Crystal structures of butyl 2-amino-5-hy­droxy-4-(4-nitro­phen­yl)benzo­furan-3-carboxyl­ate and 2-meth­oxy­ethyl 2-amino-5-hy­droxy-4-(4-nitro­phen­yl)benzo­furan-3-carboxyl­ate

Diana, R.; Tuzi, A.; Panunzi, B.; Carella, A.; Caruso, U.

doi:10.1107/S205698901900728X

Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate

R. Diana, A. Tuzi, B. Panunzi, A. Carella and U. Caruso

There are small differences in the molecular geometries of the title compounds regarding the orientation of methoxyethyl or butyl group. Common features in the two molecular structures are the presence of an intramolecular N—H

O_carbonyl hydrogen bond and the inclination of nitrobenzene ring to the benzofuran mean plane.

Keywords: crystal structure; benzofuran; anti tumoral properties.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901900728X/dx2017sup1.cif Contains datablocks global, BF1, BF2
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901900728X/dx2017BF1sup2.hkl Contains datablock BF1
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901900728X/dx2017BF1sup4.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901900728X/dx2017BF2sup3.hkl Contains datablock BF2
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901900728X/dx2017BF2sup5.cml Supplementary material

CCDC references: 1917143; 1917142

checkCIF report

Key indicators

Structure: BF1

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
Disorder in main residue
R factor = 0.093
wR factor = 0.236
Data-to-parameter ratio = 11.0

Structure: BF2

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.052
wR factor = 0.139
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Datablock: BF1



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        40% Check
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.963 Why?
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference O3       --N2       .       0.17 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N2 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C9       -C14             1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00856 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1B      .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7       ..O4       .       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17D     ..O6       .       2.74 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     13.260 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.281 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595        111 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        11% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             107.1 Degree
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         41 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 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
  14 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

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




Datablock: BF2



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.964 Why?
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.492 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        108 Report

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             106.1 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         96 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.          6 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
   6 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
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: Collect (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF1) top

Crystal data top

C₁₉H₁₈N₂O₆	Z = 2
M_r = 370.35	F(000) = 388
Triclinic, P1	D_x = 1.388 Mg m⁻³
a = 9.4420 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.558 (3) Å	Cell parameters from 134 reflections
c = 11.419 (2) Å	θ = 4.3–18.7°
α = 110.58 (2)°	µ = 0.11 mm⁻¹
β = 95.669 (19)°	T = 298 K
γ = 108.863 (19)°	Needle, yellow
V = 886.3 (4) Å³	0.48 × 0.08 × 0.01 mm

Data collection top

Bruker-Nonius KappaCCD diffractometer	3006 independent reflections
Radiation source: normal-focus sealed tube	1212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.105
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
CCD rotation images, thick slices scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −11→11
T_min = 0.925, T_max = 0.987	l = −13→13
5854 measured reflections

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)] = 0.093	Hydrogen site location: mixed
wR(F²) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ²(F_o²) + (0.0652P)²] where P = (F_o² + 2F_c²)/3
3006 reflections	(Δ/σ)_max < 0.001
274 parameters	Δρ_max = 0.23 e Å⁻³
41 restraints	Δρ_min = −0.33 e Å⁻³

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.

