The crystal structures and Hirshfeld surface analysis of 6-(naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexa­hydro­spiro­[chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zole-11,11′-indeno­[1,2-b]quinoxaline] and 6′-(naphthalen-1-yl)-6a′-nitro-6′,6a′,6b′,7′,8′,9′,10′,12a′-octa­hydro-2H-spiro­[ace­naphthyl­ene-1,12′-chromeno[3,4-a]indolizin]-2-one

The crystal structures of the title spiro derivatives are described and the analysis of the inter­molecular contacts in the crystals using Hirshfeld surface analysis and two-dimensional fingerprint plots is reported.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.164
• Data-to-parameter ratio = 19.9

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.126
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of .        216 Ang   3

Author Response: In the crystal structure, some solvent density is present. We could not find out the correct solvent molecule in the corresponding density. We try to squeeze that solvent molecule, but that solvent accessible voids is very high 216 Ang   3.

Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.2 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4       --C24      .        5.9 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........  H27<I>B</ Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  C<I>G</I> Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     23.173 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.908 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          4 Note
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 C1          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C16         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C23         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C24         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C25         (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        168 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   1 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
  14 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of .        201 Ang   3

Author Response: In the crystal structure, some solvent density is present. We could not find out the correct solvent molecule in the corresponding density. We try to squeeze that solvent molecule, but that solvent accessible voids is very high 201 Ang   3.

Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          4 Check

Author Response: The inclusion of 7 slightly disagreeable reflections in the refinments. Although slightly disagreeable, the refletions were not removed from calculations using OMIT as we flet that the difference between I(obs) and I(cal) was not so large as to necessitate their removal.

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    N2       --C18      .        5.3 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........  H13<I>A</ Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  C<I>G</I> Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.582 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595          8 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
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 C12         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C17         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C18         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C19         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C26         (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        37% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008). Software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009 for (I); WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009) for (II).

6-(Naphthalen-1-yl)-6a-nitro-6,6a,6b,7,9,11a-hexahydrospiro[chromeno[3',4':3,4]pyrrolo[1,2-c]thiazole-11,11'-indeno[1,2-b]quinoxaline] (I)

Crystal data

C37H26N4O3S	F(000) = 1264
Mr = 606.68	Dx = 1.246 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3690 (3) Å	Cell parameters from 8083 reflections
b = 13.2440 (4) Å	θ = 1.8–26.9°
c = 29.2210 (5) Å	µ = 0.14 mm^−1
β = 93.280 (2)°	T = 293 K
V = 3233.52 (16) Å^3	Block, colourless
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4209 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.061
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 28.6°, θmin = 1.4°
Tmin = 0.741, Tmax = 0.852	h = −11→10
30398 measured reflections	k = −14→17
8083 independent reflections	l = −39→39

