H1A—C18—H1B	109.5	C6—C1—H23	120.4
O2—C18—H1C	109.5	C2—C1—H23	120.4
H1A—C18—H1C	109.5	C33—C32—C31	117.81 (16)
H1B—C18—H1C	109.5	C33—C32—C35	120.83 (18)
C8—N1—C15	114.78 (13)	C31—C32—C35	121.35 (18)
C9—N2—C10	114.47 (13)	N4—C27—C26	106.32 (13)
C19—N3—C16	123.49 (13)	N4—C27—H25A	110.5
C19—N3—H3	118.3	C26—C27—H25A	110.5
C16—N3—H3	118.3	N4—C27—H25B	110.5
C28—N4—C27	112.91 (14)	C26—C27—H25B	110.5
C28—N4—C7	116.08 (13)	H25A—C27—H25B	108.7
C27—N4—C7	108.12 (12)	C33—C34—C29	121.44 (16)
C17—O2—C18	115.42 (15)	C33—C34—H26	119.3
N1—C8—C9	122.96 (14)	C29—C34—H26	119.3
N1—C8—C7	126.40 (13)	C32—C31—C30	121.19 (16)
C9—C8—C7	110.64 (13)	C32—C31—H27	119.4
N3—C16—C17	111.13 (12)	C30—C31—H27	119.4
N3—C16—C26	112.04 (11)	C32—C33—C34	121.02 (16)
C17—C16—C26	112.59 (12)	C32—C33—H28	119.5
N3—C16—C7	107.65 (11)	C34—C33—H28	119.5
C17—C16—C7	110.42 (11)	C12—C11—C10	120.40 (19)
C26—C16—C7	102.58 (11)	C12—C11—H29	119.8
C30—C29—C34	117.49 (14)	C10—C11—H29	119.8
C30—C29—C26	120.39 (14)	C3—C4—C5	118.55 (16)
C34—C29—C26	122.01 (14)	C3—C4—H30	120.7
C1—C6—C5	119.04 (14)	C5—C4—H30	120.7
C1—C6—C7	130.03 (14)	C20—C25—C24	120.62 (19)
C5—C6—C7	110.92 (13)	C20—C25—H31	119.7
N4—C7—C8	112.45 (12)	C24—C25—H31	119.7
N4—C7—C6	117.15 (12)	C4—C3—C2	120.44 (16)
C8—C7—C6	100.68 (11)	C4—C3—H32	119.8
N4—C7—C16	99.76 (11)	C2—C3—H32	119.8
C8—C7—C16	114.22 (12)	C22—C21—C20	119.6 (2)
C6—C7—C16	113.29 (12)	C22—C21—H33	120.2
N2—C9—C8	123.90 (14)	C20—C21—H33	120.2
N2—C9—C5	127.69 (14)	N4—C28—H34A	109.5
C8—C9—C5	108.40 (13)	N4—C28—H34B	109.5
C4—C5—C6	121.54 (15)	H34A—C28—H34B	109.5
C4—C5—C9	129.34 (15)	N4—C28—H34C	109.5
C6—C5—C9	109.11 (13)	H34A—C28—H34C	109.5
C29—C26—C27	115.40 (13)	H34B—C28—H34C	109.5
C29—C26—C16	113.57 (12)	C22—C23—C24	120.20 (19)
C27—C26—C16	103.91 (12)	C22—C23—H35	119.9
C29—C26—H15	107.9	C24—C23—H35	119.9
C27—C26—H15	107.9	C11—C12—C13	120.56 (19)
C16—C26—H15	107.9	C11—C12—H36	119.7
N2—C10—C11	119.22 (16)	C13—C12—H36	119.7
N2—C10—C15	121.76 (14)	C14—C13—C12	120.73 (19)
C11—C10—C15	119.02 (16)	C14—C13—H37	119.6
O1—C17—O2	124.37 (15)	C12—C13—H37	119.6
O1—C17—C16	125.32 (15)	C3—C2—C1	121.18 (17)
O2—C17—C16	110.03 (13)	C3—C2—H38	119.4
N1—C15—C14	119.11 (15)	C1—C2—H38	119.4
N1—C15—C10	121.81 (14)	C32—C35—H39A	109.5
C14—C15—C10	119.05 (15)	C32—C35—H39B	109.5
O3—C19—N3	122.17 (14)	H39A—C35—H39B	109.5
O3—C19—C20	122.11 (14)	C32—C35—H39C	109.5
N3—C19—C20	115.72 (14)	H39A—C35—H39C	109.5
C25—C20—C21	119.33 (16)	H39B—C35—H39C	109.5
C25—C20—C19	122.78 (15)	C23—C24—C25	119.6 (2)
C21—C20—C19	117.89 (16)	C23—C24—H40	120.2
C29—C30—C31	121.02 (16)	C25—C24—H40	120.2
C29—C30—H21	119.5	C23—C22—C21	120.6 (2)
C31—C30—H21	119.5	C23—C22—H41	119.7
C13—C14—C15	120.19 (18)	C21—C22—H41	119.7
C13—C14—H22	119.9
C15—N1—C8—C9	5.3 (2)	C9—N2—C10—C15	3.4 (2)
C15—N1—C8—C7	−174.39 (14)	C18—O2—C17—O1	2.3 (2)
C19—N3—C16—C17	39.35 (18)	C18—O2—C17—C16	176.53 (15)