Refinement. The alkyl group at O5 is disordered over two orientations. The two split positions were refined by applying DFIX and SIMU restraints on bond lengths and displacement parameters.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.0745 (7)	0.4807 (8)	0.8031 (6)	0.0708 (17)
C2	0.9991 (6)	0.3911 (6)	0.6776 (6)	0.0601 (15)
C3	0.8466 (6)	0.3990 (6)	0.6666 (5)	0.0500 (13)
C4	0.7108 (6)	0.3317 (5)	0.5697 (5)	0.0478 (13)
C5	0.5923 (6)	0.3826 (6)	0.6031 (6)	0.0546 (14)
C6	0.6039 (7)	0.4895 (6)	0.7249 (6)	0.0697 (17)
H6	0.522787	0.522558	0.741744	0.084*
C7	0.7321 (7)	0.5481 (6)	0.8216 (6)	0.0671 (17)
H7	0.740213	0.617845	0.905105	0.081*
C8	0.8479 (6)	0.4976 (6)	0.7879 (5)	0.0599 (15)
C9	0.6832 (5)	0.2043 (6)	0.4439 (5)	0.0514 (14)
C10	0.6654 (7)	0.2268 (7)	0.3306 (6)	0.0727 (18)
H10	0.671548	0.327540	0.334700	0.087*
C11	0.6393 (7)	0.1055 (8)	0.2139 (6)	0.0787 (19)
H11	0.630450	0.122599	0.138677	0.094*
C12	0.6266 (6)	−0.0422 (7)	0.2106 (6)	0.0657 (16)
C13	0.6403 (7)	−0.0701 (6)	0.3180 (6)	0.0711 (17)
H13	0.630802	−0.172387	0.312089	0.085*
C14	0.6680 (6)	0.0516 (6)	0.4354 (6)	0.0634 (16)
H14	0.676691	0.032325	0.509609	0.076*
C15	1.0806 (7)	0.3308 (6)	0.5863 (6)	0.0588 (15)
C16	1.0804 (7)	0.2212 (8)	0.3631 (6)	0.0825 (19)
H16A	1.030642	0.226635	0.287168	0.099*
H16B	1.186378	0.298045	0.390155	0.099*
C17A	1.0790 (8)	0.0602 (8)	0.3295 (7)	0.103 (2)	0.557 (13)
H17A	0.975065	−0.019365	0.308210	0.123*	0.557 (13)
H17B	1.142348	0.054603	0.398655	0.123*	0.557 (13)
C18A	1.148 (3)	0.036 (2)	0.2114 (16)	0.133 (5)	0.557 (13)
H18A	1.075824	0.031654	0.141926	0.160*	0.557 (13)
H18B	1.241883	0.129730	0.232273	0.160*	0.557 (13)
C19A	1.183 (2)	−0.1118 (16)	0.1655 (16)	0.136 (6)	0.557 (13)
H19A	1.247458	−0.112461	0.235361	0.204*	0.557 (13)
H19B	1.234537	−0.113113	0.097225	0.204*	0.557 (13)
H19C	1.088185	−0.205753	0.134145	0.204*	0.557 (13)
C17B	1.0790 (8)	0.0602 (8)	0.3295 (7)	0.103 (2)	0.443 (13)
H17C	0.972300	−0.014526	0.293379	0.123*	0.443 (13)
H17D	1.112223	0.052835	0.409518	0.123*	0.443 (13)
C18B	1.171 (3)	−0.004 (4)	0.2383 (17)	0.141 (6)	0.443 (13)
H18C	1.270102	0.079386	0.250798	0.169*	0.443 (13)
H18D	1.187648	−0.095011	0.248124	0.169*	0.443 (13)
C19B	1.068 (3)	−0.055 (3)	0.111 (2)	0.162 (7)	0.443 (13)
H19D	0.970732	−0.136990	0.102475	0.244*	0.443 (13)
H19E	1.114365	−0.098113	0.043673	0.244*	0.443 (13)
H19F	1.050918	0.036411	0.105986	0.244*	0.443 (13)
N1	1.2139 (7)	0.5123 (8)	0.8657 (6)	0.094 (2)
H1A	1.283 (8)	0.475 (8)	0.821 (7)	0.112*
H1B	1.255 (8)	0.560 (8)	0.944 (7)	0.112*
N2	0.5962 (7)	−0.1744 (8)	0.0885 (6)	0.0949 (19)
O1	0.9885 (5)	0.5479 (5)	0.8716 (4)	0.0757 (12)
O2	0.4613 (5)	0.3189 (5)	0.5099 (4)	0.0776 (13)
H2	0.406 (6)	0.356 (7)	0.561 (5)	0.093*
O3	0.5829 (9)	−0.1520 (9)	−0.0083 (6)	0.172 (3)
O4	0.5908 (9)	−0.3032 (7)	0.0850 (6)	0.164 (3)
O5	1.0027 (4)	0.2678 (5)	0.4653 (4)	0.0728 (12)
O6	1.2162 (4)	0.3471 (5)	0.6150 (4)	0.0753 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.060 (4)	0.093 (4)	0.064 (5)	0.033 (4)	0.005 (3)	0.035 (3)
C2	0.056 (4)	0.075 (4)	0.055 (4)	0.031 (3)	0.009 (3)	0.029 (3)
C3	0.055 (3)	0.049 (3)	0.054 (4)	0.025 (3)	0.018 (3)	0.023 (3)
C4	0.047 (3)	0.053 (3)	0.047 (3)	0.025 (3)	0.008 (3)	0.018 (3)
C5	0.048 (3)	0.049 (3)	0.063 (4)	0.021 (3)	0.007 (3)	0.018 (3)
C6	0.059 (4)	0.069 (4)	0.082 (5)	0.036 (3)	0.024 (3)	0.019 (3)
C7	0.077 (5)	0.071 (4)	0.059 (4)	0.039 (3)	0.028 (3)	0.020 (3)
C8	0.055 (4)	0.064 (3)	0.053 (4)	0.023 (3)	0.002 (3)	0.018 (3)
C9	0.044 (3)	0.064 (3)	0.054 (4)	0.031 (3)	0.005 (2)	0.024 (3)
C10	0.095 (5)	0.075 (4)	0.064 (5)	0.053 (3)	0.009 (3)	0.030 (3)
C11	0.104 (5)	0.095 (4)	0.042 (4)	0.054 (4)	0.003 (3)	0.025 (3)
C12	0.071 (4)	0.070 (4)	0.046 (4)	0.035 (3)	0.004 (3)	0.007 (3)
C13	0.092 (5)	0.060 (3)	0.065 (5)	0.035 (3)	0.025 (3)	0.023 (3)
C14	0.085 (4)	0.060 (3)	0.063 (4)	0.036 (3)	0.025 (3)	0.036 (3)
C15	0.053 (4)	0.057 (3)	0.066 (4)	0.021 (3)	0.004 (3)	0.027 (3)
C16	0.083 (5)	0.109 (5)	0.082 (5)	0.055 (4)	0.031 (4)	0.049 (4)
C17A	0.110 (6)	0.092 (5)	0.113 (7)	0.059 (4)	0.034 (5)	0.030 (4)
C18A	0.191 (12)	0.135 (11)	0.116 (11)	0.133 (8)	0.046 (9)	0.032 (7)
C19A	0.197 (13)	0.123 (9)	0.116 (11)	0.100 (9)	0.062 (9)	0.039 (8)
C17B	0.110 (6)	0.092 (5)	0.113 (7)	0.059 (4)	0.034 (5)	0.030 (4)
C18B	0.195 (13)	0.137 (12)	0.126 (11)	0.137 (9)	0.038 (10)	0.025 (9)
C19B	0.206 (14)	0.155 (13)	0.127 (13)	0.108 (10)	0.037 (11)	0.023 (10)
N1	0.068 (4)	0.129 (5)	0.071 (4)	0.041 (3)	−0.011 (3)	0.031 (4)
N2	0.118 (5)	0.103 (5)	0.066 (5)	0.064 (4)	0.013 (4)	0.020 (4)
O1	0.080 (3)	0.091 (3)	0.050 (3)	0.040 (2)	0.008 (2)	0.018 (2)
O2	0.063 (3)	0.091 (3)	0.086 (3)	0.049 (2)	0.016 (2)	0.027 (2)
O3	0.267 (8)	0.201 (6)	0.065 (4)	0.165 (6)	−0.002 (5)	0.016 (4)
O4	0.294 (9)	0.092 (3)	0.119 (5)	0.086 (5)	0.094 (5)	0.033 (4)
O5	0.062 (3)	0.102 (3)	0.061 (3)	0.046 (2)	0.019 (2)	0.027 (2)
O6	0.050 (2)	0.100 (3)	0.087 (3)	0.041 (2)	0.013 (2)	0.041 (2)