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0738P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
8083 reflections	Δρmax = 0.36 e Å^−3
406 parameters	Δρmin = −0.34 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
C1	0.1161 (2)	0.24359 (15)	0.30919 (6)	0.0494 (5)
C2	0.0918 (2)	0.23613 (16)	0.25673 (7)	0.0541 (5)
C3	0.1107 (3)	0.15404 (18)	0.22850 (7)	0.0671 (6)
H3	0.139426	0.091580	0.240969	0.081*
C4	0.0865 (3)	0.1652 (2)	0.18134 (8)	0.0849 (8)
H4	0.098128	0.109992	0.162138	0.102*
C5	0.0448 (3)	0.2591 (3)	0.16285 (9)	0.0936 (9)
H5	0.031066	0.266237	0.131206	0.112*
C6	0.0239 (3)	0.3398 (2)	0.18991 (9)	0.0859 (8)
H6	−0.007778	0.401526	0.177193	0.103*
C7	0.0505 (2)	0.32971 (17)	0.23738 (7)	0.0614 (6)
C8	0.0423 (2)	0.40471 (18)	0.27342 (8)	0.0610 (6)
C9	0.0036 (3)	0.55087 (19)	0.31022 (12)	0.0825 (8)
C10	−0.0465 (4)	0.6527 (2)	0.31060 (17)	0.1145 (11)
H10	−0.076570	0.684749	0.283137	0.137*
C11	−0.0510 (5)	0.7035 (3)	0.3502 (2)	0.1415 (17)
H11	−0.084652	0.770462	0.349812	0.170*
C12	−0.0066 (5)	0.6582 (3)	0.3912 (2)	0.1382 (15)
H12	−0.010154	0.695207	0.418145	0.166*
C13	0.0430 (4)	0.5595 (2)	0.39324 (12)	0.1058 (10)
H13	0.073851	0.529893	0.421227	0.127*
C14	0.0463 (3)	0.50397 (19)	0.35256 (10)	0.0750 (7)
C15	0.0833 (2)	0.35657 (16)	0.31577 (8)	0.0541 (5)
C16	0.2865 (2)	0.20774 (14)	0.32709 (6)	0.0472 (5)
H16	0.325781	0.161182	0.304208	0.057*
C17	0.4111 (2)	0.28888 (15)	0.33502 (7)	0.0517 (5)
C18	0.4752 (2)	0.33919 (18)	0.29859 (8)	0.0670 (6)
H18	0.439990	0.323138	0.268711	0.080*
C19	0.5897 (3)	0.4123 (2)	0.30622 (9)	0.0801 (7)
H19	0.631402	0.445264	0.281466	0.096*
C20	0.6434 (3)	0.4371 (2)	0.35007 (10)	0.0846 (8)
H20	0.720422	0.487177	0.355019	0.102*
C21	0.5830 (3)	0.38786 (18)	0.38640 (9)	0.0722 (7)
H21	0.619996	0.403698	0.416151	0.087*
C22	0.4672 (2)	0.31471 (16)	0.37893 (7)	0.0556 (5)
C23	0.2641 (2)	0.21920 (14)	0.41284 (6)	0.0472 (5)
H23	0.182414	0.271326	0.406921	0.057*
C24	0.25919 (19)	0.14506 (12)	0.37099 (6)	0.0446 (4)
C25	0.0895 (2)	0.10286 (14)	0.36166 (6)	0.0482 (5)
H25	0.040553	0.091076	0.390862	0.058*
C26	0.0710 (3)	0.00792 (16)	0.33174 (7)	0.0591 (5)
H26A	0.088186	−0.052686	0.350003	0.071*
H26B	0.146009	0.008585	0.307642	0.071*
C27	−0.1468 (2)	0.15173 (17)	0.31845 (8)	0.0665 (6)
H27A	−0.174584	0.186668	0.289926	0.080*
H27B	−0.228995	0.165400	0.339706	0.080*
C28	0.2370 (2)	0.17076 (14)	0.45860 (6)	0.0466 (5)
C29	0.3636 (3)	0.12777 (16)	0.48297 (7)	0.0579 (5)
H29	0.463434	0.127450	0.470563	0.069*
C30	0.3470 (3)	0.08386 (17)	0.52642 (7)	0.0670 (6)
H30	0.435212	0.056120	0.542655	0.080*
C31	0.2015 (3)	0.08258 (16)	0.54417 (7)	0.0621 (6)
H31	0.190245	0.052815	0.572633	0.074*
C32	0.0676 (2)	0.12492 (14)	0.52078 (6)	0.0523 (5)
C33	−0.0829 (3)	0.12485 (18)	0.53942 (7)	0.0656 (6)
H33	−0.094090	0.094106	0.567672	0.079*
C34	−0.2109 (3)	0.1675 (2)	0.51796 (8)	0.0789 (7)
H34	−0.309462	0.165333	0.531071	0.095*
C35	−0.1964 (3)	0.21564 (19)	0.47545 (8)	0.0747 (7)
H35	−0.285147	0.246448	0.460805	0.090*
C36	−0.0535 (2)	0.21727 (16)	0.45578 (7)	0.0582 (5)
H36	−0.045876	0.249053	0.427606	0.070*
C37	0.0839 (2)	0.17177 (13)	0.47715 (6)	0.0460 (5)
N1	0.0872 (2)	0.40293 (14)	0.35511 (7)	0.0660 (5)
N2	0.0036 (2)	0.49945 (16)	0.26964 (8)	0.0773 (6)
N3	0.00650 (17)	0.18572 (12)	0.33735 (5)	0.0503 (4)
N4	0.37670 (19)	0.06748 (12)	0.37895 (5)	0.0512 (4)
O1	0.41679 (16)	0.26684 (11)	0.41708 (4)	0.0619 (4)
O2	0.51538 (18)	0.08236 (11)	0.36905 (6)	0.0754 (5)
O3	0.33881 (17)	−0.01166 (11)	0.39739 (5)	0.0637 (4)
S1	−0.13165 (8)	0.01440 (5)	0.30819 (2)	0.0791 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0494 (11)	0.0584 (13)	0.0412 (10)	−0.0039 (9)	0.0084 (9)	0.0061 (9)
C2	0.0503 (12)	0.0696 (14)	0.0425 (11)	−0.0071 (10)	0.0034 (9)	0.0093 (10)
C3	0.0787 (15)	0.0808 (16)	0.0424 (12)	−0.0018 (12)	0.0073 (11)	0.0045 (11)
C4	0.0974 (19)	0.110 (2)	0.0471 (14)	−0.0118 (16)	0.0034 (13)	−0.0004 (14)
C5	0.113 (2)	0.125 (3)	0.0428 (14)	−0.0156 (18)	0.0011 (14)	0.0160 (17)
C6	0.0889 (19)	0.106 (2)	0.0622 (17)	−0.0077 (15)	−0.0052 (14)	0.0348 (16)
C7	0.0522 (13)	0.0786 (16)	0.0534 (13)	−0.0104 (11)	0.0015 (10)	0.0171 (12)
C8	0.0456 (12)	0.0651 (16)	0.0719 (15)	−0.0070 (10)	0.0005 (10)	0.0185 (12)
C9	0.0619 (16)	0.0558 (17)	0.130 (3)	−0.0140 (12)	0.0078 (16)	0.0102 (17)
C10	0.100 (2)	0.059 (2)	0.184 (4)	−0.0076 (16)	0.007 (2)	0.015 (2)
C11	0.134 (3)	0.056 (2)	0.235 (6)	−0.007 (2)	0.020 (3)	−0.013 (3)
C12	0.135 (3)	0.079 (3)	0.201 (5)	−0.013 (2)	0.019 (3)	−0.057 (3)
C13	0.113 (2)	0.075 (2)	0.129 (3)	−0.0083 (16)	0.0026 (19)	−0.0351 (18)
C14	0.0578 (15)	0.0589 (17)	0.109 (2)	−0.0086 (11)	0.0058 (13)	−0.0062 (15)
C15	0.0417 (11)	0.0601 (14)	0.0606 (13)	−0.0059 (9)	0.0040 (9)	0.0053 (11)
C16	0.0443 (11)	0.0593 (12)	0.0388 (10)	−0.0001 (9)	0.0087 (8)	0.0067 (9)
C17	0.0411 (11)	0.0617 (13)	0.0528 (12)	−0.0031 (9)	0.0087 (9)	0.0111 (10)
C18	0.0544 (13)	0.0859 (16)	0.0617 (14)	−0.0054 (12)	0.0137 (10)	0.0237 (12)
C19	0.0638 (15)	0.100 (2)	0.0775 (18)	−0.0176 (14)	0.0161 (13)	0.0349 (14)
C20	0.0656 (16)	0.0879 (19)	0.101 (2)	−0.0264 (13)	0.0080 (14)	0.0270 (15)
C21	0.0594 (14)	0.0815 (16)	0.0751 (16)	−0.0216 (12)	−0.0003 (12)	0.0125 (12)
C22	0.0478 (11)	0.0656 (14)	0.0536 (13)	−0.0129 (10)	0.0062 (9)	0.0096 (10)
C23	0.0471 (11)	0.0532 (12)	0.0414 (10)	−0.0103 (9)	0.0039 (8)	0.0013 (8)
C24	0.0446 (11)	0.0522 (11)	0.0374 (10)	−0.0006 (9)	0.0064 (8)	0.0052 (8)
C25	0.0511 (11)	0.0581 (12)	0.0357 (10)	−0.0109 (9)	0.0063 (8)	0.0007 (9)
C26	0.0691 (14)	0.0637 (14)	0.0451 (11)	−0.0129 (10)	0.0079 (10)	−0.0040 (9)
C27	0.0500 (13)	0.0894 (17)	0.0599 (14)	−0.0130 (11)	0.0024 (10)	0.0090 (11)
C28	0.0513 (12)	0.0513 (11)	0.0372 (10)	−0.0065 (9)	0.0027 (9)	−0.0014 (8)
C29	0.0536 (12)	0.0751 (14)	0.0451 (11)	−0.0008 (11)	0.0038 (10)	0.0002 (10)
C30	0.0722 (16)	0.0801 (16)	0.0479 (12)	0.0037 (12)	−0.0027 (11)	0.0071 (11)
C31	0.0766 (16)	0.0703 (15)	0.0394 (11)	−0.0079 (12)	0.0037 (11)	0.0063 (10)
C32	0.0638 (13)	0.0558 (12)	0.0376 (10)	−0.0159 (10)	0.0047 (10)	−0.0043 (9)
C33	0.0643 (15)	0.0885 (17)	0.0446 (12)	−0.0236 (12)	0.0082 (11)	−0.0002 (11)
C34	0.0611 (15)	0.118 (2)	0.0595 (15)	−0.0158 (14)	0.0195 (12)	−0.0035 (14)
C35	0.0548 (14)	0.1079 (19)	0.0618 (15)	0.0005 (12)	0.0062 (11)	0.0050 (13)
C36	0.0548 (13)	0.0741 (14)	0.0461 (11)	−0.0036 (11)	0.0069 (10)	0.0040 (10)
C37	0.0506 (11)	0.0487 (11)	0.0389 (10)	−0.0108 (9)	0.0036 (9)	−0.0045 (8)
N1	0.0608 (11)	0.0621 (13)	0.0754 (14)	−0.0053 (9)	0.0074 (10)	−0.0065 (10)
N2	0.0665 (13)	0.0621 (14)	0.1031 (18)	−0.0071 (10)	0.0031 (11)	0.0214 (12)
N3	0.0424 (9)	0.0652 (11)	0.0437 (9)	−0.0082 (8)	0.0065 (7)	0.0062 (8)
N4	0.0532 (11)	0.0584 (11)	0.0425 (9)	−0.0018 (9)	0.0063 (8)	0.0021 (8)
O1	0.0589 (9)	0.0785 (10)	0.0483 (8)	−0.0286 (7)	0.0026 (6)	0.0055 (7)
O2	0.0502 (9)	0.0822 (11)	0.0953 (12)	0.0063 (7)	0.0185 (8)	0.0192 (9)
O3	0.0709 (10)	0.0622 (9)	0.0586 (9)	−0.0008 (7)	0.0085 (7)	0.0144 (7)
S1	0.0740 (4)	0.0978 (5)	0.0647 (4)	−0.0289 (3)	−0.0022 (3)	−0.0161 (3)

