Crystal structure of 2-amino-5,6,7,8-tetra­hydro-7,7-dimethyl-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbo­nitrile

Both six-membered rings of the fused heterocyclic system of the title compound display envelope conformations. Two hydrogen bonds involving the amino group lead to a double-layer structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.086
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B      ..N2       .       2.69 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.842 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C3       --C9       .        7.3 s.u.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         17 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
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 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
   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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).

2-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbonitrile

Crystal data

C22H20N2O2	F(000) = 1456
Mr = 344.40	Dx = 1.257 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 25.3144 (3) Å	Cell parameters from 35871 reflections
b = 9.25765 (11) Å	θ = 3.5–77.4°
c = 15.6778 (2) Å	µ = 0.65 mm^−1
β = 97.8724 (10)°	T = 100 K
V = 3639.51 (8) Å^3	Lath, colourless
Z = 8	0.08 × 0.05 × 0.02 mm

Data collection

XtaLAB Synergy, HyPix diffractometer	3856 independent reflections
Radiation source: micro-focus sealed X-ray tube	3694 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.030
ω scans	θmax = 77.6°, θmin = 3.5°
Absorption correction: multi-scan (CrysalisPro; Rigaku OD, 2021)	h = −31→31
Tmin = 0.826, Tmax = 1.000	k = −11→11
61093 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0362P)^2 + 2.6486P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3856 reflections	Δρmax = 0.22 e Å^−3
245 parameters	Δρmin = −0.20 e Å^−3
1 restraint

Special details

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

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

24.6913 (0.0028) x - 2.0266 (0.0045) y - 2.5063 (0.0065) z = 7.9737 (0.0050)

* -0.0099 (0.0006) C4A * -0.0265 (0.0007) C5 * 0.0300 (0.0005) C6 * -0.0353 (0.0005) C8 * 0.0417 (0.0007) C8A -0.6525 (0.0015) C7

Rms deviation of fitted atoms = 0.0306

23.4020 (0.0039) x - 3.5289 (0.0034) y - 1.8463 (0.0073) z = 7.1162 (0.0054)

Angle to previous plane (with approximate esd) = 9.967 ( 0.036 )

* -0.0423 (0.0006) O1 * 0.0228 (0.0006) C2 * -0.0021 (0.0005) C3 * -0.0200 (0.0005) C4A * 0.0415 (0.0006) C8A -0.3166 (0.0014) C4

Rms deviation of fitted atoms = 0.0298

- 6.0033 (0.0056) x - 6.6409 (0.0023) y + 10.6832 (0.0042) z = 0.1010 (0.0050)

Angle to previous plane (with approximate esd) = 86.556 ( 0.027 )

* -0.0188 (0.0008) C12 * -0.0048 (0.0008) C13 * 0.0149 (0.0009) C14 * 0.0098 (0.0010) C15 * -0.0015 (0.0011) C16 * -0.0151 (0.0011) C17 * -0.0093 (0.0011) C18 * 0.0169 (0.0011) C19 * 0.0111 (0.0010) C20 * -0.0032 (0.0010) C21

