Crystal structures of two substituted thia­zolidine derivatives

Viswanathan, V.; Rao, N.S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S2056989016011336

Crystal structures of two substituted thiazolidine derivatives

V. Viswanathan, N. S. Rao, R. Raghunathan and D. Velmurugan

In both compounds, namely 2′-ferrocenyl-6′-methyl-6a'-nitro-6′,6a',6b',7′,9′,11a'-hexahydro-2H-spiro[acenaphthylene-1,11′-chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazol]-2-one, (I), and 6′-(4-methoxyphenyl)-6a'-nitro-6′,6a',6b',7′,9′,11a'-hexahydro-2H-spiro[acenaphthylene-1,11′-chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazol]-2-one, (II), an intramolecular C—H

O hydrogen bond forms an S(7) ring motif. In (I), molecules are linked via two different C—H

O hydrogen bonds, forming chains along [001] and [100]. In (II), they are linked through C—H

O hydrogen bonds, forming dimers with an $R_{2}^{2}$ (10) ring motif while C—H

π interactions link the molecules in a head-to-tail fashion, forming chains along the a-axis direction.

Keywords: crystal structure; thiazolidine derivative; ferrocenyl; acenaphthylene; chromane; hydrogen bonding; C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016011336/bg2588sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011336/bg2588Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011336/bg2588IIsup3.hkl Contains datablock II

CCDC references: 1023737; 1023726

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.097
Data-to-parameter ratio = 18.2

Structure: II

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.037
wR factor = 0.105
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C27 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Fe1 Check

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 The Model has Chirality at C12     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C15     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C16     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C17     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C24     (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          13 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
   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
   0 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 A
PLAT737_ALERT_1_A D...A   Calc  3.1789(18), Rep   3.178(19) ......        9.9 s.u.-R
              C24  -O1          1.555   1.555 ............     #   70 Check

Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         S1 Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 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 C12     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C15     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C16     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C17     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C24     (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         21 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          18 Note

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 6'-Ferrocenyl-6a'-nitro-6',6a',6b',7',9',11a'-hexahydro-2H-spiro[acenaphthylene-1,11'-chromeno[3',4':3,4]pyrrolo[1,2-c]thiazol]-2-one top