Geometric parameters (Å, º)

C1—N3	1.481 (2)	C20—H20	0.9300
C1—C15	1.535 (3)	C21—C22	1.379 (3)
C1—C2	1.538 (3)	C21—H21	0.9300
C1—C16	1.564 (3)	C22—O1	1.369 (2)
C2—C3	1.379 (3)	C23—O1	1.424 (2)
C2—C7	1.397 (3)	C23—C28	1.512 (2)
C3—C4	1.389 (3)	C23—C24	1.567 (2)
C3—H3	0.9300	C23—H23	0.9800
C4—C5	1.393 (4)	C24—N4	1.4321 (9)
C4—H4	0.9300	C24—C25	1.536 (2)
C5—C6	1.347 (4)	C25—N3	1.461 (2)
C5—H5	0.9300	C25—C26	1.534 (3)
C6—C7	1.399 (3)	C25—H25	0.9800
C6—H6	0.9300	C26—S1	1.795 (2)
C7—C8	1.452 (3)	C26—H26A	0.9700
C8—N2	1.299 (3)	C26—H26B	0.9700
C8—C15	1.417 (3)	C27—N3	1.439 (2)
C9—N2	1.367 (3)	C27—S1	1.849 (2)
C9—C10	1.412 (4)	C27—H27A	0.9700
C9—C14	1.412 (4)	C27—H27B	0.9700
C10—C11	1.340 (6)	C28—C29	1.366 (3)
C10—H10	0.9300	C28—C37	1.420 (3)
C11—C12	1.373 (6)	C29—C30	1.411 (3)
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.372 (5)	C30—C31	1.351 (3)
C12—H12	0.9300	C30—H30	0.9300
C13—C14	1.399 (4)	C31—C32	1.396 (3)
C13—H13	0.9300	C31—H31	0.9300
C14—N1	1.382 (3)	C32—C33	1.401 (3)
C15—N1	1.302 (3)	C32—C37	1.431 (3)
C16—C17	1.506 (3)	C33—C34	1.335 (3)
C16—C24	1.556 (2)	C33—H33	0.9300
C16—H16	0.9800	C34—C35	1.408 (3)
C17—C22	1.384 (3)	C34—H34	0.9300
C17—C18	1.389 (3)	C35—C36	1.356 (3)
C18—C19	1.371 (3)	C35—H35	0.9300
C18—H18	0.9300	C36—C37	1.412 (3)
C19—C20	1.374 (3)	C36—H36	0.9300
C19—H19	0.9300	N4—O2	1.2279 (19)
C20—C21	1.368 (3)	N4—O3	1.2285 (19)
N3—C1—C15	108.30 (15)	C21—C22—C17	121.22 (19)
N3—C1—C2	118.02 (15)	O1—C23—C28	106.87 (14)
C15—C1—C2	99.97 (15)	O1—C23—C24	109.20 (14)
N3—C1—C16	103.82 (14)	C28—C23—C24	115.20 (15)
C15—C1—C16	114.83 (15)	O1—C23—H23	108.5
C2—C1—C16	112.33 (15)	C28—C23—H23	108.5
C3—C2—C7	119.43 (19)	C24—C23—H23	108.5
C3—C2—C1	129.31 (19)	N4—C24—C25	112.77 (15)
C7—C2—C1	111.21 (18)	N4—C24—C16	112.63 (14)
C2—C3—C4	119.6 (2)	C25—C24—C16	103.05 (13)
C2—C3—H3	120.2	N4—C24—C23	109.61 (14)
C4—C3—H3	120.2	C25—C24—C23	110.44 (13)
C3—C4—C5	119.9 (2)	C16—C24—C23	108.10 (14)
C3—C4—H4	120.0	N3—C25—C26	107.98 (15)
C5—C4—H4	120.0	N3—C25—C24	102.83 (13)
C6—C5—C4	121.3 (2)	C26—C25—C24	117.50 (16)
C6—C5—H5	119.4	N3—C25—H25	109.4
C4—C5—H5	119.4	C26—C25—H25	109.4
C5—C6—C7	119.2 (2)	C24—C25—H25	109.4
C5—C6—H6	120.4	C25—C26—S1	104.00 (14)
C7—C6—H6	120.4	C25—C26—H26A	111.0
C2—C7—C6	120.5 (2)	S1—C26—H26A	111.0
C2—C7—C8	109.52 (19)	C25—C26—H26B	111.0
C6—C7—C8	130.0 (2)	S1—C26—H26B	111.0
N2—C8—C15	123.8 (2)	H26A—C26—H26B	109.0
N2—C8—C7	128.4 (2)	N3—C27—S1	107.58 (14)
C15—C8—C7	107.9 (2)	N3—C27—H27A	110.2
N2—C9—C10	119.8 (3)	S1—C27—H27A	110.2
N2—C9—C14	121.9 (2)	N3—C27—H27B	110.2
C10—C9—C14	118.3 (3)	S1—C27—H27B	110.2
C11—C10—C9	120.6 (4)	H27A—C27—H27B	108.5
C11—C10—H10	119.7	C29—C28—C37	119.65 (17)
C9—C10—H10	119.7	C29—C28—C23	119.15 (17)
C10—C11—C12	120.9 (4)	C37—C28—C23	121.18 (16)
C10—C11—H11	119.5	C28—C29—C30	121.9 (2)
C12—C11—H11	119.5	C28—C29—H29	119.1
C13—C12—C11	121.4 (4)	C30—C29—H29	119.1
C13—C12—H12	119.3	C31—C30—C29	119.2 (2)
C11—C12—H12	119.3	C31—C30—H30	120.4
C12—C13—C14	118.9 (4)	C29—C30—H30	120.4
C12—C13—H13	120.5	C30—C31—C32	121.53 (19)
C14—C13—H13	120.5	C30—C31—H31	119.2
N1—C14—C13	118.7 (3)	C32—C31—H31	119.2
N1—C14—C9	121.5 (2)	C31—C32—C33	121.59 (19)
C13—C14—C9	119.8 (3)	C31—C32—C37	119.71 (18)
N1—C15—C8	123.5 (2)	C33—C32—C37	118.69 (19)
N1—C15—C1	125.07 (19)	C34—C33—C32	122.1 (2)
C8—C15—C1	111.42 (19)	C34—C33—H33	118.9
C17—C16—C24	112.77 (15)	C32—C33—H33	118.9
C17—C16—C1	116.40 (16)	C33—C34—C35	119.9 (2)
C24—C16—C1	105.28 (13)	C33—C34—H34	120.0
C17—C16—H16	107.3	C35—C34—H34	120.0
C24—C16—H16	107.3	C36—C35—C34	120.2 (2)
C1—C16—H16	107.3	C36—C35—H35	119.9
C22—C17—C18	117.82 (19)	C34—C35—H35	119.9
C22—C17—C16	120.94 (16)	C35—C36—C37	121.41 (19)
C18—C17—C16	121.24 (19)	C35—C36—H36	119.3
C19—C18—C17	120.7 (2)	C37—C36—H36	119.3
C19—C18—H18	119.6	C36—C37—C28	124.43 (17)
C17—C18—H18	119.6	C36—C37—C32	117.55 (17)
C18—C19—C20	120.6 (2)	C28—C37—C32	118.01 (17)
C18—C19—H19	119.7	C15—N1—C14	114.5 (2)
C20—C19—H19	119.7	C8—N2—C9	114.8 (2)
C21—C20—C19	119.6 (2)	C27—N3—C25	109.89 (15)
C21—C20—H20	120.2	C27—N3—C1	121.03 (15)