Geometric parameters (Å, º) top

C1—N1	1.318 (7)	C16—C17B	1.445 (8)
C1—O1	1.339 (7)	C16—C17A	1.445 (8)
C1—C2	1.355 (8)	C16—O5	1.454 (7)
C2—C15	1.427 (8)	C16—H16A	0.9700
C2—C3	1.462 (7)	C16—H16B	0.9700
C3—C8	1.370 (7)	C17A—C18A	1.530 (9)
C3—C4	1.403 (7)	C17A—H17A	0.9700
C4—C5	1.393 (7)	C17A—H17B	0.9700
C4—C9	1.451 (7)	C18A—C19A	1.484 (9)
C5—O2	1.353 (6)	C18A—H18A	0.9700
C5—C6	1.375 (8)	C18A—H18B	0.9700
C6—C7	1.364 (8)	C19A—H19A	0.9600
C6—H6	0.9300	C19A—H19B	0.9600
C7—C8	1.368 (7)	C19A—H19C	0.9600
C7—H7	0.9300	C17B—C18B	1.516 (10)
C8—O1	1.386 (6)	C17B—H17C	0.9700
C9—C14	1.386 (7)	C17B—H17D	0.9700
C9—C10	1.387 (7)	C18B—C19B	1.487 (10)
C10—C11	1.359 (8)	C18B—H18C	0.9700
C10—H10	0.9300	C18B—H18D	0.9700
C11—C12	1.364 (8)	C19B—H19D	0.9600
C11—H11	0.9300	C19B—H19E	0.9600
C12—C13	1.346 (8)	C19B—H19F	0.9600
C12—N2	1.439 (8)	N1—H1A	0.95 (7)
C13—C14	1.362 (7)	N1—H1B	0.83 (7)
C13—H13	0.9300	N2—O3	1.199 (8)
C14—H14	0.9300	N2—O4	1.202 (7)
C15—O6	1.235 (6)	O2—H2	0.88 (2)
C15—O5	1.319 (6)