Crystal data top

[Fe(C₅H₅)(C₂₉H₂₁N₂O₄S)]	F(000) = 1272
M_r = 614.48	D_x = 1.477 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.782 (5) Å	Cell parameters from 6900 reflections
b = 16.741 (5) Å	θ = 1.9–28.3°
c = 14.147 (5) Å	µ = 0.67 mm⁻¹
β = 98.013 (5)°	T = 293 K
V = 2763.1 (17) Å³	Block, colourless
Z = 4	0.19 × 0.16 × 0.11 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	5281 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
ω and φ scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→12
T_min = 0.746, T_max = 0.845	k = −22→20
25994 measured reflections	l = −16→18
6900 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0472P)² + 0.6353P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6900 reflections	Δρ_max = 0.29 e Å⁻³
379 parameters	Δρ_min = −0.33 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.17168 (14)	0.29715 (10)	0.34129 (12)	0.0382 (4)
C2	0.27528 (15)	0.26349 (12)	0.30982 (13)	0.0437 (4)
C3	0.36894 (17)	0.29875 (15)	0.27815 (15)	0.0580 (5)
H3	0.3751	0.3540	0.2741	0.070*
C4	0.45406 (18)	0.24843 (19)	0.25235 (17)	0.0714 (7)
H4	0.5173	0.2713	0.2301	0.086*
C5	0.44852 (18)	0.16710 (18)	0.25835 (16)	0.0683 (7)
H5	0.5081	0.1363	0.2412	0.082*
C6	0.35397 (17)	0.12899 (14)	0.29018 (14)	0.0536 (5)
C7	0.3351 (2)	0.04678 (15)	0.30007 (16)	0.0660 (6)
H7	0.3897	0.0103	0.2855	0.079*
C8	0.2377 (2)	0.02016 (13)	0.33066 (17)	0.0649 (6)
H8	0.2277	−0.0346	0.3372	0.078*
C9	0.15032 (19)	0.07272 (11)	0.35320 (15)	0.0528 (5)
H9	0.0834	0.0526	0.3720	0.063*
C10	0.16661 (15)	0.15301 (10)	0.34672 (12)	0.0397 (4)
C11	0.26808 (15)	0.18037 (11)	0.31521 (12)	0.0409 (4)
C12	0.09371 (13)	0.22504 (9)	0.36526 (11)	0.0327 (3)
C13	0.13859 (17)	0.19957 (12)	0.54151 (13)	0.0478 (4)
H13A	0.1502	0.2351	0.5961	0.057*
H13B	0.2128	0.1863	0.5235	0.057*
C14	−0.06611 (17)	0.13300 (11)	0.49327 (14)	0.0489 (5)
H14A	−0.0738	0.1007	0.4358	0.059*
H14B	−0.1330	0.1248	0.5250	0.059*
C15	−0.05289 (14)	0.22215 (9)	0.46914 (11)	0.0344 (3)
H15	−0.0782	0.2554	0.5193	0.041*
C16	−0.10955 (13)	0.25086 (9)	0.37114 (11)	0.0302 (3)
C17	−0.02634 (13)	0.22598 (9)	0.30174 (11)	0.0305 (3)
H17	−0.0450	0.1711	0.2810	0.037*
C18	−0.03280 (14)	0.27774 (10)	0.21409 (11)	0.0335 (3)
C19	0.02668 (16)	0.25728 (12)	0.13894 (13)	0.0445 (4)
H19	0.0699	0.2106	0.1426	0.053*
C20	0.02230 (19)	0.30546 (14)	0.05904 (14)	0.0562 (5)
H20	0.0621	0.2911	0.0093	0.067*