C19—C20—H20	120.2	C25—N3—C1	111.50 (14)
C20—C21—C22	120.0 (2)	O2—N4—O3	120.76 (14)
C20—C21—H21	120.0	O2—N4—C24	119.74 (16)
C22—C21—H21	120.0	O3—N4—C24	119.43 (15)
O1—C22—C21	116.28 (19)	C22—O1—C23	116.79 (14)
O1—C22—C17	122.44 (17)	C26—S1—C27	93.26 (9)
N3—C1—C2—C3	−66.0 (3)	C28—C23—C24—N4	−57.8 (2)
C15—C1—C2—C3	176.9 (2)	O1—C23—C24—C25	−172.68 (14)
C16—C1—C2—C3	54.7 (3)	C28—C23—C24—C25	67.09 (19)
N3—C1—C2—C7	116.51 (19)	O1—C23—C24—C16	−60.63 (17)
C15—C1—C2—C7	−0.53 (19)	C28—C23—C24—C16	179.14 (14)
C16—C1—C2—C7	−122.75 (17)	N4—C24—C25—N3	−158.22 (14)
C7—C2—C3—C4	−0.8 (3)	C16—C24—C25—N3	−36.51 (16)
C1—C2—C3—C4	−178.1 (2)	C23—C24—C25—N3	78.75 (16)
C2—C3—C4—C5	0.6 (4)	N4—C24—C25—C26	−39.8 (2)
C3—C4—C5—C6	−1.4 (4)	C16—C24—C25—C26	81.88 (18)
C4—C5—C6—C7	2.4 (4)	C23—C24—C25—C26	−162.86 (16)
C3—C2—C7—C6	1.8 (3)	N3—C25—C26—S1	−39.77 (16)
C1—C2—C7—C6	179.58 (19)	C24—C25—C26—S1	−155.37 (13)
C3—C2—C7—C8	−178.23 (18)	O1—C23—C28—C29	−37.1 (2)
C1—C2—C7—C8	−0.5 (2)	C24—C23—C28—C29	84.4 (2)
C5—C6—C7—C2	−2.6 (3)	O1—C23—C28—C37	141.13 (16)
C5—C6—C7—C8	177.5 (2)	C24—C23—C28—C37	−97.4 (2)
C2—C7—C8—N2	−177.9 (2)	C37—C28—C29—C30	0.0 (3)
C6—C7—C8—N2	2.0 (4)	C23—C28—C29—C30	178.23 (18)
C2—C7—C8—C15	1.4 (2)	C28—C29—C30—C31	1.2 (3)
C6—C7—C8—C15	−178.7 (2)	C29—C30—C31—C32	−0.9 (3)
N2—C9—C10—C11	178.4 (3)	C30—C31—C32—C33	−179.1 (2)
C14—C9—C10—C11	0.9 (4)	C30—C31—C32—C37	−0.6 (3)
C9—C10—C11—C12	0.3 (6)	C31—C32—C33—C34	178.2 (2)
C10—C11—C12—C13	−0.4 (6)	C37—C32—C33—C34	−0.4 (3)
C11—C12—C13—C14	−0.7 (5)	C32—C33—C34—C35	−0.9 (4)
C12—C13—C14—N1	−176.2 (3)	C33—C34—C35—C36	1.2 (4)
C12—C13—C14—C9	1.8 (4)	C34—C35—C36—C37	−0.4 (3)
N2—C9—C14—N1	−1.4 (3)	C35—C36—C37—C28	−179.9 (2)
C10—C9—C14—N1	176.1 (2)	C35—C36—C37—C32	−0.9 (3)
N2—C9—C14—C13	−179.4 (2)	C29—C28—C37—C36	177.57 (18)
C10—C9—C14—C13	−1.9 (4)	C23—C28—C37—C36	−0.6 (3)
N2—C8—C15—N1	−0.5 (3)	C29—C28—C37—C32	−1.4 (3)
C7—C8—C15—N1	−179.83 (18)	C23—C28—C37—C32	−179.62 (16)
N2—C8—C15—C1	177.54 (18)	C31—C32—C37—C36	−177.34 (18)
C7—C8—C15—C1	−1.8 (2)	C33—C32—C37—C36	1.3 (3)
N3—C1—C15—N1	55.3 (2)	C31—C32—C37—C28	1.7 (3)
C2—C1—C15—N1	179.41 (18)	C33—C32—C37—C28	−179.68 (17)
C16—C1—C15—N1	−60.2 (2)	C8—C15—N1—C14	0.6 (3)
N3—C1—C15—C8	−122.67 (17)	C1—C15—N1—C14	−177.19 (18)
C2—C1—C15—C8	1.42 (19)	C13—C14—N1—C15	178.3 (2)
C16—C1—C15—C8	121.85 (17)	C9—C14—N1—C15	0.3 (3)
N3—C1—C16—C17	−135.76 (16)	C15—C8—N2—C9	−0.5 (3)
C15—C1—C16—C17	−17.7 (2)	C7—C8—N2—C9	178.7 (2)
C2—C1—C16—C17	95.63 (19)	C10—C9—N2—C8	−176.0 (2)
N3—C1—C16—C24	−10.06 (18)	C14—C9—N2—C8	1.4 (3)
C15—C1—C16—C24	107.98 (17)	S1—C27—N3—C25	−27.14 (18)
C2—C1—C16—C24	−138.67 (16)	S1—C27—N3—C1	105.11 (17)
C24—C16—C17—C22	−12.0 (3)	C26—C25—N3—C27	44.43 (19)
C1—C16—C17—C22	109.8 (2)	C24—C25—N3—C27	169.30 (15)
C24—C16—C17—C18	167.06 (17)	C26—C25—N3—C1	−92.60 (17)
C1—C16—C17—C18	−71.1 (2)	C24—C25—N3—C1	32.28 (18)
C22—C17—C18—C19	−0.3 (3)	C15—C1—N3—C27	92.1 (2)
C16—C17—C18—C19	−179.3 (2)	C2—C1—N3—C27	−20.4 (3)
C17—C18—C19—C20	0.0 (4)	C16—C1—N3—C27	−145.47 (17)
C18—C19—C20—C21	0.6 (4)	C15—C1—N3—C25	−136.36 (16)
C19—C20—C21—C22	−0.9 (4)	C2—C1—N3—C25	111.15 (18)
C20—C21—C22—O1	178.0 (2)	C16—C1—N3—C25	−13.90 (19)
C20—C21—C22—C17	0.7 (4)	C25—C24—N4—O2	151.16 (16)
C18—C17—C22—O1	−177.23 (18)	C16—C24—N4—O2	35.0 (2)
C16—C17—C22—O1	1.8 (3)	C23—C24—N4—O2	−85.35 (19)
C18—C17—C22—C21	−0.1 (3)	C25—C24—N4—O3	−31.9 (2)
C16—C17—C22—C21	179.00 (19)	C16—C24—N4—O3	−147.98 (16)
C17—C16—C24—N4	−81.57 (19)	C23—C24—N4—O3	91.63 (18)
C1—C16—C24—N4	150.52 (15)	C21—C22—O1—C23	158.47 (18)
C17—C16—C24—C25	156.62 (15)	C17—C22—O1—C23	−24.2 (3)
C1—C16—C24—C25	28.71 (18)	C28—C23—O1—C22	179.04 (16)
C17—C16—C24—C23	39.69 (19)	C24—C23—O1—C22	53.8 (2)
C1—C16—C24—C23	−88.23 (16)	C25—C26—S1—C27	20.61 (14)
O1—C23—C24—N4	62.48 (18)	N3—C27—S1—C26	2.64 (15)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···S1^i	0.93	2.78	3.640 (3)	156
C23—H23···N1	0.98	2.41	3.267 (3)	145
C27—H27B···O2^ii	0.97	2.59	3.393 (3)	140
C30—H30···O3^iii	0.93	2.57	3.480 (3)	166
C33—H33···O3^iv	0.93	2.58	3.274 (3)	131
C20—H20···Cg1^v	0.93	2.81	3.706 (3)	163

