Crystal structure, Hirshfeld surface analysis and computational study of a rhodamine B–salicyl­aldehyde Schiff base derivative

The mol­ecular structure of the title compound comprises two parts, xanthene and iso­indole, sharing a central quaternary carbon atom. Both the xanthene and iso­indole moieties are nearly planar and are almost perpendicular.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.099
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT355_ALERT_3_C Long   O-H (X0.82,N0.98A)  O3       - H3       .       1.02 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31      ..O3       .       2.77 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.386 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        112 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         29 Note

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 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.         19 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
   5 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3',6'-Bis(diethylamino)-2-[(2-hydroxybenzylidene)amino]spiro[isoindoline-1,9'-xanthen]-3-one

Crystal data

C35H36N4O3	F(000) = 1192
Mr = 560.68	Dx = 1.306 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 9.3903 (7) Å	Cell parameters from 9681 reflections
b = 26.8178 (19) Å	θ = 3.9–72.1°
c = 11.5639 (8) Å	µ = 0.67 mm^−1
β = 101.635 (2)°	T = 100 K
V = 2852.3 (4) Å^3	Block, clear light violet
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXIII CCD diffractometer	5462 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 72.2°, θmin = 5.1°
Tmin = 0.673, Tmax = 0.754	h = −11→11
64500 measured reflections	k = −33→31
5508 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0366P)^2 + 1.6105P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
5508 reflections	Δρmax = 0.26 e Å^−3
387 parameters	Δρmin = −0.25 e Å^−3
0 restraints

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
O1	0.63421 (9)	0.53998 (3)	0.51482 (7)	0.01990 (19)
O2	0.35333 (10)	0.71057 (3)	0.15605 (8)	0.0258 (2)
O3	0.85258 (11)	0.67163 (4)	0.47128 (9)	0.0341 (2)
N3	0.47258 (11)	0.64737 (4)	0.27590 (9)	0.0182 (2)
N2	0.78424 (11)	0.43998 (4)	0.22361 (9)	0.0203 (2)
N4	0.61281 (11)	0.66475 (4)	0.30950 (9)	0.0197 (2)
