Synthesis, crystal structure and aggregation-induced emission of a new pyrene-based compound, 3,3-diphenyl-2-[4-(pyren-1-yl)phen­yl]acrylo­nitrile

There are alternating relatively strong and weak intermolecular π–π interactions between adjacent pyrene ring systems, forming a one-dimensional supramolecular structure. The compound is weakly fluorescent in THF solution, but it is highly emissive in the condensed phase, revealing distinct aggregation-induced emission (AIE) characteristics.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.104
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         13 Note

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..N1               2.73 Ang.

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT230_ALERT_2_G Hirshfeld Test Diff for   C1       --C2        .        7.9 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 Info

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

3,3-Diphenyl-2-[4-(pyren-1-yl)phenyl]acrylonitrile

Crystal data

C37H23N	Z = 2
Mr = 481.51	F(000) = 504
Triclinic, P1	Dx = 1.283 Mg m^−3
a = 9.2277 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6445 (3) Å	Cell parameters from 2445 reflections
c = 14.639 (2) Å	θ = 3.0–26.4°
α = 105.169 (2)°	µ = 0.07 mm^−1
β = 94.806 (2)°	T = 123 K
γ = 113.255 (2)°	Block, yellow
V = 1246.38 (18) Å^3	0.12 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	4402 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
φ and ω scans	θmax = 26.4°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2015)	h = −11→11
Tmin = 0.981, Tmax = 0.995	k = −13→13
22549 measured reflections	l = −17→18
5093 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0589P)^2 + 0.2438P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
5093 reflections	Δρmax = 0.22 e Å^−3
343 parameters	Δρmin = −0.19 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
N1	1.02807 (12)	0.88812 (10)	0.68529 (7)	0.0324 (2)
C1	0.94092 (13)	0.76789 (11)	0.65188 (7)	0.0229 (2)
C2	0.83242 (12)	0.61531 (11)	0.61689 (7)	0.0196 (2)
C3	0.77520 (11)	0.54507 (11)	0.52005 (7)	0.0191 (2)
C4	0.80379 (11)	0.62187 (11)	0.44699 (7)	0.0200 (2)
C5	0.79817 (13)	0.75520 (12)	0.46234 (8)	0.0241 (2)
H5	0.7715	0.7965	0.5187	0.029*