C21	−0.04142 (19)	0.37487 (13)	0.05351 (13)	0.0556 (5)
H21	−0.0439	0.4075	0.0000	0.067*
C22	−0.10152 (17)	0.39641 (11)	0.12664 (12)	0.0462 (4)
H22	−0.1445	0.4432	0.1228	0.055*
C23	−0.09665 (14)	0.34702 (10)	0.20609 (11)	0.0351 (3)
C24	−0.12592 (14)	0.34274 (9)	0.36993 (10)	0.0310 (3)
H24	−0.0518	0.3674	0.3930	0.037*
C25	−0.21170 (15)	0.37219 (9)	0.43064 (11)	0.0360 (4)
C26	−0.1857 (2)	0.41094 (13)	0.52068 (13)	0.0546 (5)
H26	−0.1090	0.4222	0.5545	0.065*
C27	−0.2915 (2)	0.43003 (14)	0.55249 (15)	0.0691 (7)
H27	−0.3003	0.4579	0.6119	0.083*
C28	−0.3806 (2)	0.40483 (13)	0.48430 (18)	0.0621 (6)
H28	−0.4625	0.4114	0.4878	0.074*
C29	−0.33282 (16)	0.36859 (11)	0.40861 (16)	0.0476 (4)
H29	−0.3759	0.3454	0.3508	0.057*
C30	−0.1999 (2)	0.54692 (11)	0.33192 (16)	0.0600 (6)
H30	−0.1325	0.5299	0.3037	0.072*
C31	−0.1986 (2)	0.59003 (12)	0.41768 (18)	0.0629 (6)
H31	−0.1301	0.6078	0.4598	0.075*
C32	−0.3126 (2)	0.60257 (11)	0.43236 (16)	0.0586 (6)
H32	−0.3377	0.6305	0.4867	0.070*
C33	−0.3842 (2)	0.56757 (12)	0.35621 (16)	0.0595 (5)
H33	−0.4682	0.5671	0.3477	0.071*
C34	−0.3144 (2)	0.53302 (12)	0.29394 (14)	0.0591 (6)
H34	−0.3413	0.5048	0.2343	0.071*
N1	0.06793 (12)	0.23745 (8)	0.46323 (9)	0.0346 (3)
N2	−0.22575 (12)	0.21372 (8)	0.34208 (11)	0.0363 (3)
O1	0.14788 (12)	0.36653 (7)	0.35017 (10)	0.0508 (3)
O2	−0.16222 (11)	0.37057 (7)	0.27473 (8)	0.0390 (3)
O3	−0.26393 (11)	0.21596 (8)	0.25751 (9)	0.0492 (3)
O4	−0.27784 (11)	0.18748 (9)	0.40367 (11)	0.0580 (4)
S1	0.06376 (5)	0.10735 (3)	0.57181 (4)	0.06071 (16)
Fe1	−0.27986 (2)	0.48313 (2)	0.42494 (2)	0.03501 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0313 (9)	0.0423 (9)	0.0401 (9)	−0.0019 (7)	0.0014 (7)	−0.0009 (7)
C2	0.0288 (9)	0.0600 (11)	0.0413 (9)	−0.0012 (8)	0.0016 (7)	−0.0017 (8)
C3	0.0392 (11)	0.0821 (15)	0.0526 (12)	−0.0127 (10)	0.0066 (9)	−0.0002 (10)
C4	0.0352 (11)	0.125 (2)	0.0563 (13)	−0.0084 (13)	0.0130 (10)	−0.0133 (14)
C5	0.0345 (11)	0.117 (2)	0.0537 (13)	0.0167 (12)	0.0063 (9)	−0.0229 (13)
C6	0.0384 (10)	0.0803 (15)	0.0400 (10)	0.0192 (10)	−0.0023 (8)	−0.0148 (9)
C7	0.0633 (15)	0.0755 (15)	0.0566 (13)	0.0355 (12)	−0.0007 (11)	−0.0184 (11)
C8	0.0830 (17)	0.0436 (11)	0.0657 (14)	0.0229 (11)	0.0015 (13)	−0.0096 (9)
C9	0.0585 (13)	0.0423 (10)	0.0584 (12)	0.0086 (9)	0.0105 (10)	−0.0052 (9)
C10	0.0375 (9)	0.0413 (9)	0.0400 (9)	0.0090 (7)	0.0044 (7)	−0.0042 (7)