N1	0.54337 (12)	0.63079 (4)	0.84325 (9)	0.0228 (2)
C27	0.22734 (13)	0.63956 (4)	0.22148 (10)	0.0181 (2)
C12	0.52489 (12)	0.55798 (4)	0.31027 (10)	0.0163 (2)
C9	0.56210 (12)	0.58015 (4)	0.55053 (10)	0.0167 (2)
C22	0.27539 (12)	0.59856 (4)	0.29156 (10)	0.0165 (2)
C8	0.46927 (12)	0.61076 (4)	0.47253 (10)	0.0165 (2)
C13	0.61868 (12)	0.53104 (4)	0.39588 (10)	0.0163 (2)
C17	0.70486 (13)	0.49250 (4)	0.36853 (10)	0.0174 (2)
H17	0.767903	0.475358	0.430372	0.021*
C28	0.35267 (13)	0.67139 (4)	0.21032 (10)	0.0185 (2)
C16	0.70031 (12)	0.47851 (4)	0.25124 (10)	0.0173 (2)
C10	0.58838 (13)	0.58696 (5)	0.67180 (10)	0.0188 (2)
H10	0.652938	0.565077	0.721574	0.023*
C11	0.43818 (12)	0.60188 (4)	0.34033 (10)	0.0165 (2)
C7	0.40438 (13)	0.64983 (5)	0.52325 (11)	0.0199 (3)
H7	0.340634	0.671699	0.472730	0.024*
C5	0.52106 (13)	0.62564 (5)	0.72189 (11)	0.0190 (2)
C6	0.42897 (13)	0.65798 (5)	0.64345 (11)	0.0212 (3)
H6	0.383917	0.685408	0.673746	0.025*
C24	0.03086 (13)	0.57033 (5)	0.26884 (11)	0.0219 (3)
H24	−0.038019	0.546594	0.284338	0.026*
C23	0.17839 (13)	0.56257 (5)	0.31441 (10)	0.0190 (2)
H23	0.211332	0.533686	0.359496	0.023*
C15	0.60465 (13)	0.50567 (5)	0.16302 (11)	0.0207 (3)
H15	0.598389	0.497589	0.082170	0.025*
C26	0.08054 (14)	0.64726 (5)	0.17477 (11)	0.0219 (3)
H26	0.048406	0.675417	0.126699	0.026*
C14	0.52070 (13)	0.54367 (5)	0.19346 (11)	0.0203 (3)
H14	0.457022	0.560945	0.132251	0.024*
C25	−0.01736 (13)	0.61228 (5)	0.20097 (11)	0.0231 (3)
H25	−0.118581	0.617015	0.172246	0.028*
C29	0.66197 (14)	0.69802 (5)	0.24752 (11)	0.0226 (3)
H29	0.603743	0.709238	0.175314	0.027*
C21	0.88015 (14)	0.41198 (5)	0.31614 (11)	0.0228 (3)
H21A	0.901201	0.379277	0.283556	0.027*
H21B	0.827910	0.405544	0.380933	0.027*
C30	0.80710 (15)	0.71842 (5)	0.28840 (12)	0.0249 (3)
C4	0.67041 (14)	0.60808 (5)	0.91783 (11)	0.0250 (3)
H4A	0.670275	0.571911	0.900719	0.030*
H4B	0.663083	0.612091	1.001535	0.030*
C19	0.78644 (15)	0.42836 (5)	0.10088 (11)	0.0230 (3)
H19A	0.685046	0.427015	0.055715	0.028*
H19B	0.829533	0.394843	0.097343	0.028*
C2	0.46026 (14)	0.66609 (5)	0.89867 (11)	0.0236 (3)
H2A	0.454398	0.653305	0.977887	0.028*
H2B	0.359964	0.667543	0.851350	0.028*
C35	0.89543 (15)	0.70507 (5)	0.39724 (13)	0.0284 (3)
C3	0.81405 (15)	0.63038 (6)	0.90053 (12)	0.0310 (3)
H3A	0.820426	0.627884	0.817176	0.046*
