Ethyl 2-amino-4-(2-methoxy­phen­yl)-4H-benzo[h]chromene-3-carboxyl­ate

The title compound, C₂₃H₂₁NO₄, was synthesized by the reaction of 1-naphthol with ethyl cyano­acetate and 2-methoxy­benzaldehyde in ethanol under microwave irradiation. In the mol­ecular structure, there is an intra­molecular N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.187
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C22     ..       6.67 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    -   C22     ..       5.95 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C20     ..       5.47 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21A   ..  CG3     ..       2.96 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Ethyl 2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate

Crystal data

C23H21NO4	Z = 2
Mr = 375.41	F(000) = 396
Triclinic, P1	Dx = 1.297 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9960 (14) Å	Cell parameters from 25 reflections
b = 10.542 (2) Å	θ = 10–13°
c = 13.522 (3) Å	µ = 0.09 mm^−1
α = 101.45 (3)°	T = 293 K
β = 96.33 (3)°	Block, colourless
γ = 96.82 (3)°	0.4 × 0.3 × 0.2 mm
V = 961.3 (3) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.051
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.6°
Graphite monochromator	h = 0→8
ω/2θ scans	k = −12→12
4100 measured reflections	l = −16→16
3775 independent reflections	3 standard reflections every 200 reflections
2310 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.09P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3775 reflections	Δρmax = 0.23 e Å^−3
262 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5852 (2)	0.72409 (16)	0.59936 (13)	0.0624 (5)
O2	0.2646 (3)	0.67207 (19)	0.54931 (15)	0.0746 (6)
O3	0.2670 (2)	0.34957 (15)	0.68622 (13)	0.0562 (5)
O4	0.4026 (3)	0.5735 (2)	0.87238 (14)	0.0756 (6)
N	0.0850 (3)	0.4661 (3)	0.60674 (19)	0.0673 (7)
C1	0.7846 (5)	0.9007 (3)	0.5603 (3)	0.0999 (11)
H1A	0.7868	0.9732	0.5272	0.150*
H1B	0.8667	0.8412	0.5306	0.150*
H1C	0.8308	0.9320	0.6316	0.150*
C2	0.5813 (4)	0.8317 (3)	0.5474 (2)	0.0730 (8)
H2A	0.4966	0.8911	0.5765	0.088*
H2B	0.5332	0.7990	0.4756	0.088*
C3	0.4136 (4)	0.6500 (2)	0.59612 (17)	0.0543 (6)
C4	0.4286 (3)	0.5459 (2)	0.65041 (17)	0.0486 (5)
C5	0.2668 (3)	0.4590 (2)	0.64685 (17)	0.0508 (6)
C6	0.4448 (3)	0.3168 (2)	0.72188 (17)	0.0513 (6)
C7	0.4318 (4)	0.1904 (2)	0.74412 (17)	0.0549 (6)
C8	0.2574 (4)	0.1034 (3)	0.7279 (2)	0.0685 (7)
H8A	0.1428	0.1275	0.7006	0.082*
C9	0.2555 (5)	−0.0168 (3)	0.7520 (3)	0.0871 (9)
