Crystal structure and mol­ecular Hirshfeld surface analysis of acenaphthene derivatives obeying the chlorine–methyl exchange rule

The change of substituents viz. a chlorine atom in (I) replaced by a methyl group in (II) has not induced any differences in their respective crystal packing features, confirming the validity of the chlorine–methyl exchange rule.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 20.1

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.121
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10      ..O2       .       2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16      ..O2       .       2.76 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.155 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
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 Model has Chirality at C2          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C20         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C23         (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C29      --C30      .        6.0 s.u.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H20      ..H36A     .       1.82 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H36A     ..O1       .       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10      ..O2       .       2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16      ..O2       .       2.79 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.797 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H35A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H35B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H35C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H35D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H35E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H35F       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H36A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H36B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H36C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H36D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H36E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H36F       Constrained at        0.5 Check
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C14      - C36      .       1.50 Ang.
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C20         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C23         (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
  19 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

5''-(2-Chlorobenzylidene)-4'-(2-chlorophenyl)-1'-methyldispiro[acenaphthene-1,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione (I)

Crystal data

C34H28Cl2N2O2	F(000) = 1184
Mr = 567.48	Dx = 1.373 Mg m^−3 Dm = 1.37 Mg m^−3 Dm measured by floatation method
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.6710 (4) Å	Cell parameters from 7274 reflections
b = 15.6756 (7) Å	θ = 4.8–57.2°
c = 20.2284 (9) Å	µ = 0.27 mm^−1
β = 93.036 (2)°	T = 293 K
V = 2745.6 (2) Å^3	Block, yellow
Z = 4	0.31 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer	5025 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
φ and ω scans	θmax = 29.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.771, Tmax = 1.000	k = −21→21
33739 measured reflections	l = −27→27
7274 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0458P)^2 + 1.2817P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
7274 reflections	Δρmax = 0.33 e Å^−3
361 parameters	Δρmin = −0.46 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.38200 (9)	0.88710 (4)	0.49943 (3)	0.0749 (2)
Cl2	0.53437 (6)	1.07386 (3)	0.14315 (3)	0.05500 (14)
O1	0.48210 (14)	0.92211 (9)	0.26952 (6)	0.0509 (3)
O2	0.01681 (16)	0.80480 (10)	0.10859 (7)	0.0587 (4)
N1	0.02281 (15)	0.96435 (9)	0.23726 (6)	0.0345 (3)
N2	0.32804 (16)	0.76391 (9)	0.17821 (7)	0.0379 (3)
C1	0.34543 (18)	0.93585 (10)	0.26001 (8)	0.0339 (3)
C2	0.25834 (17)	0.90781 (10)	0.19571 (7)	0.0298 (3)
C3	0.12354 (18)	0.96919 (10)	0.18237 (8)	0.0330 (3)
H3A	0.161841	1.026946	0.177987	0.040*
H3B	0.066923	0.953767	0.141473	0.040*
C4	−0.1310 (2)	0.99694 (13)	0.21990 (10)	0.0486 (4)
H4A	−0.175090	0.965861	0.182623	0.073*
H4B	−0.194961	0.990171	0.256864	0.073*
H4C	−0.124570	1.056321	0.208758	0.073*
C5	0.0931 (2)	1.00991 (11)	0.29351 (8)	0.0412 (4)
H5A	0.029809	1.002742	0.331249	0.049*
H5B	0.096552	1.070296	0.283217	0.049*
C6	0.2542 (2)	0.97887 (10)	0.31150 (8)	0.0367 (3)
C7	0.3209 (2)	0.98384 (12)	0.37223 (9)	0.0453 (4)
H7	0.419755	0.961011	0.377724	0.054*
C8	0.2571 (2)	1.02102 (12)	0.43141 (9)	0.0498 (5)
C9	0.1760 (3)	1.09734 (15)	0.42992 (11)	0.0700 (7)
H9	0.157858	1.125378	0.389746	0.084*
C10	0.1219 (4)	1.13245 (17)	0.48645 (13)	0.0900 (9)
H10	0.067945	1.183728	0.484082	0.108*
C11	0.1467 (4)	1.09265 (18)	0.54595 (12)	0.0925 (10)
H11	0.109239	1.116503	0.584021	0.111*
