Crystal structures and conformational analyses of three pyranochromene derivatives

Swaminathan, K.; Sethusankar, K.; Kumar, G.S.; Bakthadoss, M.

doi:10.1107/S2056989015012967

Crystal structures and conformational analyses of three pyranochromene derivatives

K. Swaminathan, K. Sethusankar, G. S. Kumar and M. Bakthadoss

In the crystal structures of the three title pyran–chromene derivatives, (I)–(III), molecules are linked by C—H

O hydrogen bonds which generate molecular sheets parallel to the ab plane with $R_{4}^{3}$ (28) loops in (I), inversion dimers with $R_{2}^{2}$ (10) loops in (II) and chains along the b axis with $R_{2}^{2}$ (12) ring motifs in (III).

Keywords: crystal structure; pyranochromene; coumarin derivatives; molecular sheets; inversion dimers; chains; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015012967/su5160sup1.cif Contains datablocks I, II, III, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015012967/su5160Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015012967/su5160IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015012967/su5160IIIsup4.hkl Contains datablock III
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015012967/su5160Isup5.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015012967/su5160IIsup6.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015012967/su5160IIIsup7.cml Supplementary material

CCDC references: 1410607; 1410606; 1410605

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.037
wR factor = 0.106
Data-to-parameter ratio = 12.4

Structure: II

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.047
wR factor = 0.155
Data-to-parameter ratio = 20.8

Structure: III

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.126
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         O1 Check

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C12     (Centro SPGR)          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          57 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

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

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




Datablock: II


Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C12     (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         22 Note

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

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




Datablock: III



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.325 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         17 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C8     --  C25     ..        5.3 su
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C12     (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          50 %

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

   1 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
   3 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 top

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(I) Methyl 7-oxo-14-phenyl-1H,7H,14H-pyrano[3,2-c:5,4-c']dichromene-14a(6bH)-carboxylate] top

Crystal data top

C₂₇H₂₀O₆	F(000) = 920
M_r = 440.43	D_x = 1.391 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3698 reflections
a = 9.3980 (15) Å	θ = 2.6–25.0°
b = 14.0050 (12) Å	µ = 0.10 mm⁻¹
c = 15.9890 (13) Å	T = 296 K
β = 92.048 (5)°	Block, colourless
V = 2103.1 (4) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3698 independent reflections
Radiation source: fine-focus sealed tube	2964 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω & φ scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.966, T_max = 0.976	k = −16→16
19091 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0556P)² + 0.3545P] where P = (F_o² + 2F_c²)/3
3698 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.56782 (17)	0.20825 (13)	0.27702 (12)	0.0602 (5)
H1	0.5188	0.1513	0.2680	0.072*
C2	0.55034 (19)	0.25923 (16)	0.34916 (12)	0.0673 (5)
H2	0.4893	0.2366	0.3892	0.081*
C3	0.6227 (2)	0.34377 (16)	0.36281 (11)	0.0641 (5)
H3	0.6102	0.3782	0.4117	0.077*
C4	0.71382 (17)	0.37705 (13)	0.30365 (10)	0.0527 (4)
H4	0.7636	0.4335	0.3136	0.063*
C5	0.73273 (15)	0.32771 (11)	0.22924 (9)	0.0418 (3)
C6	0.65935 (16)	0.24239 (11)	0.21752 (10)	0.0472 (4)
C7	0.77878 (16)	0.20819 (11)	0.09054 (10)	0.0473 (4)
H7A	0.7343	0.2434	0.0444	0.057*
H7B	0.8165	0.1494	0.0682	0.057*
C8	0.90161 (15)	0.26711 (10)	0.12772 (9)	0.0382 (3)
C9	0.84184 (14)	0.35891 (10)	0.16676 (9)	0.0373 (3)
H9	0.9199	0.3912	0.1977	0.045*
C10	0.79072 (15)	0.42388 (10)	0.09597 (9)	0.0377 (3)
C11	0.83533 (15)	0.41354 (10)	0.01665 (9)	0.0390 (3)
C12	1.00608 (15)	0.29584 (10)	0.05912 (9)	0.0398 (3)
H12	1.0776	0.3390	0.0844	0.048*
C13	0.69743 (15)	0.50314 (10)	0.11408 (10)	0.0406 (3)
C14	0.68064 (15)	0.54090 (10)	−0.03296 (10)	0.0436 (4)
C15	0.78006 (15)	0.47146 (10)	−0.05170 (9)	0.0416 (3)
C16	0.81551 (18)	0.45965 (12)	−0.13507 (10)	0.0519 (4)
H16	0.8829	0.4143	−0.1490	0.062*
C17	0.7513 (2)	0.51477 (13)	−0.19664 (11)	0.0594 (5)
H17	0.7757	0.5067	−0.2521	0.071*
C18	0.65055 (19)	0.58214 (13)	−0.17657 (12)	0.0592 (5)
H18	0.6063	0.6183	−0.2188	0.071*
C19	0.61517 (17)	0.59612 (12)	−0.09496 (11)	0.0534 (4)
H19	0.5482	0.6420	−0.0815	0.064*
C20	1.08306 (16)	0.21352 (10)	0.01989 (9)	0.0437 (4)
C21	1.21663 (18)	0.18833 (12)	0.05144 (12)	0.0557 (4)
H21	1.2581	0.2227	0.0957	0.067*
C22	1.2892 (2)	0.11241 (13)	0.01770 (14)	0.0712 (6)
H22	1.3792	0.0961	0.0393	0.085*
C23	1.2289 (2)	0.06125 (13)	−0.04743 (15)	0.0754 (6)
H23	1.2784	0.0108	−0.0706	0.091*
C24	1.0960 (2)	0.08450 (14)	−0.07837 (13)	0.0715 (6)
H24	1.0545	0.0487	−0.1217	0.086*
C25	1.0226 (2)	0.16088 (12)	−0.04583 (11)	0.0572 (4)
H25	0.9329	0.1769	−0.0680	0.069*
C26	0.98572 (15)	0.20813 (11)	0.19238 (9)	0.0423 (4)
C27	1.1726 (2)	0.21330 (15)	0.29418 (13)	0.0713 (5)
H27A	1.1191	0.1816	0.3360	0.107*
H27B	1.2367	0.2584	0.3206	0.107*
H27C	1.2261	0.1670	0.2641	0.107*
O1	0.67314 (12)	0.18517 (9)	0.14893 (8)	0.0638 (3)
O2	0.93013 (11)	0.34696 (7)	−0.00690 (6)	0.0466 (3)
O3	0.64390 (11)	0.55763 (7)	0.04799 (7)	0.0490 (3)
O4	0.66214 (12)	0.52699 (8)	0.18248 (7)	0.0533 (3)
O5	1.07607 (11)	0.26285 (8)	0.23656 (7)	0.0535 (3)
O6	0.97557 (13)	0.12343 (8)	0.20042 (8)	0.0613 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0410 (9)	0.0613 (11)	0.0790 (13)	0.0020 (8)	0.0107 (8)	0.0229 (10)
C2	0.0509 (10)	0.0891 (15)	0.0631 (11)	0.0121 (10)	0.0165 (9)	0.0304 (11)
C3	0.0585 (11)	0.0886 (14)	0.0459 (9)	0.0167 (10)	0.0109 (8)	0.0091 (9)
C4	0.0509 (9)	0.0614 (10)	0.0459 (9)	0.0092 (8)	0.0045 (7)	0.0014 (8)
C5	0.0351 (7)	0.0456 (8)	0.0450 (8)	0.0042 (6)	0.0036 (6)	0.0054 (7)
C6	0.0362 (8)	0.0487 (9)	0.0570 (9)	0.0018 (7)	0.0052 (7)	0.0070 (8)
C7	0.0492 (9)	0.0389 (8)	0.0540 (9)	−0.0077 (7)	0.0055 (7)	−0.0035 (7)
C8	0.0379 (8)	0.0322 (7)	0.0448 (8)	−0.0014 (6)	0.0049 (6)	−0.0016 (6)
C9	0.0339 (7)	0.0345 (7)	0.0435 (8)	−0.0020 (6)	0.0033 (6)	−0.0032 (6)
C10	0.0347 (7)	0.0305 (7)	0.0480 (8)	−0.0041 (6)	0.0031 (6)	−0.0022 (6)
C11	0.0383 (8)	0.0297 (7)	0.0492 (8)	−0.0024 (6)	0.0043 (6)	−0.0021 (6)
C12	0.0419 (8)	0.0325 (7)	0.0452 (8)	0.0012 (6)	0.0054 (6)	0.0000 (6)
C13	0.0369 (8)	0.0310 (7)	0.0539 (9)	−0.0045 (6)	0.0043 (7)	−0.0021 (7)
C14	0.0391 (8)	0.0353 (8)	0.0565 (9)	−0.0069 (6)	0.0026 (7)	0.0040 (7)
C15	0.0423 (8)	0.0328 (7)	0.0496 (8)	−0.0055 (6)	0.0004 (6)	0.0025 (6)
C16	0.0613 (10)	0.0441 (9)	0.0504 (9)	−0.0021 (8)	0.0028 (8)	0.0013 (7)
C17	0.0722 (12)	0.0556 (11)	0.0502 (10)	−0.0088 (9)	−0.0026 (8)	0.0078 (8)
C18	0.0573 (11)	0.0555 (10)	0.0640 (11)	−0.0090 (8)	−0.0109 (9)	0.0172 (9)
C19	0.0427 (9)	0.0417 (9)	0.0754 (12)	−0.0030 (7)	−0.0057 (8)	0.0122 (8)
C20	0.0482 (9)	0.0331 (8)	0.0506 (9)	0.0006 (6)	0.0143 (7)	−0.0004 (6)
C21	0.0492 (9)	0.0460 (9)	0.0726 (11)	0.0017 (7)	0.0099 (8)	−0.0053 (8)
C22	0.0588 (11)	0.0527 (11)	0.1033 (16)	0.0151 (9)	0.0186 (11)	−0.0025 (11)
C23	0.0884 (15)	0.0408 (10)	0.0995 (15)	0.0114 (10)	0.0372 (13)	−0.0086 (10)
C24	0.0917 (15)	0.0526 (11)	0.0717 (12)	−0.0006 (10)	0.0222 (11)	−0.0203 (9)
C25	0.0646 (11)	0.0512 (10)	0.0562 (10)	0.0034 (8)	0.0090 (8)	−0.0096 (8)
C26	0.0421 (8)	0.0382 (8)	0.0473 (8)	0.0019 (6)	0.0103 (7)	0.0024 (7)
C27	0.0585 (11)	0.0751 (13)	0.0790 (13)	0.0166 (10)	−0.0165 (10)	0.0123 (10)
O1	0.0535 (7)	0.0599 (7)	0.0789 (8)	−0.0232 (6)	0.0172 (6)	−0.0120 (6)
O2	0.0547 (6)	0.0411 (6)	0.0446 (6)	0.0104 (5)	0.0106 (5)	0.0027 (5)
O3	0.0476 (6)	0.0384 (6)	0.0613 (7)	0.0071 (5)	0.0075 (5)	0.0049 (5)
O4	0.0592 (7)	0.0416 (6)	0.0596 (7)	0.0046 (5)	0.0112 (5)	−0.0091 (5)
O5	0.0465 (6)	0.0464 (6)	0.0667 (7)	0.0061 (5)	−0.0100 (5)	0.0041 (5)
O6	0.0759 (8)	0.0385 (7)	0.0699 (8)	0.0000 (6)	0.0059 (6)	0.0120 (6)

