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

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901900728X/dx2017sup1.cif
Contains datablocks global, BF1, BF2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901900728X/dx2017BF1sup2.hkl
Contains datablock BF1

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901900728X/dx2017BF1sup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901900728X/dx2017BF2sup3.hkl
Contains datablock BF2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901900728X/dx2017BF2sup5.cml
Supplementary material

CCDC references: 1917143; 1917142

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.093
  • wR factor = 0.236
  • Data-to-parameter ratio = 11.0

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
C19H18N2O6Z = 2
Mr = 370.35F(000) = 388
Triclinic, P1Dx = 1.388 Mg m3
a = 9.4420 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.558 (3) ÅCell parameters from 134 reflections
c = 11.419 (2) Åθ = 4.3–18.7°
α = 110.58 (2)°µ = 0.11 mm1
β = 95.669 (19)°T = 298 K
γ = 108.863 (19)°Needle, yellow
V = 886.3 (4) Å30.48 × 0.08 × 0.01 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3006 independent reflections
Radiation source: normal-focus sealed tube1212 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.105
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 3.0°
CCD rotation images, thick slices scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 1111
Tmin = 0.925, Tmax = 0.987l = 1313
5854 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.093Hydrogen site location: mixed
wR(F2) = 0.236H atoms treated by a mixture of independent and constrained refinement
S = 1.21 w = 1/[σ2(Fo2) + (0.0652P)2]
where P = (Fo2 + 2Fc2)/3
3006 reflections(Δ/σ)max < 0.001
274 parametersΔρmax = 0.23 e Å3
41 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/UeqOcc. (<1)
C11.0745 (7)0.4807 (8)0.8031 (6)0.0708 (17)
C20.9991 (6)0.3911 (6)0.6776 (6)0.0601 (15)
C30.8466 (6)0.3990 (6)0.6666 (5)0.0500 (13)
C40.7108 (6)0.3317 (5)0.5697 (5)0.0478 (13)
C50.5923 (6)0.3826 (6)0.6031 (6)0.0546 (14)
C60.6039 (7)0.4895 (6)0.7249 (6)0.0697 (17)
H60.5227870.5225580.7417440.084*
C70.7321 (7)0.5481 (6)0.8216 (6)0.0671 (17)
H70.7402130.6178450.9051050.081*
C80.8479 (6)0.4976 (6)0.7879 (5)0.0599 (15)
C90.6832 (5)0.2043 (6)0.4439 (5)0.0514 (14)
C100.6654 (7)0.2268 (7)0.3306 (6)0.0727 (18)
H100.6715480.3275400.3347000.087*
C110.6393 (7)0.1055 (8)0.2139 (6)0.0787 (19)
H110.6304500.1225990.1386770.094*
C120.6266 (6)0.0422 (7)0.2106 (6)0.0657 (16)
C130.6403 (7)0.0701 (6)0.3180 (6)0.0711 (17)