C12	0.2269 (3)	1.01755 (16)	0.54950 (11)	0.0761 (7)
H12	0.244309	0.990238	0.590018	0.091*
C13	0.2817 (3)	0.98246 (13)	0.49292 (9)	0.0546 (5)
C14	0.40575 (19)	1.04221 (11)	0.07931 (8)	0.0395 (4)
C15	0.3746 (2)	1.09964 (13)	0.02837 (10)	0.0524 (5)
H15	0.424605	1.152112	0.028284	0.063*
C16	0.2695 (3)	1.07856 (15)	−0.02190 (10)	0.0604 (6)
H16	0.247308	1.116892	−0.056185	0.073*
C17	0.1973 (2)	1.00115 (16)	−0.02157 (10)	0.0589 (6)
H17	0.125775	0.986900	−0.055648	0.071*
C18	0.2301 (2)	0.94401 (13)	0.02908 (9)	0.0475 (4)
H18	0.180273	0.891469	0.028376	0.057*
C19	0.33571 (18)	0.96284 (11)	0.08114 (8)	0.0355 (3)
C20	0.37056 (18)	0.90127 (10)	0.13774 (7)	0.0333 (3)
H20	0.474518	0.914578	0.156241	0.040*
C21	0.3698 (2)	0.80722 (11)	0.11831 (9)	0.0418 (4)
H21A	0.294485	0.796255	0.082138	0.050*
H21B	0.470866	0.789228	0.105323	0.050*
C22	0.3020 (3)	0.67327 (12)	0.17056 (11)	0.0576 (5)
H22A	0.275049	0.649399	0.212106	0.086*
H22B	0.219323	0.663728	0.137946	0.086*
H22C	0.394350	0.646490	0.156564	0.086*
C23	0.20239 (17)	0.81269 (10)	0.20545 (8)	0.0322 (3)
C24	0.0411 (2)	0.79856 (11)	0.16774 (9)	0.0410 (4)
C25	−0.06990 (19)	0.77207 (11)	0.21615 (10)	0.0429 (4)
C26	−0.2263 (2)	0.75748 (13)	0.21054 (12)	0.0572 (5)
H26	−0.281931	0.764906	0.170370	0.069*
C27	−0.2990 (2)	0.73129 (15)	0.26675 (14)	0.0684 (7)
H27	−0.405325	0.722892	0.264134	0.082*
C28	−0.2189 (3)	0.71761 (13)	0.32545 (13)	0.0628 (6)
H28	−0.271567	0.698729	0.361561	0.075*
C29	−0.0578 (2)	0.73134 (11)	0.33300 (10)	0.0461 (4)
C30	0.0409 (3)	0.71831 (12)	0.38919 (10)	0.0526 (5)
H30	0.001188	0.698030	0.428006	0.063*
C31	0.1947 (2)	0.73521 (12)	0.38725 (9)	0.0496 (5)
H31	0.258210	0.724857	0.424875	0.060*
C32	0.2616 (2)	0.76802 (11)	0.32996 (9)	0.0410 (4)
H32	0.366809	0.779746	0.330281	0.049*
C33	0.16946 (18)	0.78193 (10)	0.27480 (8)	0.0339 (3)
C34	0.01184 (19)	0.76132 (10)	0.27645 (9)	0.0379 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1164 (5)	0.0651 (4)	0.0426 (3)	0.0162 (3)	−0.0028 (3)	0.0052 (2)
Cl2	0.0520 (3)	0.0486 (3)	0.0634 (3)	−0.0065 (2)	−0.0062 (2)	−0.0027 (2)
O1	0.0375 (6)	0.0762 (9)	0.0382 (7)	0.0023 (6)	−0.0059 (5)	−0.0024 (6)
O2	0.0606 (8)	0.0712 (10)	0.0422 (8)	−0.0164 (7)	−0.0156 (6)	0.0065 (7)
N1	0.0344 (7)	0.0376 (7)	0.0316 (7)	0.0049 (5)	0.0030 (5)	−0.0007 (6)
N2	0.0460 (8)	0.0329 (7)	0.0352 (8)	0.0044 (6)	0.0067 (6)	−0.0027 (6)
C1	0.0384 (8)	0.0354 (8)	0.0275 (8)	−0.0033 (6)	−0.0013 (6)	0.0035 (6)
C2	0.0309 (7)	0.0335 (8)	0.0252 (7)	0.0007 (6)	0.0013 (6)	0.0008 (6)
C3	0.0365 (8)	0.0355 (8)	0.0268 (8)	0.0039 (6)	−0.0005 (6)	0.0016 (6)
C4	0.0411 (9)	0.0537 (11)	0.0511 (11)	0.0131 (8)	0.0035 (8)	0.0005 (9)
C5	0.0517 (10)	0.0408 (9)	0.0315 (9)	0.0077 (7)	0.0039 (7)	−0.0038 (7)
C6	0.0465 (9)	0.0344 (8)	0.0291 (8)	−0.0030 (7)	0.0010 (7)	−0.0008 (6)
C7	0.0571 (11)	0.0466 (10)	0.0318 (9)	−0.0019 (8)	−0.0023 (8)	−0.0012 (7)
C8	0.0732 (13)	0.0468 (10)	0.0288 (9)	−0.0039 (9)	−0.0025 (8)	−0.0063 (8)
C9	0.117 (2)	0.0542 (13)	0.0381 (11)	0.0107 (13)	−0.0047 (12)	−0.0076 (9)
C10	0.153 (3)	0.0611 (15)	0.0555 (15)	0.0301 (16)	0.0057 (16)	−0.0159 (12)
C11	0.163 (3)	0.0710 (17)	0.0448 (14)	0.0170 (18)	0.0209 (16)	−0.0168 (12)
C12	0.133 (2)	0.0629 (14)	0.0337 (11)	0.0001 (15)	0.0128 (13)	−0.0019 (10)
C13	0.0821 (14)	0.0460 (11)	0.0356 (10)	−0.0045 (10)	0.0017 (9)	−0.0034 (8)
C14	0.0358 (8)	0.0465 (9)	0.0369 (9)	0.0042 (7)	0.0078 (7)	0.0023 (7)
C15	0.0570 (11)	0.0509 (11)	0.0507 (12)	0.0045 (9)	0.0165 (9)	0.0135 (9)
C16	0.0635 (13)	0.0777 (15)	0.0409 (11)	0.0173 (11)	0.0104 (9)	0.0262 (10)
C17	0.0525 (11)	0.0899 (17)	0.0337 (10)	0.0036 (11)	−0.0023 (8)	0.0126 (10)
C18	0.0463 (10)	0.0642 (12)	0.0319 (9)	−0.0031 (8)	0.0010 (7)	0.0051 (8)
C19	0.0337 (8)	0.0459 (9)	0.0275 (8)	0.0032 (7)	0.0065 (6)	0.0027 (7)
C20	0.0324 (7)	0.0403 (8)	0.0273 (8)	0.0011 (6)	0.0013 (6)	0.0002 (6)
C21	0.0485 (9)	0.0432 (9)	0.0343 (9)	0.0054 (7)	0.0075 (7)	−0.0040 (7)
C22	0.0804 (14)	0.0358 (10)	0.0577 (13)	0.0030 (9)	0.0133 (11)	−0.0059 (9)
C23	0.0335 (7)	0.0336 (8)	0.0292 (8)	0.0001 (6)	−0.0006 (6)	0.0014 (6)
C24	0.0413 (9)	0.0364 (9)	0.0443 (10)	−0.0033 (7)	−0.0059 (7)	0.0012 (7)
C25	0.0367 (8)	0.0342 (9)	0.0574 (11)	−0.0009 (7)	−0.0002 (8)	0.0006 (8)
C26	0.0391 (9)	0.0519 (11)	0.0798 (15)	−0.0016 (8)	−0.0034 (10)	−0.0004 (10)
C27	0.0395 (10)	0.0635 (14)	0.104 (2)	−0.0058 (9)	0.0173 (12)	−0.0037 (13)
C28	0.0549 (12)	0.0518 (12)	0.0851 (17)	−0.0068 (9)	0.0344 (12)	−0.0017 (11)
C29	0.0539 (10)	0.0309 (8)	0.0555 (12)	0.0016 (7)	0.0216 (9)	0.0003 (8)
C30	0.0744 (13)	0.0377 (9)	0.0482 (11)	0.0050 (9)	0.0253 (10)	0.0054 (8)
C31	0.0711 (13)	0.0406 (10)	0.0374 (10)	0.0110 (9)	0.0051 (9)	0.0074 (8)
C32	0.0461 (9)	0.0382 (9)	0.0389 (9)	0.0067 (7)	0.0033 (7)	0.0048 (7)
C33	0.0377 (8)	0.0288 (7)	0.0355 (9)	0.0029 (6)	0.0049 (6)	0.0026 (6)
C34	0.0403 (8)	0.0261 (7)	0.0479 (10)	0.0012 (6)	0.0090 (7)	0.0000 (7)

Geometric parameters (Å, º)