C19—N3—C16—C26	−87.57 (17)	N3—C16—C17—O1	−131.07 (16)
C19—N3—C16—C7	160.39 (13)	C26—C16—C17—O1	−4.4 (2)
C28—N4—C7—C8	−67.27 (17)	C7—C16—C17—O1	109.54 (17)
C27—N4—C7—C8	164.69 (12)	N3—C16—C17—O2	54.81 (16)
C28—N4—C7—C6	48.66 (19)	C26—C16—C17—O2	−178.56 (12)
C27—N4—C7—C6	−79.37 (15)	C7—C16—C17—O2	−64.57 (16)
C28—N4—C7—C16	171.29 (14)	C8—N1—C15—C14	177.13 (15)
C27—N4—C7—C16	43.26 (14)	C8—N1—C15—C10	−1.0 (2)
N1—C8—C7—N4	−50.7 (2)	N2—C10—C15—N1	−3.6 (3)
C9—C8—C7—N4	129.51 (13)	C11—C10—C15—N1	175.92 (15)
N1—C8—C7—C6	−176.22 (15)	N2—C10—C15—C14	178.32 (16)
C9—C8—C7—C6	4.03 (16)	C11—C10—C15—C14	−2.2 (2)
N1—C8—C7—C16	62.0 (2)	C16—N3—C19—O3	−4.5 (2)
C9—C8—C7—C16	−117.71 (14)	C16—N3—C19—C20	175.11 (13)
C1—C6—C7—N4	55.1 (2)	O3—C19—C20—C25	−153.06 (18)
C5—C6—C7—N4	−123.65 (14)	N3—C19—C20—C25	27.3 (2)
C1—C6—C7—C8	177.36 (17)	O3—C19—C20—C21	27.2 (2)
C5—C6—C7—C8	−1.41 (16)	N3—C19—C20—C21	−152.45 (16)
C1—C6—C7—C16	−60.2 (2)	C34—C29—C30—C31	1.7 (2)
C5—C6—C7—C16	120.99 (14)	C26—C29—C30—C31	−174.49 (15)
N3—C16—C7—N4	78.00 (13)	N1—C15—C14—C13	−175.62 (17)
C17—C16—C7—N4	−160.52 (12)	C10—C15—C14—C13	2.6 (3)
C26—C16—C7—N4	−40.32 (13)	C5—C6—C1—C2	1.5 (3)
N3—C16—C7—C8	−42.15 (16)	C7—C6—C1—C2	−177.21 (17)
C17—C16—C7—C8	79.32 (15)	C28—N4—C27—C26	−158.68 (14)
C26—C16—C7—C8	−160.48 (12)	C7—N4—C27—C26	−28.85 (16)
N3—C16—C7—C6	−156.67 (12)	C29—C26—C27—N4	−123.90 (14)
C17—C16—C7—C6	−35.19 (17)	C16—C26—C27—N4	1.11 (16)
C26—C16—C7—C6	85.01 (14)	C30—C29—C34—C33	−2.2 (3)
C10—N2—C9—C8	0.9 (2)	C26—C29—C34—C33	173.90 (16)
C10—N2—C9—C5	−179.94 (15)	C33—C32—C31—C30	−1.6 (3)
N1—C8—C9—N2	−5.7 (2)	C35—C32—C31—C30	176.85 (18)
C7—C8—C9—N2	174.02 (14)	C29—C30—C31—C32	0.2 (3)
N1—C8—C9—C5	174.98 (14)	C31—C32—C33—C34	1.1 (3)
C7—C8—C9—C5	−5.26 (17)	C35—C32—C33—C34	−177.38 (18)
C1—C6—C5—C4	−1.6 (2)	C29—C34—C33—C32	0.9 (3)
C7—C6—C5—C4	177.35 (15)	N2—C10—C11—C12	179.90 (18)
C1—C6—C5—C9	179.45 (15)	C15—C10—C11—C12	0.4 (3)
C7—C6—C5—C9	−1.63 (18)	C6—C5—C4—C3	0.4 (3)
N2—C9—C5—C4	6.1 (3)	C9—C5—C4—C3	179.20 (17)
C8—C9—C5—C4	−174.62 (17)	C21—C20—C25—C24	−1.6 (3)
N2—C9—C5—C6	−174.99 (15)	C19—C20—C25—C24	178.65 (18)
C8—C9—C5—C6	4.25 (18)	C5—C4—C3—C2	0.8 (3)
C30—C29—C26—C27	−144.82 (16)	C25—C20—C21—C22	0.8 (3)
C34—C29—C26—C27	39.2 (2)	C19—C20—C21—C22	−179.47 (17)
C30—C29—C26—C16	95.34 (17)	C10—C11—C12—C13	1.1 (3)
C34—C29—C26—C16	−80.66 (19)	C15—C14—C13—C12	−1.1 (3)
N3—C16—C26—C29	35.05 (17)	C11—C12—C13—C14	−0.8 (3)
C17—C16—C26—C29	−91.08 (15)	C4—C3—C2—C1	−0.8 (3)
C7—C16—C26—C29	150.23 (12)	C6—C1—C2—C3	−0.3 (3)
N3—C16—C26—C27	−91.12 (14)	C22—C23—C24—C25	0.5 (3)
C17—C16—C26—C27	142.74 (13)	C20—C25—C24—C23	1.0 (3)
C7—C16—C26—C27	24.05 (14)	C24—C23—C22—C21	−1.3 (4)
C9—N2—C10—C11	−176.11 (15)	C20—C21—C22—C23	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.86	2.27	2.8107 (18)	121
C21—H33···O3^i	0.93	2.54	3.347 (2)	146

Symmetry code: (i) −x+2, −y+1, −z.