N1—C1—O1	116.9 (6)	C17A—C16—H16B	109.0
N1—C1—C2	131.4 (7)	O5—C16—H16B	109.0
O1—C1—C2	111.7 (5)	H16A—C16—H16B	107.8
C1—C2—C15	119.5 (5)	C16—C17A—C18A	101.6 (7)
C1—C2—C3	106.0 (5)	C16—C17A—H17A	111.5
C15—C2—C3	133.8 (5)	C18A—C17A—H17A	111.5
C8—C3—C4	118.1 (5)	C16—C17A—H17B	111.5
C8—C3—C2	105.0 (5)	C18A—C17A—H17B	111.5
C4—C3—C2	136.9 (5)	H17A—C17A—H17B	109.3
C5—C4—C3	116.4 (5)	C19A—C18A—C17A	114.2 (11)
C5—C4—C9	119.3 (4)	C19A—C18A—H18A	108.7
C3—C4—C9	124.0 (5)	C17A—C18A—H18A	108.7
O2—C5—C6	120.6 (5)	C19A—C18A—H18B	108.7
O2—C5—C4	116.7 (5)	C17A—C18A—H18B	108.7
C6—C5—C4	122.7 (5)	H18A—C18A—H18B	107.6
C7—C6—C5	121.2 (5)	C18A—C19A—H19A	109.5
C7—C6—H6	119.4	C18A—C19A—H19B	109.5
C5—C6—H6	119.4	H19A—C19A—H19B	109.5
C6—C7—C8	115.7 (5)	C18A—C19A—H19C	109.5
C6—C7—H7	122.2	H19A—C19A—H19C	109.5
C8—C7—H7	122.2	H19B—C19A—H19C	109.5
C3—C8—C7	125.7 (5)	C16—C17B—C18B	121.7 (13)
C3—C8—O1	110.1 (5)	C16—C17B—H17C	106.9
C7—C8—O1	124.1 (5)	C18B—C17B—H17C	106.9
C14—C9—C10	118.2 (5)	C16—C17B—H17D	106.9
C14—C9—C4	119.0 (5)	C18B—C17B—H17D	106.9
C10—C9—C4	122.8 (5)	H17C—C17B—H17D	106.7
C11—C10—C9	121.7 (5)	C19B—C18B—C17B	101.0 (15)
C11—C10—H10	119.1	C19B—C18B—H18C	111.6
C9—C10—H10	119.1	C17B—C18B—H18C	111.6
C10—C11—C12	117.8 (6)	C19B—C18B—H18D	111.6
C10—C11—H11	121.1	C17B—C18B—H18D	111.6
C12—C11—H11	121.1	H18C—C18B—H18D	109.4
C13—C12—C11	122.4 (5)	C18B—C19B—H19D	109.5
C13—C12—N2	118.2 (6)	C18B—C19B—H19E	109.5
C11—C12—N2	119.4 (6)	H19D—C19B—H19E	109.5
C12—C13—C14	120.0 (5)	C18B—C19B—H19F	109.5
C12—C13—H13	120.0	H19D—C19B—H19F	109.5
C14—C13—H13	120.0	H19E—C19B—H19F	109.5
C13—C14—C9	119.8 (6)	C1—N1—H1A	121 (4)
C13—C14—H14	120.1	C1—N1—H1B	130 (5)
C9—C14—H14	120.1	H1A—N1—H1B	109 (7)
O6—C15—O5	121.8 (5)	O3—N2—O4	120.9 (7)
O6—C15—C2	124.0 (6)	O3—N2—C12	119.1 (7)
O5—C15—C2	114.0 (5)	O4—N2—C12	119.9 (7)
C17B—C16—O5	113.0 (6)	C1—O1—C8	107.1 (5)
C17A—C16—O5	113.0 (6)	C5—O2—H2	96 (4)
C17A—C16—H16A	109.0	C15—O5—C16	119.0 (5)
O5—C16—H16A	109.0

N1—C1—C2—C15	−8.7 (10)	C4—C9—C10—C11	−179.9 (5)
O1—C1—C2—C15	170.4 (5)	C9—C10—C11—C12	1.8 (9)
N1—C1—C2—C3	179.1 (7)	C10—C11—C12—C13	−0.6 (9)
O1—C1—C2—C3	−1.9 (7)	C10—C11—C12—N2	178.9 (6)
C1—C2—C3—C8	1.6 (6)	C11—C12—C13—C14	−0.1 (9)
C15—C2—C3—C8	−169.1 (6)	N2—C12—C13—C14	−179.6 (5)
C1—C2—C3—C4	−176.7 (6)	C12—C13—C14—C9	−0.5 (8)
C15—C2—C3—C4	12.7 (11)	C10—C9—C14—C13	1.7 (8)
C8—C3—C4—C5	5.3 (7)	C4—C9—C14—C13	179.3 (5)
C2—C3—C4—C5	−176.6 (6)	C1—C2—C15—O6	4.2 (9)
C8—C3—C4—C9	−168.8 (5)	C3—C2—C15—O6	173.9 (5)
C2—C3—C4—C9	9.4 (10)	C1—C2—C15—O5	−169.9 (5)
C3—C4—C5—O2	179.7 (5)	C3—C2—C15—O5	−0.2 (9)
C9—C4—C5—O2	−6.0 (7)	O5—C16—C17A—C18A	173.0 (11)
C3—C4—C5—C6	−1.7 (8)	C16—C17A—C18A—C19A	171.5 (17)
C9—C4—C5—C6	172.7 (5)	O5—C16—C17B—C18B	−171.7 (11)
O2—C5—C6—C7	176.5 (5)	C16—C17B—C18B—C19B	−81 (2)
C4—C5—C6—C7	−2.1 (9)	C13—C12—N2—O3	179.7 (7)
C5—C6—C7—C8	2.0 (9)	C11—C12—N2—O3	0.1 (10)
C4—C3—C8—C7	−5.8 (9)	C13—C12—N2—O4	−3.4 (10)
C2—C3—C8—C7	175.6 (6)	C11—C12—N2—O4	177.1 (7)
C4—C3—C8—O1	177.8 (4)	N1—C1—O1—C8	−179.4 (6)
C2—C3—C8—O1	−0.9 (6)	C2—C1—O1—C8	1.3 (7)
C6—C7—C8—C3	2.0 (9)	C3—C8—O1—C1	−0.2 (6)
C6—C7—C8—O1	177.9 (5)	C7—C8—O1—C1	−176.7 (6)
C5—C4—C9—C14	−106.8 (6)	O6—C15—O5—C16	−2.1 (8)
C3—C4—C9—C14	67.1 (7)	C2—C15—O5—C16	172.2 (5)
C5—C4—C9—C10	70.6 (7)	C17B—C16—O5—C15	85.4 (7)
C3—C4—C9—C10	−115.4 (6)	C17A—C16—O5—C15	85.4 (7)
C14—C9—C10—C11	−2.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4ⁱ	0.93	2.64	3.444 (8)	146
C11—H11···O3ⁱⁱ	0.93	2.53	3.237 (8)	133
C17B—H17D···O6	0.97	2.74	3.226 (8)	112
N1—H1A···O6	0.95 (7)	2.15 (7)	2.747 (8)	120 (6)
O2—H2···O6ⁱⁱⁱ	0.88 (2)	1.94 (3)	2.755 (6)	154 (6)