Cl1—C13	1.731 (2)	C14—C19	1.386 (2)
Cl2—C14	1.7336 (18)	C15—C16	1.369 (3)
O1—C1	1.2098 (19)	C15—H15	0.9300
O2—C24	1.208 (2)	C16—C17	1.365 (3)
N1—C5	1.450 (2)	C16—H16	0.9300
N1—C3	1.4506 (19)	C17—C18	1.379 (3)
N1—C4	1.454 (2)	C17—H17	0.9300
N2—C22	1.446 (2)	C18—C19	1.390 (2)
N2—C21	1.451 (2)	C18—H18	0.9300
N2—C23	1.462 (2)	C19—C20	1.516 (2)
C1—C6	1.501 (2)	C20—C21	1.526 (2)
C1—C2	1.533 (2)	C20—H20	0.9800
C2—C3	1.527 (2)	C21—H21A	0.9700
C2—C20	1.566 (2)	C21—H21B	0.9700
C2—C23	1.584 (2)	C22—H22A	0.9600
C3—H3A	0.9700	C22—H22B	0.9600
C3—H3B	0.9700	C22—H22C	0.9600
C4—H4A	0.9600	C23—C33	1.525 (2)
C4—H4B	0.9600	C23—C24	1.573 (2)
C4—H4C	0.9600	C24—C25	1.469 (3)
C5—C6	1.505 (2)	C25—C26	1.374 (2)
C5—H5A	0.9700	C25—C34	1.388 (3)
C5—H5B	0.9700	C26—C27	1.391 (3)
C6—C7	1.332 (2)	C26—H26	0.9300
C7—C8	1.466 (3)	C27—C28	1.360 (3)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.387 (3)	C28—C29	1.414 (3)
C8—C13	1.390 (3)	C28—H28	0.9300
C9—C10	1.374 (3)	C29—C30	1.401 (3)
C9—H9	0.9300	C29—C34	1.402 (2)
C10—C11	1.363 (4)	C30—C31	1.362 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.367 (4)	C31—C32	1.420 (2)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.377 (3)	C32—C33	1.355 (2)
C12—H12	0.9300	C32—H32	0.9300
C14—C15	1.384 (3)	C33—C34	1.406 (2)
C5—N1—C3	109.25 (13)	C16—C17—C18	120.3 (2)
C5—N1—C4	111.01 (13)	C16—C17—H17	119.9
C3—N1—C4	112.25 (13)	C18—C17—H17	119.9
C22—N2—C21	114.51 (14)	C17—C18—C19	121.78 (19)
C22—N2—C23	116.03 (14)	C17—C18—H18	119.1
C21—N2—C23	107.08 (13)	C19—C18—H18	119.1
O1—C1—C6	121.17 (15)	C14—C19—C18	116.24 (16)
O1—C1—C2	121.21 (15)	C14—C19—C20	121.46 (15)
C6—C1—C2	117.60 (13)	C18—C19—C20	122.29 (16)
C3—C2—C1	107.89 (12)	C19—C20—C21	115.01 (13)
C3—C2—C20	114.15 (12)	C19—C20—C2	114.64 (12)
C1—C2—C20	110.87 (12)	C21—C20—C2	105.17 (13)
C3—C2—C23	112.25 (12)	C19—C20—H20	107.2
C1—C2—C23	107.74 (12)	C21—C20—H20	107.2
C20—C2—C23	103.77 (12)	C2—C20—H20	107.2
N1—C3—C2	108.55 (12)	N2—C21—C20	103.58 (13)
N1—C3—H3A	110.0	N2—C21—H21A	111.0
C2—C3—H3A	110.0	C20—C21—H21A	111.0
N1—C3—H3B	110.0	N2—C21—H21B	111.0
C2—C3—H3B	110.0	C20—C21—H21B	111.0
H3A—C3—H3B	108.4	H21A—C21—H21B	109.0
N1—C4—H4A	109.5	N2—C22—H22A	109.5
N1—C4—H4B	109.5	N2—C22—H22B	109.5
H4A—C4—H4B	109.5	H22A—C22—H22B	109.5
N1—C4—H4C	109.5	N2—C22—H22C	109.5
H4A—C4—H4C	109.5	H22A—C22—H22C	109.5
H4B—C4—H4C	109.5	H22B—C22—H22C	109.5
N1—C5—C6	112.12 (13)	N2—C23—C33	111.16 (12)
N1—C5—H5A	109.2	N2—C23—C24	113.88 (13)
C6—C5—H5A	109.2	C33—C23—C24	101.34 (12)
N1—C5—H5B	109.2	N2—C23—C2	101.90 (12)
C6—C5—H5B	109.2	C33—C23—C2	119.06 (13)
H5A—C5—H5B	107.9	C24—C23—C2	110.04 (12)
C7—C6—C1	116.54 (16)	O2—C24—C25	126.70 (16)
C7—C6—C5	123.80 (16)	O2—C24—C23	124.93 (16)
C1—C6—C5	119.60 (14)	C25—C24—C23	108.28 (14)
C6—C7—C8	127.74 (18)	C26—C25—C34	120.53 (18)
C6—C7—H7	116.1	C26—C25—C24	132.12 (19)
C8—C7—H7	116.1	C34—C25—C24	107.35 (15)
C9—C8—C13	116.62 (18)	C25—C26—C27	118.0 (2)
C9—C8—C7	122.54 (18)	C25—C26—H26	121.0
C13—C8—C7	120.78 (18)	C27—C26—H26	121.0
C10—C9—C8	121.5 (2)	C28—C27—C26	121.8 (2)
C10—C9—H9	119.2	C28—C27—H27	119.1
C8—C9—H9	119.2	C26—C27—H27	119.1
C11—C10—C9	120.5 (2)	C27—C28—C29	121.7 (2)
C11—C10—H10	119.8	C27—C28—H28	119.1
C9—C10—H10	119.8	C29—C28—H28	119.1
C10—C11—C12	119.8 (2)	C30—C29—C34	116.10 (17)
C10—C11—H11	120.1	C30—C29—C28	128.53 (19)
C12—C11—H11	120.1	C34—C29—C28	115.4 (2)
C11—C12—C13	119.8 (2)	C31—C30—C29	120.33 (17)
C11—C12—H12	120.1	C31—C30—H30	119.8
C13—C12—H12	120.1	C29—C30—H30	119.8
C12—C13—C8	121.8 (2)	C30—C31—C32	122.50 (18)
C12—C13—Cl1	118.43 (17)	C30—C31—H31	118.8
C8—C13—Cl1	119.76 (15)	C32—C31—H31	118.8
