Ethyl 6′-cyano-7′-(p-tol­yl)-1′,6′,7′,7a′-tetra­hydro-3′H-spiro­[indeno­[1,2-b]quinoxaline-11,5′-pyrrolo­[1,2-c]thia­zole]-6′-carboxyl­ate

The title compound, C₃₁H₂₆N₄O₂S, crystallizes in a triclinic centrosymmetric lattice with two mol­ecules in the unit cell. The five-membered thia­zole and pyrrolidine rings adopt twisted and envelope conformations, respectively. The meth­oxy­phenyl and indeno­quinoxaline planes are oriented with a dihedral angle of 88.1 (1)° to each other. The crystal structure features C—H...N, C—H...O and C—H...S inter­molecular inter­actions forming two R₂²(16) ring motifs and a C(11) and two C₂²(14) chain motifs. The –CH₃ group of the ethyl side chain is disordered over two positions with site occupancies of 0.55 and 0.45.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.061
• wR factor = 0.151
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
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        C25 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C28 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C25      -C30             1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0046 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14      ..S1       .       3.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23A     ..N2       .       2.70 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.211 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.031 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         11 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          3 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
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 C20        Constrained at       0.55 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C20'       Constrained at       0.45 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19A       Constrained at       0.55 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19B       Constrained at       0.55 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20A       Constrained at       0.55 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20B       Constrained at       0.55 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20C       Constrained at       0.55 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19C       Constrained at       0.45 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19D       Constrained at       0.45 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20D       Constrained at       0.45 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20E       Constrained at       0.45 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20F       Constrained at       0.45 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         3% Note
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C16         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C21         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C22         (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         22 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        75% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

Ethyl 6'-cyano-7'-(p-tolyl)-1',6',7',7a'-tetrahydro-3'H-spiro[indeno[1,2-b]quinoxaline-11,5'-pyrrolo[1,2-c]thiazole]-6'-carboxylate

Crystal data

C31H26N4O2S	Z = 2
Mr = 518.62	F(000) = 544
Triclinic, P1	Dx = 1.311 Mg m^−3
a = 10.5467 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6469 (19) Å	Cell parameters from 2425 reflections
c = 12.942 (2) Å	θ = 2.2–24.7°
α = 108.321 (3)°	µ = 0.16 mm^−1
β = 102.108 (3)°	T = 293 K
γ = 110.887 (3)°	Block, colourless
V = 1313.9 (4) Å^3	0.21 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.1°
ω scans	h = −12→12
12753 measured reflections	k = −13→13
4622 independent reflections	l = −15→15
3771 reflections with I > 2σ(I)

Refinement

Refinement on F^2	22 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0638P)^2 + 0.7519P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4622 reflections	Δρmax = 0.28 e Å^−3
355 parameters	Δρmin = −0.26 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.

Refinement. All the H atoms were constrained and refined in the riding model approximation with C—H = 0.93–0.98 Å and U_iso(H) = 1.2–1.5 U_eq(parent carbon atom). The –CH₃ group of the ethyl side chain (atom C20) is disordered two positions with site occupancies of 0.55 and 0.45. The C—C distances involving the disordered methyl group were restrained to 1.500 (5) Å. The displacement parameters of the disordered atoms were restrained to be similar as the one of the atom to which they are bonded.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5961 (2)	0.9197 (2)	0.2416 (2)	0.0408 (6)
C2	0.5481 (3)	0.8168 (2)	0.1140 (2)	0.0427 (6)
C3	0.4668 (3)	0.6764 (2)	0.0615 (2)	0.0499 (6)
H3	0.4307	0.6306	0.1043	0.060*
C4	0.4402 (3)	0.6057 (3)	−0.0548 (3)	0.0574 (7)
H4	0.3862	0.5116	−0.0899	0.069*
C5	0.4918 (3)	0.6713 (3)	−0.1198 (3)	0.0621 (8)
H5	0.4720	0.6214	−0.1982	0.075*
C6	0.5729 (3)	0.8109 (3)	−0.0695 (2)	0.0591 (7)
H6	0.6081	0.8559	−0.1131	0.071*
C7	0.6005 (3)	0.8823 (3)	0.0474 (2)	0.0457 (6)
C8	0.6789 (3)	1.0287 (2)	0.1196 (2)	0.0446 (6)
C9	0.6725 (2)	1.0533 (2)	0.2330 (2)	0.0410 (6)
C10	0.7864 (3)	1.2786 (2)	0.2866 (2)	0.0500 (6)
C11	0.8413 (3)	1.4131 (3)	0.3690 (3)	0.0665 (8)
H11	0.8322	1.4301	0.4415	0.080*
C12	0.9078 (3)	1.5189 (3)	0.3436 (3)	0.0737 (10)
H12	0.9449	1.6076	0.3992	0.088*
C13	0.9205 (3)	1.4948 (3)	0.2353 (4)	0.0720 (10)
H13	0.9654	1.5680	0.2188	0.086*
C14	0.8685 (3)	1.3663 (3)	0.1527 (3)	0.0642 (8)
H14	0.8789	1.3524	0.0808	0.077*
C15	0.7989 (3)	1.2542 (3)	0.1755 (3)	0.0508 (7)
C16	0.6976 (2)	0.8932 (2)	0.3302 (2)	0.0389 (5)
C17	0.7946 (3)	1.0183 (2)	0.4386 (2)	0.0430 (6)
C18	0.7898 (3)	0.8377 (3)	0.2721 (2)	0.0425 (6)
C21	0.5848 (3)	0.7902 (2)	0.3579 (2)	0.0413 (6)
H21	0.5381	0.7027	0.2891	0.050*
C22	0.4708 (3)	0.8422 (3)	0.3620 (2)	0.0471 (6)
H22	0.4956	0.9036	0.4431	0.057*
C23	0.3105 (3)	0.7322 (3)	0.3151 (3)	0.0647 (8)
H23A	0.2636	0.7565	0.3695	0.078*
H23B	0.3072	0.6452	0.3063	0.078*
C24	0.3470 (3)	0.8973 (3)	0.2200 (3)	0.0662 (8)
H24A	0.3550	0.9121	0.1514	0.079*
H24B	0.3143	0.9586	0.2625	0.079*
C25	0.6408 (3)	0.7648 (2)	0.4626 (2)	0.0457 (6)
C26	0.5612 (4)	0.7430 (5)	0.5313 (3)	0.0890 (12)
H26	0.4753	0.7511	0.5177	0.107*
C27	0.6058 (5)	0.7094 (5)	0.6206 (4)	0.1080 (15)
H27	0.5477	0.6937	0.6647	0.130*
C28	0.7324 (4)	0.6982 (4)	0.6471 (3)	0.0708 (9)
C29	0.8159 (4)	0.7278 (4)	0.5832 (3)	0.0775 (10)
H29	0.9051	0.7259	0.6008	0.093*
C30	0.7719 (4)	0.7604 (4)	0.4930 (3)	0.0724 (9)
H30	0.8323	0.7801	0.4514	0.087*
C31	0.7813 (5)	0.6613 (5)	0.7454 (4)	0.1092 (15)
H31A	0.8405	0.7426	0.8164	0.164*
H31B	0.8369	0.6134	0.7266	0.164*
H31C	0.6976	0.6045	0.7555	0.164*
N1	0.4856 (2)	0.9211 (2)	0.2931 (2)	0.0479 (5)
N2	0.8697 (3)	1.1096 (2)	0.5250 (2)	0.0624 (6)
N3	0.7420 (2)	1.1249 (2)	0.0893 (2)	0.0533 (6)
N4	0.7208 (2)	1.1737 (2)	0.31545 (19)	0.0483 (5)
O1	0.7654 (2)	0.72191 (18)	0.23620 (16)	0.0570 (5)
O2	0.8942 (2)	0.93702 (19)	0.26587 (18)	0.0579 (5)
C19	0.9941 (4)	0.9032 (4)	0.2154 (3)	0.0799 (10)
H19A	1.0083	0.8336	0.2347	0.096*	0.55
H19B	1.0878	0.9830	0.2486	0.096*	0.55
H19C	0.9644	0.8067	0.1887	0.096*	0.45
H19D	1.0915	0.9521	0.2741	0.096*	0.45
S1	0.21886 (8)	0.72141 (9)	0.17723 (8)	0.0703 (3)
C20	0.9376 (12)	0.8542 (10)	0.0874 (5)	0.094 (3)	0.55
H20A	0.8556	0.7658	0.0531	0.141*	0.55
H20B	1.0126	0.8489	0.0579	0.141*	0.55
H20C	0.9078	0.9159	0.0679	0.141*	0.55
C20'	0.9945 (16)	0.9404 (12)	0.1157 (8)	0.096 (4)	0.45
H20D	0.8991	0.8883	0.0559	0.144*	0.45
H20E	1.0636	0.9214	0.0847	0.144*	0.45
H20F	1.0210	1.0354	0.1419	0.144*	0.45

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0386 (13)	0.0321 (12)	0.0492 (14)	0.0161 (10)	0.0146 (11)	0.0155 (11)
C2	0.0356 (12)	0.0390 (13)	0.0489 (14)	0.0191 (11)	0.0073 (11)	0.0158 (11)
C3	0.0458 (14)	0.0377 (14)	0.0531 (16)	0.0168 (12)	0.0067 (12)	0.0137 (12)
C4	0.0505 (16)	0.0403 (14)	0.0597 (18)	0.0202 (12)	0.0016 (13)	0.0078 (13)
C5	0.0635 (18)	0.0623 (19)	0.0468 (16)	0.0320 (15)	0.0090 (14)	0.0100 (14)
C6	0.0608 (17)	0.0638 (19)	0.0512 (17)	0.0312 (15)	0.0154 (14)	0.0226 (15)
C7	0.0402 (13)	0.0455 (14)	0.0480 (15)	0.0213 (11)	0.0100 (11)	0.0179 (12)
C8	0.0396 (13)	0.0438 (14)	0.0535 (15)	0.0209 (11)	0.0130 (11)	0.0247 (12)
C9	0.0349 (12)	0.0346 (13)	0.0517 (15)	0.0161 (10)	0.0119 (11)	0.0185 (11)
C10	0.0416 (14)	0.0368 (14)	0.0659 (18)	0.0155 (11)	0.0098 (12)	0.0242 (13)
C11	0.0645 (19)	0.0407 (16)	0.078 (2)	0.0171 (14)	0.0130 (16)	0.0221 (15)
C12	0.0626 (19)	0.0362 (16)	0.099 (3)	0.0111 (14)	0.0108 (18)	0.0257 (16)
C13	0.0464 (16)	0.0534 (19)	0.116 (3)	0.0134 (14)	0.0198 (18)	0.053 (2)
C14	0.0520 (16)	0.0614 (19)	0.090 (2)	0.0234 (15)	0.0243 (16)	0.0482 (18)
C15	0.0381 (13)	0.0467 (15)	0.0700 (18)	0.0183 (12)	0.0129 (12)	0.0332 (14)
C16	0.0380 (12)	0.0318 (12)	0.0446 (13)	0.0158 (10)	0.0138 (10)	0.0146 (10)
C17	0.0418 (13)	0.0365 (13)	0.0477 (15)	0.0157 (11)	0.0146 (12)	0.0178 (12)
C18	0.0397 (13)	0.0427 (15)	0.0412 (13)	0.0188 (11)	0.0098 (11)	0.0162 (11)
C21	0.0421 (13)	0.0328 (12)	0.0456 (13)	0.0149 (10)	0.0171 (11)	0.0144 (10)
C22	0.0478 (14)	0.0428 (14)	0.0521 (15)	0.0219 (12)	0.0219 (12)	0.0179 (12)
C23	0.0496 (16)	0.0700 (19)	0.089 (2)	0.0272 (15)	0.0326 (16)	0.0456 (18)
C24	0.0500 (16)	0.070 (2)	0.101 (2)	0.0348 (15)	0.0330 (16)	0.0515 (19)
C25	0.0498 (15)	0.0369 (13)	0.0495 (15)	0.0179 (11)	0.0195 (12)	0.0184 (11)
C26	0.073 (2)	0.154 (4)	0.089 (2)	0.066 (2)	0.045 (2)	0.082 (3)
C27	0.096 (3)	0.189 (5)	0.100 (3)	0.078 (3)	0.059 (2)	0.103 (3)
C28	0.084 (2)	0.083 (2)	0.0649 (19)	0.0458 (19)	0.0302 (18)	0.0444 (18)
C29	0.083 (2)	0.105 (3)	0.083 (2)	0.064 (2)	0.0364 (19)	0.058 (2)
C30	0.075 (2)	0.103 (3)	0.084 (2)	0.059 (2)	0.0445 (18)	0.063 (2)
C31	0.128 (4)	0.151 (4)	0.099 (3)	0.083 (3)	0.046 (3)	0.087 (3)
N1	0.0409 (11)	0.0403 (11)	0.0696 (14)	0.0215 (9)	0.0232 (10)	0.0265 (11)
N2	0.0628 (15)	0.0466 (14)	0.0539 (15)	0.0163 (12)	0.0083 (12)	0.0115 (12)
N3	0.0512 (13)	0.0526 (14)	0.0619 (14)	0.0235 (11)	0.0195 (11)	0.0322 (12)
N4	0.0470 (12)	0.0355 (11)	0.0569 (13)	0.0172 (10)	0.0131 (10)	0.0185 (10)
O1	0.0612 (12)	0.0411 (11)	0.0619 (12)	0.0269 (9)	0.0211 (9)	0.0107 (9)
O2	0.0519 (11)	0.0607 (12)	0.0831 (14)	0.0326 (10)	0.0390 (10)	0.0394 (11)
C19	0.078 (2)	0.107 (3)	0.104 (3)	0.063 (2)	0.062 (2)	0.062 (2)
S1	0.0417 (4)	0.0768 (6)	0.0791 (6)	0.0151 (4)	0.0168 (4)	0.0345 (5)
C20	0.100 (8)	0.143 (9)	0.089 (5)	0.091 (7)	0.048 (5)	0.059 (6)
C20'	0.112 (10)	0.141 (11)	0.082 (6)	0.084 (10)	0.062 (6)	0.056 (7)

Geometric parameters (Å, º)

C1—N1	1.461 (3)	C21—H21	0.9800
C1—C9	1.528 (3)	C22—N1	1.461 (3)
C1—C2	1.546 (3)	C22—C23	1.550 (4)
C1—C16	1.581 (3)	C22—H22	0.9800
C2—C3	1.389 (3)	C23—S1	1.784 (3)
C2—C7	1.393 (4)	C23—H23A	0.9700
C3—C4	1.378 (4)	C23—H23B	0.9700
C3—H3	0.9300	C24—N1	1.440 (3)
C4—C5	1.375 (4)	C24—S1	1.825 (3)
C4—H4	0.9300	C24—H24A	0.9700
C5—C6	1.381 (4)	C24—H24B	0.9700
C5—H5	0.9300	C25—C26	1.366 (4)
C6—C7	1.385 (4)	C25—C30	1.379 (4)
C6—H6	0.9300	C26—C27	1.378 (5)
C7—C8	1.461 (3)	C26—H26	0.9300
C8—N3	1.306 (3)	C27—C28	1.370 (5)
C8—C9	1.425 (4)	C27—H27	0.9300
C9—N4	1.299 (3)	C28—C29	1.359 (5)
C10—N4	1.379 (3)	C28—C31	1.516 (5)
C10—C11	1.404 (4)	C29—C30	1.379 (4)
C10—C15	1.420 (4)	C29—H29	0.9300
C11—C12	1.361 (4)	C30—H30	0.9300
C11—H11	0.9300	C31—H31A	0.9600
C12—C13	1.386 (5)	C31—H31B	0.9600
C12—H12	0.9300	C31—H31C	0.9600
C13—C14	1.359 (5)	O2—C19	1.454 (3)
C13—H13	0.9300	C19—C20	1.474 (5)
C14—C15	1.408 (4)	C19—C20'	1.484 (5)
C14—H14	0.9300	C19—H19A	0.9700
C15—N3	1.374 (3)	C19—H19B	0.9700
C16—C17	1.479 (3)	C19—H19C	0.9700
C16—C18	1.542 (3)	C19—H19D	0.9700
C16—C21	1.553 (3)	C20—H20A	0.9600
C17—N2	1.135 (3)	C20—H20B	0.9600
C18—O1	1.188 (3)	C20—H20C	0.9600
C18—O2	1.320 (3)	C20'—H20D	0.9600
C21—C25	1.521 (3)	C20'—H20E	0.9600
C21—C22	1.531 (3)	C20'—H20F	0.9600
N1—C1—C9	111.29 (18)	C23—C22—H22	108.4
N1—C1—C2	119.08 (19)	C22—C23—S1	108.18 (19)
C9—C1—C2	100.51 (19)	C22—C23—H23A	110.1
N1—C1—C16	100.80 (19)	S1—C23—H23A	110.1
C9—C1—C16	114.22 (18)	C22—C23—H23B	110.1
C2—C1—C16	111.61 (18)	S1—C23—H23B	110.1
C3—C2—C7	119.0 (2)	H23A—C23—H23B	108.4
C3—C2—C1	130.0 (2)	N1—C24—S1	107.03 (19)
C7—C2—C1	111.0 (2)	N1—C24—H24A	110.3
C4—C3—C2	119.2 (3)	S1—C24—H24A	110.3
C4—C3—H3	120.4	N1—C24—H24B	110.3
C2—C3—H3	120.4	S1—C24—H24B	110.3
C5—C4—C3	121.4 (3)	H24A—C24—H24B	108.6
C5—C4—H4	119.3	C26—C25—C30	116.2 (3)
C3—C4—H4	119.3	C26—C25—C21	121.0 (3)
C4—C5—C6	120.5 (3)	C30—C25—C21	122.8 (2)
C4—C5—H5	119.8	C25—C26—C27	121.2 (3)
C6—C5—H5	119.8	C25—C26—H26	119.4
C5—C6—C7	118.4 (3)	C27—C26—H26	119.4
C5—C6—H6	120.8	C28—C27—C26	122.5 (3)
C7—C6—H6	120.8	C28—C27—H27	118.7
C6—C7—C2	121.6 (2)	C26—C27—H27	118.7
C6—C7—C8	129.1 (3)	C29—C28—C27	116.2 (3)
C2—C7—C8	109.3 (2)	C29—C28—C31	121.3 (3)
N3—C8—C9	123.7 (2)	C27—C28—C31	122.4 (3)
N3—C8—C7	128.1 (2)	C28—C29—C30	121.7 (3)
C9—C8—C7	108.1 (2)	C28—C29—H29	119.1
N4—C9—C8	123.8 (2)	C30—C29—H29	119.1
N4—C9—C1	125.3 (2)	C29—C30—C25	121.9 (3)
C8—C9—C1	110.8 (2)	C29—C30—H30	119.1
N4—C10—C11	119.1 (3)	C25—C30—H30	119.1
N4—C10—C15	121.8 (2)	C28—C31—H31A	109.5
C11—C10—C15	119.1 (3)	C28—C31—H31B	109.5
C12—C11—C10	120.6 (3)	H31A—C31—H31B	109.5
C12—C11—H11	119.7	C28—C31—H31C	109.5
C10—C11—H11	119.7	H31A—C31—H31C	109.5
C11—C12—C13	120.2 (3)	H31B—C31—H31C	109.5
C11—C12—H12	119.9	C24—N1—C22	112.6 (2)
C13—C12—H12	119.9	C24—N1—C1	118.3 (2)
C14—C13—C12	121.2 (3)	C22—N1—C1	112.25 (18)
C14—C13—H13	119.4	C8—N3—C15	114.3 (2)
C12—C13—H13	119.4	C9—N4—C10	114.4 (2)
C13—C14—C15	120.3 (3)	C18—O2—C19	117.1 (2)
C13—C14—H14	119.8	O2—C19—C20	111.1 (5)
C15—C14—H14	119.8	O2—C19—C20'	109.8 (6)
N3—C15—C14	119.5 (3)	O2—C19—H19A	109.4
N3—C15—C10	121.9 (2)	C20—C19—H19A	109.4
C14—C15—C10	118.6 (3)	O2—C19—H19B	109.4
C17—C16—C18	109.64 (19)	C20—C19—H19B	109.4
C17—C16—C21	109.5 (2)	H19A—C19—H19B	108.0
C18—C16—C21	114.19 (19)	O2—C19—H19C	109.7
C17—C16—C1	111.59 (18)	C20'—C19—H19C	109.7
C18—C16—C1	109.77 (19)	O2—C19—H19D	109.7
C21—C16—C1	101.94 (18)	C20'—C19—H19D	109.7
N2—C17—C16	176.0 (3)	H19C—C19—H19D	108.2
O1—C18—O2	126.5 (2)	C23—S1—C24	90.07 (14)
O1—C18—C16	123.8 (2)	C19—C20—H20A	109.5
O2—C18—C16	109.7 (2)	C19—C20—H20B	109.5
C25—C21—C22	115.2 (2)	H20A—C20—H20B	109.5
C25—C21—C16	117.8 (2)	C19—C20—H20C	109.5
C22—C21—C16	102.65 (19)	H20A—C20—H20C	109.5
C25—C21—H21	106.8	H20B—C20—H20C	109.5
C22—C21—H21	106.8	C19—C20'—H20D	109.5
C16—C21—H21	106.8	C19—C20'—H20E	109.5
N1—C22—C21	105.81 (19)	H20D—C20'—H20E	109.5
N1—C22—C23	109.4 (2)	C19—C20'—H20F	109.5
C21—C22—C23	116.1 (2)	H20D—C20'—H20F	109.5
N1—C22—H22	108.4	H20E—C20'—H20F	109.5
C21—C22—H22	108.4
N1—C1—C2—C3	−55.0 (3)	C21—C16—C18—O2	−171.9 (2)
C9—C1—C2—C3	−176.7 (2)	C1—C16—C18—O2	74.3 (2)
C16—C1—C2—C3	61.8 (3)	C17—C16—C21—C25	−47.3 (3)
N1—C1—C2—C7	126.1 (2)	C18—C16—C21—C25	76.1 (3)
C9—C1—C2—C7	4.4 (2)	C1—C16—C21—C25	−165.60 (19)
C16—C1—C2—C7	−117.1 (2)	C17—C16—C21—C22	80.4 (2)
C7—C2—C3—C4	0.1 (4)	C18—C16—C21—C22	−156.2 (2)
C1—C2—C3—C4	−178.7 (2)	C1—C16—C21—C22	−37.9 (2)
C2—C3—C4—C5	−0.4 (4)	C25—C21—C22—N1	152.5 (2)
C3—C4—C5—C6	0.3 (4)	C16—C21—C22—N1	23.1 (2)
C4—C5—C6—C7	0.0 (4)	C25—C21—C22—C23	−86.0 (3)
C5—C6—C7—C2	−0.3 (4)	C16—C21—C22—C23	144.7 (2)
C5—C6—C7—C8	−178.2 (3)	N1—C22—C23—S1	12.8 (3)
C3—C2—C7—C6	0.2 (4)	C21—C22—C23—S1	−106.8 (2)
C1—C2—C7—C6	179.3 (2)	C22—C21—C25—C26	22.1 (4)
C3—C2—C7—C8	178.5 (2)	C16—C21—C25—C26	143.6 (3)
C1—C2—C7—C8	−2.5 (3)	C22—C21—C25—C30	−158.7 (3)
C6—C7—C8—N3	−0.8 (4)	C16—C21—C25—C30	−37.3 (4)
C2—C7—C8—N3	−178.9 (2)	C30—C25—C26—C27	−4.4 (6)
C6—C7—C8—C9	177.3 (3)	C21—C25—C26—C27	174.8 (4)
C2—C7—C8—C9	−0.8 (3)	C25—C26—C27—C28	1.2 (7)
N3—C8—C9—N4	4.4 (4)	C26—C27—C28—C29	2.7 (7)
C7—C8—C9—N4	−173.8 (2)	C26—C27—C28—C31	179.9 (4)
N3—C8—C9—C1	−178.0 (2)	C27—C28—C29—C30	−3.2 (6)
C7—C8—C9—C1	3.8 (3)	C31—C28—C29—C30	179.5 (4)
N1—C1—C9—N4	45.6 (3)	C28—C29—C30—C25	−0.1 (6)
C2—C1—C9—N4	172.7 (2)	C26—C25—C30—C29	3.9 (5)
C16—C1—C9—N4	−67.7 (3)	C21—C25—C30—C29	−175.3 (3)
N1—C1—C9—C8	−131.9 (2)	S1—C24—N1—C22	−32.2 (3)
C2—C1—C9—C8	−4.9 (2)	S1—C24—N1—C1	101.5 (2)
C16—C1—C9—C8	114.8 (2)	C21—C22—N1—C24	138.6 (2)
N4—C10—C11—C12	179.4 (3)	C23—C22—N1—C24	12.8 (3)
C15—C10—C11—C12	−1.0 (4)	C21—C22—N1—C1	2.1 (3)
C10—C11—C12—C13	0.8 (5)	C23—C22—N1—C1	−123.7 (2)
C11—C12—C13—C14	−0.6 (5)	C9—C1—N1—C24	79.0 (3)
C12—C13—C14—C15	0.6 (5)	C2—C1—N1—C24	−37.2 (3)
C13—C14—C15—N3	177.5 (3)	C16—C1—N1—C24	−159.5 (2)
C13—C14—C15—C10	−0.8 (4)	C9—C1—N1—C22	−147.2 (2)
N4—C10—C15—N3	2.4 (4)	C2—C1—N1—C22	96.6 (3)
C11—C10—C15—N3	−177.2 (2)	C16—C1—N1—C22	−25.7 (2)
N4—C10—C15—C14	−179.4 (2)	C9—C8—N3—C15	−1.9 (3)
C11—C10—C15—C14	1.0 (4)	C7—C8—N3—C15	175.9 (2)
N1—C1—C16—C17	−78.2 (2)	C14—C15—N3—C8	−179.4 (2)
C9—C1—C16—C17	41.2 (3)	C10—C15—N3—C8	−1.2 (3)
C2—C1—C16—C17	154.3 (2)	C8—C9—N4—C10	−3.0 (3)
N1—C1—C16—C18	160.00 (18)	C1—C9—N4—C10	179.8 (2)
C9—C1—C16—C18	−80.6 (2)	C11—C10—N4—C9	179.4 (2)
C2—C1—C16—C18	32.6 (3)	C15—C10—N4—C9	−0.2 (3)
N1—C1—C16—C21	38.6 (2)	O1—C18—O2—C19	−3.3 (4)
C9—C1—C16—C21	158.01 (19)	C16—C18—O2—C19	178.7 (2)
C2—C1—C16—C21	−88.8 (2)	C18—O2—C19—C20	87.4 (5)
C17—C16—C18—O1	133.3 (2)	C18—O2—C19—C20'	123.8 (6)
C21—C16—C18—O1	10.0 (3)	C22—C23—S1—C24	−26.2 (2)
C1—C16—C18—O1	−103.7 (3)	N1—C24—S1—C23	33.7 (2)
C17—C16—C18—O2	−48.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···S1^i	0.93	3.01	3.881 (4)	156
C23—H23A···N2^ii	0.97	2.70	3.610 (4)	156
C4—H4···O1^iii	0.93	2.43	3.332 (3)	162

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