H3B	0.894997	0.612070	0.948926	0.046*
H3C	0.819047	0.665505	0.924369	0.046*
C18	0.87120 (16)	0.46553 (5)	0.04151 (12)	0.0287 (3)
H18A	0.866719	0.455502	−0.040637	0.043*
H18B	0.972824	0.466195	0.083581	0.043*
H18C	0.828601	0.498805	0.043386	0.043*
C20	1.02371 (15)	0.43748 (5)	0.36756 (13)	0.0291 (3)
H20A	1.077556	0.443530	0.304608	0.044*
H20B	1.081375	0.416020	0.428003	0.044*
H20C	1.004643	0.469316	0.403179	0.044*
C1	0.52129 (17)	0.71867 (5)	0.91209 (13)	0.0319 (3)
H1A	0.517760	0.733206	0.833812	0.048*
H1B	0.622293	0.717668	0.955531	0.048*
H1C	0.463219	0.739067	0.955591	0.048*
C31	0.85986 (17)	0.75357 (5)	0.21765 (14)	0.0332 (3)
H31	0.800983	0.763165	0.144281	0.040*
C32	0.99603 (19)	0.77443 (6)	0.25302 (17)	0.0412 (4)
H32	1.031113	0.797800	0.203696	0.049*
C34	1.03266 (16)	0.72693 (6)	0.43299 (16)	0.0377 (4)
H34	1.092100	0.718219	0.506806	0.045*
C33	1.08133 (17)	0.76114 (6)	0.36078 (17)	0.0430 (4)
H33	1.174654	0.775796	0.385279	0.052*
H3	0.752 (3)	0.6591 (9)	0.431 (2)	0.069 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0224 (4)	0.0236 (4)	0.0129 (4)	0.0070 (3)	0.0017 (3)	−0.0005 (3)
O2	0.0281 (5)	0.0213 (5)	0.0272 (5)	0.0023 (4)	0.0035 (4)	0.0077 (4)
O3	0.0246 (5)	0.0390 (6)	0.0363 (6)	−0.0069 (4)	0.0001 (4)	0.0078 (4)
N3	0.0162 (5)	0.0190 (5)	0.0188 (5)	−0.0012 (4)	0.0022 (4)	0.0035 (4)
N2	0.0205 (5)	0.0219 (5)	0.0190 (5)	0.0026 (4)	0.0049 (4)	−0.0014 (4)
N4	0.0169 (5)	0.0197 (5)	0.0233 (5)	−0.0016 (4)	0.0062 (4)	−0.0019 (4)
N1	0.0207 (5)	0.0305 (6)	0.0171 (5)	0.0025 (4)	0.0034 (4)	−0.0042 (4)
C27	0.0193 (6)	0.0197 (6)	0.0148 (5)	0.0016 (5)	0.0025 (4)	−0.0018 (4)
C12	0.0140 (5)	0.0188 (6)	0.0162 (5)	−0.0012 (4)	0.0028 (4)	0.0014 (4)
C9	0.0137 (5)	0.0185 (6)	0.0180 (6)	−0.0007 (4)	0.0036 (4)	−0.0005 (4)
C22	0.0154 (6)	0.0204 (6)	0.0134 (5)	0.0012 (4)	0.0023 (4)	−0.0022 (4)
C8	0.0134 (5)	0.0195 (6)	0.0164 (6)	−0.0024 (4)	0.0024 (4)	0.0003 (4)
C13	0.0154 (5)	0.0200 (6)	0.0134 (5)	−0.0023 (4)	0.0030 (4)	0.0003 (4)
C17	0.0155 (5)	0.0206 (6)	0.0157 (5)	0.0006 (4)	0.0020 (4)	0.0026 (4)
C28	0.0211 (6)	0.0188 (6)	0.0155 (5)	0.0021 (5)	0.0031 (4)	−0.0002 (4)
C16	0.0152 (5)	0.0185 (6)	0.0190 (6)	−0.0023 (4)	0.0053 (4)	−0.0004 (4)
C10	0.0162 (5)	0.0230 (6)	0.0164 (6)	0.0005 (5)	0.0014 (4)	0.0006 (5)
C11	0.0151 (5)	0.0177 (6)	0.0163 (6)	−0.0009 (4)	0.0022 (4)	0.0028 (4)