H9A	0.1398	−0.0744	0.7398	0.105*
C10	0.4245 (6)	−0.0536 (3)	0.7945 (3)	0.0923 (11)
H10A	0.4204	−0.1345	0.8125	0.111*
C11	0.5953 (5)	0.0275 (3)	0.8101 (2)	0.0836 (9)
H11A	0.7075	0.0009	0.8379	0.100*
C12	0.6065 (4)	0.1519 (3)	0.78486 (19)	0.0637 (7)
C13	0.7822 (4)	0.2386 (3)	0.7979 (2)	0.0699 (8)
H13A	0.8973	0.2141	0.8243	0.084*
C14	0.7854 (4)	0.3569 (3)	0.77249 (19)	0.0621 (7)
H14A	0.9033	0.4115	0.7809	0.075*
C15	0.6138 (3)	0.3993 (2)	0.73355 (17)	0.0506 (6)
C16	0.6195 (3)	0.5339 (2)	0.70939 (16)	0.0503 (6)
H16A	0.7189	0.5418	0.6644	0.060*
C17	0.6856 (3)	0.6386 (2)	0.80602 (17)	0.0545 (6)
C18	0.8641 (4)	0.7172 (2)	0.8187 (2)	0.0665 (7)
H18A	0.9395	0.7075	0.7659	0.080*
C19	0.9331 (5)	0.8090 (3)	0.9067 (3)	0.0835 (9)
H19A	1.0537	0.8599	0.9131	0.100*
C20	0.8244 (6)	0.8251 (3)	0.9842 (3)	0.0918 (11)
H20A	0.8713	0.8873	1.0437	0.110*
C21	0.6441 (6)	0.7499 (3)	0.9759 (2)	0.0811 (9)
H21A	0.5697	0.7624	1.0290	0.097*
C22	0.5757 (4)	0.6554 (2)	0.88715 (19)	0.0621 (7)
C23	0.2869 (5)	0.5797 (4)	0.9540 (2)	0.0950 (11)
H23A	0.1709	0.5172	0.9326	0.143*
H23B	0.2525	0.6660	0.9719	0.143*
H23C	0.3598	0.5600	1.0121	0.143*
H2	0.080 (4)	0.538 (3)	0.579 (2)	0.083 (9)*
H1	0.005 (4)	0.397 (3)	0.594 (2)	0.072 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0610 (11)	0.0629 (11)	0.0614 (10)	−0.0026 (8)	0.0023 (8)	0.0190 (8)
O2	0.0664 (12)	0.0772 (13)	0.0825 (13)	0.0053 (9)	−0.0118 (10)	0.0380 (10)
O3	0.0442 (9)	0.0597 (10)	0.0703 (11)	0.0112 (7)	0.0043 (7)	0.0266 (8)
O4	0.0759 (13)	0.0945 (14)	0.0608 (11)	0.0247 (11)	0.0195 (9)	0.0140 (10)
N	0.0454 (13)	0.0769 (17)	0.0865 (17)	0.0066 (12)	0.0000 (11)	0.0403 (14)
C1	0.103 (3)	0.092 (2)	0.105 (3)	−0.019 (2)	0.019 (2)	0.038 (2)
C2	0.089 (2)	0.0705 (18)	0.0608 (16)	−0.0028 (15)	0.0083 (14)	0.0256 (14)
C3	0.0592 (15)	0.0567 (14)	0.0443 (12)	0.0059 (12)	−0.0004 (11)	0.0096 (10)
C4	0.0446 (13)	0.0504 (13)	0.0499 (12)	0.0084 (10)	0.0021 (10)	0.0100 (10)
C5	0.0477 (13)	0.0571 (14)	0.0501 (13)	0.0151 (11)	0.0026 (10)	0.0153 (11)
C6	0.0512 (14)	0.0557 (14)	0.0492 (13)	0.0201 (11)	0.0051 (10)	0.0100 (10)
C7	0.0648 (16)	0.0568 (14)	0.0477 (13)	0.0222 (12)	0.0106 (11)	0.0127 (11)
C8	0.0759 (19)	0.0647 (16)	0.0712 (17)	0.0170 (14)	0.0141 (14)	0.0234 (13)
C9	0.113 (3)	0.0661 (18)	0.092 (2)	0.0169 (18)	0.0211 (19)	0.0336 (17)
C10	0.136 (3)	0.067 (2)	0.092 (2)	0.039 (2)	0.028 (2)	0.0363 (17)
C11	0.110 (3)	0.083 (2)	0.0753 (19)	0.055 (2)	0.0197 (18)	0.0300 (16)
C12	0.0768 (18)	0.0687 (16)	0.0546 (14)	0.0376 (15)	0.0145 (13)	0.0159 (12)