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

6'-(nNphthalen-1-yl)-6a'-nitro-6',6a',6b',7',8',9',10',12a'-octahydro-2H-spiro[acenaphthylene-1,12'-chromeno[3,4-a]indolizin]-2-one (II)

Crystal data

C36H28N2O4	F(000) = 2320
Mr = 552.60	Dx = 1.184 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 35.7360 (5) Å	Cell parameters from 5464 reflections
b = 11.4510 (4) Å	θ = 1.8–26.9°
c = 15.3130 (3) Å	µ = 0.08 mm^−1
β = 98.378 (2)°	T = 293 K
V = 6199.4 (3) Å^3	Block, colourless
Z = 8	0.30 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4002 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.027
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 25.0°, θmin = 1.2°
Tmin = 0.742, Tmax = 0.863	h = −38→42
24488 measured reflections	k = −12→13
5464 independent reflections	l = −18→18

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)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 3.3964P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.126	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.15 e Å^−3
5464 reflections	Δρmin = −0.16 e Å^−3
380 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00076 (10)

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
C1	0.11638 (5)	0.06508 (18)	0.21020 (13)	0.0526 (5)
C2	0.08463 (6)	−0.01305 (19)	0.17739 (14)	0.0626 (6)
C3	0.05810 (7)	−0.0115 (3)	0.10306 (19)	0.0961 (9)
H3	0.057587	0.048710	0.062178	0.115*
C4	0.03208 (9)	−0.1019 (4)	0.0903 (3)	0.1207 (12)
H4	0.013886	−0.101140	0.040225	0.145*
C5	0.03227 (8)	−0.1916 (3)	0.1486 (3)	0.1065 (11)
H5	0.014260	−0.250396	0.137433	0.128*
C6	0.05926 (7)	−0.1975 (2)	0.2259 (2)	0.0786 (7)
C7	0.06434 (8)	−0.2845 (2)	0.2910 (3)	0.0942 (9)
H7	0.047848	−0.347774	0.286966	0.113*
C8	0.09285 (9)	−0.2781 (2)	0.3597 (2)	0.0951 (9)
H8	0.095799	−0.338284	0.400921	0.114*
C9	0.11834 (7)	−0.18250 (18)	0.37060 (18)	0.0755 (7)
H9	0.137421	−0.178846	0.418798	0.091*
C10	0.11421 (6)	−0.09664 (16)	0.30913 (14)	0.0542 (5)
C11	0.08490 (5)	−0.10469 (17)	0.23760 (15)	0.0588 (5)
C12	0.13643 (5)	0.01453 (15)	0.30137 (12)	0.0460 (4)
C13	0.18850 (6)	−0.06500 (19)	0.22802 (14)	0.0631 (6)
H13A	0.180208	−0.020888	0.174621	0.076*
H13B	0.176720	−0.141442	0.221732	0.076*
C14	0.23091 (6)	−0.0782 (2)	0.24037 (14)	0.0674 (6)
H14A	0.238852	−0.129872	0.289782	0.081*
H14B	0.238469	−0.113015	0.187899	0.081*
C15	0.24999 (6)	0.0384 (2)	0.25728 (14)	0.0629 (6)
H15A	0.243259	0.088851	0.206529	0.075*
H15B	0.277228	0.028152	0.266245	0.075*
C16	0.23775 (5)	0.09456 (17)	0.33870 (12)	0.0507 (5)
H16A	0.245424	0.045909	0.390051	0.061*
H16B	0.249717	0.170305	0.349153	0.061*
C17	0.19517 (5)	0.10841 (14)	0.32397 (11)	0.0405 (4)
H17	0.188258	0.159896	0.273058	0.049*
C18	0.17508 (5)	0.15277 (14)	0.40030 (10)	0.0388 (4)
C19	0.13489 (5)	0.10116 (15)	0.38040 (11)	0.0435 (4)
H19	0.129935	0.055939	0.431831	0.052*
C20	0.10467 (5)	0.19219 (17)	0.36118 (12)	0.0487 (5)
C21	0.06688 (6)	0.1676 (2)	0.36418 (15)	0.0669 (6)
H21	0.059928	0.094245	0.382387	0.080*
C22	0.03949 (7)	0.2515 (3)	0.34024 (19)	0.0896 (8)
H22	0.014138	0.234324	0.341579	0.108*
C23	0.04983 (8)	0.3603 (3)	0.3145 (2)	0.0908 (8)
H23	0.031290	0.416307	0.298034	0.109*
C24	0.08670 (7)	0.3874 (2)	0.31264 (15)	0.0703 (6)
H24	0.093426	0.461806	0.296162	0.084*
C25	0.11409 (6)	0.30341 (17)	0.33549 (12)	0.0509 (5)
C26	0.17650 (5)	0.28672 (14)	0.40757 (11)	0.0413 (4)
H26	0.202195	0.310881	0.400510	0.050*
C27	0.16712 (5)	0.34448 (14)	0.49082 (11)	0.0415 (4)
C28	0.17669 (5)	0.46539 (15)	0.50394 (12)	0.0450 (4)
C29	0.19530 (6)	0.53161 (16)	0.44563 (14)	0.0567 (5)
H29	0.201503	0.496668	0.394821	0.068*
C30	0.20438 (7)	0.64609 (18)	0.46233 (17)	0.0721 (6)
H30	0.216839	0.687805	0.423115	0.087*
C31	0.19517 (8)	0.7009 (2)	0.53741 (19)	0.0803 (7)
H31	0.201638	0.778734	0.548245	0.096*
C32	0.17682 (7)	0.64135 (19)	0.59490 (17)	0.0725 (7)
H32	0.170597	0.679086	0.644604	0.087*