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

2-Methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF2) top

Crystal data top

C₁₈H₁₆N₂O₇	F(000) = 776
M_r = 372.33	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.263 (2) Å	Cell parameters from 72 reflections
b = 9.0860 (8) Å	θ = 3.0–20.3°
c = 20.049 (4) Å	µ = 0.11 mm⁻¹
β = 111.577 (16)°	T = 298 K
V = 1738.6 (6) Å³	Plate, yellow
Z = 4	0.48 × 0.22 × 0.02 mm

Data collection top

Bruker-Nonius KappaCCD diffractometer	3784 independent reflections
Radiation source: normal-focus sealed tube	2408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD rotation images, thick slices scans	h = −8→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −11→10
T_min = 0.825, T_max = 0.927	l = −26→23
9595 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.058P)² + 0.521P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3784 reflections	Δρ_max = 0.21 e Å⁻³
254 parameters	Δρ_min = −0.18 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	0.1522 (2)	−0.1808 (2)	0.16883 (11)	0.0445 (5)
C2	0.1956 (2)	−0.0554 (2)	0.20982 (10)	0.0373 (5)
C3	0.1095 (2)	0.0632 (2)	0.16748 (10)	0.0341 (4)
C4	0.1002 (2)	0.2168 (2)	0.17400 (10)	0.0344 (4)
C5	−0.0070 (2)	0.2886 (2)	0.11922 (11)	0.0406 (5)
C6	−0.0987 (2)	0.2149 (2)	0.05940 (11)	0.0461 (5)
H6	−0.169033	0.267025	0.024435	0.055*
C7	−0.0860 (2)	0.0655 (2)	0.05158 (11)	0.0450 (5)
H7	−0.145055	0.015044	0.011512	0.054*
C8	0.0173 (2)	−0.0043 (2)	0.10548 (10)	0.0390 (5)
C9	0.2033 (2)	0.3040 (2)	0.23255 (10)	0.0340 (4)
C10	0.1601 (2)	0.3939 (2)	0.27675 (11)	0.0420 (5)
H10	0.065367	0.399616	0.269523	0.050*
C11	0.2554 (2)	0.4745 (2)	0.33092 (11)	0.0467 (5)
H11	0.225981	0.534073	0.360395	0.056*
C12	0.3945 (2)	0.4653 (2)	0.34070 (11)	0.0444 (5)
C13	0.4412 (2)	0.3798 (2)	0.29739 (12)	0.0503 (6)
H13	0.535893	0.376423	0.304353	0.060*
C14	0.3444 (2)	0.2992 (2)	0.24337 (11)	0.0440 (5)
H14	0.374444	0.240694	0.213767	0.053*
C15	0.2933 (2)	−0.0684 (2)	0.28310 (11)	0.0424 (5)
C16	0.3911 (3)	0.0471 (3)	0.39702 (12)	0.0675 (7)
H15A	0.476930	0.089810	0.395981	0.081*
H15B	0.411377	−0.052314	0.415599	0.081*
C17	0.3393 (3)	0.1360 (3)	0.44439 (12)	0.0639 (7)
H17A	0.418292	0.173723	0.484457	0.077*
H17B	0.285814	0.219097	0.417820	0.077*
C18	0.2178 (3)	0.1191 (3)	0.52447 (15)	0.0807 (9)
H18A	0.301484	0.142483	0.564594	0.121*
H18B	0.160476	0.054063	0.539727	0.121*
H18C	0.166857	0.207917	0.505670	0.121*
N1	0.1990 (3)	−0.3192 (2)	0.17972 (13)	0.0662 (7)
H1A	0.137 (3)	−0.388 (3)	0.1558 (15)	0.079*
H1B	0.258 (3)	−0.334 (3)	0.2202 (16)	0.079*
N2	0.4964 (3)	0.5494 (2)	0.39927 (11)	0.0620 (6)
O1	0.04482 (16)	−0.15477 (14)	0.10650 (8)	0.0487 (4)
O2	−0.01457 (18)	0.43883 (16)	0.12485 (9)	0.0579 (5)
H2O	−0.094 (3)	0.471 (3)	0.0929 (14)	0.069*
O3	0.4543 (2)	0.6155 (2)	0.44027 (10)	0.0856 (6)
O4	0.6174 (2)	0.5507 (3)	0.40383 (12)	0.0956 (7)
O5	0.28607 (16)	0.04351 (16)	0.32517 (7)	0.0519 (4)
O6	0.37098 (18)	−0.17310 (18)	0.30529 (9)	0.0630 (5)
O7	0.25432 (19)	0.04923 (17)	0.47021 (8)	0.0628 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0499 (13)	0.0369 (11)	0.0459 (12)	−0.0015 (9)	0.0168 (11)	0.0021 (9)
C2	0.0385 (12)	0.0333 (10)	0.0406 (11)	−0.0025 (8)	0.0150 (9)	0.0018 (8)
C3	0.0328 (11)	0.0374 (11)	0.0341 (10)	−0.0029 (8)	0.0144 (8)	0.0005 (8)
C4	0.0327 (11)	0.0378 (11)	0.0334 (10)	−0.0007 (8)	0.0130 (8)	−0.0013 (8)
C5	0.0406 (12)	0.0346 (11)	0.0448 (12)	0.0016 (8)	0.0135 (10)	0.0010 (9)
C6	0.0425 (13)	0.0489 (13)	0.0385 (11)	0.0023 (9)	0.0051 (10)	0.0056 (9)
C7	0.0481 (13)	0.0488 (13)	0.0334 (11)	−0.0085 (9)	0.0095 (9)	−0.0038 (9)
C8	0.0459 (12)	0.0353 (11)	0.0369 (11)	−0.0046 (8)	0.0165 (9)	−0.0030 (8)
C9	0.0346 (11)	0.0314 (10)	0.0344 (10)	−0.0002 (7)	0.0109 (8)	0.0015 (8)
C10	0.0382 (12)	0.0436 (12)	0.0459 (12)	−0.0009 (9)	0.0177 (10)	−0.0042 (9)
C11	0.0574 (15)	0.0434 (12)	0.0426 (12)	−0.0045 (10)	0.0221 (11)	−0.0073 (9)
C12	0.0489 (14)	0.0439 (12)	0.0357 (11)	−0.0119 (9)	0.0099 (10)	−0.0002 (9)
C13	0.0348 (12)	0.0612 (14)	0.0528 (14)	−0.0076 (10)	0.0137 (11)	−0.0026 (11)
C14	0.0367 (12)	0.0501 (12)	0.0463 (12)	−0.0006 (9)	0.0165 (10)	−0.0078 (9)
C15	0.0418 (12)	0.0391 (12)	0.0447 (12)	−0.0043 (9)	0.0142 (10)	0.0069 (9)
C16	0.0584 (17)	0.089 (2)	0.0386 (13)	−0.0056 (13)	−0.0011 (11)	0.0059 (12)
C17	0.0819 (19)	0.0544 (15)	0.0396 (13)	−0.0198 (12)	0.0039 (12)	−0.0003 (11)
C18	0.097 (2)	0.082 (2)	0.0644 (18)	−0.0044 (16)	0.0318 (17)	−0.0191 (15)
N1	0.0802 (17)	0.0332 (11)	0.0703 (15)	−0.0010 (10)	0.0100 (12)	0.0010 (10)
N2	0.0671 (16)	0.0586 (13)	0.0475 (12)	−0.0200 (11)	0.0061 (11)	−0.0018 (10)
O1	0.0610 (10)	0.0359 (8)	0.0435 (8)	−0.0051 (7)	0.0126 (7)	−0.0066 (6)
O2	0.0537 (10)	0.0383 (9)	0.0629 (11)	0.0095 (7)	−0.0005 (8)	0.0010 (7)
O3	0.1101 (17)	0.0828 (14)	0.0548 (12)	−0.0276 (12)	0.0195 (12)	−0.0262 (10)
O4	0.0596 (14)	0.1190 (18)	0.0861 (15)	−0.0335 (12)	0.0009 (11)	−0.0229 (12)
O5	0.0540 (10)	0.0558 (10)	0.0352 (8)	0.0042 (7)	0.0040 (7)	0.0019 (7)
O6	0.0615 (11)	0.0517 (10)	0.0639 (11)	0.0120 (8)	0.0091 (9)	0.0131 (8)
O7	0.0778 (12)	0.0530 (10)	0.0515 (10)	−0.0191 (8)	0.0165 (9)	−0.0113 (8)