C13	0.0641 (17)	0.089 (2)	0.0660 (16)	0.0450 (16)	0.0098 (13)	0.0194 (14)
C14	0.0499 (14)	0.0775 (18)	0.0606 (15)	0.0231 (13)	0.0030 (11)	0.0130 (13)
C15	0.0484 (13)	0.0556 (14)	0.0467 (12)	0.0158 (11)	0.0036 (10)	0.0053 (10)
C16	0.0426 (12)	0.0586 (14)	0.0483 (12)	0.0090 (10)	0.0046 (10)	0.0080 (10)
C17	0.0585 (15)	0.0544 (14)	0.0512 (13)	0.0164 (12)	−0.0004 (11)	0.0126 (11)
C18	0.0665 (17)	0.0564 (15)	0.0719 (17)	0.0055 (13)	−0.0104 (13)	0.0152 (13)
C19	0.095 (2)	0.0574 (17)	0.087 (2)	0.0016 (16)	−0.0219 (19)	0.0131 (15)
C20	0.135 (3)	0.0528 (17)	0.074 (2)	0.0123 (19)	−0.029 (2)	0.0054 (15)
C21	0.124 (3)	0.0723 (19)	0.0518 (16)	0.039 (2)	0.0078 (16)	0.0133 (14)
C22	0.0722 (18)	0.0566 (15)	0.0571 (15)	0.0198 (13)	−0.0027 (13)	0.0116 (12)
C23	0.092 (2)	0.141 (3)	0.0728 (19)	0.056 (2)	0.0362 (17)	0.0361 (19)

Geometric parameters (Å, º)

O1—C3	1.344 (3)	C9—H9A	0.9300
O1—C2	1.449 (3)	C10—C11	1.354 (5)
O2—C3	1.230 (3)	C10—H10A	0.9300
O3—C5	1.363 (3)	C11—C12	1.414 (4)
O3—C6	1.391 (3)	C11—H11A	0.9300
O4—C22	1.372 (3)	C12—C13	1.414 (4)
O4—C23	1.435 (3)	C13—C14	1.357 (4)
N—C5	1.343 (3)	C13—H13A	0.9300
N—H2	0.91 (3)	C14—C15	1.414 (3)
N—H1	0.84 (3)	C14—H14A	0.9300
C1—C2	1.494 (4)	C15—C16	1.514 (3)
C1—H1A	0.9600	C16—C17	1.521 (3)
C1—H1B	0.9600	C16—H16A	0.9800
C1—H1C	0.9600	C17—C18	1.387 (4)
C2—H2A	0.9700	C17—C22	1.403 (4)
C2—H2B	0.9700	C18—C19	1.376 (4)
C3—C4	1.443 (3)	C18—H18A	0.9300
C4—C5	1.360 (3)	C19—C20	1.356 (5)
C4—C16	1.510 (3)	C19—H19A	0.9300
C6—C15	1.356 (3)	C20—C21	1.389 (5)
C6—C7	1.418 (3)	C20—H20A	0.9300
C7—C8	1.405 (4)	C21—C22	1.396 (4)
C7—C12	1.421 (3)	C21—H21A	0.9300
C8—C9	1.368 (4)	C23—H23A	0.9600
C8—H8A	0.9300	C23—H23B	0.9600
C9—C10	1.388 (5)	C23—H23C	0.9600
C3—O1—C2	116.1 (2)	C12—C11—H11A	119.4
C5—O3—C6	118.39 (18)	C13—C12—C11	123.2 (3)
C22—O4—C23	118.9 (2)	C13—C12—C7	118.9 (2)
C5—N—H2	111.7 (19)	C11—C12—C7	117.9 (3)
C5—N—H1	117 (2)	C14—C13—C12	121.0 (2)
H2—N—H1	128 (3)	C14—C13—H13A	119.5
C2—C1—H1A	109.5	C12—C13—H13A	119.5
C2—C1—H1B	109.5	C13—C14—C15	121.6 (3)
H1A—C1—H1B	109.5	C13—C14—H14A	119.2
C2—C1—H1C	109.5	C15—C14—H14A	119.2
H1A—C1—H1C	109.5	C6—C15—C14	117.5 (2)
H1B—C1—H1C	109.5	C6—C15—C16	121.7 (2)
O1—C2—C1	107.4 (2)	C14—C15—C16	120.7 (2)
O1—C2—H2A	110.2	C4—C16—C15	110.49 (19)
C1—C2—H2A	110.2	C4—C16—C17	115.16 (18)
O1—C2—H2B	110.2	C15—C16—C17	110.03 (18)
C1—C2—H2B	110.2	C4—C16—H16A	106.9
H2A—C2—H2B	108.5	C15—C16—H16A	106.9
O2—C3—O1	120.9 (2)	C17—C16—H16A	106.9
O2—C3—C4	126.2 (2)	C18—C17—C22	117.5 (2)
O1—C3—C4	112.9 (2)	C18—C17—C16	120.4 (2)
C5—C4—C3	118.3 (2)	C22—C17—C16	122.1 (2)