C11	0.0312 (9)	0.0562 (11)	0.0340 (9)	0.0100 (8)	−0.0003 (7)	−0.0066 (7)
C12	0.0286 (8)	0.0324 (8)	0.0369 (8)	0.0029 (6)	0.0038 (6)	−0.0023 (6)
C13	0.0474 (11)	0.0517 (11)	0.0411 (10)	0.0094 (8)	−0.0045 (8)	0.0007 (8)
C14	0.0484 (11)	0.0448 (10)	0.0539 (11)	0.0039 (8)	0.0082 (9)	0.0155 (8)
C15	0.0358 (9)	0.0373 (8)	0.0307 (8)	0.0051 (7)	0.0072 (7)	0.0016 (6)
C16	0.0268 (8)	0.0320 (8)	0.0318 (8)	0.0013 (6)	0.0039 (6)	−0.0004 (6)
C17	0.0284 (8)	0.0312 (7)	0.0323 (8)	0.0007 (6)	0.0060 (6)	−0.0034 (6)
C18	0.0308 (8)	0.0406 (8)	0.0290 (8)	−0.0047 (7)	0.0039 (6)	−0.0044 (6)
C19	0.0424 (10)	0.0546 (11)	0.0384 (9)	−0.0024 (8)	0.0120 (8)	−0.0084 (8)
C20	0.0576 (13)	0.0762 (14)	0.0389 (10)	−0.0099 (11)	0.0215 (9)	−0.0057 (9)
C21	0.0658 (14)	0.0681 (13)	0.0338 (9)	−0.0130 (11)	0.0101 (9)	0.0091 (9)
C22	0.0532 (12)	0.0482 (10)	0.0364 (9)	−0.0053 (8)	0.0029 (8)	0.0054 (7)
C23	0.0352 (9)	0.0418 (9)	0.0284 (8)	−0.0051 (7)	0.0045 (6)	−0.0022 (6)
C24	0.0328 (8)	0.0317 (8)	0.0285 (7)	0.0022 (6)	0.0045 (6)	0.0005 (6)
C25	0.0406 (9)	0.0341 (8)	0.0341 (8)	0.0090 (7)	0.0083 (7)	0.0049 (6)
C26	0.0668 (13)	0.0656 (12)	0.0300 (9)	0.0278 (10)	0.0021 (9)	0.0005 (8)
C27	0.100 (2)	0.0739 (15)	0.0400 (11)	0.0418 (14)	0.0312 (13)	0.0130 (10)
C28	0.0616 (14)	0.0558 (12)	0.0778 (16)	0.0136 (10)	0.0413 (13)	0.0157 (11)
C29	0.0403 (10)	0.0371 (9)	0.0687 (12)	−0.0014 (8)	0.0191 (9)	−0.0013 (8)
C30	0.0800 (16)	0.0359 (10)	0.0717 (14)	−0.0013 (10)	0.0380 (13)	0.0044 (9)
C31	0.0682 (15)	0.0406 (10)	0.0811 (16)	−0.0106 (10)	0.0151 (12)	−0.0122 (10)
C32	0.0757 (15)	0.0358 (10)	0.0663 (14)	0.0118 (9)	0.0172 (12)	−0.0083 (9)
C33	0.0657 (14)	0.0489 (11)	0.0620 (13)	0.0194 (10)	0.0019 (11)	0.0094 (10)
C34	0.0931 (18)	0.0450 (11)	0.0387 (10)	0.0105 (11)	0.0074 (11)	0.0085 (8)
N1	0.0331 (7)	0.0372 (7)	0.0323 (7)	0.0056 (6)	0.0005 (6)	−0.0015 (5)
N2	0.0288 (7)	0.0346 (7)	0.0460 (8)	0.0028 (6)	0.0071 (6)	−0.0001 (6)
O1	0.0481 (8)	0.0373 (7)	0.0668 (9)	−0.0048 (6)	0.0071 (7)	−0.0017 (6)
O2	0.0476 (7)	0.0409 (6)	0.0292 (6)	0.0123 (5)	0.0078 (5)	0.0049 (5)
O3	0.0339 (7)	0.0675 (9)	0.0444 (7)	−0.0035 (6)	−0.0003 (6)	−0.0090 (6)
O4	0.0411 (8)	0.0710 (9)	0.0645 (9)	−0.0105 (7)	0.0165 (7)	0.0170 (7)
S1	0.0694 (4)	0.0521 (3)	0.0579 (3)	0.0147 (3)	−0.0006 (3)	0.0201 (2)
Fe1	0.03822 (15)	0.03383 (13)	0.03325 (13)	0.00572 (10)	0.00597 (10)	−0.00222 (9)