C15—C14—C19	122.37 (17)	C33—C32—C31	118.77 (17)
C15—C14—Cl2	117.45 (15)	C33—C32—H32	120.6
C19—C14—Cl2	120.17 (13)	C31—C32—H32	120.6
C16—C15—C14	119.5 (2)	C32—C33—C34	118.36 (15)
C16—C15—H15	120.3	C32—C33—C23	132.64 (15)
C14—C15—H15	120.3	C34—C33—C23	108.90 (14)
C17—C16—C15	119.85 (19)	C25—C34—C29	122.39 (17)
C17—C16—H16	120.1	C25—C34—C33	113.76 (15)
C15—C16—H16	120.1	C29—C34—C33	123.85 (17)
O1—C1—C2—C3	−151.50 (15)	C19—C20—C21—N2	−152.40 (13)
C6—C1—C2—C3	30.10 (18)	C2—C20—C21—N2	−25.30 (16)
O1—C1—C2—C20	−25.8 (2)	C22—N2—C23—C33	60.97 (19)
C6—C1—C2—C20	155.77 (13)	C21—N2—C23—C33	−169.74 (13)
O1—C1—C2—C23	87.09 (18)	C22—N2—C23—C24	−52.7 (2)
C6—C1—C2—C23	−91.31 (15)	C21—N2—C23—C24	76.57 (16)
C5—N1—C3—C2	75.82 (16)	C22—N2—C23—C2	−171.16 (15)
C4—N1—C3—C2	−160.58 (14)	C21—N2—C23—C2	−41.87 (15)
C1—C2—C3—N1	−60.62 (16)	C3—C2—C23—N2	147.45 (12)
C20—C2—C3—N1	175.67 (13)	C1—C2—C23—N2	−93.90 (14)
C23—C2—C3—N1	57.94 (16)	C20—C2—C23—N2	23.71 (14)
C3—N1—C5—C6	−54.27 (18)	C3—C2—C23—C33	−89.93 (16)
C4—N1—C5—C6	−178.59 (14)	C1—C2—C23—C33	28.72 (17)
O1—C1—C6—C7	−14.3 (2)	C20—C2—C23—C33	146.34 (13)
C2—C1—C6—C7	164.07 (15)	C3—C2—C23—C24	26.31 (17)
O1—C1—C6—C5	168.41 (16)	C1—C2—C23—C24	144.96 (13)
C2—C1—C6—C5	−13.2 (2)	C20—C2—C23—C24	−97.43 (14)
N1—C5—C6—C7	−153.17 (16)	N2—C23—C24—O2	−51.3 (2)
N1—C5—C6—C1	23.9 (2)	C33—C23—C24—O2	−170.73 (17)
C1—C6—C7—C8	−179.00 (17)	C2—C23—C24—O2	62.4 (2)
C5—C6—C7—C8	−1.9 (3)	N2—C23—C24—C25	125.47 (15)
C6—C7—C8—C9	−42.2 (3)	C33—C23—C24—C25	6.04 (16)
C6—C7—C8—C13	140.7 (2)	C2—C23—C24—C25	−120.86 (14)
C13—C8—C9—C10	−0.5 (4)	O2—C24—C25—C26	−8.4 (3)
C7—C8—C9—C10	−177.7 (3)	C23—C24—C25—C26	174.85 (19)
C8—C9—C10—C11	−0.1 (5)	O2—C24—C25—C34	171.10 (18)
C9—C10—C11—C12	0.4 (5)	C23—C24—C25—C34	−5.60 (18)
C10—C11—C12—C13	−0.2 (5)	C34—C25—C26—C27	−0.4 (3)
C11—C12—C13—C8	−0.4 (4)	C24—C25—C26—C27	179.1 (2)
C11—C12—C13—Cl1	−179.7 (2)	C25—C26—C27—C28	−2.0 (3)
C9—C8—C13—C12	0.8 (3)	C26—C27—C28—C29	1.6 (3)
C7—C8—C13—C12	178.0 (2)	C27—C28—C29—C30	−178.3 (2)
C9—C8—C13—Cl1	−179.95 (18)	C27—C28—C29—C34	1.2 (3)
C7—C8—C13—Cl1	−2.7 (3)	C34—C29—C30—C31	0.5 (3)
C19—C14—C15—C16	0.9 (3)	C28—C29—C30—C31	179.99 (19)
Cl2—C14—C15—C16	−177.66 (15)	C29—C30—C31—C32	1.4 (3)
C14—C15—C16—C17	−0.4 (3)	C30—C31—C32—C33	−1.0 (3)
C15—C16—C17—C18	−0.2 (3)	C31—C32—C33—C34	−1.4 (2)
C16—C17—C18—C19	0.3 (3)	C31—C32—C33—C23	−177.36 (16)
C15—C14—C19—C18	−0.7 (2)	N2—C23—C33—C32	50.4 (2)
Cl2—C14—C19—C18	177.79 (13)	C24—C23—C33—C32	171.78 (17)
C15—C14—C19—C20	−179.46 (15)	C2—C23—C33—C32	−67.5 (2)
Cl2—C14—C19—C20	−0.9 (2)	N2—C23—C33—C34	−125.80 (14)
C17—C18—C19—C14	0.1 (3)	C24—C23—C33—C34	−4.45 (16)
C17—C18—C19—C20	178.84 (17)	C2—C23—C33—C34	116.30 (15)
C14—C19—C20—C21	−145.35 (15)	C26—C25—C34—C29	3.3 (3)
C18—C19—C20—C21	36.0 (2)	C24—C25—C34—C29	−176.29 (15)
C14—C19—C20—C2	92.53 (18)	C26—C25—C34—C33	−177.61 (16)
C18—C19—C20—C2	−86.13 (19)	C24—C25—C34—C33	2.8 (2)
C3—C2—C20—C19	5.57 (19)	C30—C29—C34—C25	175.93 (16)
C1—C2—C20—C19	−116.52 (15)	C28—C29—C34—C25	−3.6 (2)
C23—C2—C20—C19	128.06 (14)	C30—C29—C34—C33	−3.0 (2)
C3—C2—C20—C21	−121.76 (14)	C28—C29—C34—C33	177.43 (16)
C1—C2—C20—C21	116.15 (14)	C32—C33—C34—C25	−175.52 (15)
C23—C2—C20—C21	0.73 (15)	C23—C33—C34—C25	1.33 (19)
C22—N2—C21—C20	173.28 (15)	C32—C33—C34—C29	3.5 (2)
C23—N2—C21—C20	43.13 (17)	C23—C33—C34—C29	−179.62 (15)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C25–C29/C34 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2^i	0.93	2.74	3.492 (3)	139
C16—H16···O2^ii	0.93	2.76	3.481 (3)	135
C5—H5B···Cg1^i	0.97	2.99	3.9466 (19)	168

