Different packing motifs mediated by weak inter­actions and polymorphism in the crystal structures of five 2-(benzyl­idene)benzosuberone derivatives

Seaman, L.S.; Costa, C.F. da; Souza, M.V.N. de; Wardell, S.M.S.V.; Wardell, J.L.; Harrison, W.T.A.

doi:10.1107/S2056989019014245

Different packing motifs mediated by weak interactions and polymorphism in the crystal structures of five 2-(benzylidene)benzosuberone derivatives

L. S. Seaman, C. F. da Costa, M. V. N. de Souza, S. M. S. V. Wardell, J. L. Wardell and W. T. A. Harrison

The title compounds, which differ in the substituent at the 4-position of the pendant benzene ring, show different packing motifs mediated by weak C—H

X (X = O or N) interactions. One of them is a polymorph of a known structure.

Keywords: crystal structure; suberone; polymorphism.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019014245/eb2024sup1.cif Contains datablocks I, II, III, IV, V, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019014245/eb2024Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019014245/eb2024IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019014245/eb2024IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019014245/eb2024IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019014245/eb2024Vsup6.hkl Contains datablock V

CCDC references: 1960122; 1960121; 1960120; 1960119; 1960118

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.037
wR factor = 0.093
Data-to-parameter ratio = 17.3

Structure: II

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.092
Data-to-parameter ratio = 13.5

Structure: III

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.080
Data-to-parameter ratio = 13.6

Structure: IV

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.055
wR factor = 0.165
Data-to-parameter ratio = 14.2

Structure: V

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.068
wR factor = 0.181
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.532 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
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.         21 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         35 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 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.         16 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         18 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: IV


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: V


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.14 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C16      --C19      .        5.7 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku, 2017); cell refinement: CrysAlis PRO (Rigaku, 2017); data reduction: CrysAlis PRO (Rigaku, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

6-(4-Methoxybenzylidene)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (I) top

Crystal data top

C₁₉H₁₈O₂	F(000) = 592
M_r = 278.33	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.9171 (3) Å	Cell parameters from 6994 reflections
b = 9.1262 (2) Å	θ = 3.6–30.6°
c = 15.2539 (3) Å	µ = 0.08 mm⁻¹
β = 108.618 (3)°	T = 100 K
V = 1440.24 (6) Å³	Block, colourless
Z = 4	0.20 × 0.15 × 0.05 mm

Data collection top

XtaLAB AFC12 (RCD3): Kappa single CCD diffractometer	3296 independent reflections
Radiation source: Rotating-anode X-ray tube	2843 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −13→14
T_min = 0.877, T_max = 1.000	k = −11→11
16988 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0435P)² + 0.435P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3296 reflections	Δρ_max = 0.25 e Å⁻³
191 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.21223 (10)	0.67551 (12)	0.33073 (7)	0.0185 (2)
C2	0.25289 (10)	0.51984 (12)	0.35285 (7)	0.0176 (2)
C3	0.26700 (10)	0.42493 (12)	0.27568 (7)	0.0192 (2)
H3A	0.3201	0.3384	0.3032	0.023*
H3B	0.3146	0.4809	0.2413	0.023*
C4	0.13905 (11)	0.37140 (12)	0.20672 (7)	0.0235 (2)
H4A	0.1543	0.3392	0.1491	0.028*
H4B	0.1077	0.2858	0.2333	0.028*
C5	0.03505 (11)	0.49088 (12)	0.18348 (8)	0.0228 (2)
H5A	−0.0381	0.4586	0.1296	0.027*
H5B	0.0022	0.5024	0.2365	0.027*
C6	0.08193 (10)	0.63762 (12)	0.16175 (7)	0.0187 (2)
C7	0.03877 (11)	0.69424 (13)	0.07205 (7)	0.0220 (2)
H7	−0.0170	0.6369	0.0237	0.026*
C8	0.07549 (11)	0.83208 (13)	0.05212 (8)	0.0237 (2)
H8	0.0461	0.8677	−0.0096	0.028*
C9	0.15527 (11)	0.91857 (13)	0.12212 (8)	0.0227 (2)
H9	0.1795	1.0139	0.1087	0.027*
C10	0.19928 (10)	0.86472 (12)	0.21178 (7)	0.0199 (2)
H10	0.2534	0.9237	0.2600	0.024*
C11	0.16467 (10)	0.72442 (12)	0.23167 (7)	0.0178 (2)
C12	0.28541 (10)	0.48266 (12)	0.44276 (7)	0.0184 (2)
H12	0.2785	0.5598	0.4828	0.022*
C13	0.32958 (10)	0.34296 (12)	0.48884 (7)	0.0179 (2)
C14	0.28868 (10)	0.20616 (12)	0.44938 (7)	0.0186 (2)
H14	0.2300	0.2016	0.3881	0.022*
C15	0.33124 (10)	0.07653 (12)	0.49704 (7)	0.0192 (2)
H15	0.3014	−0.0152	0.4689	0.023*
C16	0.41828 (10)	0.08253 (12)	0.58673 (7)	0.0182 (2)
C17	0.45955 (10)	0.21776 (12)	0.62786 (7)	0.0205 (2)
H17	0.5189	0.2220	0.6889	0.025*
C18	0.41448 (11)	0.34552 (12)	0.58016 (7)	0.0204 (2)
H18	0.4414	0.4371	0.6096	0.024*
C19	0.41639 (11)	−0.17646 (12)	0.60092 (8)	0.0220 (2)
H19A	0.3224	−0.1777	0.5874	0.033*
H19B	0.4555	−0.2544	0.6452	0.033*
H19C	0.4370	−0.1924	0.5436	0.033*
O1	0.21902 (8)	0.76586 (9)	0.39153 (5)	0.0253 (2)
O2	0.46646 (7)	−0.03768 (8)	0.63967 (5)	0.02142 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0175 (5)	0.0198 (5)	0.0189 (5)	−0.0002 (4)	0.0067 (4)	−0.0003 (4)
C2	0.0171 (5)	0.0181 (5)	0.0178 (5)	−0.0003 (4)	0.0058 (4)	−0.0001 (4)
C3	0.0236 (6)	0.0186 (5)	0.0166 (5)	0.0020 (4)	0.0081 (4)	0.0007 (4)
C4	0.0305 (6)	0.0199 (6)	0.0183 (5)	−0.0024 (5)	0.0054 (5)	−0.0002 (4)
C5	0.0215 (6)	0.0247 (6)	0.0204 (5)	−0.0040 (4)	0.0041 (4)	0.0002 (4)
C6	0.0165 (5)	0.0211 (5)	0.0192 (5)	0.0020 (4)	0.0065 (4)	0.0011 (4)
C7	0.0195 (5)	0.0265 (6)	0.0186 (5)	0.0036 (4)	0.0041 (4)	0.0004 (4)
C8	0.0246 (6)	0.0283 (6)	0.0192 (5)	0.0083 (5)	0.0083 (4)	0.0070 (4)
C9	0.0250 (6)	0.0203 (6)	0.0260 (6)	0.0048 (4)	0.0127 (5)	0.0057 (4)
C10	0.0196 (5)	0.0194 (5)	0.0220 (5)	0.0027 (4)	0.0086 (4)	−0.0001 (4)
C11	0.0174 (5)	0.0192 (5)	0.0182 (5)	0.0032 (4)	0.0076 (4)	0.0015 (4)
C12	0.0187 (5)	0.0193 (5)	0.0181 (5)	0.0003 (4)	0.0070 (4)	−0.0014 (4)
C13	0.0177 (5)	0.0213 (5)	0.0159 (5)	0.0009 (4)	0.0071 (4)	0.0008 (4)
C14	0.0178 (5)	0.0233 (6)	0.0142 (5)	−0.0003 (4)	0.0042 (4)	0.0008 (4)
C15	0.0200 (5)	0.0204 (5)	0.0175 (5)	−0.0015 (4)	0.0065 (4)	−0.0002 (4)
C16	0.0179 (5)	0.0218 (5)	0.0163 (5)	0.0027 (4)	0.0076 (4)	0.0037 (4)
C17	0.0193 (5)	0.0271 (6)	0.0140 (5)	0.0004 (4)	0.0037 (4)	0.0003 (4)
C18	0.0222 (5)	0.0218 (5)	0.0176 (5)	−0.0011 (4)	0.0071 (4)	−0.0024 (4)
C19	0.0241 (6)	0.0199 (5)	0.0226 (5)	0.0015 (4)	0.0081 (4)	0.0041 (4)
O1	0.0349 (5)	0.0208 (4)	0.0187 (4)	0.0036 (3)	0.0066 (3)	−0.0019 (3)
O2	0.0239 (4)	0.0209 (4)	0.0177 (4)	0.0025 (3)	0.0043 (3)	0.0037 (3)