H130.6308020.1723870.3120890.085*
C140.6680 (6)0.0516 (6)0.4354 (6)0.0634 (16)
H140.6766910.0323250.5096090.076*
C151.0806 (7)0.3308 (6)0.5863 (6)0.0588 (15)
C161.0804 (7)0.2212 (8)0.3631 (6)0.0825 (19)
H16A1.0306420.2266350.2871680.099*
H16B1.1863780.2980450.3901550.099*
C17A1.0790 (8)0.0602 (8)0.3295 (7)0.103 (2)0.557 (13)
H17A0.9750650.0193650.3082100.123*0.557 (13)
H17B1.1423480.0546030.3986550.123*0.557 (13)
C18A1.148 (3)0.036 (2)0.2114 (16)0.133 (5)0.557 (13)
H18A1.0758240.0316540.1419260.160*0.557 (13)
H18B1.2418830.1297300.2322730.160*0.557 (13)
C19A1.183 (2)0.1118 (16)0.1655 (16)0.136 (6)0.557 (13)
H19A1.2474580.1124610.2353610.204*0.557 (13)
H19B1.2345370.1131130.0972250.204*0.557 (13)
H19C1.0881850.2057530.1341450.204*0.557 (13)
C17B1.0790 (8)0.0602 (8)0.3295 (7)0.103 (2)0.443 (13)
H17C0.9723000.0145260.2933790.123*0.443 (13)
H17D1.1122230.0528350.4095180.123*0.443 (13)
C18B1.171 (3)0.004 (4)0.2383 (17)0.141 (6)0.443 (13)
H18C1.2701020.0793860.2507980.169*0.443 (13)
H18D1.1876480.0950110.2481240.169*0.443 (13)
C19B1.068 (3)0.055 (3)0.111 (2)0.162 (7)0.443 (13)
H19D0.9707320.1369900.1024750.244*0.443 (13)
H19E1.1143650.0981130.0436730.244*0.443 (13)
H19F1.0509180.0364110.1059860.244*0.443 (13)
N11.2139 (7)0.5123 (8)0.8657 (6)0.094 (2)
H1A1.283 (8)0.475 (8)0.821 (7)0.112*
H1B1.255 (8)0.560 (8)0.944 (7)0.112*
N20.5962 (7)0.1744 (8)0.0885 (6)0.0949 (19)
O10.9885 (5)0.5479 (5)0.8716 (4)0.0757 (12)
O20.4613 (5)0.3189 (5)0.5099 (4)0.0776 (13)
H20.406 (6)0.356 (7)0.561 (5)0.093*
O30.5829 (9)0.1520 (9)0.0083 (6)0.172 (3)
O40.5908 (9)0.3032 (7)0.0850 (6)0.164 (3)
O51.0027 (4)0.2678 (5)0.4653 (4)0.0728 (12)
O61.2162 (4)0.3471 (5)0.6150 (4)0.0753 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.060 (4)0.093 (4)0.064 (5)0.033 (4)0.005 (3)0.035 (3)
C20.056 (4)0.075 (4)0.055 (4)0.031 (3)0.009 (3)0.029 (3)
C30.055 (3)0.049 (3)0.054 (4)0.025 (3)0.018 (3)0.023 (3)
C40.047 (3)0.053 (3)0.047 (3)0.025 (3)0.008 (3)0.018 (3)
C50.048 (3)0.049 (3)0.063 (4)0.021 (3)0.007 (3)0.018 (3)
C60.059 (4)0.069 (4)0.082 (5)0.036 (3)0.024 (3)0.019 (3)
C70.077 (5)0.071 (4)0.059 (4)0.039 (3)0.028 (3)0.020 (3)
C80.055 (4)0.064 (3)0.053 (4)0.023 (3)0.002 (3)0.018 (3)
C90.044 (3)0.064 (3)0.054 (4)0.031 (3)0.005 (2)0.024 (3)
C100.095 (5)0.075 (4)0.064 (5)0.053 (3)0.009 (3)0.030 (3)
C110.104 (5)0.095 (4)0.042 (4)0.054 (4)0.003 (3)0.025 (3)
C120.071 (4)0.070 (4)0.046 (4)0.035 (3)0.004 (3)0.007 (3)
C130.092 (5)0.060 (3)0.065 (5)0.035 (3)0.025 (3)0.023 (3)
C140.085 (4)0.060 (3)0.063 (4)0.036 (3)0.025 (3)0.036 (3)
C150.053 (4)0.057 (3)0.066 (4)0.021 (3)0.004 (3)0.027 (3)