Geometric parameters (Å, º) top

C1—C2	1.372 (3)	C13—O3	1.3835 (18)
C1—C6	1.390 (2)	C14—O3	1.3715 (18)
C1—H1	0.9300	C14—C19	1.384 (2)
C2—C3	1.379 (3)	C14—C15	1.389 (2)
C2—H2	0.9300	C15—C16	1.395 (2)
C3—C4	1.379 (2)	C16—C17	1.374 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.393 (2)	C17—C18	1.382 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.389 (2)	C18—C19	1.372 (3)
C5—C9	1.5211 (19)	C18—H18	0.9300
C6—O1	1.368 (2)	C19—H19	0.9300
C7—O1	1.4239 (19)	C20—C21	1.382 (2)
C7—C8	1.522 (2)	C20—C25	1.388 (2)
C7—H7A	0.9700	C21—C22	1.383 (2)
C7—H7B	0.9700	C21—H21	0.9300
C8—C26	1.522 (2)	C22—C23	1.370 (3)
C8—C9	1.5438 (19)	C22—H22	0.9300
C8—C12	1.5512 (19)	C23—C24	1.366 (3)
C9—C10	1.517 (2)	C23—H23	0.9300
C9—H9	0.9800	C24—C25	1.385 (2)
C10—C11	1.358 (2)	C24—H24	0.9300
C10—C13	1.450 (2)	C25—H25	0.9300
C11—O2	1.3524 (17)	C26—O6	1.1973 (18)
C11—C15	1.443 (2)	C26—O5	1.3283 (18)
C12—O2	1.4430 (17)	C27—O5	1.4470 (19)
C12—C20	1.5094 (19)	C27—H27A	0.9600
C12—H12	0.9800	C27—H27B	0.9600
C13—O4	1.2015 (17)	C27—H27C	0.9600

