Methyl 2-amino-4-(3-nitro­phen­yl)-4H-benzo[h]chromene-3-carboxyl­ate

Tang, S.-G.; Tang, Q.-G.; Wu, W.-Y.; Guo, C.; Ji, C.-X.

doi:10.1107/S1600536806031412

Methyl 2-amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carboxylate

S.-G. Tang, Q.-G. Tang, W.-Y. Wu, C. Guo and C.-X. Ji

The title compound, C₂₁H₁₆N₂O₅, was synthesized by the reaction of 1-naphthol with methyl cyanoacetate and 3-nitrobenzaldehyde in methanol under microwave irradiation. Intermolecular C—H

O hydrogen bonds link the molecules into chains along the b axis and adjacent chains are connected via N—H

O hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031412/ci2141sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031412/ci2141Isup2.hkl Contains datablock I

CCDC reference: 620758

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.024
wR factor = 0.077
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   0 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

Computing details top

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.

Methyl 2-amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carboxylate top

Crystal data top

C₂₁H₁₆N₂O₅	Z = 2
M_r = 376.36	F(000) = 392
Triclinic, P1	D_x = 1.340 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2190 (16) Å	Cell parameters from 25 reflections
b = 9.2570 (19) Å	θ = 10–13°
c = 13.203 (3) Å	µ = 0.10 mm⁻¹
α = 71.84 (3)°	T = 293 K
β = 78.39 (3)°	Block, colourless
γ = 82.73 (3)°	0.40 × 0.30 × 0.20 mm
V = 932.8 (4) Å³

Data collection top

Enraf-Nonius CAD-4 diffractometer	2346 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.963, T_max = 0.984	l = −15→16
3739 measured reflections	3 standard reflections every 200 reflections
3658 independent reflections	intensity decay: none

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0249P)²] where P = (F_o² + 2F_c²)/3
3658 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.11 e Å⁻³

Special details top

Experimental. ¹H NMR (CDCl₃): δ 8.23 (d, 1H), 8.15 (d, 1H), 7.99 (d, 1H), 7.77 (m, 1H), 7.57 (d, 2H), 7.51 (m, 2H), 7.37 (m, 1H), 7.09 (m, 1H), 6.54 (s, 2H), 3.65 (s, 3H).