C160.083 (5)0.109 (5)0.082 (5)0.055 (4)0.031 (4)0.049 (4)
C17A0.110 (6)0.092 (5)0.113 (7)0.059 (4)0.034 (5)0.030 (4)
C18A0.191 (12)0.135 (11)0.116 (11)0.133 (8)0.046 (9)0.032 (7)
C19A0.197 (13)0.123 (9)0.116 (11)0.100 (9)0.062 (9)0.039 (8)
C17B0.110 (6)0.092 (5)0.113 (7)0.059 (4)0.034 (5)0.030 (4)
C18B0.195 (13)0.137 (12)0.126 (11)0.137 (9)0.038 (10)0.025 (9)
C19B0.206 (14)0.155 (13)0.127 (13)0.108 (10)0.037 (11)0.023 (10)
N10.068 (4)0.129 (5)0.071 (4)0.041 (3)0.011 (3)0.031 (4)
N20.118 (5)0.103 (5)0.066 (5)0.064 (4)0.013 (4)0.020 (4)
O10.080 (3)0.091 (3)0.050 (3)0.040 (2)0.008 (2)0.018 (2)
O20.063 (3)0.091 (3)0.086 (3)0.049 (2)0.016 (2)0.027 (2)
O30.267 (8)0.201 (6)0.065 (4)0.165 (6)0.002 (5)0.016 (4)
O40.294 (9)0.092 (3)0.119 (5)0.086 (5)0.094 (5)0.033 (4)
O50.062 (3)0.102 (3)0.061 (3)0.046 (2)0.019 (2)0.027 (2)
O60.050 (2)0.100 (3)0.087 (3)0.041 (2)0.013 (2)0.041 (2)
Geometric parameters (Å, º) top
C1—N11.318 (7)C16—C17B1.445 (8)
C1—O11.339 (7)C16—C17A1.445 (8)
C1—C21.355 (8)C16—O51.454 (7)
C2—C151.427 (8)C16—H16A0.9700
C2—C31.462 (7)C16—H16B0.9700
C3—C81.370 (7)C17A—C18A1.530 (9)
C3—C41.403 (7)C17A—H17A0.9700
C4—C51.393 (7)C17A—H17B0.9700
C4—C91.451 (7)C18A—C19A1.484 (9)
C5—O21.353 (6)C18A—H18A0.9700
C5—C61.375 (8)C18A—H18B0.9700
C6—C71.364 (8)C19A—H19A0.9600
C6—H60.9300C19A—H19B0.9600
C7—C81.368 (7)C19A—H19C0.9600
C7—H70.9300C17B—C18B1.516 (10)
C8—O11.386 (6)C17B—H17C0.9700
C9—C141.386 (7)C17B—H17D0.9700
C9—C101.387 (7)C18B—C19B1.487 (10)
C10—C111.359 (8)C18B—H18C0.9700
C10—H100.9300C18B—H18D0.9700
C11—C121.364 (8)C19B—H19D0.9600
C11—H110.9300C19B—H19E0.9600
C12—C131.346 (8)C19B—H19F0.9600
C12—N21.439 (8)N1—H1A0.95 (7)
C13—C141.362 (7)N1—H1B0.83 (7)
C13—H130.9300N2—O31.199 (8)
C14—H140.9300N2—O41.202 (7)
C15—O61.235 (6)O2—H20.88 (2)
C15—O51.319 (6)
N1—C1—O1116.9 (6)C17A—C16—H16B109.0
N1—C1—C2131.4 (7)O5—C16—H16B109.0
O1—C1—C2111.7 (5)H16A—C16—H16B107.8
C1—C2—C15119.5 (5)C16—C17A—C18A101.6 (7)
C1—C2—C3106.0 (5)C16—C17A—H17A111.5
C15—C2—C3133.8 (5)C18A—C17A—H17A111.5
C8—C3—C4118.1 (5)C16—C17A—H17B111.5
C8—C3—C2105.0 (5)C18A—C17A—H17B111.5
C4—C3—C2136.9 (5)H17A—C17A—H17B109.3
C5—C4—C3116.4 (5)C19A—C18A—C17A114.2 (11)
C5—C4—C9119.3 (4)C19A—C18A—H18A108.7
C3—C4—C9124.0 (5)C17A—C18A—H18A108.7
O2—C5—C6120.6 (5)C19A—C18A—H18B108.7
O2—C5—C4116.7 (5)C17A—C18A—H18B108.7
C6—C5—C4122.7 (5)H18A—C18A—H18B107.6
C7—C6—C5121.2 (5)C18A—C19A—H19A109.5
C7—C6—H6119.4C18A—C19A—H19B109.5
C5—C6—H6119.4H19A—C19A—H19B109.5
C6—C7—C8115.7 (5)C18A—C19A—H19C109.5
C6—C7—H7122.2H19A—C19A—H19C109.5
C8—C7—H7122.2H19B—C19A—H19C109.5