Geometric parameters (Å, º) top

C1—O1	1.2254 (13)	C9—H9	0.9500
C1—C2	1.4945 (15)	C10—C11	1.3955 (15)
C1—C11	1.5003 (14)	C10—H10	0.9500
C2—C12	1.3458 (15)	C12—C13	1.4614 (15)
C2—C3	1.5085 (14)	C12—H12	0.9500
C3—C4	1.5356 (15)	C13—C14	1.3959 (15)
C3—H3A	0.9900	C13—C18	1.4056 (15)
C3—H3B	0.9900	C14—C15	1.3887 (15)
C4—C5	1.5319 (16)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.3956 (15)
C4—H4B	0.9900	C15—H15	0.9500
C5—C6	1.5078 (15)	C16—O2	1.3642 (12)
C5—H5A	0.9900	C16—C17	1.3926 (15)
C5—H5B	0.9900	C17—C18	1.3793 (15)
C6—C7	1.3962 (15)	C17—H17	0.9500
C6—C11	1.4021 (15)	C18—H18	0.9500
C7—C8	1.3832 (16)	C19—O2	1.4304 (13)
C7—H7	0.9500	C19—H19A	0.9800
C8—C9	1.3885 (17)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
C9—C10	1.3869 (15)

O1—C1—C2	121.79 (10)	C8—C9—H9	120.3
O1—C1—C11	118.68 (10)	C9—C10—C11	120.47 (11)
C2—C1—C11	119.51 (9)	C9—C10—H10	119.8
C12—C2—C1	115.63 (9)	C11—C10—H10	119.8
C12—C2—C3	126.23 (10)	C10—C11—C6	120.42 (10)
C1—C2—C3	117.81 (9)	C10—C11—C1	117.47 (10)
C2—C3—C4	114.83 (9)	C6—C11—C1	121.99 (9)
C2—C3—H3A	108.6	C2—C12—C13	130.49 (10)
C4—C3—H3A	108.6	C2—C12—H12	114.8
C2—C3—H3B	108.6	C13—C12—H12	114.8
C4—C3—H3B	108.6	C14—C13—C18	117.46 (10)
H3A—C3—H3B	107.5	C14—C13—C12	124.18 (9)
C5—C4—C3	112.15 (9)	C18—C13—C12	118.30 (10)
C5—C4—H4A	109.2	C15—C14—C13	121.92 (10)
C3—C4—H4A	109.2	C15—C14—H14	119.0
C5—C4—H4B	109.2	C13—C14—H14	119.0
C3—C4—H4B	109.2	C14—C15—C16	119.28 (10)
H4A—C4—H4B	107.9	C14—C15—H15	120.4
C6—C5—C4	113.86 (9)	C16—C15—H15	120.4
C6—C5—H5A	108.8	O2—C16—C17	115.97 (9)
C4—C5—H5A	108.8	O2—C16—C15	124.19 (10)
C6—C5—H5B	108.8	C17—C16—C15	119.84 (10)
C4—C5—H5B	108.8	C18—C17—C16	120.12 (10)
H5A—C5—H5B	107.7	C18—C17—H17	119.9
C7—C6—C11	118.05 (10)	C16—C17—H17	119.9
C7—C6—C5	120.80 (10)	C17—C18—C13	121.34 (10)
C11—C6—C5	121.07 (9)	C17—C18—H18	119.3
C8—C7—C6	121.41 (11)	C13—C18—H18	119.3
C8—C7—H7	119.3	O2—C19—H19A	109.5
C6—C7—H7	119.3	O2—C19—H19B	109.5
C7—C8—C9	120.18 (10)	H19A—C19—H19B	109.5
C7—C8—H8	119.9	O2—C19—H19C	109.5
C9—C8—H8	119.9	H19A—C19—H19C	109.5
C10—C9—C8	119.45 (11)	H19B—C19—H19C	109.5
C10—C9—H9	120.3	C16—O2—C19	116.31 (8)

O1—C1—C2—C12	6.07 (15)	O1—C1—C11—C10	36.06 (14)
C11—C1—C2—C12	−175.42 (9)	C2—C1—C11—C10	−142.50 (10)
O1—C1—C2—C3	−167.73 (10)	O1—C1—C11—C6	−140.03 (11)
C11—C1—C2—C3	10.78 (14)	C2—C1—C11—C6	41.42 (14)
C12—C2—C3—C4	110.47 (12)	C1—C2—C12—C13	−179.67 (10)
C1—C2—C3—C4	−76.47 (12)	C3—C2—C12—C13	−6.47 (19)
C2—C3—C4—C5	40.48 (13)	C2—C12—C13—C14	−33.81 (17)
C3—C4—C5—C6	46.53 (12)	C2—C12—C13—C18	148.98 (11)
C4—C5—C6—C7	110.60 (11)	C18—C13—C14—C15	−1.16 (15)
C4—C5—C6—C11	−72.74 (13)	C12—C13—C14—C15	−178.38 (10)
C11—C6—C7—C8	−0.30 (16)	C13—C14—C15—C16	−0.55 (15)
C5—C6—C7—C8	176.46 (10)	C14—C15—C16—O2	−179.87 (9)
C6—C7—C8—C9	−1.05 (17)	C14—C15—C16—C17	1.11 (15)
C7—C8—C9—C10	0.97 (16)	O2—C16—C17—C18	−179.03 (9)
C8—C9—C10—C11	0.46 (16)	C15—C16—C17—C18	0.07 (15)
C9—C10—C11—C6	−1.83 (15)	C16—C17—C18—C13	−1.85 (16)
C9—C10—C11—C1	−177.98 (9)	C14—C13—C18—C17	2.36 (15)
C7—C6—C11—C10	1.73 (15)	C12—C13—C18—C17	179.75 (9)
C5—C6—C11—C10	−175.02 (10)	C17—C16—O2—C19	174.98 (9)
C7—C6—C11—C1	177.70 (9)	C15—C16—O2—C19	−4.07 (14)
C5—C6—C11—C1	0.95 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.35	3.2971 (14)	176
C19—H19A···Cg1ⁱⁱ	0.98	2.76	3.6165 (13)	146
C19—H19C···Cg2ⁱⁱⁱ	0.98	2.74	3.6029 (13)	147

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

6-(4-Ethoxybenzylidene)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (II) top

Crystal data top

C₂₀H₂₀O₂	F(000) = 624
M_r = 292.36	D_x = 1.291 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.6208 (2) Å	Cell parameters from 4578 reflections
b = 14.99690 (17) Å	θ = 3.7–69.7°
c = 8.39151 (12) Å	µ = 0.64 mm⁻¹
β = 108.6814 (17)°	T = 100 K
V = 1504.60 (4) Å³	Plate, colourless
Z = 4	0.20 × 0.11 × 0.03 mm

Data collection top

XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer	2704 independent reflections
Radiation source: Rotating-anode X-ray tube	2486 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.024
ω scans	θ_max = 68.3°, θ_min = 3.7°
Absorption correction: gaussian (CrysAlis PRO; Rigaku, 2017)	h = −14→15
T_min = 0.772, T_max = 1.000	k = −18→12
9197 measured reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0491P)² + 0.4554P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.092	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.25 e Å⁻³
2704 reflections	Δρ_min = −0.20 e Å⁻³
201 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0019 (3)
Primary atom site location: structure-invariant direct methods