C6	0.83202 (14)	0.82631 (12)	0.39420 (8)	0.0279 (2)
H6	0.8284	0.9150	0.4054	0.033*
C7	0.87130 (13)	0.76576 (12)	0.30952 (8)	0.0273 (2)
H7	0.8958	0.8144	0.2645	0.033*
C8	0.87392 (13)	0.63244 (12)	0.29233 (8)	0.0266 (2)
H8	0.8992	0.5912	0.2353	0.032*
C9	0.83892 (12)	0.56010 (11)	0.35990 (7)	0.0228 (2)
H9	0.8388	0.4698	0.3472	0.027*
C10	0.68717 (12)	0.38450 (11)	0.48036 (7)	0.0208 (2)
C11	0.54277 (13)	0.31868 (12)	0.41204 (7)	0.0265 (2)
H11	0.4995	0.3752	0.3924	0.032*
C12	0.46275 (15)	0.16898 (13)	0.37298 (8)	0.0369 (3)
H12	0.3654	0.1259	0.3282	0.044*
C13	0.52712 (17)	0.08421 (13)	0.40034 (9)	0.0420 (3)
H13	0.4735	−0.0159	0.3740	0.050*
C14	0.67154 (18)	0.14849 (13)	0.46697 (10)	0.0402 (3)
H14	0.7157	0.0914	0.4849	0.048*
C15	0.75108 (14)	0.29761 (12)	0.50735 (9)	0.0297 (3)
H15	0.8476	0.3399	0.5527	0.036*
C16	0.79833 (12)	0.55102 (10)	0.69650 (7)	0.0191 (2)
C17	0.64459 (12)	0.44808 (12)	0.69409 (8)	0.0243 (2)
H17	0.5606	0.4181	0.6418	0.029*
C18	0.61664 (12)	0.39052 (12)	0.76912 (8)	0.0251 (2)
H18	0.5137	0.3226	0.7666	0.030*
C19	0.74037 (12)	0.43273 (11)	0.84834 (7)	0.0197 (2)
C20	0.89266 (12)	0.53771 (11)	0.85158 (7)	0.0215 (2)
H20	0.9763	0.5683	0.9042	0.026*
C21	0.92078 (12)	0.59701 (11)	0.77726 (7)	0.0207 (2)
H21	1.0225	0.6683	0.7813	0.025*
C22	0.71039 (11)	0.36891 (11)	0.92838 (7)	0.0197 (2)
C23	0.65220 (12)	0.42907 (11)	1.00476 (8)	0.0228 (2)
H23	0.6337	0.5090	1.0052	0.027*
C24	0.62136 (12)	0.37253 (11)	1.07996 (7)	0.0239 (2)
H24	0.5815	0.4142	1.1296	0.029*
C25	0.64954 (11)	0.25348 (11)	1.08188 (7)	0.0205 (2)
C26	0.62014 (12)	0.19169 (12)	1.15898 (7)	0.0254 (2)
H26	0.5804	0.2318	1.2094	0.031*
C27	0.64880 (13)	0.07757 (12)	1.15974 (8)	0.0275 (2)
H27	0.6296	0.0412	1.2110	0.033*
C28	0.70848 (12)	0.01052 (11)	1.08316 (8)	0.0242 (2)
C29	0.73803 (13)	−0.10905 (12)	1.08179 (9)	0.0306 (3)
H29	0.7200	−0.1470	1.1324	0.037*
C30	0.79388 (14)	−0.17187 (12)	1.00585 (9)	0.0327 (3)
H30	0.8124	−0.2516	1.0061	0.039*
C31	0.82237 (13)	−0.11705 (12)	0.92967 (9)	0.0287 (2)
H31	0.8589	−0.1607	0.8790	0.034*
C32	0.79652 (12)	0.00371 (11)	0.92856 (8)	0.0227 (2)
C33	0.83002 (12)	0.06669 (11)	0.85275 (8)	0.0233 (2)
H33	0.8716	0.0273	0.8032	0.028*
C34	0.80244 (12)	0.18199 (11)	0.85180 (7)	0.0214 (2)