C2—C1—C6	119.48 (18)	O3—C13—C10	118.41 (13)
C2—C1—H1	120.3	O3—C14—C19	117.38 (14)
C6—C1—H1	120.3	O3—C14—C15	121.15 (13)
C1—C2—C3	120.46 (16)	C19—C14—C15	121.47 (15)
C1—C2—H2	119.8	C14—C15—C16	118.34 (14)
C3—C2—H2	119.8	C14—C15—C11	117.20 (14)
C2—C3—C4	119.76 (18)	C16—C15—C11	124.41 (14)
C2—C3—H3	120.1	C17—C16—C15	120.28 (16)
C4—C3—H3	120.1	C17—C16—H16	119.9
C3—C4—C5	121.29 (18)	C15—C16—H16	119.9
C3—C4—H4	119.4	C16—C17—C18	120.28 (17)
C5—C4—H4	119.4	C16—C17—H17	119.9
C6—C5—C4	117.66 (14)	C18—C17—H17	119.9
C6—C5—C9	120.11 (13)	C19—C18—C17	120.62 (16)
C4—C5—C9	121.88 (14)	C19—C18—H18	119.7
O1—C6—C5	123.45 (13)	C17—C18—H18	119.7
O1—C6—C1	115.20 (15)	C18—C19—C14	119.00 (16)
C5—C6—C1	121.34 (16)	C18—C19—H19	120.5
O1—C7—C8	113.79 (13)	C14—C19—H19	120.5
O1—C7—H7A	108.8	C21—C20—C25	118.86 (14)
C8—C7—H7A	108.8	C21—C20—C12	119.07 (14)
O1—C7—H7B	108.8	C25—C20—C12	122.05 (14)
C8—C7—H7B	108.8	C20—C21—C22	120.54 (18)
H7A—C7—H7B	107.7	C20—C21—H21	119.7
C7—C8—C26	109.83 (12)	C22—C21—H21	119.7
C7—C8—C9	109.12 (12)	C23—C22—C21	120.14 (19)
C26—C8—C9	111.40 (11)	C23—C22—H22	119.9
C7—C8—C12	110.78 (12)	C21—C22—H22	119.9
C26—C8—C12	107.13 (11)	C24—C23—C22	119.91 (17)
C9—C8—C12	108.57 (11)	C24—C23—H23	120.0
C10—C9—C5	117.35 (11)	C22—C23—H23	120.0
C10—C9—C8	107.94 (11)	C23—C24—C25	120.64 (19)
C5—C9—C8	106.85 (11)	C23—C24—H24	119.7
C10—C9—H9	108.1	C25—C24—H24	119.7
C5—C9—H9	108.1	C24—C25—C20	119.90 (18)
C8—C9—H9	108.1	C24—C25—H25	120.0
C11—C10—C13	118.51 (13)	C20—C25—H25	120.0
C11—C10—C9	122.20 (12)	O6—C26—O5	124.50 (15)
C13—C10—C9	119.20 (12)	O6—C26—C8	124.68 (14)
O2—C11—C10	124.21 (13)	O5—C26—C8	110.77 (12)
O2—C11—C15	113.56 (12)	O5—C27—H27A	109.5
C10—C11—C15	122.19 (13)	O5—C27—H27B	109.5
O2—C12—C20	107.87 (11)	H27A—C27—H27B	109.5
O2—C12—C8	109.69 (11)	O5—C27—H27C	109.5
C20—C12—C8	114.87 (11)	H27A—C27—H27C	109.5
O2—C12—H12	108.1	H27B—C27—H27C	109.5
C20—C12—H12	108.1	C6—O1—C7	118.76 (12)
C8—C12—H12	108.1	C11—O2—C12	116.87 (11)
O4—C13—O3	115.93 (13)	C14—O3—C13	121.98 (11)
O4—C13—C10	125.67 (14)	C26—O5—C27	115.86 (13)

C6—C1—C2—C3	0.0 (3)	O3—C14—C15—C11	4.2 (2)
C1—C2—C3—C4	−0.3 (3)	C19—C14—C15—C11	−176.08 (13)
C2—C3—C4—C5	1.1 (3)	O2—C11—C15—C14	179.24 (12)
C3—C4—C5—C6	−1.6 (2)	C10—C11—C15—C14	1.6 (2)
C3—C4—C5—C9	−174.77 (15)	O2—C11—C15—C16	1.9 (2)
C4—C5—C6—O1	−177.19 (14)	C10—C11—C15—C16	−175.73 (14)
C9—C5—C6—O1	−3.9 (2)	C14—C15—C16—C17	−1.0 (2)
C4—C5—C6—C1	1.4 (2)	C11—C15—C16—C17	176.29 (14)
C9—C5—C6—C1	174.64 (14)	C15—C16—C17—C18	−0.3 (3)
C2—C1—C6—O1	178.06 (15)	C16—C17—C18—C19	1.2 (3)
C2—C1—C6—C5	−0.6 (2)	C17—C18—C19—C14	−0.8 (2)
O1—C7—C8—C26	66.18 (16)	O3—C14—C19—C18	179.25 (14)
O1—C7—C8—C9	−56.20 (16)	C15—C14—C19—C18	−0.5 (2)
O1—C7—C8—C12	−175.67 (12)	O2—C12—C20—C21	142.93 (14)
C6—C5—C9—C10	93.17 (16)	C8—C12—C20—C21	−94.41 (17)
C4—C5—C9—C10	−93.83 (17)	O2—C12—C20—C25	−38.48 (18)
C6—C5—C9—C8	−28.10 (18)	C8—C12—C20—C25	84.17 (18)
C4—C5—C9—C8	144.90 (14)	C25—C20—C21—C22	0.5 (2)
C7—C8—C9—C10	−71.67 (14)	C12—C20—C21—C22	179.09 (15)
C26—C8—C9—C10	166.90 (11)	C20—C21—C22—C23	−0.1 (3)
C12—C8—C9—C10	49.16 (14)	C21—C22—C23—C24	−0.9 (3)
C7—C8—C9—C5	55.38 (15)	C22—C23—C24—C25	1.5 (3)
C26—C8—C9—C5	−66.05 (14)	C23—C24—C25—C20	−1.2 (3)
C12—C8—C9—C5	176.21 (11)	C21—C20—C25—C24	0.2 (2)
C5—C9—C10—C11	−140.03 (14)	C12—C20—C25—C24	−178.41 (15)
C8—C9—C10—C11	−19.34 (17)	C7—C8—C26—O6	14.1 (2)
C5—C9—C10—C13	43.55 (18)	C9—C8—C26—O6	135.12 (15)
C8—C9—C10—C13	164.25 (12)	C12—C8—C26—O6	−106.27 (16)
C13—C10—C11—O2	175.09 (12)	C7—C8—C26—O5	−168.35 (12)
C9—C10—C11—O2	−1.4 (2)	C9—C8—C26—O5	−47.33 (15)
C13—C10—C11—C15	−7.5 (2)	C12—C8—C26—O5	71.28 (14)
C9—C10—C11—C15	176.06 (12)	C5—C6—O1—C7	7.0 (2)
C7—C8—C12—O2	56.60 (15)	C1—C6—O1—C7	−171.66 (14)
C26—C8—C12—O2	176.37 (11)	C8—C7—O1—C6	24.1 (2)
C9—C8—C12—O2	−63.21 (14)	C10—C11—O2—C12	−11.38 (19)
C7—C8—C12—C20	−65.08 (16)	C15—C11—O2—C12	171.01 (11)
C26—C8—C12—C20	54.69 (16)	C20—C12—O2—C11	169.19 (11)
C9—C8—C12—C20	175.12 (12)	C8—C12—O2—C11	43.41 (15)
C11—C10—C13—O4	−171.57 (14)	C19—C14—O3—C13	176.57 (12)
C9—C10—C13—O4	5.0 (2)	C15—C14—O3—C13	−3.7 (2)
C11—C10—C13—O3	7.88 (19)	O4—C13—O3—C14	177.07 (13)
C9—C10—C13—O3	−175.57 (11)	C10—C13—O3—C14	−2.43 (19)
O3—C14—C15—C16	−178.36 (13)	O6—C26—O5—C27	3.7 (2)
C19—C14—C15—C16	1.4 (2)	C8—C26—O5—C27	−173.81 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C14–C19 and C1–C6, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.93	2.58	3.411 (2)	149
C27—H27C···O4ⁱⁱ	0.96	2.37	3.053 (2)	128
C12—H12···Cg1ⁱⁱⁱ	0.98	2.73	3.6861 (17)	166
C18—H18···Cg2^iv	0.93	2.84	3.674 (2)	150

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

(II) Methyl 1-oxo-6-phenyl-2,3,4,12b-tetrahydro-1H,6H-chromeno[3,4-c]chromene-6a(7H)-carboxylate] top