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.29882 (10)	0.41642 (7)	0.43555 (14)	0.0187 (3)
C2	0.34088 (9)	0.37739 (8)	0.60870 (14)	0.0181 (3)
C3	0.27266 (9)	0.30342 (8)	0.64912 (14)	0.0183 (3)
H3A	0.3219	0.2668	0.7414	0.022*
H3B	0.2438	0.2646	0.5492	0.022*
C4	0.17406 (9)	0.33720 (8)	0.70118 (14)	0.0196 (3)
H4A	0.2021	0.3603	0.8178	0.024*
H4B	0.1226	0.2870	0.6990	0.024*
C5	0.10987 (10)	0.41143 (8)	0.58327 (14)	0.0203 (3)
H5A	0.0363	0.4193	0.6001	0.024*
H5B	0.1517	0.4680	0.6155	0.024*
C6	0.09109 (10)	0.39437 (7)	0.39855 (14)	0.0187 (3)
C7	−0.01602 (10)	0.37634 (8)	0.28964 (15)	0.0218 (3)
H7	−0.0757	0.3683	0.3342	0.026*
C8	−0.03708 (10)	0.36985 (8)	0.11691 (15)	0.0239 (3)
H8	−0.1104	0.3564	0.0451	0.029*
C9	0.04853 (10)	0.38295 (8)	0.04913 (15)	0.0233 (3)
H9	0.0337	0.3808	−0.0692	0.028*
C10	0.15569 (10)	0.39914 (8)	0.15573 (14)	0.0201 (3)
H10	0.2145	0.4080	0.1097	0.024*
C11	0.17889 (10)	0.40265 (7)	0.33013 (14)	0.0183 (3)
C12	0.43722 (9)	0.41219 (8)	0.71077 (14)	0.0182 (3)
H12	0.4688	0.4565	0.6587	0.022*
C13	0.50252 (10)	0.39471 (7)	0.88640 (14)	0.0183 (3)
C14	0.46487 (10)	0.35195 (8)	1.00672 (15)	0.0207 (3)
H14	0.3911	0.3284	0.9737	0.025*
C15	0.53262 (10)	0.34296 (8)	1.17341 (15)	0.0209 (3)
H15	0.5052	0.3134	1.2523	0.025*
C16	0.64063 (10)	0.37742 (7)	1.22393 (14)	0.0186 (3)
C17	0.67988 (9)	0.42064 (8)	1.10640 (14)	0.0193 (3)
H17	0.7537	0.4441	1.1399	0.023*
C18	0.61171 (10)	0.42937 (8)	0.94187 (14)	0.0186 (3)
H18	0.6393	0.4597	0.8639	0.022*
C19	0.67659 (10)	0.33225 (8)	1.51117 (15)	0.0229 (3)
H19A	0.6531	0.2700	1.4798	0.028*
H19B	0.6122	0.3655	1.5247	0.028*
C20	0.77366 (11)	0.33441 (9)	1.67216 (15)	0.0271 (3)
H20A	0.7515	0.3069	1.7626	0.041*
H20B	0.7960	0.3964	1.7018	0.041*
H20C	0.8367	0.3014	1.6569	0.041*
O1	0.36138 (7)	0.45674 (6)	0.37458 (10)	0.0264 (2)
O2	0.71428 (7)	0.37337 (6)	1.38349 (10)	0.0217 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0219 (6)	0.0195 (6)	0.0159 (6)	−0.0012 (4)	0.0076 (5)	−0.0007 (4)
C2	0.0192 (6)	0.0212 (6)	0.0155 (6)	0.0017 (4)	0.0077 (5)	0.0005 (4)
C3	0.0182 (6)	0.0208 (6)	0.0155 (5)	−0.0006 (4)	0.0049 (4)	0.0011 (4)
C4	0.0195 (6)	0.0250 (6)	0.0154 (5)	−0.0014 (5)	0.0071 (5)	0.0005 (4)
C5	0.0196 (6)	0.0251 (6)	0.0171 (6)	0.0020 (5)	0.0072 (5)	−0.0011 (4)
C6	0.0204 (6)	0.0187 (5)	0.0171 (6)	0.0027 (4)	0.0059 (5)	0.0012 (4)
C7	0.0203 (6)	0.0255 (6)	0.0203 (6)	0.0027 (5)	0.0073 (5)	−0.0004 (5)
C8	0.0197 (6)	0.0297 (6)	0.0195 (6)	0.0019 (5)	0.0023 (5)	−0.0015 (5)
C9	0.0260 (6)	0.0279 (6)	0.0144 (6)	0.0027 (5)	0.0045 (5)	−0.0007 (5)
C10	0.0233 (6)	0.0213 (6)	0.0169 (6)	0.0008 (5)	0.0081 (5)	0.0007 (4)
C11	0.0205 (6)	0.0173 (5)	0.0167 (6)	0.0004 (4)	0.0056 (5)	0.0002 (4)
C12	0.0184 (6)	0.0207 (6)	0.0176 (6)	0.0010 (4)	0.0087 (5)	0.0007 (4)
C13	0.0188 (6)	0.0198 (5)	0.0170 (6)	0.0010 (4)	0.0067 (5)	−0.0008 (4)
C14	0.0169 (6)	0.0258 (6)	0.0195 (6)	−0.0022 (5)	0.0063 (5)	0.0001 (5)
C15	0.0216 (6)	0.0254 (6)	0.0175 (6)	−0.0014 (5)	0.0090 (5)	0.0022 (4)
C16	0.0202 (6)	0.0200 (6)	0.0149 (6)	0.0026 (4)	0.0049 (5)	−0.0009 (4)
C17	0.0174 (6)	0.0220 (6)	0.0187 (6)	−0.0008 (4)	0.0060 (5)	−0.0012 (4)
C18	0.0205 (6)	0.0199 (6)	0.0173 (6)	0.0003 (4)	0.0089 (5)	0.0002 (4)
C19	0.0277 (6)	0.0260 (6)	0.0160 (6)	−0.0015 (5)	0.0084 (5)	0.0017 (5)
C20	0.0329 (7)	0.0287 (7)	0.0174 (6)	−0.0010 (5)	0.0049 (5)	0.0016 (5)
O1	0.0244 (5)	0.0366 (5)	0.0183 (4)	−0.0081 (4)	0.0071 (3)	0.0043 (4)
O2	0.0207 (4)	0.0296 (5)	0.0137 (4)	−0.0018 (3)	0.0041 (3)	0.0025 (3)

Geometric parameters (Å, º) top

C1—O1	1.2286 (14)	C10—C11	1.3985 (16)
C1—C2	1.4971 (16)	C10—H10	0.9500
C1—C11	1.5027 (16)	C12—C13	1.4635 (16)
C2—C12	1.3481 (17)	C12—H12	0.9500
C2—C3	1.5079 (16)	C13—C14	1.4014 (16)
C3—C4	1.5311 (15)	C13—C18	1.4053 (17)
C3—H3A	0.9900	C14—C15	1.3927 (16)
C3—H3B	0.9900	C14—H14	0.9500
C4—C5	1.5365 (16)	C15—C16	1.3909 (17)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—O2	1.3650 (14)
C5—C6	1.5130 (16)	C16—C17	1.3968 (16)
C5—H5A	0.9900	C17—C18	1.3794 (16)
C5—H5B	0.9900	C17—H17	0.9500
C6—C7	1.3944 (17)	C18—H18	0.9500
C6—C11	1.4074 (16)	C19—O2	1.4426 (14)
C7—C8	1.3908 (17)	C19—C20	1.5056 (17)
C7—H7	0.9500	C19—H19A	0.9900
C8—C9	1.3868 (18)	C19—H19B	0.9900
C8—H8	0.9500	C20—H20A	0.9800
C9—C10	1.3832 (18)	C20—H20B	0.9800
C9—H9	0.9500	C20—H20C	0.9800

O1—C1—C2	121.41 (10)	C11—C10—H10	119.4
O1—C1—C11	118.88 (10)	C10—C11—C6	119.69 (11)
C2—C1—C11	119.65 (10)	C10—C11—C1	117.07 (10)
C12—C2—C1	115.63 (10)	C6—C11—C1	123.24 (10)
C12—C2—C3	127.28 (10)	C2—C12—C13	132.29 (11)
C1—C2—C3	117.09 (10)	C2—C12—H12	113.9
C2—C3—C4	113.30 (9)	C13—C12—H12	113.9
C2—C3—H3A	108.9	C14—C13—C18	116.96 (11)
C4—C3—H3A	108.9	C14—C13—C12	126.59 (11)
C2—C3—H3B	108.9	C18—C13—C12	116.32 (10)
C4—C3—H3B	108.9	C15—C14—C13	121.81 (11)
H3A—C3—H3B	107.7	C15—C14—H14	119.1
C3—C4—C5	111.41 (9)	C13—C14—H14	119.1
C3—C4—H4A	109.3	C16—C15—C14	119.77 (11)
C5—C4—H4A	109.3	C16—C15—H15	120.1
C3—C4—H4B	109.3	C14—C15—H15	120.1
C5—C4—H4B	109.3	O2—C16—C15	125.13 (10)
H4A—C4—H4B	108.0	O2—C16—C17	115.41 (10)
C6—C5—C4	114.49 (10)	C15—C16—C17	119.46 (11)
C6—C5—H5A	108.6	C18—C17—C16	120.15 (11)
C4—C5—H5A	108.6	C18—C17—H17	119.9
C6—C5—H5B	108.6	C16—C17—H17	119.9
C4—C5—H5B	108.6	C17—C18—C13	121.83 (10)
H5A—C5—H5B	107.6	C17—C18—H18	119.1
C7—C6—C11	118.32 (11)	C13—C18—H18	119.1
C7—C6—C5	120.34 (11)	O2—C19—C20	106.86 (10)
C11—C6—C5	121.17 (10)	O2—C19—H19A	110.3
C8—C7—C6	121.21 (11)	C20—C19—H19A	110.3
C8—C7—H7	119.4	O2—C19—H19B	110.3
C6—C7—H7	119.4	C20—C19—H19B	110.3
C9—C8—C7	120.24 (11)	H19A—C19—H19B	108.6
C9—C8—H8	119.9	C19—C20—H20A	109.5
C7—C8—H8	119.9	C19—C20—H20B	109.5
C10—C9—C8	119.24 (11)	H20A—C20—H20B	109.5
C10—C9—H9	120.4	C19—C20—H20C	109.5
C8—C9—H9	120.4	H20A—C20—H20C	109.5
C9—C10—C11	121.14 (11)	H20B—C20—H20C	109.5
C9—C10—H10	119.4	C16—O2—C19	117.69 (9)