H34	0.8242	0.2193	0.8011	0.026*
C35	0.74010 (11)	0.24854 (10)	0.92750 (7)	0.0182 (2)
C36	0.70957 (11)	0.19041 (11)	1.00497 (7)	0.0187 (2)
C37	0.73828 (11)	0.06826 (11)	1.00549 (7)	0.0205 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0421 (6)	0.0230 (5)	0.0248 (5)	0.0069 (4)	0.0025 (4)	0.0092 (4)
C1	0.0288 (5)	0.0241 (6)	0.0177 (5)	0.0112 (5)	0.0060 (4)	0.0100 (4)
C2	0.0196 (5)	0.0189 (5)	0.0221 (5)	0.0087 (4)	0.0052 (4)	0.0087 (4)
C3	0.0165 (4)	0.0208 (5)	0.0224 (5)	0.0093 (4)	0.0049 (4)	0.0085 (4)
C4	0.0171 (4)	0.0214 (5)	0.0199 (5)	0.0067 (4)	0.0027 (4)	0.0073 (4)
C5	0.0273 (5)	0.0268 (5)	0.0221 (5)	0.0139 (4)	0.0077 (4)	0.0097 (4)
C6	0.0331 (6)	0.0272 (6)	0.0292 (6)	0.0151 (5)	0.0082 (5)	0.0144 (5)
C7	0.0278 (5)	0.0326 (6)	0.0236 (5)	0.0101 (5)	0.0072 (4)	0.0163 (5)
C8	0.0252 (5)	0.0317 (6)	0.0202 (5)	0.0095 (5)	0.0067 (4)	0.0078 (4)
C9	0.0220 (5)	0.0221 (5)	0.0225 (5)	0.0084 (4)	0.0044 (4)	0.0062 (4)
C10	0.0214 (5)	0.0210 (5)	0.0201 (5)	0.0081 (4)	0.0083 (4)	0.0073 (4)
C11	0.0244 (5)	0.0308 (6)	0.0204 (5)	0.0081 (4)	0.0067 (4)	0.0076 (4)
C12	0.0323 (6)	0.0337 (6)	0.0232 (6)	−0.0020 (5)	0.0087 (5)	0.0006 (5)
C13	0.0559 (8)	0.0195 (6)	0.0365 (7)	0.0037 (6)	0.0234 (6)	0.0025 (5)
C14	0.0576 (8)	0.0267 (6)	0.0465 (7)	0.0232 (6)	0.0239 (6)	0.0157 (6)
C15	0.0318 (6)	0.0273 (6)	0.0342 (6)	0.0154 (5)	0.0088 (5)	0.0117 (5)
C16	0.0218 (5)	0.0177 (5)	0.0199 (5)	0.0099 (4)	0.0054 (4)	0.0072 (4)
C17	0.0193 (5)	0.0295 (6)	0.0234 (5)	0.0082 (4)	0.0008 (4)	0.0121 (4)
C18	0.0174 (5)	0.0274 (5)	0.0280 (5)	0.0049 (4)	0.0031 (4)	0.0133 (4)
C19	0.0214 (5)	0.0188 (5)	0.0212 (5)	0.0101 (4)	0.0053 (4)	0.0080 (4)
C20	0.0201 (5)	0.0218 (5)	0.0198 (5)	0.0070 (4)	0.0007 (4)	0.0067 (4)
C21	0.0192 (5)	0.0176 (5)	0.0227 (5)	0.0049 (4)	0.0045 (4)	0.0069 (4)
C22	0.0154 (4)	0.0203 (5)	0.0196 (5)	0.0042 (4)	0.0009 (4)	0.0071 (4)
C23	0.0213 (5)	0.0206 (5)	0.0260 (5)	0.0089 (4)	0.0048 (4)	0.0071 (4)
C24	0.0215 (5)	0.0254 (5)	0.0201 (5)	0.0078 (4)	0.0057 (4)	0.0034 (4)
C25	0.0153 (4)	0.0222 (5)	0.0170 (5)	0.0024 (4)	0.0008 (4)	0.0054 (4)
C26	0.0197 (5)	0.0317 (6)	0.0163 (5)	0.0033 (4)	0.0028 (4)	0.0070 (4)
C27	0.0211 (5)	0.0332 (6)	0.0207 (5)	0.0010 (4)	0.0005 (4)	0.0149 (4)
C28	0.0168 (5)	0.0236 (5)	0.0252 (5)	0.0010 (4)	−0.0032 (4)	0.0113 (4)