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

1'-Methyl-5''-(2-methylbenzylidene)-4'-(2-methylphenyl)dispiro[acenaphthene-1,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione (II)

Crystal data

C36H34N2O2	F(000) = 1120
Mr = 526.65	Dx = 1.240 Mg m^−3 Dm = 1.24 Mg m^−3 Dm measured by floatation method
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7507 (5) Å	Cell parameters from 5358 reflections
b = 15.9089 (8) Å	θ = 4.7–42.0°
c = 20.2879 (10) Å	µ = 0.08 mm^−1
β = 92.935 (2)°	T = 293 K
V = 2820.7 (3) Å^3	Block, yellow
Z = 4	0.32 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
φ and ω scans	θmax = 25.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.816, Tmax = 1.000	k = −19→19
28946 measured reflections	l = −24→18
5339 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)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.5169P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.121	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.17 e Å^−3
5339 reflections	Δρmin = −0.15 e Å^−3
362 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0040 (6)

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	Occ. (<1)
O1	0.47706 (15)	0.91884 (10)	0.26949 (6)	0.0632 (4)
O2	0.01075 (17)	0.80552 (10)	0.11060 (7)	0.0749 (5)
N1	0.02197 (15)	0.96279 (9)	0.23966 (7)	0.0438 (4)
N2	0.32038 (17)	0.76401 (9)	0.17891 (7)	0.0488 (4)
C1	0.3410 (2)	0.93366 (11)	0.26053 (8)	0.0434 (4)
C2	0.25341 (18)	0.90633 (11)	0.19667 (8)	0.0377 (4)
C3	0.12046 (19)	0.96732 (11)	0.18425 (8)	0.0420 (4)
H3A	0.159005	1.024095	0.179771	0.050*
H3B	0.063116	0.952451	0.143748	0.050*
C4	−0.1307 (2)	0.99492 (14)	0.22319 (10)	0.0619 (6)
H4A	−0.175538	0.964127	0.186372	0.093*
H4B	−0.192980	0.988480	0.260484	0.093*
H4C	−0.124579	1.053358	0.211850	0.093*
C5	0.0937 (2)	1.00778 (12)	0.29519 (9)	0.0529 (5)
H5A	0.032387	1.000780	0.333317	0.063*
H5B	0.096585	1.067257	0.284807	0.063*
C6	0.2541 (2)	0.97734 (11)	0.31209 (8)	0.0459 (4)
C7	0.3224 (2)	0.98436 (13)	0.37200 (9)	0.0566 (5)
H7	0.420638	0.962182	0.376842	0.068*
C8	0.2630 (3)	1.02252 (14)	0.43153 (9)	0.0637 (6)
C9	0.1907 (3)	1.09994 (16)	0.42926 (11)	0.0862 (8)
H9	0.176292	1.127477	0.388985	0.103*
C10	0.1399 (4)	1.13691 (19)	0.48527 (13)	0.1125 (11)
H10	0.092416	1.189186	0.482807	0.135*
C11	0.1595 (4)	1.0966 (2)	0.54474 (13)	0.1158 (11)
H11	0.124439	1.121064	0.582782	0.139*
C12	0.2304 (4)	1.02073 (18)	0.54774 (12)	0.1011 (10)
H12	0.242808	0.993784	0.588346	0.121*
C13	0.2852 (3)	0.98180 (14)	0.49223 (10)	0.0736 (7)
C14	0.4072 (2)	1.03916 (12)	0.08230 (9)	0.0477 (5)
C15	0.3741 (2)	1.09458 (14)	0.03059 (10)	0.0627 (6)
H15	0.425474	1.145727	0.029917	0.075*
C16	0.2684 (3)	1.07634 (17)	−0.01936 (11)	0.0716 (7)
H16	0.247654	1.114850	−0.053129	0.086*
C17	0.1933 (2)	1.00083 (17)	−0.01915 (10)	0.0693 (6)
H17	0.121043	0.987782	−0.052809	0.083*
C18	0.2252 (2)	0.94425 (14)	0.03112 (9)	0.0563 (5)
H18	0.173963	0.893017	0.030703	0.068*
C19	0.33151 (19)	0.96161 (12)	0.08224 (8)	0.0429 (4)
C20	0.36354 (19)	0.89945 (11)	0.13800 (8)	0.0420 (4)
H20	0.466999	0.911443	0.156377	0.050*
C21	0.3607 (2)	0.80656 (12)	0.11868 (9)	0.0529 (5)
H21A	0.284808	0.796067	0.083082	0.063*
H21B	0.460023	0.788322	0.105068	0.063*
C22	0.2938 (3)	0.67430 (13)	0.17162 (11)	0.0731 (7)
H22A	0.268011	0.651006	0.213260	0.110*
H22B	0.211144	0.664885	0.139531	0.110*
H22C	0.384812	0.647695	0.157250	0.110*
C23	0.19669 (19)	0.81255 (11)	0.20669 (8)	0.0422 (4)
C24	0.0359 (2)	0.79910 (12)	0.16969 (10)	0.0523 (5)
C25	−0.0735 (2)	0.77254 (12)	0.21815 (10)	0.0540 (5)
C26	−0.2285 (2)	0.75824 (14)	0.21310 (13)	0.0723 (6)
H26	−0.284279	0.766562	0.173375	0.087*
C27	−0.2998 (3)	0.73101 (16)	0.26895 (16)	0.0843 (8)
H27	−0.405192	0.722827	0.266586	0.101*
C28	−0.2194 (3)	0.71598 (14)	0.32708 (14)	0.0765 (7)
H28	−0.270670	0.696290	0.363029	0.092*
C29	−0.0593 (2)	0.72969 (12)	0.33393 (11)	0.0580 (5)
C30	0.0395 (3)	0.71575 (13)	0.38964 (11)	0.0661 (6)
H30	0.000748	0.694837	0.428213	0.079*