O1—C1—C2—C12	20.55 (16)	O1—C1—C11—C10	27.78 (16)
C11—C1—C2—C12	−162.35 (10)	C2—C1—C11—C10	−149.40 (11)
O1—C1—C2—C3	−158.66 (11)	O1—C1—C11—C6	−151.50 (11)
C11—C1—C2—C3	18.45 (15)	C2—C1—C11—C6	31.33 (16)
C12—C2—C3—C4	97.96 (14)	C1—C2—C12—C13	177.92 (11)
C1—C2—C3—C4	−82.94 (12)	C3—C2—C12—C13	−3.0 (2)
C2—C3—C4—C5	45.35 (13)	C2—C12—C13—C14	−17.9 (2)
C3—C4—C5—C6	42.50 (13)	C2—C12—C13—C18	166.41 (12)
C4—C5—C6—C7	110.32 (12)	C18—C13—C14—C15	−0.80 (17)
C4—C5—C6—C11	−74.39 (14)	C12—C13—C14—C15	−176.51 (11)
C11—C6—C7—C8	−2.33 (17)	C13—C14—C15—C16	0.32 (18)
C5—C6—C7—C8	173.09 (11)	C14—C15—C16—O2	179.45 (11)
C6—C7—C8—C9	−1.20 (18)	C14—C15—C16—C17	−0.06 (17)
C7—C8—C9—C10	2.45 (18)	O2—C16—C17—C18	−179.24 (10)
C8—C9—C10—C11	−0.12 (18)	C15—C16—C17—C18	0.32 (17)
C9—C10—C11—C6	−3.44 (17)	C16—C17—C18—C13	−0.85 (17)
C9—C10—C11—C1	177.26 (11)	C14—C13—C18—C17	1.07 (17)
C7—C6—C11—C10	4.59 (16)	C12—C13—C18—C17	177.23 (10)
C5—C6—C11—C10	−170.79 (10)	C15—C16—O2—C19	−1.70 (16)
C7—C6—C11—C1	−176.16 (11)	C17—C16—O2—C19	177.83 (10)
C5—C6—C11—C1	8.46 (17)	C20—C19—O2—C16	178.58 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.95	2.36	3.2653 (14)	159
C4—H4B···Cg1ⁱⁱ	0.98	2.72	3.6429 (13)	155
C19—H19A···Cg2ⁱⁱ	0.98	2.71	3.5969 (13)	149

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

2-(4-Benzylbenzylidene)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (III) top

Crystal data top

C₂₅H₂₂O₂	Z = 2
M_r = 354.42	F(000) = 376
Triclinic, P1	D_x = 1.285 Mg m⁻³
a = 9.2870 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.8727 (2) Å	Cell parameters from 19041 reflections
c = 12.2944 (3) Å	θ = 3.9–70.3°
α = 67.098 (3)°	µ = 0.63 mm⁻¹
β = 81.472 (2)°	T = 100 K
γ = 61.989 (3)°	Block, colourless
V = 915.92 (5) Å³	0.17 × 0.11 × 0.04 mm

Data collection top

XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer	3336 independent reflections
Radiation source: Rotating-anode X-ray tube	3073 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
ω scans	θ_max = 68.2°, θ_min = 3.9°
Absorption correction: gaussian (CrysAlis PRO; Rigaku, 2017)	h = −11→11
T_min = 0.781, T_max = 1.000	k = −11→11
29818 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0343P)² + 0.2601P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.19 e Å⁻³
3336 reflections	Δρ_min = −0.16 e Å⁻³
245 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0027 (4)
Primary atom site location: structure-invariant direct methods

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.05094 (13)	0.41786 (13)	0.37210 (9)	0.0206 (2)
C2	0.11044 (12)	0.39278 (12)	0.40498 (9)	0.0201 (2)
C3	0.15112 (13)	0.53459 (13)	0.34098 (9)	0.0218 (2)
H3A	0.2299	0.5293	0.3905	0.026*
H3B	0.0507	0.6397	0.3286	0.026*
C4	0.22435 (13)	0.53175 (14)	0.22121 (9)	0.0253 (2)
H4A	0.3404	0.4482	0.2340	0.030*
H4B	0.2204	0.6406	0.1732	0.030*
C5	0.13332 (14)	0.49174 (14)	0.15296 (9)	0.0261 (2)
H5A	0.1675	0.5174	0.0702	0.031*
H5B	0.1661	0.3720	0.1880	0.031*
C6	−0.05030 (13)	0.58461 (13)	0.15292 (9)	0.0232 (2)
C7	−0.14024 (15)	0.70291 (13)	0.04850 (10)	0.0286 (3)
H7	−0.0846	0.7283	−0.0221	0.034*
C8	−0.30954 (15)	0.78425 (14)	0.04574 (10)	0.0311 (3)
H8	−0.3685	0.8652	−0.0262	0.037*
C9	−0.39279 (14)	0.74770 (14)	0.14755 (11)	0.0295 (3)
H9	−0.5087	0.8033	0.1457	0.035*
C10	−0.30610 (13)	0.62955 (13)	0.25218 (10)	0.0254 (2)
H10	−0.3632	0.6033	0.3218	0.030*
C11	−0.13575 (13)	0.54864 (12)	0.25643 (9)	0.0214 (2)
C12	0.20322 (12)	0.24621 (13)	0.48767 (9)	0.0203 (2)
H12	0.1549	0.1733	0.5162	0.024*
C13	0.36457 (13)	0.17816 (13)	0.54185 (9)	0.0208 (2)
C14	0.48036 (13)	0.23711 (13)	0.49726 (9)	0.0232 (2)
H14	0.4568	0.3274	0.4241	0.028*
C15	0.62886 (13)	0.16712 (13)	0.55709 (9)	0.0239 (2)
H15	0.7051	0.2099	0.5253	0.029*
C16	0.66527 (12)	0.03382 (13)	0.66400 (9)	0.0214 (2)
C17	0.55458 (13)	−0.03095 (12)	0.70815 (9)	0.0213 (2)
H17	0.5800	−0.1236	0.7799	0.026*
C18	0.40818 (13)	0.03976 (13)	0.64743 (9)	0.0211 (2)
H18	0.3344	−0.0065	0.6779	0.025*
C19	0.92156 (13)	0.02302 (14)	0.68813 (10)	0.0291 (3)
H19A	0.8709	0.1402	0.6798	0.035*
H19B	0.9567	0.0162	0.6096	0.035*
C20	1.06575 (13)	−0.07617 (13)	0.77387 (9)	0.0230 (2)
C21	1.18414 (13)	−0.22910 (13)	0.77295 (10)	0.0251 (2)
H21	1.1719	−0.2709	0.7190	0.030*
C22	1.31964 (13)	−0.32064 (13)	0.85007 (10)	0.0266 (2)
H22	1.3985	−0.4259	0.8499	0.032*
C23	1.34081 (13)	−0.25957 (14)	0.92737 (10)	0.0273 (3)
H23	1.4350	−0.3216	0.9791	0.033*
C24	1.22388 (14)	−0.10747 (14)	0.92885 (10)	0.0283 (3)
H24	1.2376	−0.0652	0.9819	0.034*
C25	1.08673 (13)	−0.01680 (13)	0.85305 (10)	0.0257 (2)
H25	1.0063	0.0868	0.8552	0.031*
O1	−0.11776 (9)	0.33551 (9)	0.43769 (6)	0.02637 (19)
O2	0.80574 (9)	−0.04221 (9)	0.73220 (6)	0.02490 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0216 (5)	0.0216 (5)	0.0211 (5)	−0.0107 (4)	0.0026 (4)	−0.0097 (4)
C2	0.0206 (5)	0.0227 (5)	0.0199 (5)	−0.0118 (4)	0.0035 (4)	−0.0089 (4)
C3	0.0214 (5)	0.0210 (5)	0.0235 (5)	−0.0110 (4)	0.0009 (4)	−0.0069 (4)
C4	0.0233 (6)	0.0246 (5)	0.0255 (6)	−0.0122 (5)	0.0037 (4)	−0.0060 (4)
C5	0.0296 (6)	0.0267 (6)	0.0219 (5)	−0.0135 (5)	0.0058 (4)	−0.0094 (4)
C6	0.0298 (6)	0.0209 (5)	0.0224 (5)	−0.0128 (5)	0.0001 (4)	−0.0091 (4)
C7	0.0407 (7)	0.0254 (6)	0.0226 (6)	−0.0172 (5)	−0.0016 (5)	−0.0077 (5)
C8	0.0413 (7)	0.0218 (6)	0.0280 (6)	−0.0106 (5)	−0.0124 (5)	−0.0065 (5)
C9	0.0269 (6)	0.0248 (6)	0.0362 (6)	−0.0062 (5)	−0.0092 (5)	−0.0140 (5)
C10	0.0252 (6)	0.0254 (6)	0.0291 (6)	−0.0113 (5)	−0.0011 (4)	−0.0129 (5)
C11	0.0240 (5)	0.0197 (5)	0.0232 (5)	−0.0101 (4)	−0.0012 (4)	−0.0096 (4)
C12	0.0211 (5)	0.0232 (5)	0.0205 (5)	−0.0129 (4)	0.0036 (4)	−0.0091 (4)
C13	0.0208 (5)	0.0212 (5)	0.0219 (5)	−0.0097 (4)	0.0017 (4)	−0.0092 (4)
C14	0.0227 (5)	0.0230 (5)	0.0217 (5)	−0.0114 (4)	0.0006 (4)	−0.0046 (4)
C15	0.0226 (5)	0.0256 (5)	0.0243 (5)	−0.0144 (5)	0.0030 (4)	−0.0063 (4)
C16	0.0192 (5)	0.0221 (5)	0.0230 (5)	−0.0088 (4)	−0.0002 (4)	−0.0086 (4)
C17	0.0223 (5)	0.0197 (5)	0.0210 (5)	−0.0105 (4)	0.0011 (4)	−0.0055 (4)
C18	0.0214 (5)	0.0217 (5)	0.0235 (5)	−0.0122 (4)	0.0033 (4)	−0.0092 (4)
C19	0.0242 (6)	0.0305 (6)	0.0307 (6)	−0.0183 (5)	−0.0022 (5)	−0.0008 (5)
C20	0.0205 (5)	0.0242 (5)	0.0242 (5)	−0.0146 (4)	0.0018 (4)	−0.0033 (4)
C21	0.0288 (6)	0.0261 (6)	0.0255 (6)	−0.0174 (5)	0.0023 (4)	−0.0088 (4)
C22	0.0236 (6)	0.0217 (5)	0.0303 (6)	−0.0103 (5)	0.0030 (4)	−0.0062 (5)
C23	0.0236 (6)	0.0296 (6)	0.0250 (6)	−0.0153 (5)	−0.0030 (4)	−0.0009 (5)
C24	0.0355 (6)	0.0325 (6)	0.0231 (6)	−0.0209 (5)	0.0015 (5)	−0.0093 (5)
C25	0.0260 (6)	0.0224 (5)	0.0273 (6)	−0.0115 (5)	0.0056 (4)	−0.0085 (4)
O1	0.0258 (4)	0.0314 (4)	0.0242 (4)	−0.0182 (3)	0.0011 (3)	−0.0058 (3)
O2	0.0201 (4)	0.0269 (4)	0.0257 (4)	−0.0141 (3)	−0.0028 (3)	−0.0019 (3)