C29	0.0230 (5)	0.0263 (6)	0.0361 (6)	0.0013 (4)	−0.0045 (5)	0.0180 (5)
C30	0.0257 (6)	0.0203 (5)	0.0477 (7)	0.0062 (4)	−0.0038 (5)	0.0137 (5)
C31	0.0230 (5)	0.0202 (5)	0.0377 (6)	0.0072 (4)	0.0003 (4)	0.0062 (5)
C32	0.0169 (5)	0.0194 (5)	0.0259 (5)	0.0046 (4)	−0.0015 (4)	0.0053 (4)
C33	0.0207 (5)	0.0239 (5)	0.0216 (5)	0.0087 (4)	0.0038 (4)	0.0033 (4)
C34	0.0206 (5)	0.0243 (5)	0.0169 (5)	0.0070 (4)	0.0039 (4)	0.0072 (4)
C35	0.0147 (4)	0.0185 (5)	0.0170 (5)	0.0037 (4)	0.0007 (4)	0.0050 (4)
C36	0.0142 (4)	0.0191 (5)	0.0169 (5)	0.0025 (4)	−0.0005 (3)	0.0051 (4)
C37	0.0147 (5)	0.0192 (5)	0.0212 (5)	0.0021 (4)	−0.0027 (4)	0.0069 (4)

Geometric parameters (Å, º)

N1—C1	1.1479 (14)	C19—C20	1.3953 (14)
C1—C2	1.4482 (14)	C19—C22	1.4945 (13)
C2—C3	1.3623 (14)	C20—C21	1.3881 (14)
C2—C16	1.4947 (13)	C20—H20	0.9300
C3—C4	1.4889 (13)	C21—H21	0.9300
C3—C10	1.4911 (14)	C22—C23	1.3950 (14)
C4—C5	1.4002 (15)	C22—C35	1.4094 (14)
C4—C9	1.4006 (14)	C23—C24	1.3853 (15)
C5—C6	1.3878 (14)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.3971 (15)
C6—C7	1.3876 (16)	C24—H24	0.9300
C6—H6	0.9300	C25—C36	1.4240 (14)
C7—C8	1.3852 (16)	C25—C26	1.4419 (14)
C7—H7	0.9300	C26—C27	1.3438 (17)
C8—C9	1.3898 (15)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.4369 (17)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.3926 (15)	C28—C29	1.3986 (16)
C10—C15	1.3938 (15)	C28—C37	1.4251 (14)
C11—C12	1.3909 (16)	C29—C30	1.3884 (19)
C11—H11	0.9300	C29—H29	0.9300
C12—C13	1.378 (2)	C30—C31	1.3864 (17)
C12—H12	0.9300	C30—H30	0.9300
C13—C14	1.382 (2)	C31—C32	1.4007 (15)
C13—H13	0.9300	C31—H31	0.9300
C14—C15	1.3871 (17)	C32—C37	1.4203 (15)
C14—H14	0.9300	C32—C33	1.4352 (15)
C15—H15	0.9300	C33—C34	1.3514 (15)
C16—C21	1.3967 (14)	C33—H33	0.9300
C16—C17	1.3994 (14)	C34—C35	1.4417 (14)
C17—C18	1.3868 (14)	C34—H34	0.9300
C17—H17	0.9300	C35—C36	1.4254 (13)
C18—C19	1.3967 (14)	C36—C37	1.4275 (15)
C18—H18	0.9300
N1—C1—C2	175.73 (11)	C21—C20—C19	120.78 (9)
C3—C2—C1	120.14 (9)	C21—C20—H20	119.6
C3—C2—C16	126.86 (9)	C19—C20—H20	119.6
C1—C2—C16	112.98 (8)	C20—C21—C16	120.86 (9)
C2—C3—C4	122.58 (9)	C20—C21—H21	119.6
C2—C3—C10	121.61 (9)	C16—C21—H21	119.6
C4—C3—C10	115.73 (8)	C23—C22—C35	119.64 (9)