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
C21	0.67735 (19)	0.64984 (18)	0.42582 (13)	0.0636 (5)
H21A	0.7102	0.7492	0.4179	0.095*
H21B	0.7739	0.5860	0.4090	0.095*
H21C	0.6238	0.6059	0.4990	0.095*
O1	0.04063 (11)	0.81815 (11)	0.24368 (8)	0.0507 (3)
O3	0.56180 (12)	0.66277 (11)	0.35215 (8)	0.0531 (3)
O2	0.37436 (12)	0.78315 (11)	0.45102 (9)	0.0589 (3)
C19	0.30380 (16)	0.72967 (14)	0.30047 (11)	0.0412 (3)
C12	0.38258 (16)	0.47728 (14)	0.26023 (10)	0.0380 (3)
C11	0.36092 (16)	0.65190 (14)	0.21385 (10)	0.0391 (3)
H11	0.4693	0.6885	0.1742	0.047*
C9	−0.02895 (17)	0.79999 (15)	0.08439 (11)	0.0456 (4)
C13	0.53916 (16)	0.40599 (15)	0.27069 (11)	0.0423 (4)
H13	0.6330	0.4620	0.2469	0.051*
C10	0.09126 (16)	0.76794 (14)	0.15370 (11)	0.0410 (3)
C18	0.14971 (18)	0.80299 (14)	0.31123 (11)	0.0430 (3)
N1	0.07979 (15)	0.86784 (13)	0.38829 (10)	0.0592 (4)
H1A	−0.0197	0.9100	0.3886	0.071*
H1B	0.1342	0.8674	0.4376	0.071*
C1	0.24081 (17)	0.69250 (15)	0.13429 (11)	0.0440 (4)
O4	0.83783 (14)	0.25760 (14)	0.31056 (10)	0.0742 (4)
C17	0.24588 (17)	0.38980 (16)	0.29512 (11)	0.0472 (4)
H17	0.1398	0.4366	0.2892	0.057*
C14	0.55377 (18)	0.24909 (16)	0.31745 (12)	0.0466 (4)
C20	0.41052 (18)	0.72995 (15)	0.37497 (12)	0.0442 (4)
N2	0.72215 (17)	0.17694 (16)	0.33291 (10)	0.0578 (4)
O5	0.73525 (15)	0.03737 (13)	0.36983 (11)	0.0888 (4)
C15	0.41998 (19)	0.16112 (17)	0.35171 (12)	0.0531 (4)
H15	0.4327	0.0562	0.3826	0.064*
C16	0.26594 (19)	0.23435 (17)	0.33849 (13)	0.0571 (4)
H16	0.1730	0.1773	0.3594	0.068*
C8	−0.18455 (18)	0.87638 (17)	0.10609 (13)	0.0568 (4)
H8	−0.2125	0.9091	0.1676	0.068*
C2	0.2783 (2)	0.64676 (18)	0.03931 (12)	0.0645 (5)
H2	0.3821	0.5986	0.0226	0.077*
C4	0.0092 (2)	0.74800 (18)	−0.00765 (13)	0.0591 (4)
C7	−0.2956 (2)	0.90262 (19)	0.03612 (14)	0.0705 (5)
H7	−0.3986	0.9534	0.0509	0.085*
C3	0.1670 (2)	0.6712 (2)	−0.02807 (14)	0.0739 (5)
H3	0.1946	0.6369	−0.0889	0.089*
C5	−0.1100 (2)	0.7775 (2)	−0.07686 (14)	0.0755 (5)
H5A	−0.0869	0.7431	−0.1377	0.091*
C6	−0.2573 (2)	0.8553 (2)	−0.05531 (16)	0.0814 (6)
H6	−0.3330	0.8768	−0.1026	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C21	0.0490 (10)	0.0779 (11)	0.0747 (12)	−0.0001 (9)	−0.0325 (9)	−0.0260 (9)
O1	0.0375 (6)	0.0637 (6)	0.0559 (7)	0.0149 (5)	−0.0163 (5)	−0.0267 (5)
O3	0.0394 (6)	0.0604 (6)	0.0679 (7)	0.0054 (5)	−0.0211 (5)	−0.0268 (5)
O2	0.0556 (7)	0.0652 (7)	0.0696 (7)	0.0087 (5)	−0.0231 (6)	−0.0368 (6)
C12	0.0344 (8)	0.0423 (8)	0.0412 (8)	0.0088 (6)	−0.0127 (7)	−0.0183 (6)
C11	0.0283 (7)	0.0438 (8)	0.0433 (8)	0.0069 (6)	−0.0076 (6)	−0.0130 (6)
C9	0.0391 (8)	0.0464 (8)	0.0458 (9)	0.0031 (7)	−0.0108 (7)	−0.0059 (7)
C13	0.0341 (8)	0.0478 (8)	0.0475 (9)	0.0078 (7)	−0.0091 (7)	−0.0203 (7)
C10	0.0378 (8)	0.0404 (8)	0.0422 (8)	0.0060 (6)	−0.0114 (7)	−0.0090 (7)
C18	0.0429 (9)	0.0404 (8)	0.0487 (9)	0.0035 (7)	−0.0130 (7)	−0.0167 (7)
N1	0.0462 (8)	0.0710 (9)	0.0738 (9)	0.0170 (7)	−0.0185 (7)	−0.0437 (8)
C1	0.0392 (8)	0.0489 (8)	0.0417 (9)	0.0086 (7)	−0.0110 (7)	−0.0121 (7)
C17	0.0357 (8)	0.0482 (9)	0.0609 (10)	0.0038 (7)	−0.0158 (7)	−0.0185 (8)
C14	0.0428 (9)	0.0484 (9)	0.0529 (10)	0.0174 (7)	−0.0168 (7)	−0.0238 (7)
C19	0.0361 (8)	0.0403 (8)	0.0483 (9)	0.0047 (6)	−0.0132 (7)	−0.0137 (7)
C20	0.0401 (9)	0.0364 (8)	0.0535 (10)	0.0021 (7)	−0.0126 (8)	−0.0129 (7)
N2	0.0482 (15)	0.0646 (17)	0.0819 (16)	0.0264 (13)	−0.0161 (13)	−0.0260 (14)
O4	0.0397 (12)	0.0909 (18)	0.0918 (18)	0.0189 (12)	−0.0188 (12)	−0.0258 (14)
O5	0.0734 (16)	0.0582 (15)	0.109 (2)	0.0364 (12)	−0.0293 (15)	−0.0219 (15)
C15	0.0554 (10)	0.0423 (8)	0.0646 (11)	0.0063 (8)	−0.0180 (9)	−0.0189 (8)
C16	0.0475 (10)	0.0507 (10)	0.0763 (12)	−0.0062 (8)	−0.0185 (9)	−0.0173 (8)
C8	0.0447 (9)	0.0657 (10)	0.0561 (10)	0.0085 (8)	−0.0151 (8)	−0.0133 (8)
C2	0.0609 (11)	0.0823 (12)	0.0507 (10)	0.0277 (9)	−0.0167 (9)	−0.0282 (9)
C4	0.0606 (11)	0.0704 (11)	0.0475 (10)	0.0055 (9)	−0.0228 (9)	−0.0147 (8)
C7	0.0451 (10)	0.0856 (13)	0.0749 (13)	0.0091 (9)	−0.0238 (10)	−0.0120 (10)
C3	0.0777 (13)	0.0958 (13)	0.0549 (11)	0.0283 (11)	−0.0254 (10)	−0.0361 (10)
C5	0.0727 (13)	0.1002 (14)	0.0584 (12)	0.0096 (11)	−0.0312 (10)	−0.0236 (10)
C6	0.0680 (13)	0.1093 (15)	0.0685 (13)	0.0075 (12)	−0.0403 (11)	−0.0158 (12)