Rms deviation of fitted atoms = 0.0119

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

	x	y	z	Uiso*/Ueq
O1	0.42046 (3)	0.54277 (7)	0.46059 (4)	0.01878 (16)
C2	0.44459 (4)	0.67304 (10)	0.48220 (6)	0.01719 (19)
N1	0.45324 (4)	0.74447 (10)	0.41141 (6)	0.02197 (19)
H01	0.4646 (6)	0.8361 (15)	0.4146 (9)	0.038 (4)*
H02	0.4446 (6)	0.7028 (15)	0.3594 (8)	0.036 (4)*
C3	0.45648 (4)	0.71509 (10)	0.56594 (6)	0.0174 (2)
C4	0.43643 (4)	0.63303 (11)	0.63906 (6)	0.0175 (2)
H4	0.465617	0.629568	0.688927	0.021*
C4A	0.42383 (4)	0.48120 (10)	0.60884 (6)	0.0172 (2)
C5	0.42044 (4)	0.36809 (11)	0.67350 (6)	0.0198 (2)
O2	0.42982 (3)	0.39810 (8)	0.75024 (5)	0.02716 (18)
C6	0.40710 (4)	0.21643 (11)	0.64222 (7)	0.0231 (2)
H6A	0.389602	0.164811	0.686041	0.028*
H6B	0.440604	0.164729	0.636056	0.028*
C7	0.37033 (4)	0.21205 (11)	0.55576 (7)	0.0223 (2)
C8	0.39608 (4)	0.30239 (11)	0.49014 (6)	0.0204 (2)
H8A	0.426832	0.248784	0.473153	0.025*
H8B	0.369856	0.316614	0.437883	0.025*
C8A	0.41454 (4)	0.44589 (10)	0.52524 (6)	0.01697 (19)
C9	0.48381 (4)	0.84661 (11)	0.58446 (6)	0.0183 (2)
N2	0.50703 (4)	0.95261 (10)	0.60116 (6)	0.0238 (2)
C10	0.36359 (5)	0.05655 (12)	0.52270 (8)	0.0311 (3)
H10A	0.338967	0.055087	0.468724	0.047*
H10B	0.349210	−0.003296	0.565660	0.047*
H10C	0.398300	0.018361	0.512555	0.047*
C11	0.31556 (4)	0.27340 (14)	0.56747 (8)	0.0312 (3)
H11A	0.320032	0.368819	0.594563	0.047*
H11B	0.298005	0.208440	0.604174	0.047*
H11C	0.293616	0.282185	0.511149	0.047*
C12	0.33761 (4)	0.68876 (11)	0.62556 (6)	0.0203 (2)
H12	0.332117	0.622111	0.579111	0.024*
C13	0.38823 (4)	0.70882 (11)	0.66778 (6)	0.0189 (2)
C14	0.39613 (5)	0.80926 (12)	0.73650 (7)	0.0265 (2)
H14	0.430947	0.823540	0.766542	0.032*
C15	0.35431 (5)	0.88596 (13)	0.76020 (7)	0.0330 (3)
H15	0.360637	0.953461	0.806098	0.040*
C16	0.30184 (5)	0.86665 (13)	0.71766 (7)	0.0308 (3)
C17	0.25720 (6)	0.94476 (16)	0.73986 (9)	0.0462 (4)
H17	0.262423	1.014310	0.784776	0.055*
C18	0.20725 (6)	0.92164 (18)	0.69796 (10)	0.0517 (4)
H18	0.178037	0.975221	0.713572	0.062*
C19	0.19874 (5)	0.81873 (17)	0.63165 (10)	0.0460 (4)
H19	0.163632	0.801759	0.603416	0.055*
C20	0.24071 (5)	0.74252 (14)	0.60733 (8)	0.0336 (3)
H20	0.234466	0.674176	0.561864	0.040*
C21	0.29329 (4)	0.76481 (12)	0.64938 (7)	0.0249 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0252 (4)	0.0155 (3)	0.0155 (3)	−0.0050 (3)	0.0022 (3)	0.0003 (3)
C2	0.0174 (4)	0.0155 (4)	0.0189 (5)	−0.0018 (3)	0.0030 (3)	−0.0002 (4)
N1	0.0322 (5)	0.0182 (4)	0.0159 (4)	−0.0071 (4)	0.0049 (3)	−0.0012 (3)
C3	0.0179 (4)	0.0165 (5)	0.0176 (5)	−0.0017 (4)	0.0024 (3)	0.0004 (4)
C4	0.0204 (5)	0.0176 (5)	0.0141 (4)	−0.0018 (4)	0.0005 (3)	0.0008 (4)
C4A	0.0162 (4)	0.0164 (5)	0.0190 (5)	0.0003 (3)	0.0025 (3)	0.0014 (4)
C5	0.0195 (5)	0.0199 (5)	0.0204 (5)	0.0019 (4)	0.0036 (4)	0.0030 (4)
O2	0.0386 (4)	0.0249 (4)	0.0177 (4)	0.0001 (3)	0.0028 (3)	0.0039 (3)
C6	0.0281 (5)	0.0175 (5)	0.0238 (5)	−0.0008 (4)	0.0038 (4)	0.0050 (4)
C7	0.0246 (5)	0.0179 (5)	0.0247 (5)	−0.0042 (4)	0.0042 (4)	0.0025 (4)
C8	0.0238 (5)	0.0171 (5)	0.0207 (5)	−0.0023 (4)	0.0042 (4)	−0.0006 (4)
C8A	0.0163 (4)	0.0160 (4)	0.0189 (5)	0.0003 (3)	0.0036 (3)	0.0030 (4)
C9	0.0196 (5)	0.0203 (5)	0.0148 (4)	0.0007 (4)	0.0023 (3)	0.0008 (4)
N2	0.0290 (5)	0.0208 (4)	0.0210 (4)	−0.0049 (4)	0.0018 (3)	−0.0004 (3)
C10	0.0423 (7)	0.0197 (5)	0.0308 (6)	−0.0092 (5)	0.0036 (5)	0.0022 (4)
C11	0.0219 (5)	0.0343 (6)	0.0380 (6)	−0.0061 (5)	0.0062 (5)	0.0034 (5)
C12	0.0256 (5)	0.0172 (5)	0.0188 (5)	0.0001 (4)	0.0054 (4)	0.0007 (4)
C13	0.0265 (5)	0.0162 (5)	0.0148 (4)	−0.0013 (4)	0.0057 (4)	0.0018 (4)
C14	0.0361 (6)	0.0251 (5)	0.0183 (5)	−0.0046 (4)	0.0041 (4)	−0.0030 (4)
C15	0.0524 (7)	0.0264 (6)	0.0228 (5)	0.0005 (5)	0.0143 (5)	−0.0063 (4)
C16	0.0433 (7)	0.0259 (6)	0.0274 (6)	0.0071 (5)	0.0193 (5)	0.0043 (5)
C17	0.0621 (9)	0.0411 (8)	0.0421 (7)	0.0186 (7)	0.0304 (7)	0.0038 (6)
C18	0.0496 (8)	0.0577 (9)	0.0551 (9)	0.0287 (7)	0.0329 (7)	0.0181 (7)
C19	0.0308 (7)	0.0577 (9)	0.0527 (8)	0.0146 (6)	0.0174 (6)	0.0211 (7)
C20	0.0270 (6)	0.0363 (6)	0.0391 (7)	0.0045 (5)	0.0098 (5)	0.0102 (5)
C21	0.0291 (5)	0.0219 (5)	0.0261 (5)	0.0029 (4)	0.0121 (4)	0.0071 (4)