C5—C4—C9	118.34 (9)	C23—C22—C19	119.62 (9)
C5—C4—C3	122.32 (9)	C35—C22—C19	120.74 (9)
C9—C4—C3	119.33 (9)	C24—C23—C22	121.53 (10)
C6—C5—C4	120.63 (10)	C24—C23—H23	119.2
C6—C5—H5	119.7	C22—C23—H23	119.2
C4—C5—H5	119.7	C23—C24—C25	120.60 (9)
C7—C6—C5	120.35 (10)	C23—C24—H24	119.7
C7—C6—H6	119.8	C25—C24—H24	119.7
C5—C6—H6	119.8	C24—C25—C36	118.98 (9)
C8—C7—C6	119.69 (10)	C24—C25—C26	122.48 (10)
C8—C7—H7	120.2	C36—C25—C26	118.54 (10)
C6—C7—H7	120.2	C27—C26—C25	121.57 (10)
C7—C8—C9	120.26 (10)	C27—C26—H26	119.2
C7—C8—H8	119.9	C25—C26—H26	119.2
C9—C8—H8	119.9	C26—C27—C28	121.50 (9)
C8—C9—C4	120.67 (10)	C26—C27—H27	119.3
C8—C9—H9	119.7	C28—C27—H27	119.3
C4—C9—H9	119.7	C29—C28—C37	118.84 (10)
C11—C10—C15	118.72 (10)	C29—C28—C27	122.65 (10)
C11—C10—C3	120.39 (9)	C37—C28—C27	118.52 (10)
C15—C10—C3	120.83 (9)	C30—C29—C28	120.91 (10)
C12—C11—C10	120.46 (11)	C30—C29—H29	119.5
C12—C11—H11	119.8	C28—C29—H29	119.5
C10—C11—H11	119.8	C31—C30—C29	120.71 (10)
C13—C12—C11	120.26 (12)	C31—C30—H30	119.6
C13—C12—H12	119.9	C29—C30—H30	119.6
C11—C12—H12	119.9	C30—C31—C32	120.40 (11)
C12—C13—C14	119.74 (11)	C30—C31—H31	119.8
C12—C13—H13	120.1	C32—C31—H31	119.8
C14—C13—H13	120.1	C31—C32—C37	119.40 (10)
C13—C14—C15	120.42 (12)	C31—C32—C33	122.04 (10)
C13—C14—H14	119.8	C37—C32—C33	118.55 (9)
C15—C14—H14	119.8	C34—C33—C32	121.47 (9)
C14—C15—C10	120.38 (11)	C34—C33—H33	119.3
C14—C15—H15	119.8	C32—C33—H33	119.3
C10—C15—H15	119.8	C33—C34—C35	121.57 (9)
C21—C16—C17	118.43 (9)	C33—C34—H34	119.2
C21—C16—C2	119.78 (9)	C35—C34—H34	119.2
C17—C16—C2	121.76 (9)	C22—C35—C36	119.10 (9)
C18—C17—C16	120.43 (9)	C22—C35—C34	122.76 (9)
C18—C17—H17	119.8	C36—C35—C34	118.13 (9)
C16—C17—H17	119.8	C25—C36—C35	120.14 (9)
C17—C18—C19	121.18 (9)	C25—C36—C37	119.75 (9)
C17—C18—H18	119.4	C35—C36—C37	120.11 (9)
C19—C18—H18	119.4	C32—C37—C28	119.74 (10)
C20—C19—C18	118.26 (9)	C32—C37—C36	120.13 (9)
C20—C19—C22	120.70 (9)	C28—C37—C36	120.13 (10)
C18—C19—C22	121.04 (9)
C1—C2—C3—C4	−7.36 (15)	C35—C22—C23—C24	−0.53 (15)
C16—C2—C3—C4	173.99 (9)	C19—C22—C23—C24	179.41 (9)
C1—C2—C3—C10	169.22 (9)	C22—C23—C24—C25	0.67 (15)
C16—C2—C3—C10	−9.43 (15)	C23—C24—C25—C36	−0.39 (15)
C2—C3—C4—C5	−39.58 (14)	C23—C24—C25—C26	179.60 (9)
C10—C3—C4—C5	143.65 (10)	C24—C25—C26—C27	−179.66 (10)