Crystal data top

C₂₄H₂₂O₅	F(000) = 824
M_r = 390.42	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5466 reflections
a = 11.1694 (10) Å	θ = 2.1–29.8°
b = 20.1405 (19) Å	µ = 0.09 mm⁻¹
c = 8.5835 (7) Å	T = 296 K
β = 96.453 (3)°	Block, colourless
V = 1918.7 (3) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5466 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω & φ scans	θ_max = 29.8°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.968, T_max = 0.977	k = −28→27
23342 measured reflections	l = −10→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0894P)² + 0.1805P] where P = (F_o² + 2F_c²)/3
5466 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.31613 (14)	0.23586 (8)	0.65866 (19)	0.0508 (4)
H1	0.2975	0.2790	0.6860	0.061*
C2	0.42353 (15)	0.20782 (10)	0.7195 (2)	0.0593 (4)
H2	0.4769	0.2317	0.7894	0.071*
C3	0.45178 (15)	0.14467 (10)	0.6769 (2)	0.0601 (4)
H3	0.5257	0.1262	0.7147	0.072*
C4	0.37039 (13)	0.10856 (8)	0.57786 (18)	0.0478 (4)
H4	0.3898	0.0653	0.5521	0.057*
C5	0.25975 (11)	0.13496 (7)	0.51513 (14)	0.0348 (3)
C6	0.23532 (12)	0.19988 (7)	0.55629 (16)	0.0379 (3)
C7	0.05795 (12)	0.20179 (7)	0.37858 (16)	0.0374 (3)
H7A	0.0956	0.2085	0.2833	0.045*
H7B	−0.0206	0.2229	0.3648	0.045*
C8	0.04229 (11)	0.12785 (6)	0.40481 (14)	0.0311 (3)
C9	0.16596 (11)	0.09252 (6)	0.41771 (14)	0.0316 (3)
H9	0.1580	0.0510	0.4751	0.038*
C10	0.20028 (12)	0.07429 (7)	0.25652 (15)	0.0376 (3)
C11	0.12973 (14)	0.08917 (8)	0.12367 (16)	0.0436 (3)
C12	−0.03692 (12)	0.09634 (7)	0.26444 (15)	0.0360 (3)
H12	−0.0339	0.0480	0.2781	0.043*
C13	0.29831 (14)	0.02678 (8)	0.2427 (2)	0.0486 (4)
C14	0.33358 (18)	0.01282 (12)	0.0817 (2)	0.0733 (6)
H14A	0.4203	0.0074	0.0892	0.088*
H14B	0.2971	−0.0288	0.0442	0.088*
C15	0.29703 (19)	0.06569 (12)	−0.0346 (2)	0.0751 (6)
H15A	0.3138	0.0513	−0.1378	0.090*
H15B	0.3437	0.1055	−0.0077	0.090*
C16	0.16417 (17)	0.08128 (11)	−0.03816 (19)	0.0652 (5)
H16A	0.1460	0.1219	−0.0968	0.078*
H16B	0.1173	0.0457	−0.0911	0.078*
C17	−0.16701 (13)	0.11648 (7)	0.23894 (16)	0.0418 (3)
C18	−0.20700 (17)	0.16855 (9)	0.1421 (2)	0.0578 (4)
H18	−0.1527	0.1939	0.0927	0.069*
C19	−0.3299 (2)	0.18263 (11)	0.1194 (3)	0.0842 (7)
H19	−0.3580	0.2171	0.0530	0.101*
C20	−0.40961 (19)	0.14608 (13)	0.1939 (4)	0.0922 (8)
H20	−0.4914	0.1560	0.1778	0.111*
C21	−0.37047 (17)	0.09518 (12)	0.2915 (3)	0.0804 (6)
H21	−0.4249	0.0709	0.3432	0.096*
C22	−0.24989 (14)	0.08015 (9)	0.3127 (2)	0.0560 (4)
H22	−0.2232	0.0450	0.3778	0.067*
C23	−0.01905 (11)	0.11340 (6)	0.55155 (15)	0.0326 (3)
C24	−0.16103 (16)	0.14882 (9)	0.7159 (2)	0.0607 (5)
H24A	−0.2197	0.1152	0.6843	0.091*
H24B	−0.2013	0.1887	0.7425	0.091*
H24C	−0.1091	0.1336	0.8055	0.091*
O1	0.12981 (9)	0.23212 (5)	0.50640 (12)	0.0447 (3)
O2	0.01594 (10)	0.11195 (6)	0.12316 (11)	0.0471 (3)
O3	0.34448 (11)	−0.00487 (7)	0.35498 (15)	0.0625 (3)
O4	−0.00799 (10)	0.06241 (5)	0.62305 (12)	0.0489 (3)
O5	−0.09014 (9)	0.16233 (5)	0.58848 (12)	0.0466 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0511 (9)	0.0473 (9)	0.0540 (9)	−0.0135 (7)	0.0058 (7)	−0.0108 (7)
C2	0.0479 (9)	0.0697 (12)	0.0575 (10)	−0.0193 (8)	−0.0071 (7)	−0.0041 (8)
C3	0.0403 (8)	0.0725 (12)	0.0642 (11)	−0.0054 (8)	−0.0084 (7)	0.0036 (9)
C4	0.0381 (7)	0.0530 (9)	0.0513 (9)	0.0026 (6)	−0.0001 (6)	−0.0004 (7)
C5	0.0338 (6)	0.0405 (7)	0.0303 (6)	−0.0017 (5)	0.0050 (5)	0.0011 (5)
C6	0.0361 (6)	0.0402 (7)	0.0383 (7)	−0.0044 (6)	0.0073 (5)	−0.0010 (5)
C7	0.0396 (7)	0.0326 (7)	0.0395 (7)	0.0011 (5)	0.0027 (5)	0.0026 (5)
C8	0.0317 (6)	0.0307 (6)	0.0305 (6)	0.0009 (5)	0.0025 (4)	0.0004 (5)
C9	0.0313 (6)	0.0316 (6)	0.0321 (6)	0.0024 (5)	0.0042 (5)	0.0006 (5)
C10	0.0394 (7)	0.0379 (7)	0.0368 (7)	−0.0015 (5)	0.0093 (5)	−0.0062 (5)
C11	0.0485 (8)	0.0467 (8)	0.0363 (7)	−0.0030 (6)	0.0082 (6)	−0.0066 (6)
C12	0.0384 (7)	0.0362 (7)	0.0323 (6)	0.0013 (5)	−0.0008 (5)	−0.0007 (5)
C13	0.0414 (8)	0.0502 (9)	0.0558 (9)	0.0002 (7)	0.0134 (7)	−0.0153 (7)
C14	0.0639 (11)	0.0924 (15)	0.0681 (12)	0.0066 (11)	0.0268 (9)	−0.0283 (11)
C15	0.0785 (13)	0.0995 (16)	0.0534 (11)	−0.0132 (12)	0.0334 (9)	−0.0195 (11)
C16	0.0760 (12)	0.0876 (14)	0.0339 (8)	−0.0055 (10)	0.0145 (8)	−0.0095 (8)
C17	0.0397 (7)	0.0412 (8)	0.0416 (7)	0.0045 (6)	−0.0079 (6)	−0.0072 (6)
C18	0.0592 (10)	0.0520 (10)	0.0576 (10)	0.0109 (8)	−0.0144 (8)	−0.0001 (7)
C19	0.0760 (14)	0.0629 (13)	0.1027 (17)	0.0275 (11)	−0.0389 (13)	−0.0101 (11)
C20	0.0431 (10)	0.0777 (16)	0.148 (2)	0.0128 (10)	−0.0234 (13)	−0.0324 (16)
C21	0.0398 (9)	0.0790 (15)	0.1203 (18)	−0.0055 (9)	0.0004 (11)	−0.0154 (13)
C22	0.0415 (8)	0.0573 (10)	0.0675 (11)	−0.0033 (7)	−0.0016 (7)	−0.0020 (8)
C23	0.0316 (6)	0.0338 (6)	0.0323 (6)	−0.0011 (5)	0.0027 (5)	−0.0029 (5)
C24	0.0606 (10)	0.0591 (10)	0.0691 (11)	0.0022 (8)	0.0366 (9)	−0.0021 (8)
O1	0.0432 (5)	0.0339 (5)	0.0560 (6)	−0.0005 (4)	0.0013 (4)	−0.0096 (4)
O2	0.0518 (6)	0.0586 (7)	0.0300 (5)	0.0053 (5)	0.0010 (4)	0.0005 (4)
O3	0.0557 (7)	0.0606 (8)	0.0711 (8)	0.0213 (6)	0.0069 (6)	−0.0092 (6)
O4	0.0620 (7)	0.0429 (6)	0.0442 (6)	0.0077 (5)	0.0161 (5)	0.0094 (4)
O5	0.0472 (6)	0.0415 (6)	0.0549 (6)	0.0055 (4)	0.0223 (5)	0.0020 (4)