Geometric parameters (Å, º) top

C1—N1	1.335 (3)	C12—N2	1.468 (3)
C1—O1	1.349 (3)	C13—C14	1.380 (3)
C1—C2	1.380 (3)	C13—H13	0.9300
C2—C15	1.447 (3)	C14—H14	0.9300
C2—C3	1.453 (3)	C15—O6	1.216 (2)
C3—C8	1.397 (3)	C15—O5	1.341 (2)
C3—C4	1.409 (3)	C16—O5	1.448 (3)
C4—C5	1.397 (3)	C16—C17	1.486 (4)
C4—C9	1.487 (3)	C16—H15A	0.9700
C5—O2	1.375 (2)	C16—H15B	0.9700
C5—C6	1.393 (3)	C17—O7	1.408 (3)
C6—C7	1.378 (3)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—C8	1.361 (3)	C18—O7	1.424 (3)
C7—H7	0.9300	C18—H18A	0.9600
C8—O1	1.394 (2)	C18—H18B	0.9600
C9—C14	1.384 (3)	C18—H18C	0.9600
C9—C10	1.392 (3)	N1—H1A	0.89 (3)
C10—C11	1.375 (3)	N1—H1B	0.83 (3)
C10—H10	0.9300	N2—O4	1.212 (3)
C11—C12	1.370 (3)	N2—O3	1.218 (3)
C11—H11	0.9300	O2—H2O	0.88 (3)
C12—C13	1.376 (3)