Geometric parameters (Å, º)

O1—C2	1.3733 (11)	C17—C18	1.359 (2)
O1—C8A	1.3769 (11)	C18—C19	1.405 (2)
C2—N1	1.3355 (13)	C19—C20	1.3724 (18)
C2—C3	1.3628 (13)	C20—C21	1.4172 (17)
C3—C9	1.4109 (13)	N1—H01	0.895 (13)
C3—C4	1.5193 (13)	N1—H02	0.901 (13)
C4—C4A	1.5035 (13)	C4—H4	1.0000
C4—C13	1.5278 (14)	C6—H6A	0.9900
C4A—C8A	1.3400 (14)	C6—H6B	0.9900
C4A—C5	1.4681 (13)	C8—H8A	0.9900
C5—O2	1.2259 (13)	C8—H8B	0.9900
C5—C6	1.5101 (14)	C10—H10A	0.9800
C6—C7	1.5362 (15)	C10—H10B	0.9800
C7—C10	1.5316 (15)	C10—H10C	0.9800
C7—C11	1.5323 (15)	C11—H11A	0.9800
C7—C8	1.5384 (14)	C11—H11B	0.9800
C8—C8A	1.4885 (13)	C11—H11C	0.9800
C9—N2	1.1553 (13)	C12—H12	0.9500
C12—C13	1.3721 (14)	C14—H14	0.9500
C12—C21	1.4173 (14)	C15—H15	0.9500
C13—C14	1.4164 (14)	C17—H17	0.9500
C14—C15	1.3678 (17)	C18—H18	0.9500
C15—C16	1.4135 (18)	C19—H19	0.9500
C16—C21	1.4206 (17)	C20—H20	0.9500
C16—C17	1.4244 (17)
C2—O1—C8A	118.69 (7)	C12—C21—C16	118.93 (10)
N1—C2—C3	128.28 (9)	C2—N1—H01	120.8 (9)
N1—C2—O1	110.35 (8)	C2—N1—H02	119.5 (9)
C3—C2—O1	121.37 (9)	H01—N1—H02	119.5 (13)
C2—C3—C9	118.82 (9)	C4A—C4—H4	108.6
C2—C3—C4	122.11 (9)	C3—C4—H4	108.6
C9—C3—C4	118.77 (8)	C13—C4—H4	108.6
C4A—C4—C3	107.94 (8)	C5—C6—H6A	109.0
C4A—C4—C13	112.25 (8)	C7—C6—H6A	109.0
C3—C4—C13	110.83 (8)	C5—C6—H6B	109.0
C8A—C4A—C5	118.84 (9)	C7—C6—H6B	109.0
C8A—C4A—C4	122.52 (9)	H6A—C6—H6B	107.8
C5—C4A—C4	118.63 (8)	C8A—C8—H8A	109.2
O2—C5—C4A	119.62 (9)	C7—C8—H8A	109.2
O2—C5—C6	122.28 (9)	C8A—C8—H8B	109.2
C4A—C5—C6	118.07 (9)	C7—C8—H8B	109.2
C5—C6—C7	113.12 (8)	H8A—C8—H8B	107.9
C10—C7—C11	109.17 (9)	C7—C10—H10A	109.5
C10—C7—C6	110.45 (9)	C7—C10—H10B	109.5
C11—C7—C6	109.48 (9)	H10A—C10—H10B	109.5
C10—C7—C8	108.80 (9)	C7—C10—H10C	109.5
C11—C7—C8	110.60 (9)	H10A—C10—H10C	109.5
C6—C7—C8	108.34 (8)	H10B—C10—H10C	109.5
C8A—C8—C7	112.23 (8)	C7—C11—H11A	109.5
C4A—C8A—O1	122.61 (9)	C7—C11—H11B	109.5
C4A—C8A—C8	125.70 (9)	H11A—C11—H11B	109.5
O1—C8A—C8	111.69 (8)	C7—C11—H11C	109.5
N2—C9—C3	178.34 (11)	H11A—C11—H11C	109.5
C13—C12—C21	121.76 (10)	H11B—C11—H11C	109.5
C12—C13—C14	118.75 (10)	C13—C12—H12	119.1
C12—C13—C4	121.77 (9)	C21—C12—H12	119.1
C14—C13—C4	119.37 (9)	C15—C14—H14	119.5
C15—C14—C13	120.90 (11)	C13—C14—H14	119.5