Geometric parameters (Å, º) top

C1—C2	1.375 (2)	C13—O3	1.220 (2)
C1—C6	1.391 (2)	C13—C14	1.506 (2)
C1—H1	0.9300	C14—C15	1.485 (3)
C2—C3	1.370 (3)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C3—C4	1.380 (2)	C15—C16	1.514 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.3965 (19)	C15—H15B	0.9700
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.389 (2)	C16—H16B	0.9700
C5—C9	1.5265 (18)	C17—C18	1.381 (2)
C6—O1	1.3712 (17)	C17—C22	1.388 (2)
C7—O1	1.4224 (16)	C18—C19	1.394 (3)
C7—C8	1.5190 (18)	C18—H18	0.9300
C7—H7A	0.9700	C19—C20	1.368 (4)
C7—H7B	0.9700	C19—H19	0.9300
C8—C23	1.5280 (17)	C20—C21	1.365 (4)
C8—C9	1.5467 (17)	C20—H20	0.9300
C8—C12	1.5484 (18)	C21—C22	1.372 (2)
C9—C10	1.5216 (17)	C21—H21	0.9300
C9—H9	0.9800	C22—H22	0.9300
C10—C11	1.345 (2)	C23—O4	1.1957 (16)
C10—C13	1.469 (2)	C23—O5	1.3262 (15)
C11—O2	1.3508 (18)	C24—O5	1.4465 (17)
C11—C16	1.491 (2)	C24—H24A	0.9600
C12—O2	1.4418 (16)	C24—H24B	0.9600
C12—C17	1.5008 (19)	C24—H24C	0.9600
C12—H12	0.9800

C2—C1—C6	120.18 (16)	C10—C13—C14	118.02 (16)
C2—C1—H1	119.9	C15—C14—C13	113.74 (16)
C6—C1—H1	119.9	C15—C14—H14A	108.8
C3—C2—C1	119.83 (15)	C13—C14—H14A	108.8
C3—C2—H2	120.1	C15—C14—H14B	108.8
C1—C2—H2	120.1	C13—C14—H14B	108.8
C2—C3—C4	119.87 (16)	H14A—C14—H14B	107.7
C2—C3—H3	120.1	C14—C15—C16	110.94 (16)
C4—C3—H3	120.1	C14—C15—H15A	109.5
C3—C4—C5	122.02 (16)	C16—C15—H15A	109.5
C3—C4—H4	119.0	C14—C15—H15B	109.5
C5—C4—H4	119.0	C16—C15—H15B	109.5
C6—C5—C4	116.79 (13)	H15A—C15—H15B	108.0
C6—C5—C9	121.60 (11)	C11—C16—C15	110.98 (15)
C4—C5—C9	121.41 (13)	C11—C16—H16A	109.4
O1—C6—C5	123.54 (12)	C15—C16—H16A	109.4
O1—C6—C1	115.13 (13)	C11—C16—H16B	109.4
C5—C6—C1	121.26 (14)	C15—C16—H16B	109.4
O1—C7—C8	111.79 (11)	H16A—C16—H16B	108.0
O1—C7—H7A	109.3	C18—C17—C22	119.22 (15)
C8—C7—H7A	109.3	C18—C17—C12	122.37 (15)
O1—C7—H7B	109.3	C22—C17—C12	118.39 (13)
C8—C7—H7B	109.3	C17—C18—C19	119.0 (2)
H7A—C7—H7B	107.9	C17—C18—H18	120.5
C7—C8—C23	112.26 (10)	C19—C18—H18	120.5
C7—C8—C9	110.17 (10)	C20—C19—C18	120.5 (2)
C23—C8—C9	109.45 (10)	C20—C19—H19	119.8
C7—C8—C12	110.59 (10)	C18—C19—H19	119.8
C23—C8—C12	107.06 (10)	C21—C20—C19	120.75 (19)
C9—C8—C12	107.14 (10)	C21—C20—H20	119.6
C10—C9—C5	113.94 (10)	C19—C20—H20	119.6
C10—C9—C8	111.11 (10)	C20—C21—C22	119.3 (2)
C5—C9—C8	109.51 (10)	C20—C21—H21	120.4
C10—C9—H9	107.3	C22—C21—H21	120.4
C5—C9—H9	107.3	C21—C22—C17	121.21 (19)
C8—C9—H9	107.3	C21—C22—H22	119.4
C11—C10—C13	116.61 (12)	C17—C22—H22	119.4
C11—C10—C9	122.25 (12)	O4—C23—O5	123.07 (12)
C13—C10—C9	119.78 (12)	O4—C23—C8	123.83 (11)
C10—C11—O2	122.67 (12)	O5—C23—C8	113.04 (11)
C10—C11—C16	125.32 (15)	O5—C24—H24A	109.5
O2—C11—C16	111.99 (13)	O5—C24—H24B	109.5
O2—C12—C17	107.44 (11)	H24A—C24—H24B	109.5
O2—C12—C8	108.24 (10)	O5—C24—H24C	109.5
C17—C12—C8	117.51 (11)	H24A—C24—H24C	109.5
O2—C12—H12	107.8	H24B—C24—H24C	109.5
C17—C12—H12	107.8	C6—O1—C7	115.35 (10)
C8—C12—H12	107.8	C11—O2—C12	113.41 (10)
O3—C13—C10	121.98 (14)	C23—O5—C24	115.74 (12)
O3—C13—C14	119.76 (15)