Geometric parameters (Å, º) top

C1—O1	1.2294 (12)	C13—C14	1.4001 (14)
C1—C2	1.4914 (14)	C13—C18	1.4042 (15)
C1—C11	1.5025 (14)	C14—C15	1.3895 (15)
C2—C12	1.3467 (15)	C14—H14	0.9500
C2—C3	1.5077 (14)	C15—C16	1.3933 (15)
C3—C4	1.5326 (15)	C15—H15	0.9500
C3—H3A	0.9900	C16—O2	1.3723 (12)
C3—H3B	0.9900	C16—C17	1.3936 (14)
C4—C5	1.5352 (15)	C17—C18	1.3774 (14)
C4—H4A	0.9900	C17—H17	0.9500
C4—H4B	0.9900	C18—H18	0.9500
C5—C6	1.5099 (15)	C19—O2	1.4392 (12)
C5—H5A	0.9900	C19—C20	1.4990 (15)
C5—H5B	0.9900	C19—H19A	0.9900
C6—C7	1.3945 (15)	C19—H19B	0.9900
C6—C11	1.4102 (15)	C20—C25	1.3916 (16)
C7—C8	1.3881 (17)	C20—C21	1.3925 (16)
C7—H7	0.9500	C21—C22	1.3849 (16)
C8—C9	1.3850 (18)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.3850 (16)
C9—C10	1.3859 (16)	C22—H22	0.9500
C9—H9	0.9500	C23—C24	1.3850 (17)
C10—C11	1.3960 (15)	C23—H23	0.9500
C10—H10	0.9500	C24—C25	1.3871 (16)
C12—C13	1.4637 (14)	C24—H24	0.9500
C12—H12	0.9500	C25—H25	0.9500

O1—C1—C2	121.81 (9)	C13—C12—H12	114.0
O1—C1—C11	118.85 (9)	C14—C13—C18	116.95 (9)
C2—C1—C11	119.33 (9)	C14—C13—C12	125.98 (9)
C12—C2—C1	116.43 (9)	C18—C13—C12	117.06 (9)
C12—C2—C3	127.54 (9)	C15—C14—C13	121.79 (10)
C1—C2—C3	116.03 (9)	C15—C14—H14	119.1
C2—C3—C4	111.93 (9)	C13—C14—H14	119.1
C2—C3—H3A	109.2	C14—C15—C16	119.59 (10)
C4—C3—H3A	109.2	C14—C15—H15	120.2
C2—C3—H3B	109.2	C16—C15—H15	120.2
C4—C3—H3B	109.2	O2—C16—C15	124.70 (9)
H3A—C3—H3B	107.9	O2—C16—C17	115.57 (9)
C3—C4—C5	112.28 (9)	C15—C16—C17	119.73 (10)
C3—C4—H4A	109.1	C18—C17—C16	119.83 (10)
C5—C4—H4A	109.1	C18—C17—H17	120.1
C3—C4—H4B	109.1	C16—C17—H17	120.1
C5—C4—H4B	109.1	C17—C18—C13	122.01 (9)
H4A—C4—H4B	107.9	C17—C18—H18	119.0
C6—C5—C4	114.06 (9)	C13—C18—H18	119.0
C6—C5—H5A	108.7	O2—C19—C20	108.38 (8)
C4—C5—H5A	108.7	O2—C19—H19A	110.0
C6—C5—H5B	108.7	C20—C19—H19A	110.0
C4—C5—H5B	108.7	O2—C19—H19B	110.0
H5A—C5—H5B	107.6	C20—C19—H19B	110.0
C7—C6—C11	118.30 (10)	H19A—C19—H19B	108.4
C7—C6—C5	120.45 (10)	C25—C20—C21	118.80 (10)
C11—C6—C5	121.17 (9)	C25—C20—C19	121.35 (10)
C8—C7—C6	121.25 (11)	C21—C20—C19	119.83 (10)
C8—C7—H7	119.4	C22—C21—C20	120.46 (10)
C6—C7—H7	119.4	C22—C21—H21	119.8
C9—C8—C7	120.17 (10)	C20—C21—H21	119.8
C9—C8—H8	119.9	C21—C22—C23	120.37 (10)
C7—C8—H8	119.9	C21—C22—H22	119.8
C8—C9—C10	119.62 (11)	C23—C22—H22	119.8
C8—C9—H9	120.2	C24—C23—C22	119.60 (10)
C10—C9—H9	120.2	C24—C23—H23	120.2
C9—C10—C11	120.72 (11)	C22—C23—H23	120.2
C9—C10—H10	119.6	C23—C24—C25	120.12 (10)
C11—C10—H10	119.6	C23—C24—H24	119.9
C10—C11—C6	119.92 (10)	C25—C24—H24	119.9
C10—C11—C1	117.49 (9)	C24—C25—C20	120.64 (10)
C6—C11—C1	122.50 (9)	C24—C25—H25	119.7
C2—C12—C13	132.05 (9)	C20—C25—H25	119.7
C2—C12—H12	114.0	C16—O2—C19	116.40 (8)

O1—C1—C2—C12	20.98 (15)	C3—C2—C12—C13	0.73 (19)
C11—C1—C2—C12	−159.81 (9)	C2—C12—C13—C14	−17.70 (19)
O1—C1—C2—C3	−159.38 (10)	C2—C12—C13—C18	163.17 (11)
C11—C1—C2—C3	19.82 (13)	C18—C13—C14—C15	−2.86 (16)
C12—C2—C3—C4	95.36 (13)	C12—C13—C14—C15	178.01 (10)
C1—C2—C3—C4	−84.23 (11)	C13—C14—C15—C16	0.48 (16)
C2—C3—C4—C5	43.11 (12)	C14—C15—C16—O2	−178.18 (10)
C3—C4—C5—C6	45.09 (12)	C14—C15—C16—C17	1.83 (16)
C4—C5—C6—C7	112.75 (11)	O2—C16—C17—C18	178.36 (9)
C4—C5—C6—C11	−70.46 (13)	C15—C16—C17—C18	−1.65 (16)
C11—C6—C7—C8	0.23 (16)	C16—C17—C18—C13	−0.86 (16)
C5—C6—C7—C8	177.11 (10)	C14—C13—C18—C17	3.06 (15)
C6—C7—C8—C9	−0.60 (17)	C12—C13—C18—C17	−177.73 (9)
C7—C8—C9—C10	0.04 (16)	O2—C19—C20—C25	−102.31 (11)
C8—C9—C10—C11	0.89 (16)	O2—C19—C20—C21	79.43 (12)
C9—C10—C11—C6	−1.26 (15)	C25—C20—C21—C22	0.41 (15)
C9—C10—C11—C1	−177.85 (9)	C19—C20—C21—C22	178.72 (9)
C7—C6—C11—C10	0.69 (15)	C20—C21—C22—C23	−1.38 (16)
C5—C6—C11—C10	−176.17 (9)	C21—C22—C23—C24	1.27 (16)
C7—C6—C11—C1	177.10 (9)	C22—C23—C24—C25	−0.20 (16)
C5—C6—C11—C1	0.25 (15)	C23—C24—C25—C20	−0.77 (16)
O1—C1—C11—C10	32.34 (14)	C21—C20—C25—C24	0.67 (16)
C2—C1—C11—C10	−146.89 (10)	C19—C20—C25—C24	−177.61 (10)
O1—C1—C11—C6	−144.16 (10)	C15—C16—O2—C19	0.07 (15)
C2—C1—C11—C6	36.61 (14)	C17—C16—O2—C19	−179.94 (9)
C1—C2—C12—C13	−179.68 (10)	C20—C19—O2—C16	−179.68 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.40	3.3477 (13)	176
C18—H18···Cg3ⁱⁱ	0.95	2.64	3.5147 (13)	153