C7	0.0173 (6)	0.0210 (6)	0.0206 (6)	0.0011 (5)	0.0017 (5)	0.0008 (5)
C5	0.0152 (5)	0.0238 (6)	0.0178 (6)	−0.0035 (5)	0.0030 (4)	−0.0027 (5)
C6	0.0187 (6)	0.0220 (6)	0.0230 (6)	0.0005 (5)	0.0049 (5)	−0.0042 (5)
C24	0.0182 (6)	0.0286 (7)	0.0190 (6)	−0.0046 (5)	0.0043 (5)	−0.0040 (5)
C23	0.0190 (6)	0.0223 (6)	0.0155 (5)	−0.0009 (5)	0.0031 (4)	0.0000 (4)
C15	0.0204 (6)	0.0270 (6)	0.0146 (6)	0.0005 (5)	0.0030 (5)	−0.0011 (5)
C26	0.0207 (6)	0.0237 (6)	0.0193 (6)	0.0055 (5)	−0.0010 (5)	−0.0020 (5)
C14	0.0184 (6)	0.0260 (6)	0.0152 (6)	0.0022 (5)	0.0004 (4)	0.0030 (5)
C25	0.0154 (6)	0.0310 (7)	0.0211 (6)	0.0033 (5)	−0.0005 (5)	−0.0059 (5)
C29	0.0251 (6)	0.0210 (6)	0.0233 (6)	0.0005 (5)	0.0089 (5)	0.0002 (5)
C21	0.0251 (6)	0.0182 (6)	0.0251 (6)	0.0039 (5)	0.0051 (5)	0.0008 (5)
C30	0.0247 (6)	0.0198 (6)	0.0337 (7)	−0.0014 (5)	0.0140 (5)	−0.0049 (5)
C4	0.0279 (7)	0.0312 (7)	0.0150 (6)	0.0024 (5)	0.0024 (5)	−0.0011 (5)
C19	0.0266 (6)	0.0218 (6)	0.0216 (6)	0.0006 (5)	0.0070 (5)	−0.0046 (5)
C2	0.0243 (6)	0.0268 (7)	0.0209 (6)	−0.0003 (5)	0.0077 (5)	−0.0025 (5)
C35	0.0245 (7)	0.0244 (7)	0.0389 (8)	−0.0034 (5)	0.0127 (6)	−0.0033 (6)
C3	0.0224 (7)	0.0430 (8)	0.0256 (7)	0.0025 (6)	0.0001 (5)	−0.0057 (6)
C18	0.0343 (7)	0.0289 (7)	0.0266 (7)	0.0014 (6)	0.0148 (6)	−0.0016 (5)
C20	0.0221 (7)	0.0307 (7)	0.0331 (7)	0.0046 (5)	0.0025 (5)	0.0019 (6)
C1	0.0384 (8)	0.0276 (7)	0.0301 (7)	−0.0034 (6)	0.0077 (6)	−0.0012 (6)
C31	0.0397 (8)	0.0232 (7)	0.0420 (8)	−0.0045 (6)	0.0206 (7)	−0.0024 (6)
C32	0.0438 (9)	0.0266 (7)	0.0615 (11)	−0.0123 (7)	0.0304 (8)	−0.0067 (7)
C34	0.0244 (7)	0.0379 (8)	0.0513 (9)	−0.0051 (6)	0.0086 (6)	−0.0074 (7)
C33	0.0283 (8)	0.0346 (8)	0.0708 (12)	−0.0142 (6)	0.0214 (8)	−0.0154 (8)

Geometric parameters (Å, º)

O1—C9	1.3792 (14)	C15—C14	1.3768 (18)
O1—C13	1.3747 (14)	C26—H26	0.9500
O2—C28	1.2246 (15)	C26—C25	1.3890 (19)
O3—C35	1.3558 (17)	C14—H14	0.9500
O3—H3	1.02 (3)	C25—H25	0.9500
N3—N4	1.3769 (14)	C29—H29	0.9500
N3—C28	1.3833 (15)	C29—C30	1.4561 (19)
N3—C11	1.4982 (14)	C21—H21A	0.9900
N2—C16	1.3758 (16)	C21—H21B	0.9900
N2—C21	1.4599 (16)	C21—C20	1.5216 (19)
N2—C19	1.4572 (16)	C30—C35	1.407 (2)
N4—C29	1.2870 (17)	C30—C31	1.4025 (19)
N1—C5	1.3834 (16)	C4—H4A	0.9900
N1—C4	1.4569 (17)	C4—H4B	0.9900
N1—C2	1.4551 (16)	C4—C3	1.525 (2)