C31	0.1921 (3)	0.73275 (12)	0.38742 (10)	0.0618 (6)
H31	0.255708	0.721647	0.424532	0.074*
C32	0.2575 (2)	0.76681 (11)	0.33047 (9)	0.0504 (5)
H32	0.361543	0.778819	0.330644	0.060*
C33	0.1650 (2)	0.78149 (11)	0.27577 (8)	0.0430 (4)
C34	0.0085 (2)	0.76075 (11)	0.27794 (9)	0.0473 (5)
C35	0.3604 (4)	0.89722 (16)	0.49768 (11)	0.0951 (9)
H35A	0.391046	0.879874	0.454998	0.143*	0.5
H35B	0.448790	0.900568	0.527609	0.143*	0.5
H35C	0.289565	0.857078	0.513916	0.143*	0.5
H35D	0.361888	0.878473	0.542684	0.143*	0.5
H35E	0.304143	0.857779	0.470073	0.143*	0.5
H35F	0.463369	0.901268	0.483766	0.143*	0.5
C36	0.5214 (2)	1.06401 (14)	0.13658 (11)	0.0659 (6)
H36A	0.531595	1.019372	0.168344	0.099*	0.5
H36B	0.618648	1.074534	0.118366	0.099*	0.5
H36C	0.486814	1.114002	0.157740	0.099*	0.5
H36D	0.559776	1.119233	0.127956	0.099*	0.5
H36E	0.472723	1.064071	0.177934	0.099*	0.5
H36F	0.604557	1.024604	0.138560	0.099*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0476 (8)	0.0952 (11)	0.0459 (8)	0.0049 (7)	−0.0050 (6)	−0.0030 (7)
O2	0.0784 (10)	0.0890 (12)	0.0551 (10)	−0.0227 (8)	−0.0182 (8)	0.0099 (8)
N1	0.0438 (8)	0.0493 (9)	0.0386 (9)	0.0075 (7)	0.0052 (7)	0.0005 (7)
N2	0.0621 (10)	0.0420 (9)	0.0434 (9)	0.0056 (7)	0.0121 (7)	−0.0019 (7)
C1	0.0449 (11)	0.0489 (11)	0.0361 (10)	−0.0008 (8)	0.0004 (8)	0.0042 (8)
C2	0.0396 (9)	0.0432 (10)	0.0303 (9)	0.0010 (8)	0.0026 (7)	0.0004 (8)
C3	0.0471 (10)	0.0452 (10)	0.0336 (10)	0.0022 (8)	0.0018 (8)	0.0018 (8)
C4	0.0526 (12)	0.0685 (14)	0.0650 (14)	0.0164 (10)	0.0071 (10)	−0.0003 (11)
C5	0.0666 (13)	0.0533 (12)	0.0391 (11)	0.0101 (10)	0.0072 (9)	−0.0033 (9)
C6	0.0597 (11)	0.0439 (11)	0.0340 (10)	−0.0015 (9)	0.0009 (8)	0.0001 (8)
C7	0.0757 (14)	0.0559 (12)	0.0377 (11)	−0.0012 (10)	−0.0014 (10)	−0.0005 (9)
C8	0.0948 (16)	0.0596 (14)	0.0362 (12)	0.0032 (12)	−0.0021 (10)	−0.0079 (10)
C9	0.143 (2)	0.0701 (16)	0.0441 (14)	0.0211 (16)	−0.0056 (14)	−0.0085 (12)
C10	0.193 (3)	0.0801 (19)	0.0642 (18)	0.040 (2)	0.0039 (19)	−0.0204 (15)
C11	0.202 (3)	0.093 (2)	0.0542 (17)	0.028 (2)	0.0216 (18)	−0.0222 (16)
C12	0.179 (3)	0.0834 (19)	0.0420 (14)	0.013 (2)	0.0156 (16)	−0.0069 (13)
C13	0.118 (2)	0.0631 (15)	0.0393 (12)	0.0007 (14)	0.0031 (12)	−0.0062 (11)
C14	0.0447 (10)	0.0549 (12)	0.0444 (11)	0.0043 (9)	0.0126 (8)	0.0033 (9)
C15	0.0696 (14)	0.0620 (14)	0.0584 (14)	0.0034 (11)	0.0222 (11)	0.0141 (11)
C16	0.0759 (16)	0.0903 (18)	0.0497 (14)	0.0212 (14)	0.0140 (12)	0.0276 (12)
C17	0.0593 (13)	0.107 (2)	0.0415 (12)	0.0025 (13)	0.0008 (10)	0.0154 (12)
C18	0.0545 (12)	0.0767 (14)	0.0377 (11)	−0.0056 (10)	0.0028 (9)	0.0068 (10)
C19	0.0414 (10)	0.0557 (12)	0.0322 (10)	0.0019 (9)	0.0084 (8)	0.0030 (8)
C20	0.0402 (10)	0.0518 (11)	0.0342 (10)	−0.0004 (8)	0.0025 (7)	−0.0005 (8)
C21	0.0609 (12)	0.0562 (12)	0.0425 (11)	0.0046 (9)	0.0117 (9)	−0.0047 (9)
C22	0.1067 (18)	0.0462 (12)	0.0682 (15)	0.0039 (12)	0.0207 (13)	−0.0071 (11)
C23	0.0437 (10)	0.0457 (11)	0.0372 (10)	0.0020 (8)	0.0029 (8)	0.0007 (8)
C24	0.0573 (12)	0.0463 (11)	0.0524 (13)	−0.0040 (9)	−0.0057 (10)	0.0040 (9)
C25	0.0477 (11)	0.0459 (11)	0.0684 (14)	−0.0011 (9)	0.0045 (10)	0.0018 (10)
C26	0.0524 (13)	0.0648 (14)	0.0994 (19)	−0.0021 (11)	0.0012 (12)	−0.0008 (13)
C27	0.0542 (14)	0.0776 (17)	0.123 (2)	−0.0061 (13)	0.0221 (16)	−0.0055 (17)
C28	0.0690 (16)	0.0648 (15)	0.100 (2)	−0.0065 (12)	0.0418 (15)	−0.0021 (14)
C29	0.0696 (14)	0.0404 (11)	0.0664 (14)	0.0048 (10)	0.0249 (12)	0.0005 (10)
C30	0.0901 (17)	0.0501 (13)	0.0613 (14)	0.0083 (12)	0.0364 (13)	0.0071 (10)
C31	0.0919 (17)	0.0501 (12)	0.0439 (12)	0.0184 (12)	0.0088 (11)	0.0087 (9)
C32	0.0591 (12)	0.0465 (11)	0.0460 (11)	0.0112 (9)	0.0069 (9)	0.0061 (9)
C33	0.0509 (11)	0.0366 (10)	0.0422 (11)	0.0069 (8)	0.0082 (8)	0.0033 (8)
C34	0.0519 (11)	0.0349 (10)	0.0563 (12)	0.0028 (8)	0.0149 (10)	0.0026 (9)
C35	0.157 (3)	0.0752 (17)	0.0521 (14)	0.0178 (17)	−0.0015 (15)	0.0049 (12)
C36	0.0637 (13)	0.0622 (14)	0.0717 (15)	−0.0101 (11)	0.0025 (11)	−0.0023 (11)