C2—C3—C4—C9	139.89 (10)	C36—C25—C26—C27	0.33 (15)
C10—C3—C4—C9	−36.88 (12)	C25—C26—C27—C28	−0.70 (16)
C9—C4—C5—C6	−2.14 (15)	C26—C27—C28—C29	−179.46 (10)
C3—C4—C5—C6	177.33 (9)	C26—C27—C28—C37	0.40 (15)
C4—C5—C6—C7	0.29 (16)	C37—C28—C29—C30	−0.64 (15)
C5—C6—C7—C8	1.12 (17)	C27—C28—C29—C30	179.22 (10)
C6—C7—C8—C9	−0.62 (16)	C28—C29—C30—C31	0.28 (16)
C7—C8—C9—C4	−1.29 (15)	C29—C30—C31—C32	0.57 (16)
C5—C4—C9—C8	2.65 (15)	C30—C31—C32—C37	−1.02 (15)
C3—C4—C9—C8	−176.85 (9)	C30—C31—C32—C33	177.76 (9)
C2—C3—C10—C11	132.68 (10)	C31—C32—C33—C34	179.06 (10)
C4—C3—C10—C11	−50.52 (12)	C37—C32—C33—C34	−2.15 (15)
C2—C3—C10—C15	−50.29 (14)	C32—C33—C34—C35	0.84 (15)
C4—C3—C10—C15	126.51 (10)	C23—C22—C35—C36	0.13 (14)
C15—C10—C11—C12	1.15 (15)	C19—C22—C35—C36	−179.81 (8)
C3—C10—C11—C12	178.24 (9)	C23—C22—C35—C34	−179.06 (9)
C10—C11—C12—C13	−1.11 (16)	C19—C22—C35—C34	1.00 (14)
C11—C12—C13—C14	0.13 (18)	C33—C34—C35—C22	179.93 (9)
C12—C13—C14—C15	0.79 (18)	C33—C34—C35—C36	0.73 (14)
C13—C14—C15—C10	−0.73 (18)	C24—C25—C36—C35	−0.01 (14)
C11—C10—C15—C14	−0.24 (16)	C26—C25—C36—C35	180.00 (8)
C3—C10—C15—C14	−177.31 (10)	C24—C25—C36—C37	−179.68 (9)
C3—C2—C16—C21	141.70 (11)	C26—C25—C36—C37	0.33 (14)
C1—C2—C16—C21	−37.03 (13)	C22—C35—C36—C25	0.13 (14)
C3—C2—C16—C17	−40.26 (15)	C34—C35—C36—C25	179.36 (8)
C1—C2—C16—C17	141.01 (10)	C22—C35—C36—C37	179.80 (8)
C21—C16—C17—C18	−1.85 (16)	C34—C35—C36—C37	−0.97 (14)
C2—C16—C17—C18	−179.92 (10)	C31—C32—C37—C28	0.64 (14)
C16—C17—C18—C19	−0.35 (17)	C33—C32—C37—C28	−178.18 (9)
C17—C18—C19—C20	1.73 (16)	C31—C32—C37—C36	−179.31 (9)
C17—C18—C19—C22	−179.10 (10)	C33—C32—C37—C36	1.87 (14)
C18—C19—C20—C21	−0.91 (15)	C29—C28—C37—C32	0.18 (14)
C22—C19—C20—C21	179.93 (9)	C27—C28—C37—C32	−179.68 (9)
C19—C20—C21—C16	−1.31 (16)	C29—C28—C37—C36	−179.88 (9)
C17—C16—C21—C20	2.68 (15)	C27—C28—C37—C36	0.26 (14)
C2—C16—C21—C20	−179.22 (9)	C25—C36—C37—C32	179.33 (8)
C20—C19—C22—C23	93.06 (12)	C35—C36—C37—C32	−0.34 (14)
C18—C19—C22—C23	−86.08 (13)	C25—C36—C37—C28	−0.61 (14)
C20—C19—C22—C35	−87.00 (12)	C35—C36—C37—C28	179.71 (8)
C18—C19—C22—C35	93.85 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1^i	0.93	2.73	3.3563 (17)	125

Symmetry code: (i) −x+2, −y+2, −z+1.