C5—C4—C16	120.9 (2)	C19—C18—C17	122.2 (3)
C3—C4—C16	120.8 (2)	C19—C18—H18A	118.9
C4—C5—N	126.9 (2)	C17—C18—H18A	118.9
C4—C5—O3	123.66 (19)	C20—C19—C18	119.7 (3)
N—C5—O3	109.4 (2)	C20—C19—H19A	120.1
C15—C6—O3	122.4 (2)	C18—C19—H19A	120.1
C15—C6—C7	123.8 (2)	C19—C20—C21	120.8 (3)
O3—C6—C7	113.8 (2)	C19—C20—H20A	119.6
C8—C7—C6	123.5 (2)	C21—C20—H20A	119.6
C8—C7—C12	119.3 (2)	C20—C21—C22	119.3 (3)
C6—C7—C12	117.2 (2)	C20—C21—H21A	120.3
C9—C8—C7	120.3 (3)	C22—C21—H21A	120.3
C9—C8—H8A	119.8	O4—C22—C21	124.0 (3)
C7—C8—H8A	119.8	O4—C22—C17	115.6 (2)
C8—C9—C10	120.6 (3)	C21—C22—C17	120.4 (3)
C8—C9—H9A	119.7	O4—C23—H23A	109.5
C10—C9—H9A	119.7	O4—C23—H23B	109.5
C11—C10—C9	120.5 (3)	H23A—C23—H23B	109.5
C11—C10—H10A	119.8	O4—C23—H23C	109.5
C9—C10—H10A	119.8	H23A—C23—H23C	109.5
C10—C11—C12	121.3 (3)	H23B—C23—H23C	109.5
C10—C11—H11A	119.4
C3—O1—C2—C1	179.9 (2)	C12—C13—C14—C15	1.0 (4)
C2—O1—C3—O2	1.6 (3)	O3—C6—C15—C14	178.7 (2)
C2—O1—C3—C4	−179.3 (2)	C7—C6—C15—C14	−1.5 (3)
O2—C3—C4—C5	3.3 (4)	O3—C6—C15—C16	0.7 (3)
O1—C3—C4—C5	−175.7 (2)	C7—C6—C15—C16	−179.5 (2)
O2—C3—C4—C16	−176.9 (2)	C13—C14—C15—C6	−0.3 (3)
O1—C3—C4—C16	4.1 (3)	C13—C14—C15—C16	177.7 (2)
C3—C4—C5—N	−7.7 (4)	C5—C4—C16—C15	16.0 (3)
C16—C4—C5—N	172.4 (2)	C3—C4—C16—C15	−163.9 (2)
C3—C4—C5—O3	173.2 (2)	C5—C4—C16—C17	−109.5 (2)
C16—C4—C5—O3	−6.7 (3)	C3—C4—C16—C17	70.7 (3)
C6—O3—C5—C4	−7.4 (3)	C6—C15—C16—C4	−13.1 (3)
C6—O3—C5—N	173.3 (2)	C14—C15—C16—C4	169.0 (2)
C5—O3—C6—C15	10.5 (3)	C6—C15—C16—C17	115.2 (2)
C5—O3—C6—C7	−169.32 (19)	C14—C15—C16—C17	−62.8 (3)
C15—C6—C7—C8	−177.3 (2)	C4—C16—C17—C18	−122.2 (2)
O3—C6—C7—C8	2.5 (3)	C15—C16—C17—C18	112.1 (2)
C15—C6—C7—C12	2.7 (3)	C4—C16—C17—C22	61.0 (3)
O3—C6—C7—C12	−177.53 (19)	C15—C16—C17—C22	−64.6 (3)
C6—C7—C8—C9	−179.4 (2)	C22—C17—C18—C19	−0.2 (4)
C12—C7—C8—C9	0.6 (4)	C16—C17—C18—C19	−177.1 (2)
C7—C8—C9—C10	1.2 (5)	C17—C18—C19—C20	−0.4 (4)
C8—C9—C10—C11	−2.0 (5)	C18—C19—C20—C21	0.1 (5)
C9—C10—C11—C12	0.8 (5)	C19—C20—C21—C22	0.9 (4)
C10—C11—C12—C13	−178.7 (3)	C23—O4—C22—C21	−3.0 (4)
C10—C11—C12—C7	1.1 (4)	C23—O4—C22—C17	176.6 (2)
C8—C7—C12—C13	178.0 (2)	C20—C21—C22—O4	178.0 (2)
C6—C7—C12—C13	−1.9 (3)	C20—C21—C22—C17	−1.5 (4)
C8—C7—C12—C11	−1.8 (3)	C18—C17—C22—O4	−178.4 (2)
C6—C7—C12—C11	178.3 (2)	C16—C17—C22—O4	−1.6 (3)
C11—C12—C13—C14	180.0 (2)	C18—C17—C22—C21	1.2 (3)
C7—C12—C13—C14	0.2 (4)	C16—C17—C22—C21	178.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H2···O2	0.91 (3)	1.93 (3)	2.671 (4)	137 (2)
C21—H21A···Cg3^i	0.93	2.96	3.7227	141

Symmetry code: (i) −x+1, −y+1, −z.