C3—C8—C7125.7 (5)C16—C17B—C18B121.7 (13)
C3—C8—O1110.1 (5)C16—C17B—H17C106.9
C7—C8—O1124.1 (5)C18B—C17B—H17C106.9
C14—C9—C10118.2 (5)C16—C17B—H17D106.9
C14—C9—C4119.0 (5)C18B—C17B—H17D106.9
C10—C9—C4122.8 (5)H17C—C17B—H17D106.7
C11—C10—C9121.7 (5)C19B—C18B—C17B101.0 (15)
C11—C10—H10119.1C19B—C18B—H18C111.6
C9—C10—H10119.1C17B—C18B—H18C111.6
C10—C11—C12117.8 (6)C19B—C18B—H18D111.6
C10—C11—H11121.1C17B—C18B—H18D111.6
C12—C11—H11121.1H18C—C18B—H18D109.4
C13—C12—C11122.4 (5)C18B—C19B—H19D109.5
C13—C12—N2118.2 (6)C18B—C19B—H19E109.5
C11—C12—N2119.4 (6)H19D—C19B—H19E109.5
C12—C13—C14120.0 (5)C18B—C19B—H19F109.5
C12—C13—H13120.0H19D—C19B—H19F109.5
C14—C13—H13120.0H19E—C19B—H19F109.5
C13—C14—C9119.8 (6)C1—N1—H1A121 (4)
C13—C14—H14120.1C1—N1—H1B130 (5)
C9—C14—H14120.1H1A—N1—H1B109 (7)
O6—C15—O5121.8 (5)O3—N2—O4120.9 (7)
O6—C15—C2124.0 (6)O3—N2—C12119.1 (7)
O5—C15—C2114.0 (5)O4—N2—C12119.9 (7)
C17B—C16—O5113.0 (6)C1—O1—C8107.1 (5)
C17A—C16—O5113.0 (6)C5—O2—H296 (4)
C17A—C16—H16A109.0C15—O5—C16119.0 (5)
O5—C16—H16A109.0
N1—C1—C2—C158.7 (10)C4—C9—C10—C11179.9 (5)
O1—C1—C2—C15170.4 (5)C9—C10—C11—C121.8 (9)
N1—C1—C2—C3179.1 (7)C10—C11—C12—C130.6 (9)
O1—C1—C2—C31.9 (7)C10—C11—C12—N2178.9 (6)
C1—C2—C3—C81.6 (6)C11—C12—C13—C140.1 (9)
C15—C2—C3—C8169.1 (6)N2—C12—C13—C14179.6 (5)
C1—C2—C3—C4176.7 (6)C12—C13—C14—C90.5 (8)
C15—C2—C3—C412.7 (11)C10—C9—C14—C131.7 (8)
C8—C3—C4—C55.3 (7)C4—C9—C14—C13179.3 (5)
C2—C3—C4—C5176.6 (6)C1—C2—C15—O64.2 (9)
C8—C3—C4—C9168.8 (5)C3—C2—C15—O6173.9 (5)
C2—C3—C4—C99.4 (10)C1—C2—C15—O5169.9 (5)
C3—C4—C5—O2179.7 (5)C3—C2—C15—O50.2 (9)
C9—C4—C5—O26.0 (7)O5—C16—C17A—C18A173.0 (11)
C3—C4—C5—C61.7 (8)C16—C17A—C18A—C19A171.5 (17)
C9—C4—C5—C6172.7 (5)O5—C16—C17B—C18B171.7 (11)
O2—C5—C6—C7176.5 (5)C16—C17B—C18B—C19B81 (2)
C4—C5—C6—C72.1 (9)C13—C12—N2—O3179.7 (7)
C5—C6—C7—C82.0 (9)C11—C12—N2—O30.1 (10)
C4—C3—C8—C75.8 (9)C13—C12—N2—O43.4 (10)
C2—C3—C8—C7175.6 (6)C11—C12—N2—O4177.1 (7)
C4—C3—C8—O1177.8 (4)N1—C1—O1—C8179.4 (6)
C2—C3—C8—O10.9 (6)C2—C1—O1—C81.3 (7)
C6—C7—C8—C32.0 (9)C3—C8—O1—C10.2 (6)
C6—C7—C8—O1177.9 (5)C7—C8—O1—C1176.7 (6)
C5—C4—C9—C14106.8 (6)O6—C15—O5—C162.1 (8)
C3—C4—C9—C1467.1 (7)C2—C15—O5—C16172.2 (5)
C5—C4—C9—C1070.6 (7)C17B—C16—O5—C1585.4 (7)
C3—C4—C9—C10115.4 (6)C17A—C16—O5—C1585.4 (7)
C14—C9—C10—C112.4 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O4i0.932.643.444 (8)146
C11—H11···O3ii0.932.533.237 (8)133
C17B—H17D···O60.972.743.226 (8)112
N1—H1A···O60.95 (7)2.15 (7)2.747 (8)120 (6)
O2—H2···O6iii0.88 (2)1.94 (3)2.755 (6)154 (6)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y, z; (iii) x1, y, z.