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

2-(4-Chlorobenzylidene)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (IV) top

Crystal data top

C₁₈H₁₅ClO	F(000) = 592
M_r = 282.75	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 10.6273 (5) Å	Cell parameters from 4926 reflections
b = 11.6191 (4) Å	θ = 4.8–70.0°
c = 12.1114 (5) Å	µ = 2.31 mm⁻¹
β = 108.777 (4)°	T = 100 K
V = 1415.92 (11) Å³	Plate, colourless
Z = 4	0.28 × 0.20 × 0.03 mm

Data collection top

XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer	2568 independent reflections
Radiation source: Rotating-anode X-ray tube	2203 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.073
ω scans	θ_max = 68.2°, θ_min = 4.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)	h = −12→11
T_min = 0.722, T_max = 1.000	k = −13→13
11747 measured reflections	l = −14→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.1145P)² + 0.0344P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
2568 reflections	Δρ_max = 0.32 e Å⁻³
181 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2086 (2)	0.65193 (16)	0.58219 (17)	0.0292 (4)
C2	0.34239 (19)	0.67189 (16)	0.67264 (17)	0.0292 (4)
C3	0.34206 (19)	0.73875 (16)	0.77902 (17)	0.0311 (5)
H3A	0.4244	0.7207	0.8436	0.037*
H3B	0.2658	0.7131	0.8029	0.037*
C4	0.3330 (2)	0.86976 (16)	0.76058 (18)	0.0333 (5)
H4A	0.4225	0.9004	0.7685	0.040*
H4B	0.3028	0.9057	0.8218	0.040*
C5	0.2366 (2)	0.90247 (17)	0.64003 (18)	0.0323 (5)
H5A	0.2215	0.9866	0.6372	0.039*
H5B	0.2775	0.8829	0.5796	0.039*
C6	0.1047 (2)	0.84132 (17)	0.61283 (17)	0.0301 (5)
C7	−0.0085 (2)	0.90160 (19)	0.61159 (17)	0.0353 (5)
H7	−0.0024	0.9820	0.6268	0.042*
C8	−0.1309 (2)	0.84680 (19)	0.58856 (19)	0.0367 (5)
H8	−0.2071	0.8896	0.5885	0.044*
C9	−0.1412 (2)	0.72966 (19)	0.56571 (17)	0.0361 (5)
H9	−0.2242	0.6917	0.5506	0.043*
C10	−0.0297 (2)	0.66851 (18)	0.56509 (17)	0.0330 (5)
H10	−0.0369	0.5884	0.5486	0.040*
C11	0.09310 (19)	0.72291 (16)	0.58837 (16)	0.0294 (5)
C12	0.4476 (2)	0.62505 (16)	0.65047 (18)	0.0317 (5)
H12	0.4264	0.5825	0.5798	0.038*
C13	0.5893 (2)	0.62893 (16)	0.71748 (18)	0.0303 (5)
C14	0.6506 (2)	0.71561 (17)	0.79718 (18)	0.0334 (5)
H14	0.5983	0.7765	0.8116	0.040*
C15	0.7861 (2)	0.71376 (17)	0.85517 (18)	0.0339 (5)
H15	0.8263	0.7730	0.9090	0.041*
C16	0.8629 (2)	0.62534 (17)	0.83450 (19)	0.0341 (5)
C17	0.8062 (2)	0.53886 (18)	0.75589 (19)	0.0391 (5)
H17	0.8593	0.4783	0.7421	0.047*
C18	0.6709 (2)	0.54195 (18)	0.69764 (18)	0.0360 (5)
H18	0.6321	0.4833	0.6425	0.043*
O1	0.19203 (14)	0.57880 (12)	0.50600 (12)	0.0347 (4)
Cl1	1.03346 (5)	0.62611 (5)	0.90563 (5)	0.0469 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0308 (11)	0.0267 (9)	0.0297 (10)	−0.0017 (8)	0.0091 (8)	0.0023 (8)
C2	0.0292 (10)	0.0258 (9)	0.0307 (10)	−0.0012 (7)	0.0068 (8)	0.0018 (7)
C3	0.0273 (10)	0.0325 (10)	0.0309 (10)	0.0007 (8)	0.0056 (8)	−0.0006 (8)
C4	0.0274 (11)	0.0321 (11)	0.0371 (12)	−0.0021 (8)	0.0056 (9)	−0.0064 (8)
C5	0.0308 (11)	0.0277 (9)	0.0362 (11)	−0.0004 (8)	0.0076 (9)	−0.0006 (8)
C6	0.0289 (11)	0.0296 (10)	0.0295 (10)	−0.0005 (8)	0.0063 (8)	0.0004 (8)
C7	0.0330 (11)	0.0362 (11)	0.0330 (11)	0.0017 (9)	0.0056 (9)	−0.0004 (9)
C8	0.0286 (11)	0.0469 (12)	0.0328 (11)	0.0045 (9)	0.0074 (9)	−0.0001 (9)
C9	0.0289 (11)	0.0455 (12)	0.0312 (11)	−0.0047 (9)	0.0059 (9)	0.0015 (9)
C10	0.0323 (11)	0.0344 (11)	0.0295 (10)	−0.0043 (8)	0.0062 (8)	0.0008 (8)
C11	0.0280 (11)	0.0318 (10)	0.0263 (10)	0.0004 (8)	0.0058 (8)	0.0017 (7)
C12	0.0350 (12)	0.0274 (10)	0.0303 (11)	−0.0015 (8)	0.0073 (9)	0.0008 (7)
C13	0.0306 (11)	0.0317 (10)	0.0284 (10)	0.0020 (8)	0.0090 (9)	0.0025 (8)
C14	0.0296 (11)	0.0314 (10)	0.0384 (11)	0.0005 (8)	0.0099 (9)	−0.0030 (8)
C15	0.0325 (11)	0.0338 (10)	0.0350 (11)	−0.0023 (8)	0.0101 (9)	−0.0016 (8)
C16	0.0281 (11)	0.0383 (11)	0.0356 (12)	0.0005 (8)	0.0099 (9)	0.0045 (8)
C17	0.0339 (11)	0.0373 (12)	0.0465 (13)	0.0049 (9)	0.0134 (10)	−0.0025 (9)
C18	0.0334 (11)	0.0344 (11)	0.0397 (12)	−0.0005 (8)	0.0110 (9)	−0.0059 (8)
O1	0.0348 (8)	0.0318 (8)	0.0354 (8)	−0.0029 (6)	0.0083 (6)	−0.0060 (6)
Cl1	0.0268 (4)	0.0552 (4)	0.0545 (4)	0.0032 (2)	0.0071 (3)	0.0000 (2)

Geometric parameters (Å, º) top

C1—O1	1.225 (2)	C8—H8	0.9500
C1—C11	1.501 (3)	C9—C10	1.384 (3)
C1—C2	1.507 (3)	C9—H9	0.9500
C2—C12	1.346 (3)	C10—C11	1.395 (3)
C2—C3	1.506 (3)	C10—H10	0.9500
C3—C4	1.537 (3)	C12—C13	1.464 (3)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C18	1.402 (3)
C4—C5	1.537 (3)	C13—C14	1.402 (3)
C4—H4A	0.9900	C14—C15	1.385 (3)
C4—H4B	0.9900	C14—H14	0.9500
C5—C6	1.510 (3)	C15—C16	1.384 (3)
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C16—C17	1.382 (3)
C6—C7	1.388 (3)	C16—Cl1	1.739 (2)
C6—C11	1.404 (3)	C17—C18	1.383 (3)
C7—C8	1.393 (3)	C17—H17	0.9500
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.386 (3)