C6—C1—C2—C3	1.1 (3)	C11—C10—C13—O3	−158.15 (16)
C1—C2—C3—C4	−2.5 (3)	C9—C10—C13—O3	8.8 (2)
C2—C3—C4—C5	1.7 (3)	C11—C10—C13—C14	16.1 (2)
C3—C4—C5—C6	0.4 (2)	C9—C10—C13—C14	−176.91 (14)
C3—C4—C5—C9	−174.44 (14)	O3—C13—C14—C15	−164.40 (17)
C4—C5—C6—O1	−178.79 (12)	C10—C13—C14—C15	21.2 (2)
C9—C5—C6—O1	−3.93 (19)	C13—C14—C15—C16	−52.5 (2)
C4—C5—C6—C1	−1.78 (19)	C10—C11—C16—C15	−10.0 (3)
C9—C5—C6—C1	173.08 (12)	O2—C11—C16—C15	171.53 (16)
C2—C1—C6—O1	178.29 (13)	C14—C15—C16—C11	46.8 (2)
C2—C1—C6—C5	1.0 (2)	O2—C12—C17—C18	−30.11 (18)
O1—C7—C8—C23	60.13 (14)	C8—C12—C17—C18	92.13 (16)
O1—C7—C8—C9	−62.12 (13)	O2—C12—C17—C22	148.25 (13)
O1—C7—C8—C12	179.62 (10)	C8—C12—C17—C22	−89.51 (17)
C6—C5—C9—C10	114.47 (13)	C22—C17—C18—C19	−0.9 (2)
C4—C5—C9—C10	−70.91 (16)	C12—C17—C18—C19	177.47 (16)
C6—C5—C9—C8	−10.65 (16)	C17—C18—C19—C20	1.0 (3)
C4—C5—C9—C8	163.97 (12)	C18—C19—C20—C21	−0.1 (4)
C7—C8—C9—C10	−85.59 (13)	C19—C20—C21—C22	−1.0 (4)
C23—C8—C9—C10	150.52 (11)	C20—C21—C22—C17	1.2 (3)
C12—C8—C9—C10	34.77 (14)	C18—C17—C22—C21	−0.2 (3)
C7—C8—C9—C5	41.15 (13)	C12—C17—C22—C21	−178.62 (16)
C23—C8—C9—C5	−82.74 (12)	C7—C8—C23—O4	−155.62 (13)
C12—C8—C9—C5	161.51 (10)	C9—C8—C23—O4	−32.96 (17)
C5—C9—C10—C11	−123.25 (14)	C12—C8—C23—O4	82.84 (15)
C8—C9—C10—C11	1.02 (18)	C7—C8—C23—O5	26.93 (15)
C5—C9—C10—C13	70.53 (16)	C9—C8—C23—O5	149.59 (11)
C8—C9—C10—C13	−165.20 (12)	C12—C8—C23—O5	−94.61 (12)
C13—C10—C11—O2	156.24 (14)	C5—C6—O1—C7	−15.15 (18)
C9—C10—C11—O2	−10.4 (2)	C1—C6—O1—C7	167.68 (12)
C13—C10—C11—C16	−22.1 (2)	C8—C7—O1—C6	48.13 (15)
C9—C10—C11—C16	171.31 (15)	C10—C11—O2—C12	−21.3 (2)
C7—C8—C12—O2	54.74 (13)	C16—C11—O2—C12	157.21 (13)
C23—C8—C12—O2	177.32 (10)	C17—C12—O2—C11	−172.70 (12)
C9—C8—C12—O2	−65.35 (13)	C8—C12—O2—C11	59.47 (14)
C7—C8—C12—C17	−67.09 (15)	O4—C23—O5—C24	−4.0 (2)
C23—C8—C12—C17	55.49 (15)	C8—C23—O5—C24	173.49 (12)
C9—C8—C12—C17	172.82 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3	0.93	2.22	2.973 (2)	138
C12—H12···O4ⁱ	0.98	2.41	3.3613 (18)	164

Symmetry code: (i) −x, −y, −z+1.

(III) 6-(4-Ethylphenyl)-2,4-dimethyl-1,3-dioxo-2,3,4,12b-tetrahydro-1H,6H-chromeno[4',3':4,5]pyrano[2,3-d]pyrimidine-6a(7H)-carbonitrile] top