C33	0.16703 (5)	0.52252 (17)	0.58021 (13)	0.0540 (5)
C34	0.14859 (6)	0.4597 (2)	0.64003 (14)	0.0643 (6)
H34	0.142673	0.496707	0.690319	0.077*
C35	0.13925 (6)	0.3460 (2)	0.62578 (14)	0.0633 (6)
H35	0.126694	0.305819	0.665609	0.076*
C36	0.14858 (5)	0.28885 (17)	0.55064 (12)	0.0522 (5)
H36	0.141920	0.210833	0.541431	0.063*
N1	0.17683 (4)	−0.00441 (12)	0.30412 (9)	0.0443 (4)
N2	0.19688 (4)	0.10032 (13)	0.48422 (9)	0.0446 (4)
O1	0.12667 (4)	0.14930 (13)	0.17294 (9)	0.0709 (4)
O2	0.22409 (4)	0.15545 (12)	0.51946 (8)	0.0571 (4)
O3	0.18748 (4)	0.00476 (11)	0.50940 (9)	0.0627 (4)
O4	0.15134 (4)	0.33150 (10)	0.33224 (8)	0.0487 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0576 (12)	0.0525 (11)	0.0461 (11)	−0.0046 (9)	0.0021 (9)	−0.0045 (9)
C2	0.0584 (13)	0.0660 (13)	0.0601 (13)	−0.0069 (10)	−0.0020 (10)	−0.0108 (11)
C3	0.0794 (17)	0.114 (2)	0.0852 (19)	−0.0180 (16)	−0.0215 (14)	−0.0094 (16)
C4	0.091 (2)	0.142 (3)	0.117 (3)	−0.032 (2)	−0.0279 (19)	−0.026 (2)
C5	0.0661 (17)	0.105 (2)	0.143 (3)	−0.0336 (16)	−0.0011 (19)	−0.044 (2)
C6	0.0606 (14)	0.0592 (14)	0.119 (2)	−0.0139 (11)	0.0230 (15)	−0.0269 (15)
C7	0.0746 (18)	0.0551 (15)	0.160 (3)	−0.0212 (13)	0.0402 (19)	−0.0172 (18)
C8	0.106 (2)	0.0475 (14)	0.138 (3)	−0.0099 (14)	0.037 (2)	0.0152 (15)
C9	0.0815 (16)	0.0490 (12)	0.0959 (18)	−0.0076 (11)	0.0127 (13)	0.0128 (12)
C10	0.0586 (12)	0.0402 (10)	0.0649 (13)	−0.0048 (9)	0.0127 (10)	−0.0030 (9)
C11	0.0490 (11)	0.0521 (12)	0.0761 (14)	−0.0082 (9)	0.0121 (10)	−0.0218 (11)
C12	0.0542 (11)	0.0382 (9)	0.0442 (10)	−0.0071 (8)	0.0031 (8)	−0.0002 (8)
C13	0.0747 (14)	0.0630 (13)	0.0510 (12)	−0.0012 (11)	0.0066 (10)	−0.0232 (10)
C14	0.0704 (14)	0.0788 (15)	0.0544 (12)	0.0128 (12)	0.0134 (11)	−0.0214 (11)
C15	0.0594 (12)	0.0819 (15)	0.0490 (11)	0.0065 (11)	0.0135 (9)	−0.0075 (11)
C16	0.0515 (11)	0.0555 (11)	0.0457 (10)	−0.0018 (9)	0.0096 (8)	−0.0066 (9)
C17	0.0497 (10)	0.0397 (9)	0.0320 (8)	−0.0028 (8)	0.0053 (7)	−0.0003 (7)
C18	0.0494 (10)	0.0364 (9)	0.0304 (8)	0.0001 (7)	0.0054 (7)	0.0016 (7)
C19	0.0505 (10)	0.0409 (9)	0.0399 (9)	−0.0043 (8)	0.0096 (8)	0.0022 (8)
C20	0.0476 (11)	0.0550 (11)	0.0435 (10)	0.0018 (9)	0.0062 (8)	−0.0027 (9)
C21	0.0538 (13)	0.0753 (15)	0.0722 (14)	−0.0007 (11)	0.0108 (11)	−0.0047 (12)
C22	0.0497 (13)	0.113 (2)	0.105 (2)	0.0131 (14)	0.0077 (13)	−0.0040 (18)
C23	0.0709 (18)	0.090 (2)	0.108 (2)	0.0287 (15)	0.0020 (15)	0.0058 (17)
C24	0.0750 (16)	0.0622 (13)	0.0709 (15)	0.0183 (12)	0.0017 (12)	0.0036 (11)
C25	0.0569 (12)	0.0527 (11)	0.0420 (10)	0.0078 (9)	0.0037 (9)	−0.0003 (9)
C26	0.0485 (10)	0.0374 (9)	0.0385 (9)	−0.0019 (8)	0.0075 (8)	0.0025 (7)
C27	0.0442 (10)	0.0399 (9)	0.0406 (9)	0.0026 (7)	0.0064 (8)	−0.0017 (8)
C28	0.0449 (10)	0.0399 (10)	0.0486 (10)	0.0050 (8)	0.0018 (8)	−0.0051 (8)
C29	0.0663 (13)	0.0409 (10)	0.0635 (13)	−0.0014 (9)	0.0117 (10)	−0.0022 (9)
C30	0.0810 (16)	0.0437 (12)	0.0903 (17)	−0.0069 (11)	0.0079 (13)	0.0020 (12)
C31	0.0918 (18)	0.0391 (12)	0.104 (2)	0.0025 (11)	−0.0069 (15)	−0.0148 (13)
C32	0.0802 (16)	0.0533 (13)	0.0797 (16)	0.0144 (12)	−0.0028 (13)	−0.0254 (12)
C33	0.0525 (11)	0.0490 (11)	0.0578 (12)	0.0125 (9)	−0.0005 (9)	−0.0120 (9)
C34	0.0679 (14)	0.0736 (15)	0.0543 (12)	0.0145 (11)	0.0183 (11)	−0.0170 (11)
C35	0.0673 (13)	0.0734 (15)	0.0537 (12)	0.0045 (11)	0.0240 (10)	−0.0015 (11)
C36	0.0613 (12)	0.0479 (11)	0.0494 (11)	0.0010 (9)	0.0142 (9)	−0.0020 (9)
N1	0.0514 (9)	0.0416 (8)	0.0400 (8)	−0.0027 (7)	0.0073 (7)	−0.0072 (6)
N2	0.0598 (10)	0.0397 (8)	0.0342 (8)	0.0023 (7)	0.0069 (7)	−0.0012 (7)
O1	0.0850 (10)	0.0700 (10)	0.0530 (8)	−0.0173 (8)	−0.0057 (7)	0.0154 (8)
O2	0.0614 (8)	0.0619 (9)	0.0445 (7)	−0.0041 (7)	−0.0042 (6)	−0.0052 (6)
O3	0.0911 (10)	0.0452 (8)	0.0497 (8)	−0.0023 (7)	0.0028 (7)	0.0117 (6)
O4	0.0599 (8)	0.0432 (7)	0.0428 (7)	0.0028 (6)	0.0073 (6)	0.0067 (5)

Geometric parameters (Å, º)