Geometric parameters (Å, º) top

C1—O1	1.205 (2)	C19—H19	0.9300
C1—C2	1.469 (2)	C20—C21	1.380 (3)
C1—C12	1.582 (2)	C20—H20	0.9300
C2—C3	1.380 (3)	C21—C22	1.380 (3)
C2—C11	1.397 (3)	C21—H21	0.9300
C3—C4	1.397 (3)	C22—C23	1.390 (2)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.366 (4)	C23—O2	1.3799 (19)
C4—H4	0.9300	C24—O2	1.4330 (19)
C5—C6	1.411 (3)	C24—C25	1.498 (2)
C5—H5	0.9300	C24—H24	0.9800
C6—C7	1.404 (3)	C25—C29	1.419 (3)
C6—C11	1.410 (2)	C25—C26	1.424 (3)
C7—C8	1.357 (4)	C25—Fe1	2.0206 (16)
C7—H7	0.9300	C26—C27	1.419 (3)
C8—C9	1.424 (3)	C26—Fe1	2.0263 (19)
C8—H8	0.9300	C26—H26	0.9800
C9—C10	1.363 (3)	C27—C28	1.388 (4)
C9—H9	0.9300	C27—Fe1	2.033 (2)
C10—C11	1.409 (3)	C27—H27	0.9800
C10—C12	1.524 (2)	C28—C29	1.414 (3)
C12—N1	1.474 (2)	C28—Fe1	2.027 (2)
C12—C17	1.566 (2)	C28—H28	0.9800
C13—N1	1.437 (2)	C29—Fe1	2.0197 (19)
C13—S1	1.857 (2)	C29—H29	0.9800
C13—H13A	0.9700	C30—C34	1.401 (3)
C13—H13B	0.9700	C30—C31	1.410 (3)
C14—C15	1.544 (2)	C30—Fe1	2.026 (2)
C14—S1	1.813 (2)	C30—H30	0.9800
C14—H14A	0.9700	C31—C32	1.403 (3)
C14—H14B	0.9700	C31—Fe1	2.039 (2)
C15—N1	1.460 (2)	C31—H31	0.9800
C15—C16	1.530 (2)	C32—C33	1.401 (3)
C15—H15	0.9800	C32—Fe1	2.042 (2)
C16—N2	1.508 (2)	C32—H32	0.9800
C16—C17	1.538 (2)	C33—C34	1.410 (3)
C16—C24	1.550 (2)	C33—Fe1	2.030 (2)
C17—C18	1.506 (2)	C33—H33	0.9800
C17—H17	0.9800	C34—Fe1	2.022 (2)
C18—C23	1.378 (2)	C34—H34	0.9800
C18—C19	1.395 (2)	N2—O4	1.2158 (19)
C19—C20	1.384 (3)	N2—O3	1.2186 (19)