2-Methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF2) top
Crystal data top
C18H16N2O7F(000) = 776
Mr = 372.33Dx = 1.422 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.263 (2) ÅCell parameters from 72 reflections
b = 9.0860 (8) Åθ = 3.0–20.3°
c = 20.049 (4) ŵ = 0.11 mm1
β = 111.577 (16)°T = 298 K
V = 1738.6 (6) Å3Plate, yellow
Z = 40.48 × 0.22 × 0.02 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3784 independent reflections
Radiation source: normal-focus sealed tube2408 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD rotation images, thick slices scansh = 813
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 1110
Tmin = 0.825, Tmax = 0.927l = 2623
9595 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.058P)2 + 0.521P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3784 reflectionsΔρmax = 0.21 e Å3
254 parametersΔρmin = 0.18 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1522 (2)0.1808 (2)0.16883 (11)0.0445 (5)
C20.1956 (2)0.0554 (2)0.20982 (10)0.0373 (5)
C30.1095 (2)0.0632 (2)0.16748 (10)0.0341 (4)
C40.1002 (2)0.2168 (2)0.17400 (10)0.0344 (4)
C50.0070 (2)0.2886 (2)0.11922 (11)0.0406 (5)
C60.0987 (2)0.2149 (2)0.05940 (11)0.0461 (5)
H60.1690330.2670250.0244350.055*
C70.0860 (2)0.0655 (2)0.05158 (11)0.0450 (5)
H70.1450550.0150440.0115120.054*
C80.0173 (2)0.0043 (2)0.10548 (10)0.0390 (5)
C90.2033 (2)0.3040 (2)0.23255 (10)0.0340 (4)
C100.1601 (2)0.3939 (2)0.27675 (11)0.0420 (5)
H100.0653670.3996160.2695230.050*
C110.2554 (2)0.4745 (2)0.33092 (11)0.0467 (5)
H110.2259810.5340730.3603950.056*
C120.3945 (2)0.4653 (2)0.34070 (11)0.0444 (5)
C130.4412 (2)0.3798 (2)0.29739 (12)0.0503 (6)
H130.5358930.3764230.3043530.060*
C140.3444 (2)0.2992 (2)0.24337 (11)0.0440 (5)
H140.3744440.2406940.2137670.053*
C150.2933 (2)0.0684 (2)0.28310 (11)0.0424 (5)
C160.3911 (3)0.0471 (3)0.39702 (12)0.0675 (7)
H15A0.4769300.0898100.3959810.081*
H15B0.4113770.0523140.4155990.081*
C170.3393 (3)0.1360 (3)0.44439 (12)0.0639 (7)
H17A0.4182920.1737230.4844570.077*
H17B0.2858140.2190970.4178200.077*
C180.2178 (3)0.1191 (3)0.52447 (15)0.0807 (9)
H18A0.3014840.1424830.5645940.121*
H18B0.1604760.0540630.5397270.121*
H18C0.1668570.2079170.5056700.121*
N10.1990 (3)0.3192 (2)0.17972 (13)0.0662 (7)
H1A0.137 (3)0.388 (3)0.1558 (15)0.079*
H1B0.258 (3)0.334 (3)0.2202 (16)0.079*