C1—O1	1.205 (2)	C18—N2	1.526 (2)
C1—C2	1.474 (3)	C18—C26	1.538 (2)
C1—C12	1.583 (3)	C18—C19	1.542 (2)
C2—C3	1.371 (3)	C19—C20	1.499 (3)
C2—C11	1.396 (3)	C19—H19	0.9800
C3—C4	1.386 (4)	C20—C21	1.387 (3)
C3—H3	0.9300	C20—C25	1.389 (3)
C4—C5	1.361 (5)	C21—C22	1.382 (3)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.416 (4)	C22—C23	1.374 (4)
C5—H5	0.9300	C22—H22	0.9300
C6—C11	1.398 (3)	C23—C24	1.358 (4)
C6—C7	1.402 (4)	C23—H23	0.9300
C7—C8	1.356 (4)	C24—C25	1.381 (3)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.419 (3)	C25—O4	1.377 (2)
C8—H8	0.9300	C26—O4	1.449 (2)
C9—C10	1.354 (3)	C26—C27	1.516 (2)
C9—H9	0.9300	C26—H26	0.9800
C10—C11	1.404 (3)	C27—C36	1.364 (3)
C10—C12	1.514 (2)	C27—C28	1.433 (2)
C12—N1	1.454 (2)	C28—C29	1.410 (3)
C12—C19	1.572 (2)	C28—C33	1.424 (3)
C13—N1	1.468 (2)	C29—C30	1.366 (3)
C13—C14	1.507 (3)	C29—H29	0.9300
C13—H13A	0.9700	C30—C31	1.391 (4)
C13—H13B	0.9700	C30—H30	0.9300
C14—C15	1.504 (3)	C31—C32	1.356 (4)
C14—H14A	0.9700	C31—H31	0.9300
C14—H14B	0.9700	C32—C33	1.415 (3)
C15—C16	1.523 (3)	C32—H32	0.9300
C15—H15A	0.9700	C33—C34	1.403 (3)
C15—H15B	0.9700	C34—C35	1.353 (3)
C16—C17	1.514 (2)	C34—H34	0.9300
C16—H16A	0.9700	C35—C36	1.405 (3)
C16—H16B	0.9700	C35—H35	0.9300
C17—N1	1.461 (2)	C36—H36	0.9300
C17—C18	1.544 (2)	N2—O2	1.2174 (18)
C17—H17	0.9800	N2—O3	1.2233 (18)
O1—C1—C2	126.65 (19)	C26—C18—C19	114.61 (14)
O1—C1—C12	125.46 (17)	N2—C18—C17	105.74 (13)
C2—C1—C12	107.79 (17)	C26—C18—C17	111.64 (13)
C3—C2—C11	119.7 (2)	C19—C18—C17	104.29 (13)
C3—C2—C1	132.8 (2)	C20—C19—C18	113.32 (14)
C11—C2—C1	107.47 (17)	C20—C19—C12	113.13 (14)
C2—C3—C4	118.5 (3)	C18—C19—C12	104.94 (13)
C2—C3—H3	120.8	C20—C19—H19	108.4
C4—C3—H3	120.8	C18—C19—H19	108.4
C5—C4—C3	122.1 (3)	C12—C19—H19	108.4
C5—C4—H4	118.9	C21—C20—C25	118.24 (18)
C3—C4—H4	118.9	C21—C20—C19	121.96 (18)
C4—C5—C6	121.5 (3)	C25—C20—C19	119.73 (16)
C4—C5—H5	119.2	C22—C21—C20	120.4 (2)
C6—C5—H5	119.2	C22—C21—H21	119.8
C11—C6—C7	115.8 (2)	C20—C21—H21	119.8
C11—C6—C5	115.1 (3)	C23—C22—C21	119.8 (2)
C7—C6—C5	129.1 (3)	C23—C22—H22	120.1
C8—C7—C6	121.2 (2)	C21—C22—H22	120.1
C8—C7—H7	119.4	C24—C23—C22	121.0 (2)
C6—C7—H7	119.4	C24—C23—H23	119.5
C7—C8—C9	122.0 (3)	C22—C23—H23	119.5
C7—C8—H8	119.0	C23—C24—C25	119.3 (2)
C9—C8—H8	119.0	C23—C24—H24	120.3
C10—C9—C8	118.4 (3)	C25—C24—H24	120.3
C10—C9—H9	120.8	O4—C25—C24	118.78 (18)
C8—C9—H9	120.8	O4—C25—C20	119.99 (16)
C9—C10—C11	119.21 (19)	C24—C25—C20	121.2 (2)
C9—C10—C12	131.26 (19)	O4—C26—C27	109.11 (13)
C11—C10—C12	109.53 (17)	O4—C26—C18	106.57 (13)
C2—C11—C6	123.1 (2)	C27—C26—C18	119.13 (14)
C2—C11—C10	113.48 (17)	O4—C26—H26	107.2
C6—C11—C10	123.4 (2)	C27—C26—H26	107.2
N1—C12—C10	113.71 (15)	C18—C26—H26	107.2
N1—C12—C19	102.58 (13)	C36—C27—C28	119.11 (16)
C10—C12—C19	113.12 (15)	C36—C27—C26	123.32 (16)
N1—C12—C1	113.58 (15)	C28—C27—C26	117.49 (15)
C10—C12—C1	101.61 (15)	C29—C28—C33	117.74 (17)
C19—C12—C1	112.70 (14)	C29—C28—C27	123.77 (17)
N1—C13—C14	110.15 (16)	C33—C28—C27	118.49 (17)
N1—C13—H13A	109.6	C30—C29—C28	121.3 (2)
C14—C13—H13A	109.6	C30—C29—H29	119.4
N1—C13—H13B	109.6	C28—C29—H29	119.4
C14—C13—H13B	109.6	C29—C30—C31	120.6 (2)
H13A—C13—H13B	108.1	C29—C30—H30	119.7
C15—C14—C13	110.80 (18)	C31—C30—H30	119.7
C15—C14—H14A	109.5	C32—C31—C30	120.3 (2)
C13—C14—H14A	109.5	C32—C31—H31	119.8
C15—C14—H14B	109.5	C30—C31—H31	119.8
C13—C14—H14B	109.5	C31—C32—C33	120.8 (2)
H14A—C14—H14B	108.1	C31—C32—H32	119.6
C14—C15—C16	109.79 (17)	C33—C32—H32	119.6
C14—C15—H15A	109.7	C34—C33—C32	121.2 (2)
C16—C15—H15A	109.7	C34—C33—C28	119.54 (18)
C14—C15—H15B	109.7	C32—C33—C28	119.2 (2)
C16—C15—H15B	109.7	C35—C34—C33	121.09 (19)
H15A—C15—H15B	108.2	C35—C34—H34	119.5
C17—C16—C15	108.95 (15)	C33—C34—H34	119.5
C17—C16—H16A	109.9	C34—C35—C36	119.8 (2)
C15—C16—H16A	109.9	C34—C35—H35	120.1
C17—C16—H16B	109.9	C36—C35—H35	120.1
C15—C16—H16B	109.9	C27—C36—C35	121.92 (18)
H16A—C16—H16B	108.3	C27—C36—H36	119.0