C27—C22	1.3864 (17)	C19—H19A	0.9900
C27—C28	1.4803 (17)	C19—H19B	0.9900
C27—C26	1.3907 (17)	C19—C18	1.5227 (18)
C12—C13	1.3879 (16)	C2—H2A	0.9900
C12—C11	1.5113 (16)	C2—H2B	0.9900
C12—C14	1.3970 (17)	C2—C1	1.5183 (19)
C9—C8	1.3892 (17)	C35—C34	1.400 (2)
C9—C10	1.3861 (17)	C3—H3A	0.9800
C22—C11	1.5215 (16)	C3—H3B	0.9800
C22—C23	1.3885 (17)	C3—H3C	0.9800
C8—C11	1.5163 (16)	C18—H18A	0.9800
C8—C7	1.3990 (17)	C18—H18B	0.9800
C13—C17	1.3878 (17)	C18—H18C	0.9800
C17—H17	0.9500	C20—H20A	0.9800
C17—C16	1.3997 (17)	C20—H20B	0.9800
C16—C15	1.4172 (17)	C20—H20C	0.9800
C10—H10	0.9500	C1—H1A	0.9800
C10—C5	1.3996 (17)	C1—H1B	0.9800
C7—H7	0.9500	C1—H1C	0.9800
C7—C6	1.3798 (18)	C31—H31	0.9500
C5—C6	1.4165 (18)	C31—C32	1.380 (2)
C6—H6	0.9500	C32—H32	0.9500
C24—H24	0.9500	C32—C33	1.385 (3)
C24—C23	1.3949 (17)	C34—H34	0.9500
C24—C25	1.3941 (19)	C34—C33	1.379 (2)
C23—H23	0.9500	C33—H33	0.9500
C15—H15	0.9500
C13—O1—C9	118.45 (9)	C24—C25—H25	119.5
C35—O3—H3	107.4 (13)	C26—C25—C24	120.91 (11)
N4—N3—C28	128.56 (10)	C26—C25—H25	119.5
N4—N3—C11	115.17 (9)	N4—C29—H29	120.1
C28—N3—C11	114.74 (9)	N4—C29—C30	119.81 (12)
C16—N2—C21	120.92 (10)	C30—C29—H29	120.1
C16—N2—C19	120.53 (10)	N2—C21—H21A	108.5
C19—N2—C21	118.42 (10)	N2—C21—H21B	108.5
C29—N4—N3	120.51 (11)	N2—C21—C20	114.97 (11)
C5—N1—C4	119.81 (10)	H21A—C21—H21B	107.5
C5—N1—C2	121.79 (11)	C20—C21—H21A	108.5
C2—N1—C4	117.32 (10)	C20—C21—H21B	108.5
C22—C27—C28	109.72 (10)	C35—C30—C29	122.63 (12)
C22—C27—C26	121.67 (12)	C31—C30—C29	118.74 (13)
C26—C27—C28	128.59 (11)	C31—C30—C35	118.62 (13)
C13—C12—C11	122.36 (10)	N1—C4—H4A	108.9
C13—C12—C14	115.90 (11)	N1—C4—H4B	108.9
C14—C12—C11	121.66 (10)	N1—C4—C3	113.50 (11)
O1—C9—C8	123.28 (10)	H4A—C4—H4B	107.7
O1—C9—C10	114.06 (10)	C3—C4—H4A	108.9
C10—C9—C8	122.65 (11)	C3—C4—H4B	108.9
C27—C22—C11	110.76 (10)	N2—C19—H19A	108.7
C27—C22—C23	120.92 (11)	N2—C19—H19B	108.7
C23—C22—C11	128.22 (11)	N2—C19—C18	114.24 (11)
C9—C8—C11	122.00 (11)	H19A—C19—H19B	107.6
C9—C8—C7	116.08 (11)	C18—C19—H19A	108.7
C7—C8—C11	121.92 (10)	C18—C19—H19B	108.7
O1—C13—C12	123.16 (11)	N1—C2—H2A	108.5
O1—C13—C17	114.14 (10)	N1—C2—H2B	108.5
C12—C13—C17	122.71 (11)	N1—C2—C1	115.10 (11)
C13—C17—H17	119.5	H2A—C2—H2B	107.5
C13—C17—C16	121.01 (11)	C1—C2—H2A	108.5
C16—C17—H17	119.5	C1—C2—H2B	108.5