N1—C1—O1	116.06 (19)	C12—C13—H13	120.8
N1—C1—C2	131.5 (2)	C14—C13—H13	120.8
O1—C1—C2	112.45 (17)	C13—C14—C9	121.09 (19)
C1—C2—C15	119.26 (18)	C13—C14—H14	119.5
C1—C2—C3	105.70 (17)	C9—C14—H14	119.5
C15—C2—C3	134.37 (17)	O6—C15—O5	122.9 (2)
C8—C3—C4	118.08 (17)	O6—C15—C2	123.5 (2)
C8—C3—C2	105.17 (16)	O5—C15—C2	113.51 (17)
C4—C3—C2	136.74 (17)	O5—C16—C17	109.8 (2)
C5—C4—C3	116.75 (17)	O5—C16—H15A	109.7
C5—C4—C9	119.87 (17)	C17—C16—H15A	109.7
C3—C4—C9	123.23 (17)	O5—C16—H15B	109.7
O2—C5—C6	120.48 (18)	C17—C16—H15B	109.7
O2—C5—C4	116.78 (18)	H15A—C16—H15B	108.2
C6—C5—C4	122.66 (18)	O7—C17—C16	110.3 (2)
C7—C6—C5	120.60 (19)	O7—C17—H17A	109.6
C7—C6—H6	119.7	C16—C17—H17A	109.6
C5—C6—H6	119.7	O7—C17—H17B	109.6
C8—C7—C6	116.59 (19)	C16—C17—H17B	109.6
C8—C7—H7	121.7	H17A—C17—H17B	108.1
C6—C7—H7	121.7	O7—C18—H18A	109.5
C7—C8—O1	124.28 (18)	O7—C18—H18B	109.5
C7—C8—C3	125.21 (18)	H18A—C18—H18B	109.5
O1—C8—C3	110.50 (17)	O7—C18—H18C	109.5
C14—C9—C10	118.59 (18)	H18A—C18—H18C	109.5
C14—C9—C4	120.45 (17)	H18B—C18—H18C	109.5
C10—C9—C4	120.95 (17)	C1—N1—H1A	115.4 (19)
C11—C10—C9	120.97 (19)	C1—N1—H1B	114 (2)
C11—C10—H10	119.5	H1A—N1—H1B	122 (3)
C9—C10—H10	119.5	O4—N2—O3	123.5 (2)
C12—C11—C10	118.8 (2)	O4—N2—C12	118.3 (2)
C12—C11—H11	120.6	O3—N2—C12	118.1 (2)
C10—C11—H11	120.6	C1—O1—C8	106.12 (15)
C11—C12—C13	122.05 (19)	C5—O2—H2O	109.6 (17)
C11—C12—N2	118.8 (2)	C15—O5—C16	116.75 (18)
C13—C12—N2	119.2 (2)	C17—O7—C18	113.83 (19)
C12—C13—C14	118.5 (2)

N1—C1—C2—C15	−11.7 (4)	C3—C4—C9—C10	−124.6 (2)
O1—C1—C2—C15	169.66 (17)	C14—C9—C10—C11	−1.2 (3)
N1—C1—C2—C3	176.4 (2)	C4—C9—C10—C11	179.96 (18)
O1—C1—C2—C3	−2.2 (2)	C9—C10—C11—C12	0.2 (3)
C1—C2—C3—C8	2.4 (2)	C10—C11—C12—C13	1.0 (3)
C15—C2—C3—C8	−167.7 (2)	C10—C11—C12—N2	−179.02 (19)
C1—C2—C3—C4	−176.8 (2)	C11—C12—C13—C14	−1.2 (3)
C15—C2—C3—C4	13.2 (4)	N2—C12—C13—C14	178.81 (19)
C8—C3—C4—C5	3.6 (3)	C12—C13—C14—C9	0.2 (3)
C2—C3—C4—C5	−177.3 (2)	C10—C9—C14—C13	0.9 (3)
C8—C3—C4—C9	−171.97 (18)	C4—C9—C14—C13	179.83 (19)
C2—C3—C4—C9	7.1 (3)	C1—C2—C15—O6	22.3 (3)
C3—C4—C5—O2	−178.79 (17)	C3—C2—C15—O6	−168.7 (2)
C9—C4—C5—O2	−3.0 (3)	C1—C2—C15—O5	−155.14 (19)
C3—C4—C5—C6	−2.0 (3)	C3—C2—C15—O5	13.9 (3)
C9—C4—C5—C6	173.74 (19)	O5—C16—C17—O7	83.6 (2)
O2—C5—C6—C7	176.1 (2)	C11—C12—N2—O4	−173.8 (2)
C4—C5—C6—C7	−0.5 (3)	C13—C12—N2—O4	6.2 (3)
C5—C6—C7—C8	1.4 (3)	C11—C12—N2—O3	5.4 (3)
C6—C7—C8—O1	179.86 (19)	C13—C12—N2—O3	−174.5 (2)
C6—C7—C8—C3	0.5 (3)	N1—C1—O1—C8	−177.8 (2)
C4—C3—C8—C7	−3.0 (3)	C2—C1—O1—C8	1.1 (2)
C2—C3—C8—C7	177.62 (19)	C7—C8—O1—C1	−178.9 (2)
C4—C3—C8—O1	177.49 (16)	C3—C8—O1—C1	0.6 (2)
C2—C3—C8—O1	−1.8 (2)	O6—C15—O5—C16	9.3 (3)
C5—C4—C9—C14	−118.9 (2)	C2—C15—O5—C16	−173.19 (18)
C3—C4—C9—C14	56.5 (3)	C17—C16—O5—C15	−157.75 (19)
C5—C4—C9—C10	59.9 (3)	C16—C17—O7—C18	170.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the O1/C1/C2/C3/C8 and C3–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.97	2.49	3.366 (3)	150
N1—H1A···O2ⁱⁱ	0.89 (3)	2.14 (3)	3.013 (3)	165 (3)
N1—H1B···O6	0.83 (3)	2.22 (3)	2.819 (3)	129 (3)
O2—H2O···O7ⁱⁱⁱ	0.88 (3)	1.81 (3)	2.691 (2)	176 (3)
C10—H10···Cg1ⁱⁱⁱ	0.93	2.76	3.521 (3)	139
C11—H11···Cg2ⁱⁱⁱ	0.93	2.80	3.601 (3)	145