Geometric parameters (Å, º) top

C21—O3	1.4604 (16)	N1—H1B	0.86
C21—H21A	0.96	C1—C2	1.4104 (19)
C21—H21B	0.96	O4—N2	1.2157 (16)
C21—H21C	0.96	C17—C16	1.3748 (19)
O1—C18	1.3531 (16)	C17—H17	0.93
O1—C10	1.3773 (16)	C14—C15	1.369 (2)
O3—C20	1.3393 (16)	C14—N2	1.4824 (17)
O2—C20	1.2207 (16)	N2—O5	1.2296 (16)
C19—C18	1.3619 (18)	C15—C16	1.3751 (19)
C19—C20	1.4445 (18)	C15—H15	0.93
C19—C11	1.5027 (18)	C16—H16	0.93
C12—C13	1.3822 (17)	C8—C7	1.3743 (19)
C12—C17	1.3855 (18)	C8—H8	0.93
C12—C11	1.5406 (17)	C2—C3	1.352 (2)
C11—C1	1.5154 (18)	C2—H2	0.93
C11—H11	0.98	C4—C5	1.416 (2)
C9—C8	1.4027 (19)	C4—C3	1.417 (2)
C9—C4	1.407 (2)	C7—C6	1.375 (2)
C9—C10	1.4219 (18)	C7—H7	0.93
C13—C14	1.3900 (19)	C3—H3	0.93
C13—H13	0.93	C5—C6	1.354 (2)
C10—C1	1.3534 (18)	C5—H5A	0.93
C18—N1	1.3356 (17)	C6—H6	0.93
N1—H1A	0.86

O3—C21—H21A	109.5	C16—C17—H17	119.8
O3—C21—H21B	109.5	C12—C17—H17	119.8
H21A—C21—H21B	109.5	C15—C14—C13	122.87 (13)
O3—C21—H21C	109.5	C15—C14—N2	119.54 (13)
H21A—C21—H21C	109.5	C13—C14—N2	117.57 (14)
H21B—C21—H21C	109.5	O2—C20—O3	121.28 (13)
C18—O1—C10	118.82 (10)	O2—C20—C19	126.67 (13)
C20—O3—C21	116.65 (12)	O3—C20—C19	112.05 (12)
C18—C19—C20	117.61 (13)	O4—N2—O5	123.83 (13)
C18—C19—C11	121.16 (12)	O4—N2—C14	118.98 (13)
C20—C19—C11	121.23 (12)	O5—N2—C14	117.18 (15)
C13—C12—C17	118.97 (12)	C14—C15—C16	117.21 (13)
C13—C12—C11	120.17 (12)	C14—C15—H15	121.4
C17—C12—C11	120.83 (12)	C16—C15—H15	121.4
C19—C11—C1	110.81 (11)	C17—C16—C15	121.65 (15)
C19—C11—C12	112.62 (11)	C17—C16—H16	119.2
C1—C11—C12	109.37 (11)	C15—C16—H16	119.2
C19—C11—H11	108.0	C7—C8—C9	119.75 (16)
C1—C11—H11	108.0	C7—C8—H8	120.1
C12—C11—H11	108.0	C9—C8—H8	120.1
C8—C9—C4	119.22 (14)	C3—C2—C1	121.66 (15)
C8—C9—C10	122.72 (14)	C3—C2—H2	119.2
C4—C9—C10	118.02 (13)	C1—C2—H2	119.2
C12—C13—C14	118.80 (14)	C9—C4—C5	118.73 (15)
C12—C13—H13	120.6	C9—C4—C3	118.31 (14)
C14—C13—H13	120.6	C5—C4—C3	122.94 (16)
C1—C10—O1	122.87 (12)	C6—C7—C8	121.22 (16)
C1—C10—C9	123.20 (13)	C6—C7—H7	119.4
O1—C10—C9	113.92 (12)	C8—C7—H7	119.4
N1—C18—O1	109.02 (12)	C2—C3—C4	121.19 (15)
N1—C18—C19	127.22 (14)	C2—C3—H3	119.4
O1—C18—C19	123.74 (12)	C4—C3—H3	119.4
C18—N1—H1A	120.0	C6—C5—C4	120.62 (17)
C18—N1—H1B	120.0	C6—C5—H5A	119.7
H1A—N1—H1B	120.0	C4—C5—H5A	119.7
C10—C1—C2	117.56 (13)	C5—C6—C7	120.41 (17)
C10—C1—C11	121.49 (12)	C5—C6—H6	119.8
C2—C1—C11	120.90 (12)	C7—C6—H6	119.8
C16—C17—C12	120.48 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.86	2.22	3.0750 (18)	173
N1—H1B···O2	0.86	2.05	2.6616 (16)	127
C15—H15···O2ⁱⁱ	0.93	2.48	3.373 (2)	161
C21—H21A···O5ⁱⁱⁱ	0.96	2.57	3.504 (2)	165
C21—H21C···Cg1^iv	0.96	2.83	3.5675 (19)	134

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Methyl 2-amino-4-(3-nitro­phen­yl)-4H-benzo[h]chromene-3-carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

Methyl 2-amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carboxylate