Geometric parameters (Å, º)

O1—C1	1.218 (2)	C17—H17	0.9300
O2—C24	1.212 (2)	C18—C19	1.385 (2)
N1—C5	1.450 (2)	C18—H18	0.9300
N1—C3	1.453 (2)	C19—C20	1.518 (2)
N1—C4	1.454 (2)	C20—C21	1.529 (3)
N2—C22	1.452 (2)	C20—H20	0.9800
N2—C21	1.456 (2)	C21—H21A	0.9700
N2—C23	1.466 (2)	C21—H21B	0.9700
C1—C6	1.496 (2)	C22—H22A	0.9600
C1—C2	1.534 (2)	C22—H22B	0.9600
C2—C3	1.526 (2)	C22—H22C	0.9600
C2—C20	1.573 (2)	C23—C33	1.525 (2)
C2—C23	1.589 (2)	C23—C24	1.575 (3)
C3—H3A	0.9700	C24—C25	1.469 (3)
C3—H3B	0.9700	C25—C26	1.374 (3)
C4—H4A	0.9600	C25—C34	1.390 (3)
C4—H4B	0.9600	C26—C27	1.390 (3)
C4—H4C	0.9600	C26—H26	0.9300
C5—C6	1.508 (3)	C27—C28	1.363 (3)
C5—H5A	0.9700	C27—H27	0.9300
C5—H5B	0.9700	C28—C29	1.417 (3)
C6—C7	1.331 (2)	C28—H28	0.9300
C7—C8	1.470 (3)	C29—C34	1.398 (3)
C7—H7	0.9300	C29—C30	1.405 (3)
C8—C9	1.384 (3)	C30—C31	1.366 (3)
C8—C13	1.396 (3)	C30—H30	0.9300
C9—C10	1.374 (3)	C31—C32	1.423 (3)
C9—H9	0.9300	C31—H31	0.9300
C10—C11	1.369 (4)	C32—C33	1.360 (2)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.358 (4)	C33—C34	1.412 (2)
C11—H11	0.9300	C35—H35A	0.9600
C12—C13	1.392 (3)	C35—H35B	0.9600
C12—H12	0.9300	C35—H35C	0.9600
C13—C35	1.500 (3)	C35—H35D	0.9600
C14—C15	1.390 (3)	C35—H35E	0.9600
C14—C19	1.400 (3)	C35—H35F	0.9600
C14—C36	1.501 (3)	C36—H36A	0.9600
C15—C16	1.368 (3)	C36—H36B	0.9600
C15—H15	0.9300	C36—H36C	0.9600
C16—C17	1.369 (3)	C36—H36D	0.9600
C16—H16	0.9300	C36—H36E	0.9600
C17—C18	1.378 (3)	C36—H36F	0.9600
C5—N1—C3	109.05 (14)	C19—C20—C21	116.01 (14)
C5—N1—C4	111.16 (15)	C19—C20—C2	114.95 (14)
C3—N1—C4	112.30 (14)	C21—C20—C2	104.99 (14)
C22—N2—C21	114.57 (15)	C19—C20—H20	106.8
C22—N2—C23	116.08 (15)	C21—C20—H20	106.8
C21—N2—C23	107.05 (13)	C2—C20—H20	106.8
O1—C1—C6	120.91 (16)	N2—C21—C20	103.63 (13)
O1—C1—C2	120.90 (16)	N2—C21—H21A	111.0
C6—C1—C2	118.18 (15)	C20—C21—H21A	111.0
C3—C2—C1	107.64 (14)	N2—C21—H21B	111.0
C3—C2—C20	114.25 (13)	C20—C21—H21B	111.0
C1—C2—C20	111.07 (13)	H21A—C21—H21B	109.0
C3—C2—C23	112.19 (13)	N2—C22—H22A	109.5
C1—C2—C23	107.70 (13)	N2—C22—H22B	109.5
C20—C2—C23	103.83 (13)	H22A—C22—H22B	109.5
N1—C3—C2	108.55 (13)	N2—C22—H22C	109.5
N1—C3—H3A	110.0	H22A—C22—H22C	109.5
C2—C3—H3A	110.0	H22B—C22—H22C	109.5
N1—C3—H3B	110.0	N2—C23—C33	110.81 (14)
C2—C3—H3B	110.0	N2—C23—C24	113.84 (14)
H3A—C3—H3B	108.4	C33—C23—C24	101.21 (14)
N1—C4—H4A	109.5	N2—C23—C2	101.76 (13)
N1—C4—H4B	109.5	C33—C23—C2	119.65 (14)
H4A—C4—H4B	109.5	C24—C23—C2	110.12 (13)
N1—C4—H4C	109.5	O2—C24—C25	126.46 (18)
H4A—C4—H4C	109.5	O2—C24—C23	124.94 (17)
H4B—C4—H4C	109.5	C25—C24—C23	108.48 (16)
N1—C5—C6	112.26 (15)	C26—C25—C34	120.42 (19)
N1—C5—H5A	109.2	C26—C25—C24	132.3 (2)
C6—C5—H5A	109.2	C34—C25—C24	107.31 (16)
N1—C5—H5B	109.2	C25—C26—C27	118.3 (2)
C6—C5—H5B	109.2	C25—C26—H26	120.9
H5A—C5—H5B	107.9	C27—C26—H26	120.9
C7—C6—C1	117.20 (17)	C28—C27—C26	121.8 (2)
C7—C6—C5	123.34 (17)	C28—C27—H27	119.1
C1—C6—C5	119.41 (15)	C26—C27—H27	119.1
C6—C7—C8	128.6 (2)	C27—C28—C29	121.4 (2)
C6—C7—H7	115.7	C27—C28—H28	119.3
C8—C7—H7	115.7	C29—C28—H28	119.3
C9—C8—C13	119.01 (19)	C34—C29—C30	116.11 (19)
C9—C8—C7	121.34 (19)	C34—C29—C28	115.7 (2)
C13—C8—C7	119.6 (2)	C30—C29—C28	128.2 (2)
C10—C9—C8	121.3 (2)	C31—C30—C29	120.30 (19)
C10—C9—H9	119.3	C31—C30—H30	119.8
C8—C9—H9	119.3	C29—C30—H30	119.8
C11—C10—C9	119.8 (3)	C30—C31—C32	122.5 (2)
C11—C10—H10	120.1	C30—C31—H31	118.8
C9—C10—H10	120.1	C32—C31—H31	118.8
C12—C11—C10	119.5 (2)	C33—C32—C31	118.75 (19)
C12—C11—H11	120.3	C33—C32—H32	120.6
C10—C11—H11	120.3	C31—C32—H32	120.6
C11—C12—C13	122.4 (2)	C32—C33—C34	118.17 (17)
C11—C12—H12	118.8	C32—C33—C23	132.64 (16)
C13—C12—H12	118.8	C34—C33—C23	109.07 (15)
C12—C13—C8	118.0 (2)	C25—C34—C29	122.33 (19)
C12—C13—C35	120.5 (2)	C25—C34—C33	113.55 (16)
C8—C13—C35	121.46 (19)	C29—C34—C33	124.10 (19)
C15—C14—C19	118.55 (18)	C13—C35—H35A	109.5
C15—C14—C36	119.47 (18)	C13—C35—H35B	109.5