O1—C1—C2	128.05 (16)	C25—C26—H26	126.3
O1—C1—C12	124.22 (15)	Fe1—C26—H26	126.3
C2—C1—C12	107.71 (14)	C28—C27—C26	108.86 (19)
C3—C2—C11	120.08 (18)	C28—C27—Fe1	69.77 (12)
C3—C2—C1	132.09 (19)	C26—C27—Fe1	69.27 (11)
C11—C2—C1	107.83 (15)	C28—C27—H27	125.6
C2—C3—C4	117.6 (2)	C26—C27—H27	125.6
C2—C3—H3	121.2	Fe1—C27—H27	125.6
C4—C3—H3	121.2	C27—C28—C29	108.34 (19)
C5—C4—C3	122.9 (2)	C27—C28—Fe1	70.25 (13)
C5—C4—H4	118.6	C29—C28—Fe1	69.27 (11)
C3—C4—H4	118.6	C27—C28—H28	125.8
C4—C5—C6	121.1 (2)	C29—C28—H28	125.8
C4—C5—H5	119.4	Fe1—C28—H28	125.8
C6—C5—H5	119.4	C28—C29—C25	108.0 (2)
C7—C6—C11	116.3 (2)	C28—C29—Fe1	69.84 (12)
C7—C6—C5	128.2 (2)	C25—C29—Fe1	69.47 (10)
C11—C6—C5	115.5 (2)	C28—C29—H29	126.0
C8—C7—C6	120.43 (19)	C25—C29—H29	126.0
C8—C7—H7	119.8	Fe1—C29—H29	126.0
C6—C7—H7	119.8	C34—C30—C31	108.0 (2)
C7—C8—C9	122.6 (2)	C34—C30—Fe1	69.59 (12)
C7—C8—H8	118.7	C31—C30—Fe1	70.19 (12)
C9—C8—H8	118.7	C34—C30—H30	126.0
C10—C9—C8	118.8 (2)	C31—C30—H30	126.0
C10—C9—H9	120.6	Fe1—C30—H30	126.0
C8—C9—H9	120.6	C32—C31—C30	108.0 (2)
C9—C10—C11	118.39 (16)	C32—C31—Fe1	70.00 (12)
C9—C10—C12	132.91 (17)	C30—C31—Fe1	69.22 (11)
C11—C10—C12	108.70 (15)	C32—C31—H31	126.0
C2—C11—C10	113.68 (15)	C30—C31—H31	126.0
C2—C11—C6	122.87 (18)	Fe1—C31—H31	126.0
C10—C11—C6	123.45 (19)	C33—C32—C31	108.0 (2)
N1—C12—C10	117.90 (13)	C33—C32—Fe1	69.43 (11)
N1—C12—C17	104.47 (12)	C31—C32—Fe1	69.79 (11)
C10—C12—C17	113.24 (13)	C33—C32—H32	126.0
N1—C12—C1	107.21 (13)	C31—C32—H32	126.0
C10—C12—C1	102.06 (13)	Fe1—C32—H32	126.0
C17—C12—C1	111.98 (13)	C32—C33—C34	108.1 (2)
N1—C13—S1	107.58 (13)	C32—C33—Fe1	70.32 (12)
N1—C13—H13A	110.2	C34—C33—Fe1	69.32 (12)
S1—C13—H13A	110.2	C32—C33—H33	125.9
N1—C13—H13B	110.2	C34—C33—H33	125.9
S1—C13—H13B	110.2	Fe1—C33—H33	125.9
H13A—C13—H13B	108.5	C30—C34—C33	107.9 (2)
C15—C14—S1	105.19 (13)	C30—C34—Fe1	69.93 (12)
C15—C14—H14A	110.7	C33—C34—Fe1	69.95 (12)
S1—C14—H14A	110.7	C30—C34—H34	126.1
C15—C14—H14B	110.7	C33—C34—H34	126.1
S1—C14—H14B	110.7	Fe1—C34—H34	126.1
H14A—C14—H14B	108.8	C13—N1—C15	110.07 (14)
N1—C15—C16	101.46 (12)	C13—N1—C12	119.29 (14)
N1—C15—C14	108.15 (13)	C15—N1—C12	111.06 (13)
C16—C15—C14	117.35 (14)	O4—N2—O3	124.10 (15)