O1—C1—C11	119.82 (18)	C7—C8—H8	120.1
O1—C1—C2	121.84 (18)	C10—C9—C8	119.48 (19)
C11—C1—C2	118.33 (16)	C10—C9—H9	120.3
C12—C2—C3	127.61 (18)	C8—C9—H9	120.3
C12—C2—C1	116.26 (17)	C9—C10—C11	120.90 (19)
C3—C2—C1	116.09 (16)	C9—C10—H10	119.6
C2—C3—C4	113.82 (16)	C11—C10—H10	119.6
C2—C3—H3A	108.8	C10—C11—C6	119.99 (18)
C4—C3—H3A	108.8	C10—C11—C1	117.91 (17)
C2—C3—H3B	108.8	C6—C11—C1	122.07 (17)
C4—C3—H3B	108.8	C2—C12—C13	130.51 (18)
H3A—C3—H3B	107.7	C2—C12—H12	114.7
C3—C4—C5	111.98 (16)	C13—C12—H12	114.7
C3—C4—H4A	109.2	C18—C13—C14	117.39 (19)
C5—C4—H4A	109.2	C18—C13—C12	117.75 (18)
C3—C4—H4B	109.2	C14—C13—C12	124.81 (17)
C5—C4—H4B	109.2	C15—C14—C13	120.99 (18)
H4A—C4—H4B	107.9	C15—C14—H14	119.5
C6—C5—C4	112.27 (17)	C13—C14—H14	119.5
C6—C5—H5A	109.1	C16—C15—C14	119.82 (19)
C4—C5—H5A	109.1	C16—C15—H15	120.1
C6—C5—H5B	109.1	C14—C15—H15	120.1
C4—C5—H5B	109.1	C17—C16—C15	120.9 (2)
H5A—C5—H5B	107.9	C17—C16—Cl1	119.91 (16)
C7—C6—C11	118.35 (19)	C15—C16—Cl1	119.19 (17)
C7—C6—C5	120.36 (18)	C16—C17—C18	118.90 (19)
C11—C6—C5	121.30 (18)	C16—C17—H17	120.6
C6—C7—C8	121.4 (2)	C18—C17—H17	120.6
C6—C7—H7	119.3	C17—C18—C13	122.0 (2)
C8—C7—H7	119.3	C17—C18—H18	119.0
C9—C8—C7	119.8 (2)	C13—C18—H18	119.0
C9—C8—H8	120.1

O1—C1—C2—C12	14.6 (3)	C5—C6—C11—C1	−3.0 (3)
C11—C1—C2—C12	−166.52 (17)	O1—C1—C11—C10	38.8 (3)
O1—C1—C2—C3	−163.47 (18)	C2—C1—C11—C10	−140.10 (18)
C11—C1—C2—C3	15.4 (2)	O1—C1—C11—C6	−139.2 (2)
C12—C2—C3—C4	101.3 (2)	C2—C1—C11—C6	42.0 (3)
C1—C2—C3—C4	−80.8 (2)	C3—C2—C12—C13	−3.2 (3)
C2—C3—C4—C5	39.8 (2)	C1—C2—C12—C13	178.97 (18)
C3—C4—C5—C6	48.7 (2)	C2—C12—C13—C18	157.7 (2)
C4—C5—C6—C7	108.5 (2)	C2—C12—C13—C14	−24.7 (3)
C4—C5—C6—C11	−71.4 (2)	C18—C13—C14—C15	−1.1 (3)
C11—C6—C7—C8	1.0 (3)	C12—C13—C14—C15	−178.65 (19)
C5—C6—C7—C8	−178.97 (19)	C13—C14—C15—C16	0.0 (3)
C6—C7—C8—C9	−0.3 (3)	C14—C15—C16—C17	0.5 (3)
C7—C8—C9—C10	−0.5 (3)	C14—C15—C16—Cl1	178.57 (16)
C8—C9—C10—C11	0.7 (3)	C15—C16—C17—C18	0.1 (3)
C9—C10—C11—C6	0.0 (3)	Cl1—C16—C17—C18	−178.02 (16)
C9—C10—C11—C1	−177.98 (18)	C16—C17—C18—C13	−1.2 (3)
C7—C6—C11—C10	−0.8 (3)	C14—C13—C18—C17	1.6 (3)
C5—C6—C11—C10	179.14 (17)	C12—C13—C18—C17	179.39 (18)
C7—C6—C11—C1	177.07 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.95	2.50	3.319 (2)	145
C3—H3A···Cg1ⁱⁱ	0.99	2.83	3.572 (2)	132

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

6-(4-Cyanobenzylidene)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (V) top

Crystal data top

C₁₉H₁₅NO	F(000) = 576
M_r = 273.32	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.4725 (4) Å	Cell parameters from 3885 reflections
b = 7.1718 (2) Å	θ = 5.7–69.4°
c = 15.9983 (5) Å	µ = 0.64 mm⁻¹
β = 106.120 (3)°	T = 100 K
V = 1374.79 (8) Å³	Block, colourless
Z = 4	0.17 × 0.10 × 0.03 mm

Data collection top

XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer	2511 independent reflections
Radiation source: Rotating-anode X-ray tube	2302 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.059
ω scans	θ_max = 68.2°, θ_min = 3.7°
Absorption correction: gaussian (CrysAlis PRO; Rigaku, 2017)	h = −14→15
T_min = 0.895, T_max = 1.000	k = −7→8
9732 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.181	w = 1/[σ²(F_o²) + (0.1396P)² + 0.1712P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2511 reflections	Δρ_max = 0.49 e Å⁻³
190 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.34825 (12)	0.5911 (2)	0.45058 (9)	0.0284 (4)
C2	0.29525 (12)	0.4044 (2)	0.42080 (9)	0.0275 (4)
C3	0.32674 (12)	0.3153 (2)	0.34549 (9)	0.0279 (4)
H3A	0.3150	0.1790	0.3474	0.033*
H3B	0.4073	0.3366	0.3529	0.033*
C4	0.26091 (13)	0.3882 (2)	0.25527 (10)	0.0292 (4)
H4A	0.3080	0.3783	0.2148	0.035*
H4B	0.1941	0.3093	0.2323	0.035*
C5	0.22444 (13)	0.5911 (2)	0.25887 (10)	0.0296 (4)
H5A	0.1850	0.6337	0.1994	0.036*
H5B	0.1717	0.5993	0.2950	0.036*
C6	0.32277 (12)	0.7168 (2)	0.29642 (9)	0.0279 (4)
C7	0.35894 (13)	0.8371 (2)	0.24193 (10)	0.0304 (4)
H7	0.3192	0.8421	0.1820	0.037*
C8	0.45193 (14)	0.9506 (2)	0.27303 (11)	0.0319 (4)
H8	0.4759	1.0306	0.2344	0.038*
C9	0.50973 (13)	0.9462 (2)	0.36109 (11)	0.0318 (4)
H9	0.5734	1.0232	0.3829	0.038*
C10	0.47389 (13)	0.8293 (2)	0.41635 (10)	0.0305 (4)
H10	0.5128	0.8279	0.4765	0.037*
C11	0.38136 (12)	0.7129 (2)	0.38553 (10)	0.0279 (4)
C12	0.23202 (13)	0.3273 (2)	0.46664 (10)	0.0294 (4)
H12	0.2248	0.3944	0.5160	0.035*
C13	0.17236 (13)	0.1477 (2)	0.44785 (10)	0.0284 (4)
C14	0.11644 (13)	0.0939 (2)	0.36261 (10)	0.0304 (4)
H14	0.1162	0.1752	0.3157	0.036*
C15	0.06168 (13)	−0.0752 (2)	0.34565 (10)	0.0304 (4)
H15	0.0252	−0.1102	0.2874	0.036*
C16	0.05996 (12)	−0.1944 (2)	0.41403 (10)	0.0288 (4)
C17	0.11421 (14)	−0.1427 (2)	0.49975 (10)	0.0327 (4)
H17	0.1138	−0.2237	0.5466	0.039*
C18	0.16847 (13)	0.0273 (2)	0.51552 (10)	0.0320 (4)
H18	0.2040	0.0630	0.5738	0.038*
C19	−0.00015 (13)	−0.3676 (2)	0.39548 (10)	0.0308 (4)
N1	−0.05047 (12)	−0.5036 (2)	0.37711 (9)	0.0374 (4)
O1	0.36770 (11)	0.63971 (17)	0.52639 (7)	0.0376 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0239 (8)	0.0341 (9)	0.0233 (8)	0.0023 (6)	0.0002 (6)	−0.0017 (6)
C2	0.0235 (7)	0.0299 (8)	0.0234 (8)	0.0018 (6)	−0.0028 (6)	0.0020 (6)
C3	0.0228 (7)	0.0306 (8)	0.0273 (8)	0.0001 (6)	0.0020 (6)	−0.0004 (6)
C4	0.0263 (8)	0.0345 (9)	0.0243 (8)	−0.0036 (6)	0.0030 (6)	−0.0032 (6)
C5	0.0256 (8)	0.0356 (9)	0.0231 (8)	−0.0009 (6)	−0.0009 (6)	0.0006 (6)
C6	0.0248 (8)	0.0304 (8)	0.0264 (8)	0.0042 (6)	0.0034 (6)	−0.0011 (6)
C7	0.0278 (8)	0.0311 (8)	0.0307 (9)	0.0048 (6)	0.0054 (7)	0.0001 (6)
C8	0.0314 (8)	0.0286 (8)	0.0375 (9)	0.0031 (6)	0.0122 (7)	0.0008 (6)
C9	0.0244 (8)	0.0305 (8)	0.0391 (9)	−0.0001 (6)	0.0065 (7)	−0.0044 (7)
C10	0.0254 (8)	0.0307 (8)	0.0317 (9)	0.0019 (6)	0.0016 (6)	−0.0038 (6)
C11	0.0235 (7)	0.0288 (8)	0.0292 (8)	0.0015 (6)	0.0035 (6)	−0.0021 (6)
C12	0.0272 (8)	0.0323 (8)	0.0243 (8)	0.0018 (6)	−0.0002 (6)	−0.0001 (6)
C13	0.0236 (8)	0.0321 (9)	0.0277 (8)	0.0015 (6)	0.0042 (6)	−0.0011 (6)
C14	0.0274 (8)	0.0340 (9)	0.0257 (8)	−0.0011 (6)	0.0009 (6)	0.0060 (6)
C15	0.0263 (8)	0.0354 (9)	0.0248 (8)	−0.0013 (6)	−0.0006 (6)	0.0005 (6)
C16	0.0239 (7)	0.0300 (8)	0.0294 (8)	0.0004 (6)	0.0025 (6)	0.0006 (6)
C17	0.0332 (8)	0.0359 (9)	0.0256 (8)	−0.0014 (7)	0.0027 (7)	0.0045 (6)
C18	0.0312 (8)	0.0371 (9)	0.0245 (8)	−0.0022 (7)	0.0024 (6)	−0.0005 (6)
C19	0.0300 (8)	0.0339 (9)	0.0259 (8)	0.0023 (7)	0.0033 (6)	0.0036 (6)
N1	0.0377 (8)	0.0359 (9)	0.0338 (8)	−0.0053 (6)	0.0018 (6)	0.0021 (6)
O1	0.0426 (7)	0.0412 (7)	0.0259 (6)	−0.0094 (5)	0.0042 (5)	−0.0047 (5)