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

Interaction energies for BF1-molA (kJ mol^-1) top

R is the distance between molecular centroids (mean atomic position) in Å and N is the number of molecules at that distance. Total energies are the sum of the four energy components, scaled according to the appropriate scale factor⁽^a⁾.

N	symop	R	E_elec	E_pol	E_disp	E_rep	E_total	interaction
2	x, y, z	12.04	-9.1	-2.5	-14.1	9.1	-18.1	C7—H7···O4ⁱ
1	-x, -y, -z	10.51	-8.2	-3.0	-11.7	13.1	-12.9	C11—H11···O3ⁱⁱ
1	-x, -y, -z	11.10	-3.2	-1.9	-12.2	2.8	-13.6
2	x, y, z	12.43	-3.3	-1.4	-5.4	1.0	-8.6
1	-x, -y, -z	12.97	8.5	-1.0	-2.3	0.5	6.5	N2—O4···O4ⁱⁱⁱ
1	-x, -y, -z	5.99	-27.6	-3.7	-67.7	35.8	-68.8	N1—H1A···O4^iv
1	-x, -y, -z	6.67	-8.0	-3.0	-43.4	22.8	-34.4
2	x, y, z	9.44	-42.2	-10.7	-27.7	52.0	-44.5	O2—H2···O6^v
1	-x, -y, -z	5.08	-13.2	-1.5	-76.1	36.5	-58.7	C10—H10···O6^vi
1	-x, -y, -z	9.63	1.5	-1.2	-14.8	3.4	-10.1
1	-x, -y, -z	11.07	-0.5	-1.9	-14.6	4.5	-11.9

Notes: (a) Energy Model: CE_B3LYP···B3LYP/6-31G(d,p) electron densities. Scale factors for benchmarked energy model (Mackenzie et al. 2017): k_ele = 1.057; k_pol = 0.740; k_disp = 0.871; k_rep= 0.61. Symmetry codes: (i) x, 1 + y, 1 + z; (ii) 1 - x, -y, -z; (iii) 1 - x, -1 - y, -z; (iv) 2 - x, -y, 1 - z; (v) -1 + x, y, z; (vi) 2 - x, 1 - y, 1 - z.

Interaction energies for BF2 (kJ mol^-1) top

N	symop	R	E_elec	E_pol	E_disp	E_rep	E_total	interaction
1	-x, -y, -z	10.65	-2.1	-0.6	-21.2	12.0	-13.7
2	-x, y + 1/2, -z + 1/2	6.41	-70.6	-16.2	-59.8	98.4	-77.9	O2—H2O···O7ⁱ
2	x, -y + 1/2, z + 1/2	11.49	-4.5	-1.4	-6.2	4.1	-8.6
2	x, y, z	9.09	-23.5	-7.2	-29.9	35.7	-34.2	N1—H1A···O2ⁱⁱ
1	-x, -y, -z	12.21	-1.4	-0.1	-2.2	0.2	-3.3
2	x, -y + 1/2, z + 1/2	10.11	-1.4	-0.4	-13.6	5.3	-10.4
2	-x, y + 1/2, -zz + 1/2	7.42	-8.0	-2.5	-26.4	13.6	-25.0
1	-x, -y, -z	9.34	-6.5	-0.8	-22.8	12.2	-19.9
2	x, -y + 1/2, z + 1/2	12.67	2.2	-0.3	-3.1	0.6	-0.2
1	-x, -y, -z	10.57	-17.3	-6.8	-22.2	26.4	-26.3	C17—H17A···O3ⁱⁱⁱ

Notes: (a) Energy Model: CE_B3LYP···B3LYP/6-31G(d,p) electron densities. Scale factors for benchmarked energy model (Mackenzie et al. 2017): k_ele = 1.057; k_pol = 0.740; k_disp = 0.871; k_rep= 0.61. Symmetry codes: (i) -x, 1/2 + y, 1/2 - z; (ii) x, -1 + y, z; (iii) 1 - x, 1 - y, 1 - z.

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Crystal structures of butyl 2-amino-5-hy­droxy-4-(4-nitro­phen­yl)benzo­furan-3-carboxyl­ate and 2-meth­oxy­ethyl 2-amino-5-hy­droxy-4-(4-nitro­phen­yl)benzo­furan-3-carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate