1-Methyl-4′-(3-nitro­phenyl)-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-indan-2,1′′,3′′-trione

The pyrrolidine ring of the title compound, C₂₆H₁₉N₃O₅, adopts an envelope conformation. The molecular structure is stabilized by C—H...O interactions and the packing of the mol­ecules is stabilized by an N—H...O hydrogen bond and C—H...O intermolecular interactions. A dimer is formed between symmetry-related mol­ecules through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.163
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           27.98
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4747
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5218
           Completeness (_total/calc)             90.97%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N21
PLAT432_ALERT_2_C Short Inter X...Y Contact  C8     ..  C8       =       3.18 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C19    ..  O23      =      98.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C24    ..  O22      =      98.00 Deg.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

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, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-Methyl-4'-(3-nitrophenyl)-1H-indole-3-spiro-2'-pyrrolidine-3'- spiro-2''-indan-2,1'',3''-trione

Crystal data

C26H19N3O5	Z = 2
Mr = 453.44	F(000) = 472
Triclinic, P1	Dx = 1.392 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7610 (6) Å	Cell parameters from 2386 reflections
b = 11.6696 (10) Å	θ = 2.4–27.2°
c = 11.9952 (9) Å	µ = 0.10 mm^−1
α = 93.392 (2)°	T = 293 K
β = 91.092 (1)°	Needles, yellow
γ = 93.660 (1)°	0.21 × 0.16 × 0.14 mm
V = 1081.98 (15) Å^3

Data collection

CCD Area Detector diffractometer	4747 independent reflections
Radiation source: fine-focus sealed tube	3472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.980, Tmax = 0.986	k = −13→14
6822 measured reflections	l = −10→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0932P)^2 + 0.165P] where P = (Fo^2 + 2Fc^2)/3
4747 reflections	(Δ/σ)max < 0.000
307 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 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
N1	0.0636 (2)	0.02827 (15)	0.14814 (14)	0.0613 (5)
H1	−0.0160	−0.0161	0.1142	0.074*
C2	0.1514 (3)	0.11612 (18)	0.10045 (17)	0.0560 (5)
O3	0.1462 (2)	0.13715 (14)	0.00201 (12)	0.0722 (5)
C4	0.2656 (2)	0.18439 (16)	0.19517 (14)	0.0465 (4)
C5	0.2429 (2)	0.10601 (15)	0.28967 (15)	0.0454 (4)
C6	0.3245 (2)	0.10738 (16)	0.39291 (17)	0.0527 (5)
H6	0.4108	0.1640	0.4137	0.063*
C7	0.2763 (3)	0.02350 (18)	0.46520 (18)	0.0605 (5)
H7	0.3303	0.0239	0.5351	0.073*
C8	0.1484 (3)	−0.06093 (18)	0.4342 (2)	0.0644 (6)
H8	0.1161	−0.1157	0.4844	0.077*
C9	0.0678 (3)	−0.06564 (17)	0.33022 (19)	0.0620 (5)
H9	−0.0170	−0.1232	0.3091	0.074*
C10	0.1176 (2)	0.01804 (16)	0.25889 (16)	0.0506 (4)
C11	0.2000 (2)	0.30860 (15)	0.21580 (14)	0.0435 (4)
C12	0.2879 (2)	0.37348 (17)	0.12103 (15)	0.0498 (4)
H12	0.2127	0.3581	0.0546	0.060*
C13	0.4519 (3)	0.31045 (19)	0.09801 (19)	0.0652 (6)
H13A	0.4559	0.2852	0.0197	0.078*
H13B	0.5538	0.3607	0.1173	0.078*
N14	0.44401 (19)	0.21205 (13)	0.16730 (13)	0.0500 (4)
C15	0.5400 (3)	0.1160 (2)	0.1256 (2)	0.0767 (7)
H15A	0.5282	0.0550	0.1758	0.115*
H15B	0.6598	0.1408	0.1206	0.115*
H15C	0.4954	0.0889	0.0530	0.115*
C16	0.3070 (2)	0.50315 (16)	0.14180 (14)	0.0472 (4)
C17	0.1677 (3)	0.56849 (19)	0.11844 (16)	0.0567 (5)
H17	0.0650	0.5311	0.0908	0.068*
C18	0.1773 (3)	0.6870 (2)	0.13506 (18)	0.0649 (5)
H18	0.0819	0.7278	0.1185	0.078*
C19	0.3270 (3)	0.74446 (19)	0.17598 (18)	0.0646 (6)
H19	0.3352	0.8241	0.1883	0.078*
C20	0.4643 (3)	0.68013 (18)	0.19809 (16)	0.0586 (5)
N21	0.6288 (3)	0.7408 (2)	0.23596 (19)	0.0862 (7)
O22	0.7586 (3)	0.6863 (2)	0.2372 (2)	0.1137 (8)
O23	0.6306 (4)	0.8442 (2)	0.2582 (3)	0.1482 (11)
C24	0.4578 (3)	0.56196 (18)	0.18234 (16)	0.0561 (5)
H24	0.5542	0.5221	0.1988	0.067*
C25	0.0016 (2)	0.31102 (16)	0.21594 (15)	0.0483 (4)
O26	−0.09065 (18)	0.30536 (16)	0.13356 (12)	0.0714 (5)
C27	−0.0520 (2)	0.32635 (15)	0.33292 (15)	0.0459 (4)
C28	−0.2186 (3)	0.32476 (18)	0.37410 (18)	0.0579 (5)
H28	−0.3153	0.3109	0.3270	0.069*
C29	−0.2339 (3)	0.34456 (19)	0.48762 (19)	0.0647 (6)
H29	−0.3433	0.3455	0.5178	0.078*
C30	−0.0903 (3)	0.36305 (18)	0.55766 (17)	0.0620 (5)
H30	−0.1056	0.3739	0.6342	0.074*
C31	0.0754 (3)	0.36588 (16)	0.51733 (15)	0.0520 (4)
H31	0.1714	0.3794	0.5649	0.062*
C32	0.0924 (2)	0.34762 (15)	0.40279 (14)	0.0441 (4)
C33	0.2507 (2)	0.35300 (14)	0.33584 (14)	0.0412 (4)
O34	0.39307 (16)	0.38840 (12)	0.36893 (11)	0.0534 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0585 (10)	0.0641 (10)	0.0556 (10)	−0.0203 (8)	−0.0027 (7)	−0.0167 (8)
C2	0.0564 (11)	0.0596 (12)	0.0483 (10)	−0.0072 (9)	−0.0011 (8)	−0.0149 (8)
O3	0.0861 (11)	0.0806 (11)	0.0447 (8)	−0.0177 (8)	−0.0061 (7)	−0.0126 (7)
C4	0.0441 (9)	0.0506 (10)	0.0421 (9)	−0.0051 (7)	0.0009 (7)	−0.0107 (7)
C5	0.0421 (9)	0.0410 (9)	0.0512 (10)	−0.0021 (7)	0.0019 (7)	−0.0080 (7)
C6	0.0475 (10)	0.0491 (10)	0.0601 (11)	−0.0002 (8)	−0.0059 (8)	−0.0027 (8)
C7	0.0646 (12)	0.0580 (12)	0.0598 (12)	0.0097 (9)	−0.0034 (9)	0.0050 (9)
C8	0.0715 (14)	0.0496 (11)	0.0726 (14)	0.0042 (10)	0.0138 (11)	0.0033 (10)
C9	0.0609 (12)	0.0488 (11)	0.0732 (14)	−0.0101 (9)	0.0122 (10)	−0.0095 (10)
C10	0.0459 (10)	0.0485 (10)	0.0550 (11)	−0.0038 (8)	0.0042 (8)	−0.0126 (8)
C11	0.0408 (9)	0.0498 (9)	0.0383 (8)	−0.0032 (7)	0.0002 (6)	−0.0036 (7)
C12	0.0508 (10)	0.0585 (11)	0.0387 (9)	−0.0041 (8)	0.0023 (7)	−0.0006 (8)
C13	0.0666 (13)	0.0662 (13)	0.0630 (13)	0.0032 (10)	0.0252 (10)	0.0001 (10)
N14	0.0458 (8)	0.0477 (8)	0.0546 (9)	−0.0022 (6)	0.0095 (7)	−0.0103 (7)
C15	0.0667 (14)	0.0587 (13)	0.1022 (18)	0.0031 (10)	0.0252 (13)	−0.0224 (12)
C16	0.0487 (10)	0.0573 (11)	0.0351 (8)	−0.0028 (8)	0.0027 (7)	0.0044 (7)
C17	0.0505 (11)	0.0714 (13)	0.0474 (10)	−0.0001 (9)	−0.0016 (8)	0.0006 (9)
C18	0.0652 (13)	0.0691 (14)	0.0622 (13)	0.0144 (10)	0.0093 (10)	0.0069 (10)
C19	0.0789 (15)	0.0565 (12)	0.0578 (12)	−0.0006 (11)	0.0166 (10)	−0.0014 (9)
C20	0.0651 (12)	0.0630 (13)	0.0452 (10)	−0.0139 (10)	−0.0008 (9)	0.0018 (9)
N21	0.0834 (16)	0.0845 (16)	0.0854 (15)	−0.0264 (13)	−0.0166 (12)	0.0011 (12)
O22	0.0803 (14)	0.1120 (17)	0.145 (2)	−0.0256 (12)	−0.0423 (13)	0.0251 (14)
O23	0.139 (2)	0.0982 (18)	0.193 (3)	−0.0374 (15)	−0.0220 (19)	−0.0522 (18)
C24	0.0511 (11)	0.0657 (13)	0.0512 (11)	−0.0017 (9)	−0.0047 (8)	0.0100 (9)
C25	0.0425 (9)	0.0546 (10)	0.0468 (10)	−0.0028 (8)	−0.0010 (7)	0.0027 (8)
O26	0.0492 (8)	0.1128 (13)	0.0504 (8)	−0.0042 (8)	−0.0107 (6)	0.0035 (8)
C27	0.0438 (9)	0.0478 (10)	0.0465 (10)	0.0035 (7)	0.0033 (7)	0.0048 (7)
C28	0.0459 (10)	0.0640 (12)	0.0650 (12)	0.0042 (9)	0.0076 (9)	0.0114 (10)
C29	0.0605 (13)	0.0664 (13)	0.0685 (13)	0.0044 (10)	0.0236 (10)	0.0080 (10)
C30	0.0847 (15)	0.0540 (11)	0.0485 (11)	0.0050 (10)	0.0223 (10)	0.0049 (9)
C31	0.0650 (12)	0.0490 (10)	0.0420 (9)	0.0045 (8)	0.0026 (8)	0.0020 (8)
C32	0.0481 (9)	0.0413 (9)	0.0430 (9)	0.0043 (7)	0.0039 (7)	0.0018 (7)
C33	0.0430 (9)	0.0394 (8)	0.0405 (8)	0.0022 (7)	−0.0017 (7)	−0.0019 (7)
O34	0.0449 (7)	0.0613 (8)	0.0513 (7)	−0.0023 (6)	−0.0056 (5)	−0.0105 (6)

Geometric parameters (Å, º)

N1—C2	1.355 (3)	C15—H15B	0.9600
N1—C10	1.399 (3)	C15—H15C	0.9600
N1—H1	0.8600	C16—C24	1.384 (3)
C2—O3	1.221 (2)	C16—C17	1.396 (3)
C2—C4	1.573 (2)	C17—C18	1.382 (3)
C4—N14	1.451 (2)	C17—H17	0.9300
C4—C5	1.504 (3)	C18—C19	1.372 (3)
C4—C11	1.574 (3)	C18—H18	0.9300
C5—C6	1.379 (3)	C19—C20	1.372 (3)
C5—C10	1.396 (2)	C19—H19	0.9300
C6—C7	1.384 (3)	C20—C24	1.378 (3)
C6—H6	0.9300	C20—N21	1.471 (3)
C7—C8	1.382 (3)	N21—O23	1.220 (3)
C7—H7	0.9300	N21—O22	1.226 (3)
C8—C9	1.381 (3)	C24—H24	0.9300
C8—H8	0.9300	C25—O26	1.206 (2)
C9—C10	1.378 (3)	C25—C27	1.475 (3)
C9—H9	0.9300	C27—C32	1.387 (2)
C11—C33	1.536 (2)	C27—C28	1.393 (3)
C11—C25	1.542 (2)	C28—C29	1.376 (3)
C11—C12	1.548 (2)	C28—H28	0.9300
C12—C16	1.516 (3)	C29—C30	1.381 (3)
C12—C13	1.531 (3)	C29—H29	0.9300
C12—H12	0.9800	C30—C31	1.382 (3)
C13—N14	1.456 (3)	C30—H30	0.9300
C13—H13A	0.9700	C31—C32	1.388 (2)
C13—H13B	0.9700	C31—H31	0.9300
N14—C15	1.454 (3)	C32—C33	1.480 (2)
C15—H15A	0.9600	C33—O34	1.206 (2)
C2—N1—C10	112.19 (15)	N14—C15—H15A	109.5
C2—N1—H1	123.9	N14—C15—H15B	109.5
C10—N1—H1	123.9	H15A—C15—H15B	109.5
O3—C2—N1	126.58 (17)	N14—C15—H15C	109.5
O3—C2—C4	126.19 (18)	H15A—C15—H15C	109.5
N1—C2—C4	107.21 (16)	H15B—C15—H15C	109.5
N14—C4—C5	114.48 (15)	C24—C16—C17	117.19 (19)
N14—C4—C2	115.57 (15)	C24—C16—C12	123.33 (17)
C5—C4—C2	101.12 (14)	C17—C16—C12	119.48 (16)
N14—C4—C11	100.67 (13)	C18—C17—C16	122.23 (19)
C5—C4—C11	116.09 (14)	C18—C17—H17	118.9
C2—C4—C11	109.50 (15)	C16—C17—H17	118.9
C6—C5—C10	119.36 (18)	C19—C18—C17	120.2 (2)
C6—C5—C4	131.39 (15)	C19—C18—H18	119.9
C10—C5—C4	109.24 (15)	C17—C18—H18	119.9
C5—C6—C7	119.17 (17)	C18—C19—C20	117.5 (2)
C5—C6—H6	120.4	C18—C19—H19	121.2
C7—C6—H6	120.4	C20—C19—H19	121.2
C8—C7—C6	120.5 (2)	C19—C20—C24	123.37 (19)
C8—C7—H7	119.8	C19—C20—N21	118.3 (2)
C6—C7—H7	119.8	C24—C20—N21	118.3 (2)
C9—C8—C7	121.4 (2)	O23—N21—O22	123.4 (2)
C9—C8—H8	119.3	O23—N21—C20	118.1 (3)
C7—C8—H8	119.3	O22—N21—C20	118.4 (2)
C10—C9—C8	117.55 (18)	C20—C24—C16	119.52 (19)
C10—C9—H9	121.2	C20—C24—H24	120.2
C8—C9—H9	121.2	C16—C24—H24	120.2
C9—C10—C5	122.03 (18)	O26—C25—C27	126.87 (17)
C9—C10—N1	128.50 (17)	O26—C25—C11	125.03 (17)
C5—C10—N1	109.41 (17)	C27—C25—C11	108.06 (14)
C33—C11—C25	102.15 (13)	C32—C27—C28	121.68 (17)
C33—C11—C12	116.40 (14)	C32—C27—C25	109.87 (15)
C25—C11—C12	114.49 (15)	C28—C27—C25	128.42 (17)
C33—C11—C4	108.53 (13)	C29—C28—C27	116.99 (19)
C25—C11—C4	113.69 (14)	C29—C28—H28	121.5
C12—C11—C4	101.90 (14)	C27—C28—H28	121.5
C16—C12—C13	117.70 (16)	C28—C29—C30	121.43 (19)
C16—C12—C11	114.71 (14)	C28—C29—H29	119.3
C13—C12—C11	104.40 (16)	C30—C29—H29	119.3
C16—C12—H12	106.4	C29—C30—C31	121.89 (18)
C13—C12—H12	106.4	C29—C30—H30	119.1
C11—C12—H12	106.4	C31—C30—H30	119.1
N14—C13—C12	106.28 (15)	C30—C31—C32	117.21 (18)
N14—C13—H13A	110.5	C30—C31—H31	121.4
C12—C13—H13A	110.5	C32—C31—H31	121.4
N14—C13—H13B	110.5	C27—C32—C31	120.76 (17)
C12—C13—H13B	110.5	C27—C32—C33	109.97 (15)
H13A—C13—H13B	108.7	C31—C32—C33	129.18 (17)
C4—N14—C15	116.02 (16)	O34—C33—C32	126.16 (16)
C4—N14—C13	109.10 (16)	O34—C33—C11	126.14 (16)
C15—N14—C13	114.71 (17)	C32—C33—C11	107.69 (14)
C10—N1—C2—O3	171.0 (2)	C12—C13—N14—C15	154.39 (17)
C10—N1—C2—C4	−7.5 (2)	C13—C12—C16—C24	−25.3 (3)
O3—C2—C4—N14	−45.3 (3)	C11—C12—C16—C24	98.2 (2)
N1—C2—C4—N14	133.19 (18)	C13—C12—C16—C17	154.07 (18)
O3—C2—C4—C5	−169.5 (2)	C11—C12—C16—C17	−82.5 (2)
N1—C2—C4—C5	9.0 (2)	C24—C16—C17—C18	−0.3 (3)
O3—C2—C4—C11	67.4 (3)	C12—C16—C17—C18	−179.68 (17)
N1—C2—C4—C11	−114.04 (18)	C16—C17—C18—C19	−0.1 (3)
N14—C4—C5—C6	46.0 (3)	C17—C18—C19—C20	0.6 (3)
C2—C4—C5—C6	170.9 (2)	C18—C19—C20—C24	−0.7 (3)
C11—C4—C5—C6	−70.7 (2)	C18—C19—C20—N21	176.60 (19)
N14—C4—C5—C10	−132.51 (16)	C19—C20—N21—O23	8.3 (4)
C2—C4—C5—C10	−7.57 (19)	C24—C20—N21—O23	−174.3 (3)
C11—C4—C5—C10	110.79 (17)	C19—C20—N21—O22	−167.6 (2)
C10—C5—C6—C7	−2.1 (3)	C24—C20—N21—O22	9.9 (3)
C4—C5—C6—C7	179.57 (19)	C19—C20—C24—C16	0.3 (3)
C5—C6—C7—C8	0.3 (3)	N21—C20—C24—C16	−177.01 (18)
C6—C7—C8—C9	1.3 (3)	C17—C16—C24—C20	0.2 (3)
C7—C8—C9—C10	−1.0 (3)	C12—C16—C24—C20	179.58 (17)
C8—C9—C10—C5	−0.9 (3)	C33—C11—C25—O26	164.22 (19)
C8—C9—C10—N1	175.9 (2)	C12—C11—C25—O26	37.5 (3)
C6—C5—C10—C9	2.4 (3)	C4—C11—C25—O26	−79.1 (2)
C4—C5—C10—C9	−178.85 (18)	C33—C11—C25—C27	−13.39 (18)
C6—C5—C10—N1	−174.91 (17)	C12—C11—C25—C27	−140.10 (15)
C4—C5—C10—N1	3.8 (2)	C4—C11—C25—C27	103.32 (16)
C2—N1—C10—C9	−174.5 (2)	O26—C25—C27—C32	−170.3 (2)
C2—N1—C10—C5	2.6 (2)	C11—C25—C27—C32	7.3 (2)
N14—C4—C11—C33	−82.95 (15)	O26—C25—C27—C28	7.8 (3)
C5—C4—C11—C33	41.22 (19)	C11—C25—C27—C28	−174.64 (18)
C2—C4—C11—C33	154.87 (14)	C32—C27—C28—C29	−0.4 (3)
N14—C4—C11—C25	164.13 (14)	C25—C27—C28—C29	−178.27 (19)
C5—C4—C11—C25	−71.70 (18)	C27—C28—C29—C30	−1.2 (3)
C2—C4—C11—C25	41.95 (19)	C28—C29—C30—C31	1.9 (3)
N14—C4—C11—C12	40.41 (15)	C29—C30—C31—C32	−0.9 (3)
C5—C4—C11—C12	164.58 (14)	C28—C27—C32—C31	1.3 (3)
C2—C4—C11—C12	−81.76 (16)	C25—C27—C32—C31	179.54 (16)
C33—C11—C12—C16	−40.2 (2)	C28—C27—C32—C33	−175.65 (16)
C25—C11—C12—C16	78.79 (19)	C25—C27—C32—C33	2.6 (2)
C4—C11—C12—C16	−158.03 (15)	C30—C31—C32—C27	−0.6 (3)
C33—C11—C12—C13	90.10 (18)	C30—C31—C32—C33	175.68 (17)
C25—C11—C12—C13	−150.94 (16)	C27—C32—C33—O34	166.96 (17)
C4—C11—C12—C13	−27.76 (17)	C31—C32—C33—O34	−9.7 (3)
C16—C12—C13—N14	133.65 (17)	C27—C32—C33—C11	−11.45 (19)
C11—C12—C13—N14	5.2 (2)	C31—C32—C33—C11	171.91 (17)
C5—C4—N14—C15	63.9 (2)	C25—C11—C33—O34	−163.61 (17)
C2—C4—N14—C15	−53.0 (3)	C12—C11—C33—O34	−38.1 (3)
C11—C4—N14—C15	−170.79 (18)	C4—C11—C33—O34	76.0 (2)
C5—C4—N14—C13	−164.67 (15)	C25—C11—C33—C32	14.80 (17)
C2—C4—N14—C13	78.4 (2)	C12—C11—C33—C32	140.27 (15)
C11—C4—N14—C13	−39.40 (17)	C4—C11—C33—C32	−105.57 (15)
C12—C13—N14—C4	22.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.86	2.12	2.949 (2)	162
C28—H28···O34^ii	0.93	2.54	3.150 (2)	124
C31—H31···O22^iii	0.93	2.60	3.296 (3)	133
C19—H19···O23	0.93	2.42	2.703 (4)	98
C24—H24···O22	0.93	2.43	2.717 (3)	98

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