Crystal data top

C₂₅H₂₃N₃O₄	F(000) = 904
M_r = 429.46	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3715 reflections
a = 11.4471 (5) Å	θ = 2.1–25.0°
b = 11.2076 (4) Å	µ = 0.09 mm⁻¹
c = 16.5407 (7) Å	T = 296 K
β = 91.990 (2)°	Block, colourless
V = 2120.80 (15) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3715 independent reflections
Radiation source: fine-focus sealed tube	2814 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω & φ scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
T_min = 0.968, T_max = 0.977	k = −10→13
18281 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0576P)² + 0.8627P] where P = (F_o² + 2F_c²)/3
3715 reflections	(Δ/σ)_max = 0.007
292 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.1534 (2)	−0.1733 (2)	0.02179 (14)	0.0590 (6)
H1	0.1589	−0.1965	−0.0319	0.071*
C2	0.0885 (2)	−0.2402 (2)	0.07377 (15)	0.0609 (6)
H2	0.0507	−0.3091	0.0555	0.073*
C3	0.0802 (2)	−0.2042 (2)	0.15302 (15)	0.0565 (6)
H3	0.0371	−0.2493	0.1886	0.068*
C4	0.13542 (17)	−0.10173 (18)	0.17962 (13)	0.0465 (5)
H4	0.1289	−0.0786	0.2333	0.056*
C5	0.20076 (16)	−0.03175 (17)	0.12840 (11)	0.0396 (4)
C6	0.21040 (18)	−0.07139 (18)	0.04949 (12)	0.0468 (5)
C7	0.35811 (18)	0.06931 (19)	0.02593 (12)	0.0468 (5)
H7A	0.3918	0.1143	−0.0176	0.056*
H7B	0.4205	0.0255	0.0538	0.056*
C8	0.30204 (16)	0.15565 (17)	0.08532 (11)	0.0373 (4)
C9	0.25965 (16)	0.08300 (17)	0.15816 (11)	0.0372 (4)
H9	0.3287	0.0606	0.1915	0.045*
C10	0.18416 (15)	0.16192 (16)	0.20870 (11)	0.0359 (4)
C11	0.13384 (15)	0.26105 (17)	0.17771 (10)	0.0353 (4)
C12	0.19681 (16)	0.22106 (17)	0.04440 (11)	0.0374 (4)
H12	0.1394	0.1608	0.0267	0.045*
C13	0.17301 (16)	0.13736 (17)	0.29330 (11)	0.0391 (4)
C14	0.04976 (16)	0.31618 (18)	0.30307 (12)	0.0409 (5)
C15	0.01236 (19)	0.44176 (19)	0.18395 (13)	0.0522 (5)
H15A	0.0704	0.4894	0.1586	0.078*
H15B	−0.0251	0.4883	0.2243	0.078*
H15C	−0.0449	0.4159	0.1439	0.078*
C16	0.0767 (2)	0.1869 (2)	0.41949 (12)	0.0571 (6)
H16A	0.1301	0.2304	0.4545	0.086*
H16B	0.0866	0.1029	0.4287	0.086*
H16C	−0.0021	0.2094	0.4306	0.086*
C17	0.22490 (16)	0.29571 (17)	−0.02756 (11)	0.0378 (4)
C18	0.2163 (2)	0.24542 (19)	−0.10328 (12)	0.0496 (5)
H18	0.1908	0.1670	−0.1091	0.059*
C19	0.2453 (2)	0.31004 (19)	−0.17082 (12)	0.0556 (6)
H19	0.2390	0.2742	−0.2215	0.067*
C20	0.28318 (19)	0.42640 (18)	−0.16474 (12)	0.0474 (5)
C21	0.29008 (19)	0.47620 (18)	−0.08850 (12)	0.0490 (5)
H21	0.3152	0.5548	−0.0828	0.059*
C22	0.26093 (18)	0.41312 (17)	−0.02041 (12)	0.0443 (5)
H22	0.2655	0.4495	0.0301	0.053*
C23	0.3174 (3)	0.4970 (2)	−0.23790 (14)	0.0722 (7)
H23A	0.2502	0.5435	−0.2564	0.087*
H23B	0.3782	0.5528	−0.2210	0.087*
C24	0.3588 (3)	0.4293 (3)	−0.30635 (16)	0.0839 (9)
H24A	0.4161	0.3723	−0.2876	0.126*
H24B	0.3932	0.4827	−0.3441	0.126*
H24C	0.2942	0.3882	−0.3325	0.126*
C25	0.39321 (18)	0.24049 (19)	0.11184 (12)	0.0438 (5)
N1	0.10034 (14)	0.21462 (15)	0.33494 (9)	0.0413 (4)
N2	0.06822 (13)	0.33754 (14)	0.22202 (9)	0.0395 (4)
N3	0.46792 (18)	0.3023 (2)	0.13123 (13)	0.0693 (6)
O1	0.27450 (14)	−0.01194 (13)	−0.00673 (8)	0.0555 (4)
O2	0.14164 (11)	0.29896 (11)	0.10132 (7)	0.0415 (3)
O3	0.22107 (12)	0.05425 (13)	0.32899 (8)	0.0499 (4)
O4	−0.00801 (13)	0.38384 (13)	0.34285 (9)	0.0544 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0813 (16)	0.0442 (13)	0.0515 (13)	−0.0007 (12)	0.0011 (12)	−0.0045 (10)
C2	0.0706 (15)	0.0425 (13)	0.0691 (16)	−0.0078 (11)	−0.0053 (12)	0.0015 (12)
C3	0.0590 (13)	0.0445 (13)	0.0664 (15)	−0.0057 (10)	0.0076 (11)	0.0091 (11)
C4	0.0524 (12)	0.0405 (12)	0.0470 (11)	0.0016 (9)	0.0088 (9)	0.0058 (9)
C5	0.0433 (10)	0.0358 (11)	0.0400 (10)	0.0066 (8)	0.0066 (8)	0.0037 (8)
C6	0.0596 (12)	0.0367 (11)	0.0445 (11)	0.0040 (9)	0.0084 (10)	0.0039 (9)
C7	0.0562 (12)	0.0425 (12)	0.0427 (11)	0.0034 (10)	0.0172 (9)	0.0018 (9)
C8	0.0407 (10)	0.0363 (11)	0.0355 (10)	0.0006 (8)	0.0098 (8)	0.0019 (8)
C9	0.0405 (10)	0.0375 (11)	0.0341 (10)	0.0034 (8)	0.0081 (8)	0.0045 (8)
C10	0.0392 (9)	0.0361 (10)	0.0330 (9)	−0.0017 (8)	0.0097 (8)	0.0006 (8)
C11	0.0349 (9)	0.0385 (11)	0.0330 (9)	−0.0036 (8)	0.0081 (7)	0.0006 (8)
C12	0.0437 (10)	0.0361 (11)	0.0327 (9)	−0.0012 (8)	0.0086 (8)	0.0012 (8)
C13	0.0394 (10)	0.0402 (11)	0.0382 (10)	−0.0040 (9)	0.0080 (8)	0.0015 (9)
C14	0.0388 (10)	0.0436 (12)	0.0411 (11)	−0.0063 (9)	0.0114 (8)	−0.0045 (9)
C15	0.0535 (12)	0.0487 (13)	0.0550 (13)	0.0134 (10)	0.0117 (10)	0.0039 (10)
C16	0.0685 (14)	0.0674 (16)	0.0364 (11)	−0.0008 (12)	0.0178 (10)	0.0042 (10)
C17	0.0424 (10)	0.0369 (11)	0.0343 (10)	−0.0020 (8)	0.0051 (8)	0.0026 (8)
C18	0.0733 (14)	0.0363 (11)	0.0394 (11)	−0.0115 (10)	0.0070 (10)	−0.0011 (9)
C19	0.0886 (17)	0.0463 (13)	0.0323 (10)	−0.0067 (12)	0.0100 (10)	−0.0031 (9)
C20	0.0643 (13)	0.0396 (12)	0.0391 (11)	−0.0005 (10)	0.0109 (9)	0.0050 (9)
C21	0.0699 (14)	0.0332 (11)	0.0443 (11)	−0.0060 (10)	0.0062 (10)	0.0022 (9)
C22	0.0610 (12)	0.0363 (11)	0.0359 (10)	−0.0038 (9)	0.0050 (9)	−0.0010 (8)
C23	0.114 (2)	0.0560 (15)	0.0477 (13)	−0.0055 (14)	0.0223 (14)	0.0121 (12)
C24	0.116 (2)	0.0790 (19)	0.0596 (16)	0.0160 (17)	0.0368 (15)	0.0218 (14)
C25	0.0440 (11)	0.0488 (12)	0.0392 (10)	0.0005 (10)	0.0107 (9)	0.0037 (9)
N1	0.0469 (9)	0.0451 (10)	0.0326 (8)	−0.0020 (8)	0.0118 (7)	0.0003 (7)
N2	0.0408 (8)	0.0376 (9)	0.0409 (9)	0.0034 (7)	0.0110 (7)	0.0004 (7)
N3	0.0617 (12)	0.0812 (15)	0.0654 (13)	−0.0214 (12)	0.0054 (10)	−0.0054 (11)
O1	0.0826 (11)	0.0449 (9)	0.0402 (8)	−0.0055 (8)	0.0187 (7)	−0.0042 (7)
O2	0.0500 (8)	0.0403 (8)	0.0349 (7)	0.0083 (6)	0.0118 (6)	0.0060 (6)
O3	0.0603 (9)	0.0507 (9)	0.0390 (7)	0.0067 (7)	0.0071 (6)	0.0089 (7)
O4	0.0604 (9)	0.0524 (9)	0.0518 (9)	0.0056 (7)	0.0219 (7)	−0.0091 (7)

Geometric parameters (Å, º) top

C1—C2	1.378 (3)	C14—O4	1.215 (2)
C1—C6	1.385 (3)	C14—N1	1.374 (3)
C1—H1	0.9300	C14—N2	1.385 (2)
C2—C3	1.378 (3)	C15—N2	1.463 (3)
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.376 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.392 (3)	C16—N1	1.467 (2)
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.387 (3)	C16—H16B	0.9600
C5—C9	1.526 (3)	C16—H16C	0.9600
C6—O1	1.376 (2)	C17—C18	1.374 (3)
C7—O1	1.415 (2)	C17—C22	1.383 (3)
C7—C8	1.535 (3)	C18—C19	1.381 (3)
C7—H7A	0.9700	C18—H18	0.9300
C7—H7B	0.9700	C19—C20	1.377 (3)
C8—C25	1.468 (3)	C19—H19	0.9300
C8—C12	1.546 (3)	C20—C21	1.379 (3)
C8—C9	1.546 (2)	C20—C23	1.508 (3)
C9—C10	1.509 (2)	C21—C22	1.381 (3)
C9—H9	0.9800	C21—H21	0.9300
C10—C11	1.345 (3)	C22—H22	0.9300
C10—C13	1.436 (3)	C23—C24	1.456 (3)
C11—O2	1.339 (2)	C23—H23A	0.9700
C11—N2	1.369 (2)	C23—H23B	0.9700
C12—O2	1.445 (2)	C24—H24A	0.9600
C12—C17	1.499 (2)	C24—H24B	0.9600
C12—H12	0.9800	C24—H24C	0.9600
C13—O3	1.223 (2)	C25—N3	1.138 (3)
C13—N1	1.399 (2)