O2—C28—N3	126.36 (12)	O3—C35—C30	122.46 (12)
O2—C28—C27	128.73 (11)	O3—C35—C34	117.59 (14)
N3—C28—C27	104.91 (10)	C34—C35—C30	119.94 (14)
N2—C16—C17	121.29 (11)	C4—C3—H3A	109.5
N2—C16—C15	121.91 (11)	C4—C3—H3B	109.5
C17—C16—C15	116.80 (11)	C4—C3—H3C	109.5
C9—C10—H10	119.6	H3A—C3—H3B	109.5
C9—C10—C5	120.88 (11)	H3A—C3—H3C	109.5
C5—C10—H10	119.6	H3B—C3—H3C	109.5
N3—C11—C12	109.86 (9)	C19—C18—H18A	109.5
N3—C11—C22	99.47 (9)	C19—C18—H18B	109.5
N3—C11—C8	110.89 (9)	C19—C18—H18C	109.5
C12—C11—C22	114.63 (10)	H18A—C18—H18B	109.5
C12—C11—C8	110.56 (9)	H18A—C18—H18C	109.5
C8—C11—C22	110.96 (9)	H18B—C18—H18C	109.5
C8—C7—H7	118.6	C21—C20—H20A	109.5
C6—C7—C8	122.85 (11)	C21—C20—H20B	109.5
C6—C7—H7	118.6	C21—C20—H20C	109.5
N1—C5—C10	120.35 (11)	H20A—C20—H20B	109.5
N1—C5—C6	122.44 (11)	H20A—C20—H20C	109.5
C10—C5—C6	117.20 (11)	H20B—C20—H20C	109.5
C7—C6—C5	120.31 (11)	C2—C1—H1A	109.5
C7—C6—H6	119.8	C2—C1—H1B	109.5
C5—C6—H6	119.8	C2—C1—H1C	109.5
C23—C24—H24	119.4	H1A—C1—H1B	109.5
C25—C24—H24	119.4	H1A—C1—H1C	109.5
C25—C24—C23	121.21 (12)	H1B—C1—H1C	109.5
C22—C23—C24	117.65 (11)	C30—C31—H31	119.5
C22—C23—H23	121.2	C32—C31—C30	120.98 (16)
C24—C23—H23	121.2	C32—C31—H31	119.5
C16—C15—H15	119.7	C31—C32—H32	120.1
C14—C15—C16	120.59 (11)	C31—C32—C33	119.70 (15)
C14—C15—H15	119.7	C33—C32—H32	120.1
C27—C26—H26	121.2	C35—C34—H34	120.1
C25—C26—C27	117.57 (12)	C33—C34—C35	119.83 (16)
C25—C26—H26	121.2	C33—C34—H34	120.1
C12—C14—H14	118.5	C32—C33—H33	119.5
C15—C14—C12	122.99 (11)	C34—C33—C32	120.91 (14)
C15—C14—H14	118.5	C34—C33—H33	119.5
O1—C9—C8—C11	0.75 (17)	C10—C9—C8—C11	−178.13 (11)
O1—C9—C8—C7	179.83 (10)	C10—C9—C8—C7	0.94 (17)
O1—C9—C10—C5	−178.87 (10)	C10—C5—C6—C7	2.22 (18)
O1—C13—C17—C16	179.34 (10)	C11—N3—N4—C29	168.12 (11)
O3—C35—C34—C33	179.94 (14)	C11—N3—C28—O2	175.66 (11)
N3—N4—C29—C30	175.92 (11)	C11—N3—C28—C27	−4.11 (13)
N2—C16—C15—C14	179.21 (11)	C11—C12—C13—O1	3.95 (18)
N4—N3—C28—O2	10.6 (2)	C11—C12—C13—C17	−176.23 (11)
N4—N3—C28—C27	−169.16 (11)	C11—C12—C14—C15	176.21 (11)
N4—N3—C11—C12	−66.11 (12)	C11—C22—C23—C24	173.34 (11)
N4—N3—C11—C22	173.25 (9)	C11—C8—C7—C6	178.70 (11)
N4—N3—C11—C8	56.40 (13)	C7—C8—C11—N3	56.81 (14)
N4—C29—C30—C35	−3.20 (19)	C7—C8—C11—C12	178.91 (10)
N4—C29—C30—C31	178.18 (12)	C7—C8—C11—C22	−52.75 (15)