Geometric parameters (Å, º) top

C1—O1	1.2199 (19)	C8—H8	0.9500
C1—C11	1.502 (2)	C9—C10	1.380 (2)
C1—C2	1.510 (2)	C9—H9	0.9500
C2—C12	1.337 (2)	C10—C11	1.399 (2)
C2—C3	1.509 (2)	C10—H10	0.9500
C3—C4	1.540 (2)	C12—C13	1.476 (2)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C18	1.396 (2)
C4—C5	1.531 (2)	C13—C14	1.402 (2)
C4—H4A	0.9900	C14—C15	1.381 (2)
C4—H4B	0.9900	C14—H14	0.9500
C5—C6	1.506 (2)	C15—C16	1.393 (2)
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C16—C17	1.400 (2)
C6—C7	1.388 (2)	C16—C19	1.439 (2)
C6—C11	1.410 (2)	C17—C18	1.383 (2)
C7—C8	1.391 (2)	C17—H17	0.9500
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.393 (2)	C19—N1	1.153 (2)

O1—C1—C11	120.38 (14)	C9—C8—H8	120.2
O1—C1—C2	121.05 (14)	C10—C9—C8	119.53 (15)
C11—C1—C2	118.52 (13)	C10—C9—H9	120.2
C12—C2—C3	125.92 (15)	C8—C9—H9	120.2
C12—C2—C1	117.85 (14)	C9—C10—C11	121.29 (14)
C3—C2—C1	116.04 (13)	C9—C10—H10	119.4
C2—C3—C4	114.54 (13)	C11—C10—H10	119.4
C2—C3—H3A	108.6	C10—C11—C6	119.32 (14)
C4—C3—H3A	108.6	C10—C11—C1	117.50 (14)
C2—C3—H3B	108.6	C6—C11—C1	123.17 (14)
C4—C3—H3B	108.6	C2—C12—C13	126.19 (14)
H3A—C3—H3B	107.6	C2—C12—H12	116.9
C5—C4—C3	111.96 (12)	C13—C12—H12	116.9
C5—C4—H4A	109.2	C18—C13—C14	117.97 (14)
C3—C4—H4A	109.2	C18—C13—C12	120.39 (14)
C5—C4—H4B	109.2	C14—C13—C12	121.63 (14)
C3—C4—H4B	109.2	C15—C14—C13	121.18 (14)
H4A—C4—H4B	107.9	C15—C14—H14	119.4
C6—C5—C4	111.51 (12)	C13—C14—H14	119.4
C6—C5—H5A	109.3	C14—C15—C16	119.93 (14)
C4—C5—H5A	109.3	C14—C15—H15	120.0
C6—C5—H5B	109.3	C16—C15—H15	120.0
C4—C5—H5B	109.3	C15—C16—C17	119.88 (15)
H5A—C5—H5B	108.0	C15—C16—C19	119.24 (14)
C7—C6—C11	118.67 (14)	C17—C16—C19	120.86 (14)
C7—C6—C5	119.49 (13)	C18—C17—C16	119.40 (15)
C11—C6—C5	121.83 (14)	C18—C17—H17	120.3
C6—C7—C8	121.55 (15)	C16—C17—H17	120.3
C6—C7—H7	119.2	C17—C18—C13	121.62 (14)
C8—C7—H7	119.2	C17—C18—H18	119.2
C7—C8—C9	119.64 (15)	C13—C18—H18	119.2
C7—C8—H8	120.2	N1—C19—C16	177.09 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N1ⁱ	0.95	2.54	3.438 (2)	157
C3—H3A···Cg1ⁱⁱ	0.99	2.84	3.6730 (16)	142
C8—H8···Cg1ⁱⁱⁱ	0.95	2.88	3.7868 (17)	161

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

Fingerprint contact percentages for (I) and VENQUA top

Contact type	(I)	VENQUA
H···H	54.8	55.3
C···H/H···C	28.1	29.2
O—H/H···O	15.3	14.5
C···C	1.1	0.0
C···O/O···C	0.8	0.8
O···O	0.0	0.2

Summary of the C—H···O and C—H···N hydrogen bonds and packing motifs for 2-(benzylidene)benzosuberone derivatives top

Code/refcode	Substituent(s)	Space group	φ	Donor atom(s)	Packing motif
(I)	4-OMe	P2₁/c	23.79 (3)	C15	C(8) chain
(II)	4-OEt	P2₁/c	24.60 (4)	C18	R₂²(14) loop
(III)	4-OBz	P1	33.72 (4)	C15	C(8) chain
(IV)	4-Cl	P2₁/n	29.93 (8)	C10	R₂²(10) loop
(V)	4-CN	P2₁/c	21.81 (7)	C17	R₂²(10) loop
VENQOU	4-Me	P2₁/n	29.72 (11)	C10	R₂²(10) loop
VENQUA	4-OMe	P2₁/n	35.88 (11)	C10	R₂²(10) loop
VENSIQ	4-NMe₂	P2₁/n	29.43 (11)	C10	R₂²(10) loop
XUGXOM	2-NO₂	P2₁/a	27.56 (6)	C17	C(5) chain
VENREL	3-NO₂	P1	18.54 (9)	C7,C14,C16	double chain
VENRIP	4-NO₂	P1	45.32 (9)	C9,C15	sheet
XUGYED	2-Cl	P2₁/c	28.40 (19)	C14	C(7) chain
XUGXUS	3,4-Cl	P2₁/c	39.01 (16)	C15	C(8) chain
XUGYAZ	2,4-Cl	P2₁/c	30.54 (12)	C14	C(7) chain
XUGYUT	2-OMe	P2₁	25.82 (17)	None	–
XUGYON	3,4-OMe	P1	23.48 (9)	C8,C15	sheet
XUGYIH	3,4,5-OMe	P2₁/n	35.08 (10)	C7	C(6) chain

Packing analyses carried out using PLATON (Spek, 2009); φ is the dihedral angle between the C6–C11 and C13–C18 benzene rings; for the `VEN' refcode family, see Dimmock et al. (1999); for the `XUG' family, see Dimmock et al. (2002); the donor atom labels correspond to our atom numbering scheme.

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Different packing motifs mediated by weak inter­actions and polymorphism in the crystal structures of five 2-(benzyl­idene)benzosuberone derivatives

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Different packing motifs mediated by weak interactions and polymorphism in the crystal structures of five 2-(benzylidene)benzosuberone derivatives