C19—C14—C36	121.98 (17)	H35A—C35—H35B	109.5
C16—C15—C14	122.1 (2)	C13—C35—H35C	109.5
C16—C15—H15	118.9	H35A—C35—H35C	109.5
C14—C15—H15	118.9	H35B—C35—H35C	109.5
C15—C16—C17	119.4 (2)	H35D—C35—H35E	109.5
C15—C16—H16	120.3	H35D—C35—H35F	109.5
C17—C16—H16	120.3	H35E—C35—H35F	109.5
C16—C17—C18	119.8 (2)	C14—C36—H36A	109.5
C16—C17—H17	120.1	C14—C36—H36B	109.5
C18—C17—H17	120.1	H36A—C36—H36B	109.5
C17—C18—C19	121.8 (2)	C14—C36—H36C	109.5
C17—C18—H18	119.1	H36A—C36—H36C	109.5
C19—C18—H18	119.1	H36B—C36—H36C	109.5
C18—C19—C14	118.42 (17)	H36D—C36—H36E	109.5
C18—C19—C20	121.30 (17)	H36D—C36—H36F	109.5
C14—C19—C20	120.26 (15)	H36E—C36—H36F	109.5
O1—C1—C2—C3	−152.18 (17)	C19—C20—C21—N2	−153.51 (14)
C6—C1—C2—C3	29.1 (2)	C2—C20—C21—N2	−25.45 (17)
O1—C1—C2—C20	−26.4 (2)	C22—N2—C23—C33	60.2 (2)
C6—C1—C2—C20	154.89 (15)	C21—N2—C23—C33	−170.39 (14)
O1—C1—C2—C23	86.66 (19)	C22—N2—C23—C24	−53.0 (2)
C6—C1—C2—C23	−92.04 (17)	C21—N2—C23—C24	76.33 (18)
C5—N1—C3—C2	76.18 (17)	C22—N2—C23—C2	−171.47 (15)
C4—N1—C3—C2	−160.14 (15)	C21—N2—C23—C2	−42.10 (16)
C1—C2—C3—N1	−60.49 (17)	C3—C2—C23—N2	147.72 (13)
C20—C2—C3—N1	175.66 (13)	C1—C2—C23—N2	−94.01 (15)
C23—C2—C3—N1	57.82 (17)	C20—C2—C23—N2	23.85 (15)
C3—N1—C5—C6	−54.01 (19)	C3—C2—C23—C33	−89.87 (17)
C4—N1—C5—C6	−178.36 (15)	C1—C2—C23—C33	28.4 (2)
O1—C1—C6—C7	−12.8 (3)	C20—C2—C23—C33	146.26 (14)
C2—C1—C6—C7	165.91 (16)	C3—C2—C23—C24	26.65 (18)
O1—C1—C6—C5	169.68 (17)	C1—C2—C23—C24	144.93 (14)
C2—C1—C6—C5	−11.6 (2)	C20—C2—C23—C24	−97.21 (15)
N1—C5—C6—C7	−154.62 (18)	N2—C23—C24—O2	−51.5 (2)
N1—C5—C6—C1	22.8 (2)	C33—C23—C24—O2	−170.37 (18)
C1—C6—C7—C8	−178.84 (19)	C2—C23—C24—O2	62.1 (2)
C5—C6—C7—C8	−1.4 (3)	N2—C23—C24—C25	124.97 (16)
C6—C7—C8—C9	−46.1 (3)	C33—C23—C24—C25	6.06 (18)
C6—C7—C8—C13	136.6 (2)	C2—C23—C24—C25	−121.50 (15)
C13—C8—C9—C10	−0.4 (4)	O2—C24—C25—C26	−8.7 (4)
C7—C8—C9—C10	−177.7 (3)	C23—C24—C25—C26	174.9 (2)
C8—C9—C10—C11	−0.5 (5)	O2—C24—C25—C34	170.5 (2)
C9—C10—C11—C12	0.6 (6)	C23—C24—C25—C34	−5.9 (2)
C10—C11—C12—C13	0.2 (5)	C34—C25—C26—C27	−0.7 (3)
C11—C12—C13—C8	−1.1 (5)	C24—C25—C26—C27	178.4 (2)
C11—C12—C13—C35	−179.0 (3)	C25—C26—C27—C28	−2.0 (4)
C9—C8—C13—C12	1.2 (4)	C26—C27—C28—C29	1.8 (4)
C7—C8—C13—C12	178.6 (2)	C27—C28—C29—C34	1.1 (3)
C9—C8—C13—C35	179.0 (3)	C27—C28—C29—C30	−178.6 (2)
C7—C8—C13—C35	−3.6 (4)	C34—C29—C30—C31	0.3 (3)
C19—C14—C15—C16	1.2 (3)	C28—C29—C30—C31	−179.9 (2)
C36—C14—C15—C16	−178.30 (19)	C29—C30—C31—C32	1.6 (3)
C14—C15—C16—C17	−0.7 (3)	C30—C31—C32—C33	−1.3 (3)
C15—C16—C17—C18	−0.1 (3)	C31—C32—C33—C34	−1.0 (3)
C16—C17—C18—C19	0.3 (3)	C31—C32—C33—C23	−176.46 (17)
C17—C18—C19—C14	0.3 (3)	N2—C23—C33—C32	50.5 (3)
C17—C18—C19—C20	178.85 (17)	C24—C23—C33—C32	171.57 (19)
C15—C14—C19—C18	−1.0 (3)	C2—C23—C33—C32	−67.4 (2)
C36—C14—C19—C18	178.52 (17)	N2—C23—C33—C34	−125.23 (15)
C15—C14—C19—C20	−179.60 (16)	C24—C23—C33—C34	−4.16 (17)
C36—C14—C19—C20	−0.1 (3)	C2—C23—C33—C34	116.91 (16)
C18—C19—C20—C21	36.9 (2)	C26—C25—C34—C29	3.7 (3)
C14—C19—C20—C21	−144.55 (17)	C24—C25—C34—C29	−175.53 (17)
C18—C19—C20—C2	−86.1 (2)	C26—C25—C34—C33	−177.43 (17)
C14—C19—C20—C2	92.47 (19)	C24—C25—C34—C33	3.3 (2)
C3—C2—C20—C19	6.9 (2)	C30—C29—C34—C25	175.91 (18)
C1—C2—C20—C19	−115.06 (16)	C28—C29—C34—C25	−3.9 (3)
C23—C2—C20—C19	129.45 (15)	C30—C29—C34—C33	−2.8 (3)
C3—C2—C20—C21	−121.77 (16)	C28—C29—C34—C33	177.44 (17)
C1—C2—C20—C21	116.24 (16)	C32—C33—C34—C25	−175.63 (17)
C23—C2—C20—C21	0.75 (16)	C23—C33—C34—C25	0.8 (2)
C22—N2—C21—C20	173.69 (16)	C32—C33—C34—C29	3.2 (3)
C23—N2—C21—C20	43.47 (18)	C23—C33—C34—C29	179.61 (17)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C36—H36A···O1	0.96	2.66	3.586 (3)	161
C10—H10···O2^i	0.93	2.77	3.529 (3)	140
C16—H16···O2^ii	0.93	2.79	3.530 (3)	137
C35—H35F···Cg2^iii	0.96	2.94	3.805 (4)	151

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