N1—C5—C6—C7	−176.72 (12)	C5—N1—C4—C3	65.09 (16)
C27—C22—C11—N3	−5.88 (12)	C5—N1—C2—C1	−86.26 (15)
C27—C22—C11—C12	−122.98 (11)	C23—C22—C11—N3	177.66 (11)
C27—C22—C11—C8	110.92 (11)	C23—C22—C11—C12	60.56 (16)
C27—C22—C23—C24	−2.80 (17)	C23—C22—C11—C8	−65.54 (15)
C27—C26—C25—C24	−1.80 (18)	C23—C24—C25—C26	1.20 (19)
C12—C13—C17—C16	−0.50 (18)	C26—C27—C22—C11	−174.51 (11)
C9—O1—C13—C12	−5.36 (16)	C26—C27—C22—C23	2.25 (18)
C9—O1—C13—C17	174.80 (10)	C26—C27—C28—O2	−1.4 (2)
C9—C8—C11—N3	−124.17 (12)	C26—C27—C28—N3	178.35 (12)
C9—C8—C11—C12	−2.06 (15)	C14—C12—C13—O1	−179.16 (11)
C9—C8—C11—C22	126.28 (12)	C14—C12—C13—C17	0.67 (17)
C9—C8—C7—C6	−0.38 (18)	C14—C12—C11—N3	−54.17 (14)
C9—C10—C5—N1	177.28 (11)	C14—C12—C11—C22	56.81 (15)
C9—C10—C5—C6	−1.68 (17)	C14—C12—C11—C8	−176.88 (10)
C22—C27—C28—O2	−179.82 (12)	C25—C24—C23—C22	1.12 (18)
C22—C27—C28—N3	−0.05 (13)	C29—C30—C35—O3	1.0 (2)
C22—C27—C26—C25	0.11 (18)	C29—C30—C35—C34	−178.41 (13)
C8—C9—C10—C5	0.11 (18)	C29—C30—C31—C32	179.28 (13)
C8—C7—C6—C5	−1.23 (19)	C21—N2—C16—C17	0.60 (17)
C13—O1—C9—C8	2.99 (16)	C21—N2—C16—C15	−178.94 (11)
C13—O1—C9—C10	−178.03 (10)	C21—N2—C19—C18	−102.27 (13)
C13—C12—C11—N3	122.54 (12)	C30—C35—C34—C33	−0.6 (2)
C13—C12—C11—C22	−126.47 (12)	C30—C31—C32—C33	−1.0 (2)
C13—C12—C11—C8	−0.16 (15)	C4—N1—C5—C10	20.76 (18)
C13—C12—C14—C15	−0.71 (18)	C4—N1—C5—C6	−160.34 (12)
C13—C17—C16—N2	−179.25 (11)	C4—N1—C2—C1	81.84 (15)
C13—C17—C16—C15	0.31 (17)	C19—N2—C16—C17	−175.33 (11)
C17—C16—C15—C14	−0.34 (18)	C19—N2—C16—C15	5.13 (17)
C28—N3—N4—C29	−26.88 (18)	C19—N2—C21—C20	96.50 (13)
C28—N3—C11—C12	126.76 (11)	C2—N1—C5—C10	−171.43 (11)
C28—N3—C11—C22	6.13 (12)	C2—N1—C5—C6	7.48 (18)
C28—N3—C11—C8	−110.73 (11)	C2—N1—C4—C3	−103.26 (13)
C28—C27—C22—C11	4.02 (13)	C35—C30—C31—C32	0.6 (2)
C28—C27—C22—C23	−179.22 (10)	C35—C34—C33—C32	0.2 (2)
C28—C27—C26—C25	−178.12 (12)	C31—C30—C35—O3	179.64 (12)
C16—N2—C21—C20	−79.52 (15)	C31—C30—C35—C34	0.2 (2)
C16—N2—C19—C18	73.76 (15)	C31—C32—C33—C34	0.6 (2)
C16—C15—C14—C12	0.57 (19)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C22–C27 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31···O3^i	0.95	2.77	3.4737 (19)	131
O3—H3···N4	1.02 (3)	1.72 (2)	2.6276 (15)	145 (2)
C18—H18A···Cg^ii	0.98	2.88	3.8191 (15)	161

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z.