N1—C17—C16	110.45 (14)	C35—C36—H36	119.0
N1—C17—C18	101.79 (13)	C12—N1—C17	106.72 (13)
C16—C17—C18	119.33 (14)	C12—N1—C13	116.30 (14)
N1—C17—H17	108.2	C17—N1—C13	114.36 (15)
C16—C17—H17	108.2	O2—N2—O3	124.22 (15)
C18—C17—H17	108.2	O2—N2—C18	116.50 (14)
N2—C18—C26	108.91 (13)	O3—N2—C18	119.18 (14)
N2—C18—C19	111.24 (13)	C25—O4—C26	112.30 (13)
O1—C1—C2—C3	−3.4 (4)	C12—C19—C20—C25	−99.28 (19)
C12—C1—C2—C3	179.9 (3)	C25—C20—C21—C22	1.4 (3)
O1—C1—C2—C11	174.7 (2)	C19—C20—C21—C22	−175.6 (2)
C12—C1—C2—C11	−2.0 (2)	C20—C21—C22—C23	−0.9 (4)
C11—C2—C3—C4	0.2 (4)	C21—C22—C23—C24	−0.5 (4)
C1—C2—C3—C4	178.2 (3)	C22—C23—C24—C25	1.2 (4)
C2—C3—C4—C5	−0.4 (5)	C23—C24—C25—O4	179.1 (2)
C3—C4—C5—C6	0.0 (6)	C23—C24—C25—C20	−0.7 (3)
C4—C5—C6—C11	0.7 (4)	C21—C20—C25—O4	179.57 (17)
C4—C5—C6—C7	−177.7 (3)	C19—C20—C25—O4	−3.4 (3)
C11—C6—C7—C8	−0.9 (4)	C21—C20—C25—C24	−0.6 (3)
C5—C6—C7—C8	177.4 (3)	C19—C20—C25—C24	176.42 (18)
C6—C7—C8—C9	1.6 (4)	N2—C18—C26—O4	−172.49 (12)
C7—C8—C9—C10	−1.3 (4)	C19—C18—C26—O4	−47.16 (18)
C8—C9—C10—C11	0.5 (3)	C17—C18—C26—O4	71.12 (17)
C8—C9—C10—C12	−179.6 (2)	N2—C18—C26—C27	−48.6 (2)
C3—C2—C11—C6	0.5 (3)	C19—C18—C26—C27	76.68 (19)
C1—C2—C11—C6	−177.97 (19)	C17—C18—C26—C27	−165.04 (14)
C3—C2—C11—C10	178.3 (2)	O4—C26—C27—C36	105.74 (18)
C1—C2—C11—C10	−0.2 (2)	C18—C26—C27—C36	−16.9 (2)
C7—C6—C11—C2	177.7 (2)	O4—C26—C27—C28	−70.94 (18)
C5—C6—C11—C2	−0.9 (3)	C18—C26—C27—C28	166.47 (15)
C7—C6—C11—C10	0.1 (3)	C36—C27—C28—C29	−179.01 (18)
C5—C6—C11—C10	−178.5 (2)	C26—C27—C28—C29	−2.2 (3)
C9—C10—C11—C2	−177.7 (2)	C36—C27—C28—C33	1.1 (2)
C12—C10—C11—C2	2.3 (2)	C26—C27—C28—C33	177.96 (15)
C9—C10—C11—C6	0.1 (3)	C33—C28—C29—C30	1.1 (3)
C12—C10—C11—C6	−179.87 (19)	C27—C28—C29—C30	−178.72 (19)
C9—C10—C12—N1	54.4 (3)	C28—C29—C30—C31	−0.5 (3)
C11—C10—C12—N1	−125.65 (17)	C29—C30—C31—C32	−0.4 (4)
C9—C10—C12—C19	−62.1 (3)	C30—C31—C32—C33	0.6 (4)
C11—C10—C12—C19	117.85 (17)	C31—C32—C33—C34	179.0 (2)
C9—C10—C12—C1	176.8 (2)	C31—C32—C33—C28	0.0 (3)
C11—C10—C12—C1	−3.2 (2)	C29—C28—C33—C34	−179.83 (18)
O1—C1—C12—N1	−51.1 (3)	C27—C28—C33—C34	0.0 (3)
C2—C1—C12—N1	125.63 (17)	C29—C28—C33—C32	−0.9 (3)
O1—C1—C12—C10	−173.6 (2)	C27—C28—C33—C32	178.98 (17)
C2—C1—C12—C10	3.1 (2)	C32—C33—C34—C35	180.0 (2)
O1—C1—C12—C19	65.0 (3)	C28—C33—C34—C35	−1.1 (3)
C2—C1—C12—C19	−118.25 (17)	C33—C34—C35—C36	0.9 (3)
N1—C13—C14—C15	−54.9 (2)	C28—C27—C36—C35	−1.3 (3)
C13—C14—C15—C16	58.2 (2)	C26—C27—C36—C35	−177.94 (17)
C14—C15—C16—C17	−58.6 (2)	C34—C35—C36—C27	0.3 (3)
C15—C16—C17—N1	56.9 (2)	C10—C12—N1—C17	−162.50 (15)
C15—C16—C17—C18	174.30 (16)	C19—C12—N1—C17	−40.00 (16)
N1—C17—C18—N2	85.76 (14)	C1—C12—N1—C17	81.93 (17)
C16—C17—C18—N2	−36.02 (19)	C10—C12—N1—C13	68.5 (2)
N1—C17—C18—C26	−155.94 (13)	C19—C12—N1—C13	−168.96 (15)
C16—C17—C18—C26	82.28 (19)	C1—C12—N1—C13	−47.0 (2)
N1—C17—C18—C19	−31.64 (15)	C16—C17—N1—C12	173.41 (14)
C16—C17—C18—C19	−153.42 (15)	C18—C17—N1—C12	45.67 (16)
N2—C18—C19—C20	130.92 (15)	C16—C17—N1—C13	−56.51 (19)
C26—C18—C19—C20	6.8 (2)	C18—C17—N1—C13	175.76 (15)
C17—C18—C19—C20	−115.54 (15)	C14—C13—N1—C12	−179.97 (17)
N2—C18—C19—C12	−105.17 (14)	C14—C13—N1—C17	54.9 (2)
C26—C18—C19—C12	130.73 (14)	C26—C18—N2—O2	−33.06 (19)
C17—C18—C19—C12	8.37 (16)	C19—C18—N2—O2	−160.32 (14)
N1—C12—C19—C20	142.03 (15)	C17—C18—N2—O2	87.05 (16)
C10—C12—C19—C20	−95.07 (18)	C26—C18—N2—O3	150.48 (15)
C1—C12—C19—C20	19.5 (2)	C19—C18—N2—O3	23.2 (2)
N1—C12—C19—C18	18.00 (16)	C17—C18—N2—O3	−89.41 (17)
C10—C12—C19—C18	140.90 (15)	C24—C25—O4—C26	137.77 (17)
C1—C12—C19—C18	−104.52 (16)	C20—C25—O4—C26	−42.4 (2)
C18—C19—C20—C21	−163.06 (17)	C27—C26—O4—C25	−63.81 (17)
C12—C19—C20—C21	77.6 (2)	C18—C26—O4—C25	66.03 (17)
C18—C19—C20—C25	20.0 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O3^i	0.97	2.59	3.413 (3)	143
C17—H17···O1	0.98	2.50	3.148 (2)	124
C32—H32···O1^ii	0.93	2.59	3.318 (3)	135
C35—H35···Cg1^iii	0.93	2.92	3.849 (2)	176

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