C2—C1—C6	120.0 (2)	N1—C14—N2	115.99 (16)
C2—C1—H1	120.0	N2—C15—H15A	109.5
C6—C1—H1	120.0	N2—C15—H15B	109.5
C1—C2—C3	119.4 (2)	H15A—C15—H15B	109.5
C1—C2—H2	120.3	N2—C15—H15C	109.5
C3—C2—H2	120.3	H15A—C15—H15C	109.5
C4—C3—C2	120.1 (2)	H15B—C15—H15C	109.5
C4—C3—H3	119.9	N1—C16—H16A	109.5
C2—C3—H3	119.9	N1—C16—H16B	109.5
C3—C4—C5	121.8 (2)	H16A—C16—H16B	109.5
C3—C4—H4	119.1	N1—C16—H16C	109.5
C5—C4—H4	119.1	H16A—C16—H16C	109.5
C6—C5—C4	117.03 (18)	H16B—C16—H16C	109.5
C6—C5—C9	121.66 (17)	C18—C17—C22	118.68 (17)
C4—C5—C9	121.31 (17)	C18—C17—C12	118.97 (17)
O1—C6—C1	115.57 (19)	C22—C17—C12	122.33 (17)
O1—C6—C5	122.86 (18)	C17—C18—C19	120.71 (19)
C1—C6—C5	121.6 (2)	C17—C18—H18	119.6
O1—C7—C8	110.96 (16)	C19—C18—H18	119.6
O1—C7—H7A	109.4	C20—C19—C18	121.42 (19)
C8—C7—H7A	109.4	C20—C19—H19	119.3
O1—C7—H7B	109.4	C18—C19—H19	119.3
C8—C7—H7B	109.4	C19—C20—C21	117.26 (18)
H7A—C7—H7B	108.0	C19—C20—C23	121.85 (19)
C25—C8—C7	106.91 (15)	C21—C20—C23	120.9 (2)
C25—C8—C12	111.03 (16)	C20—C21—C22	122.08 (19)
C7—C8—C12	110.82 (15)	C20—C21—H21	119.0
C25—C8—C9	110.33 (15)	C22—C21—H21	119.0
C7—C8—C9	108.43 (16)	C21—C22—C17	119.83 (18)
C12—C8—C9	109.27 (14)	C21—C22—H22	120.1
C10—C9—C5	114.68 (15)	C17—C22—H22	120.1
C10—C9—C8	108.92 (15)	C24—C23—C20	116.8 (2)
C5—C9—C8	109.86 (15)	C24—C23—H23A	108.1
C10—C9—H9	107.7	C20—C23—H23A	108.1
C5—C9—H9	107.7	C24—C23—H23B	108.1
C8—C9—H9	107.7	C20—C23—H23B	108.1
C11—C10—C13	118.58 (17)	H23A—C23—H23B	107.3
C11—C10—C9	121.25 (16)	C23—C24—H24A	109.5
C13—C10—C9	119.96 (16)	C23—C24—H24B	109.5
O2—C11—C10	125.46 (16)	H24A—C24—H24B	109.5
O2—C11—N2	111.24 (16)	C23—C24—H24C	109.5
C10—C11—N2	123.29 (16)	H24A—C24—H24C	109.5
O2—C12—C17	106.90 (14)	H24B—C24—H24C	109.5
O2—C12—C8	110.65 (14)	N3—C25—C8	176.6 (2)
C17—C12—C8	115.27 (15)	C14—N1—C13	125.03 (16)
O2—C12—H12	107.9	C14—N1—C16	116.85 (16)
C17—C12—H12	107.9	C13—N1—C16	118.12 (17)
C8—C12—H12	107.9	C11—N2—C14	120.98 (16)
O3—C13—N1	119.93 (17)	C11—N2—C15	120.60 (16)
O3—C13—C10	124.23 (17)	C14—N2—C15	118.38 (16)
N1—C13—C10	115.83 (17)	C6—O1—C7	115.02 (15)
O4—C14—N1	122.65 (18)	C11—O2—C12	117.91 (14)
O4—C14—N2	121.36 (19)

C6—C1—C2—C3	0.6 (4)	C9—C10—C13—N1	−179.40 (15)
C1—C2—C3—C4	0.6 (3)	O2—C12—C17—C18	−144.56 (18)
C2—C3—C4—C5	−0.1 (3)	C8—C12—C17—C18	92.0 (2)
C3—C4—C5—C6	−1.6 (3)	O2—C12—C17—C22	36.5 (2)
C3—C4—C5—C9	178.79 (18)	C8—C12—C17—C22	−87.0 (2)
C2—C1—C6—O1	178.9 (2)	C22—C17—C18—C19	1.2 (3)
C2—C1—C6—C5	−2.3 (3)	C12—C17—C18—C19	−177.8 (2)
C4—C5—C6—O1	−178.57 (18)	C17—C18—C19—C20	−0.2 (4)
C9—C5—C6—O1	1.1 (3)	C18—C19—C20—C21	−0.6 (3)
C4—C5—C6—C1	2.8 (3)	C18—C19—C20—C23	178.7 (2)
C9—C5—C6—C1	−177.61 (19)	C19—C20—C21—C22	0.2 (3)
O1—C7—C8—C25	−176.52 (15)	C23—C20—C21—C22	−179.1 (2)
O1—C7—C8—C12	−55.4 (2)	C20—C21—C22—C17	0.8 (3)
O1—C7—C8—C9	64.5 (2)	C18—C17—C22—C21	−1.5 (3)
C6—C5—C9—C10	135.93 (18)	C12—C17—C22—C21	177.45 (18)
C4—C5—C9—C10	−44.5 (2)	C19—C20—C23—C24	−26.5 (4)
C6—C5—C9—C8	12.9 (2)	C21—C20—C23—C24	152.7 (3)
C4—C5—C9—C8	−167.51 (17)	O4—C14—N1—C13	−176.16 (18)
C25—C8—C9—C10	74.10 (19)	N2—C14—N1—C13	3.9 (3)
C7—C8—C9—C10	−169.13 (15)	O4—C14—N1—C16	3.1 (3)
C12—C8—C9—C10	−48.2 (2)	N2—C14—N1—C16	−176.82 (17)
C25—C8—C9—C5	−159.52 (15)	O3—C13—N1—C14	174.31 (18)
C7—C8—C9—C5	−42.75 (19)	C10—C13—N1—C14	−6.6 (3)
C12—C8—C9—C5	78.14 (18)	O3—C13—N1—C16	−4.9 (3)
C5—C9—C10—C11	−103.3 (2)	C10—C13—N1—C16	174.15 (17)
C8—C9—C10—C11	20.3 (2)	O2—C11—N2—C14	−179.32 (15)
C5—C9—C10—C13	82.0 (2)	C10—C11—N2—C14	0.0 (3)
C8—C9—C10—C13	−154.41 (16)	O2—C11—N2—C15	2.9 (2)
C13—C10—C11—O2	176.38 (16)	C10—C11—N2—C15	−177.83 (18)
C9—C10—C11—O2	1.6 (3)	O4—C14—N2—C11	179.73 (17)
C13—C10—C11—N2	−2.8 (3)	N1—C14—N2—C11	−0.4 (3)
C9—C10—C11—N2	−177.56 (16)	O4—C14—N2—C15	−2.4 (3)
C25—C8—C12—O2	−63.45 (19)	N1—C14—N2—C15	177.48 (16)
C7—C8—C12—O2	177.89 (14)	C1—C6—O1—C7	−162.40 (19)
C9—C8—C12—O2	58.46 (19)	C5—C6—O1—C7	18.9 (3)
C25—C8—C12—C17	58.0 (2)	C8—C7—O1—C6	−51.8 (2)
C7—C8—C12—C17	−60.7 (2)	C10—C11—O2—C12	7.7 (3)
C9—C8—C12—C17	179.90 (15)	N2—C11—O2—C12	−173.07 (14)
C11—C10—C13—O3	−175.21 (18)	C17—C12—O2—C11	−164.19 (15)
C9—C10—C13—O3	−0.4 (3)	C8—C12—O2—C11	−37.9 (2)
C11—C10—C13—N1	5.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C14–C19 and C1–C6, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3	0.93	2.39	3.155 (3)	139
C7—H7B···O4ⁱ	0.97	2.52	3.423 (3)	156
C15—H15A···O3ⁱⁱ	0.96	2.50	3.315 (3)	143
C16—H16C···Cg1ⁱⁱⁱ	0.96	2.93	3.739 (2)	143
C24—H24A···Cg2^iv	0.96	2.70	3.634 (3)	164

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

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