N1—C15—H15	109.8	O4—N2—C16	118.91 (14)
C16—C15—H15	109.8	O3—N2—C16	116.87 (13)
C14—C15—H15	109.8	C23—O2—C24	116.45 (12)
N2—C16—C15	112.49 (13)	C14—S1—C13	92.80 (9)
N2—C16—C17	110.46 (12)	C29—Fe1—C25	41.12 (8)
C15—C16—C17	104.88 (12)	C29—Fe1—C34	105.54 (9)
N2—C16—C24	107.42 (12)	C25—Fe1—C34	116.39 (8)
C15—C16—C24	111.08 (12)	C29—Fe1—C30	126.18 (8)
C17—C16—C24	110.55 (12)	C25—Fe1—C30	106.99 (8)
C18—C17—C16	113.96 (13)	C34—Fe1—C30	40.48 (10)
C18—C17—C12	114.58 (13)	C29—Fe1—C26	69.01 (9)
C16—C17—C12	103.97 (12)	C25—Fe1—C26	41.21 (7)
C18—C17—H17	108.0	C34—Fe1—C26	151.72 (9)
C16—C17—H17	108.0	C30—Fe1—C26	119.19 (10)
C12—C17—H17	108.0	C29—Fe1—C28	40.89 (8)
C23—C18—C19	118.06 (16)	C25—Fe1—C28	68.99 (8)
C23—C18—C17	121.07 (14)	C34—Fe1—C28	126.31 (11)
C19—C18—C17	120.87 (15)	C30—Fe1—C28	164.13 (11)
C20—C19—C18	120.93 (19)	C26—Fe1—C28	68.58 (10)
C20—C19—H19	119.5	C29—Fe1—C33	116.71 (9)
C18—C19—H19	119.5	C25—Fe1—C33	150.45 (8)
C21—C20—C19	119.68 (17)	C34—Fe1—C33	40.73 (9)
C21—C20—H20	120.2	C30—Fe1—C33	68.12 (10)
C19—C20—H20	120.2	C26—Fe1—C33	166.86 (8)
C20—C21—C22	120.62 (18)	C28—Fe1—C33	107.36 (10)
C20—C21—H21	119.7	C29—Fe1—C27	68.18 (10)
C22—C21—H21	119.7	C25—Fe1—C27	68.80 (7)
C21—C22—C23	118.88 (19)	C34—Fe1—C27	164.63 (11)
C21—C22—H22	120.6	C30—Fe1—C27	154.40 (12)
C23—C22—H22	120.6	C26—Fe1—C27	40.93 (9)
C18—C23—O2	122.36 (14)	C28—Fe1—C27	39.98 (10)
C18—C23—C22	121.83 (16)	C33—Fe1—C27	128.18 (9)
O2—C23—C22	115.78 (15)	C29—Fe1—C31	165.30 (8)
O2—C24—C25	107.16 (13)	C25—Fe1—C31	128.46 (9)
O2—C24—C16	110.69 (12)	C34—Fe1—C31	68.11 (10)
C25—C24—C16	114.40 (13)	C30—Fe1—C31	40.58 (9)
O2—C24—H24	108.1	C26—Fe1—C31	109.88 (10)
C25—C24—H24	108.1	C28—Fe1—C31	153.45 (9)
C16—C24—H24	108.1	C33—Fe1—C31	67.79 (10)
C29—C25—C26	107.44 (16)	C27—Fe1—C31	121.25 (11)
C29—C25—C24	126.76 (16)	C29—Fe1—C32	151.41 (9)
C26—C25—C24	125.79 (17)	C25—Fe1—C32	167.14 (9)
C29—C25—Fe1	69.41 (10)	C34—Fe1—C32	68.12 (9)
C26—C25—Fe1	69.61 (10)	C30—Fe1—C32	68.01 (9)
C24—C25—Fe1	125.15 (11)	C26—Fe1—C32	129.74 (9)
C27—C26—C25	107.3 (2)	C28—Fe1—C32	119.10 (9)
C27—C26—Fe1	69.80 (12)	C33—Fe1—C32	40.25 (9)
C25—C26—Fe1	69.18 (10)	C27—Fe1—C32	110.24 (9)
C27—C26—H26	126.3	C31—Fe1—C32	40.22 (9)