C14—C15—C16	121.22 (11)	C14—C15—H15	119.4
C15—C16—C21	118.42 (10)	C16—C15—H15	119.4
C15—C16—C17	123.10 (12)	C18—C17—H17	119.4
C21—C16—C17	118.48 (13)	C16—C17—H17	119.4
C18—C17—C16	121.23 (14)	C17—C18—H18	119.9
C17—C18—C19	120.17 (12)	C19—C18—H18	119.9
C20—C19—C18	120.53 (14)	C20—C19—H19	119.7
C19—C20—C21	120.63 (13)	C18—C19—H19	119.7
C20—C21—C12	122.14 (11)	C19—C20—H20	119.7
C20—C21—C16	118.93 (11)	C21—C20—H20	119.7
C8A—O1—C2—N1	171.82 (8)	C4—C4A—C8A—C8	−172.89 (9)
C8A—O1—C2—C3	−8.36 (13)	C2—O1—C8A—C4A	10.40 (13)
N1—C2—C3—C9	−3.54 (16)	C2—O1—C8A—C8	−170.59 (8)
O1—C2—C3—C9	176.67 (9)	C7—C8—C8A—C4A	19.52 (14)
N1—C2—C3—C4	170.13 (10)	C7—C8—C8A—O1	−159.46 (8)
O1—C2—C3—C4	−9.65 (14)	C21—C12—C13—C14	−0.51 (15)
C2—C3—C4—C4A	22.65 (13)	C21—C12—C13—C4	−176.64 (9)
C9—C3—C4—C4A	−163.67 (8)	C4A—C4—C13—C12	−37.80 (12)
C2—C3—C4—C13	−100.65 (11)	C3—C4—C13—C12	82.98 (11)
C9—C3—C4—C13	73.03 (11)	C4A—C4—C13—C14	146.09 (9)
C3—C4—C4A—C8A	−20.86 (12)	C3—C4—C13—C14	−93.12 (11)
C13—C4—C4A—C8A	101.57 (11)	C12—C13—C14—C15	−0.50 (16)
C3—C4—C4A—C5	160.51 (8)	C4—C13—C14—C15	175.72 (10)
C13—C4—C4A—C5	−77.05 (11)	C13—C14—C15—C16	0.66 (17)
C8A—C4A—C5—O2	178.62 (9)	C14—C15—C16—C21	0.19 (17)
C4—C4A—C5—O2	−2.71 (14)	C14—C15—C16—C17	−179.62 (12)
C8A—C4A—C5—C6	0.61 (14)	C15—C16—C17—C18	−179.19 (13)
C4—C4A—C5—C6	179.28 (8)	C21—C16—C17—C18	0.99 (19)
O2—C5—C6—C7	150.21 (10)	C16—C17—C18—C19	0.3 (2)
C4A—C5—C6—C7	−31.83 (13)	C17—C18—C19—C20	−1.2 (2)
C5—C6—C7—C10	173.48 (9)	C18—C19—C20—C21	0.8 (2)
C5—C6—C7—C11	−66.28 (11)	C19—C20—C21—C12	−179.56 (11)
C5—C6—C7—C8	54.40 (11)	C19—C20—C21—C16	0.47 (17)
C10—C7—C8—C8A	−167.89 (9)	C13—C12—C21—C20	−178.63 (10)
C11—C7—C8—C8A	72.21 (11)	C13—C12—C21—C16	1.34 (15)
C6—C7—C8—C8A	−47.78 (11)	C15—C16—C21—C20	178.82 (10)
C5—C4A—C8A—O1	−175.40 (8)	C17—C16—C21—C20	−1.36 (16)
C4—C4A—C8A—O1	5.99 (15)	C15—C16—C21—C12	−1.16 (16)
C5—C4A—C8A—C8	5.73 (15)	C17—C16—C21—C12	178.66 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···N2^i	0.90 (1)	2.11 (1)	2.9948 (12)	170 (1)
N1—H02···O2^ii	0.90 (1)	1.94 (1)	2.8404 (11)	176 (1)
C6—H6B···N2^iii	0.99	2.69	3.6366 (14)	160

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