O1—C1—C2—C3	−3.5 (3)	C21—C22—C23—C18	0.6 (3)
C12—C1—C2—C3	177.9 (2)	C21—C22—C23—O2	−177.60 (17)
O1—C1—C2—C11	177.00 (18)	N2—C16—C24—O2	−65.60 (15)
C12—C1—C2—C11	−1.61 (19)	C15—C16—C24—O2	171.00 (12)
C11—C2—C3—C4	0.0 (3)	C17—C16—C24—O2	54.99 (17)
C1—C2—C3—C4	−179.4 (2)	N2—C16—C24—C25	55.58 (17)
C2—C3—C4—C5	−0.8 (3)	C15—C16—C24—C25	−67.83 (18)
C3—C4—C5—C6	1.0 (4)	C17—C16—C24—C25	176.16 (13)
C4—C5—C6—C7	179.8 (2)	O2—C24—C25—C29	46.3 (2)
C4—C5—C6—C11	−0.3 (3)	C16—C24—C25—C29	−76.8 (2)
C11—C6—C7—C8	1.1 (3)	O2—C24—C25—C26	−132.02 (17)
C5—C6—C7—C8	−179.0 (2)	C16—C24—C25—C26	104.88 (19)
C6—C7—C8—C9	0.6 (4)	O2—C24—C25—Fe1	−43.03 (18)
C7—C8—C9—C10	−2.1 (3)	C16—C24—C25—Fe1	−166.13 (11)
C8—C9—C10—C11	1.8 (3)	C29—C25—C26—C27	0.3 (2)
C8—C9—C10—C12	−179.70 (19)	C24—C25—C26—C27	178.93 (16)
C3—C2—C11—C10	−178.66 (17)	Fe1—C25—C26—C27	59.64 (14)
C1—C2—C11—C10	0.9 (2)	C29—C25—C26—Fe1	−59.33 (12)
C3—C2—C11—C6	0.6 (3)	C24—C25—C26—Fe1	119.29 (16)
C1—C2—C11—C6	−179.89 (16)	C25—C26—C27—C28	−0.6 (2)
C9—C10—C11—C2	179.08 (17)	Fe1—C26—C27—C28	58.67 (15)
C12—C10—C11—C2	0.3 (2)	C25—C26—C27—Fe1	−59.25 (13)
C9—C10—C11—C6	−0.1 (3)	C26—C27—C28—C29	0.6 (2)
C12—C10—C11—C6	−178.96 (16)	Fe1—C27—C28—C29	58.98 (14)
C7—C6—C11—C2	179.51 (18)	C26—C27—C28—Fe1	−58.37 (15)
C5—C6—C11—C2	−0.4 (3)	C27—C28—C29—C25	−0.4 (2)
C7—C6—C11—C10	−1.3 (3)	Fe1—C28—C29—C25	59.17 (12)
C5—C6—C11—C10	178.75 (18)	C27—C28—C29—Fe1	−59.59 (15)
C9—C10—C12—N1	63.2 (3)	C26—C25—C29—C28	0.1 (2)
C11—C10—C12—N1	−118.28 (16)	C24—C25—C29—C28	−178.55 (16)
C9—C10—C12—C17	−59.2 (3)	Fe1—C25—C29—C28	−59.40 (13)
C11—C10—C12—C17	119.36 (15)	C26—C25—C29—Fe1	59.46 (13)
C9—C10—C12—C1	−179.8 (2)	C24—C25—C29—Fe1	−119.15 (16)
C11—C10—C12—C1	−1.18 (17)	C34—C30—C31—C32	0.0 (2)
O1—C1—C12—N1	−52.4 (2)	Fe1—C30—C31—C32	−59.50 (15)
C2—C1—C12—N1	126.23 (14)	C34—C30—C31—Fe1	59.54 (14)
O1—C1—C12—C10	−177.00 (17)	C30—C31—C32—C33	−0.1 (2)
C2—C1—C12—C10	1.68 (17)	Fe1—C31—C32—C33	−59.08 (15)
O1—C1—C12—C17	61.6 (2)	C30—C31—C32—Fe1	59.01 (15)
C2—C1—C12—C17	−119.74 (15)	C31—C32—C33—C34	0.1 (2)
S1—C14—C15—N1	34.99 (16)	Fe1—C32—C33—C34	−59.23 (14)
S1—C14—C15—C16	148.88 (12)	C31—C32—C33—Fe1	59.30 (15)
N1—C15—C16—N2	157.43 (12)	C31—C30—C34—C33	0.0 (2)
C14—C15—C16—N2	39.87 (19)	Fe1—C30—C34—C33	59.93 (14)
N1—C15—C16—C17	37.33 (15)	C31—C30—C34—Fe1	−59.92 (15)
C14—C15—C16—C17	−80.23 (17)	C32—C33—C34—C30	−0.1 (2)
N1—C15—C16—C24	−82.12 (14)	Fe1—C33—C34—C30	−59.91 (14)
C14—C15—C16—C24	160.32 (14)	C32—C33—C34—Fe1	59.86 (15)
N2—C16—C17—C18	85.38 (16)	S1—C13—N1—C15	31.86 (16)
C15—C16—C17—C18	−153.19 (13)	S1—C13—N1—C12	−98.21 (16)
C24—C16—C17—C18	−33.38 (18)	C16—C15—N1—C13	−168.36 (13)
N2—C16—C17—C12	−149.19 (12)	C14—C15—N1—C13	−44.33 (18)
C15—C16—C17—C12	−27.75 (15)	C16—C15—N1—C12	−34.03 (15)
C24—C16—C17—C12	92.05 (14)	C14—C15—N1—C12	90.01 (16)
N1—C12—C17—C18	132.57 (13)	C10—C12—N1—C13	19.8 (2)
C10—C12—C17—C18	−97.87 (16)	C17—C12—N1—C13	146.48 (15)
C1—C12—C17—C18	16.87 (18)	C1—C12—N1—C13	−94.53 (17)
N1—C12—C17—C16	7.54 (15)	C10—C12—N1—C15	−109.86 (16)
C10—C12—C17—C16	137.10 (14)	C17—C12—N1—C15	16.86 (16)
C1—C12—C17—C16	−108.16 (14)	C1—C12—N1—C15	135.85 (13)
C16—C17—C18—C23	8.6 (2)	C15—C16—N2—O4	22.38 (19)
C12—C17—C18—C23	−111.04 (17)	C17—C16—N2—O4	139.20 (15)
C16—C17—C18—C19	−172.07 (15)	C24—C16—N2—O4	−100.16 (16)
C12—C17—C18—C19	68.33 (19)	C15—C16—N2—O3	−161.40 (13)
C23—C18—C19—C20	0.4 (3)	C17—C16—N2—O3	−44.58 (18)
C17—C18—C19—C20	−178.95 (17)	C24—C16—N2—O3	76.06 (16)
C18—C19—C20—C21	0.2 (3)	C18—C23—O2—C24	26.5 (2)
C19—C20—C21—C22	−0.5 (3)	C22—C23—O2—C24	−155.38 (15)
C20—C21—C22—C23	0.1 (3)	C25—C24—O2—C23	−177.50 (13)
C19—C18—C23—O2	177.22 (15)	C16—C24—O2—C23	−52.13 (18)
C17—C18—C23—O2	−3.4 (2)	C15—C14—S1—C13	−14.50 (13)
C19—C18—C23—C22	−0.8 (3)	N1—C13—S1—C14	−8.95 (14)
C17—C18—C23—C22	178.54 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O3ⁱ	0.97	2.50	3.417 (3)	157
C20—H20···O4ⁱⁱ	0.93	2.59	3.440 (3)	152
C24—H24···O1	0.98	2.51	3.301 (3)	138

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

(II) 6'-(4-Methoxyphenyl)-6a'-nitro-6',6a',6b',7',9',11a'-hexahydro-2H-spiro[acenaphthylene-1,11'-chromeno[3',4':3,4]pyrrolo[1,2-c]thiazol]-2-one top