N20.4964 (3)0.5494 (2)0.39927 (11)0.0620 (6)
O10.04482 (16)0.15477 (14)0.10650 (8)0.0487 (4)
O20.01457 (18)0.43883 (16)0.12485 (9)0.0579 (5)
H2O0.094 (3)0.471 (3)0.0929 (14)0.069*
O30.4543 (2)0.6155 (2)0.44027 (10)0.0856 (6)
O40.6174 (2)0.5507 (3)0.40383 (12)0.0956 (7)
O50.28607 (16)0.04351 (16)0.32517 (7)0.0519 (4)
O60.37098 (18)0.17310 (18)0.30529 (9)0.0630 (5)
O70.25432 (19)0.04923 (17)0.47021 (8)0.0628 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0499 (13)0.0369 (11)0.0459 (12)0.0015 (9)0.0168 (11)0.0021 (9)
C20.0385 (12)0.0333 (10)0.0406 (11)0.0025 (8)0.0150 (9)0.0018 (8)
C30.0328 (11)0.0374 (11)0.0341 (10)0.0029 (8)0.0144 (8)0.0005 (8)
C40.0327 (11)0.0378 (11)0.0334 (10)0.0007 (8)0.0130 (8)0.0013 (8)
C50.0406 (12)0.0346 (11)0.0448 (12)0.0016 (8)0.0135 (10)0.0010 (9)
C60.0425 (13)0.0489 (13)0.0385 (11)0.0023 (9)0.0051 (10)0.0056 (9)
C70.0481 (13)0.0488 (13)0.0334 (11)0.0085 (9)0.0095 (9)0.0038 (9)
C80.0459 (12)0.0353 (11)0.0369 (11)0.0046 (8)0.0165 (9)0.0030 (8)
C90.0346 (11)0.0314 (10)0.0344 (10)0.0002 (7)0.0109 (8)0.0015 (8)
C100.0382 (12)0.0436 (12)0.0459 (12)0.0009 (9)0.0177 (10)0.0042 (9)
C110.0574 (15)0.0434 (12)0.0426 (12)0.0045 (10)0.0221 (11)0.0073 (9)
C120.0489 (14)0.0439 (12)0.0357 (11)0.0119 (9)0.0099 (10)0.0002 (9)
C130.0348 (12)0.0612 (14)0.0528 (14)0.0076 (10)0.0137 (11)0.0026 (11)
C140.0367 (12)0.0501 (12)0.0463 (12)0.0006 (9)0.0165 (10)0.0078 (9)
C150.0418 (12)0.0391 (12)0.0447 (12)0.0043 (9)0.0142 (10)0.0069 (9)
C160.0584 (17)0.089 (2)0.0386 (13)0.0056 (13)0.0011 (11)0.0059 (12)
C170.0819 (19)0.0544 (15)0.0396 (13)0.0198 (12)0.0039 (12)0.0003 (11)
C180.097 (2)0.082 (2)0.0644 (18)0.0044 (16)0.0318 (17)0.0191 (15)
N10.0802 (17)0.0332 (11)0.0703 (15)0.0010 (10)0.0100 (12)0.0010 (10)
N20.0671 (16)0.0586 (13)0.0475 (12)0.0200 (11)0.0061 (11)0.0018 (10)
O10.0610 (10)0.0359 (8)0.0435 (8)0.0051 (7)0.0126 (7)0.0066 (6)
O20.0537 (10)0.0383 (9)0.0629 (11)0.0095 (7)0.0005 (8)0.0010 (7)
O30.1101 (17)0.0828 (14)0.0548 (12)0.0276 (12)0.0195 (12)0.0262 (10)
O40.0596 (14)0.1190 (18)0.0861 (15)0.0335 (12)0.0009 (11)0.0229 (12)
O50.0540 (10)0.0558 (10)0.0352 (8)0.0042 (7)0.0040 (7)0.0019 (7)
O60.0615 (11)0.0517 (10)0.0639 (11)0.0120 (8)0.0091 (9)0.0131 (8)
O70.0778 (12)0.0530 (10)0.0515 (10)0.0191 (8)0.0165 (9)0.0113 (8)
Geometric parameters (Å, º) top
C1—N11.335 (3)C12—N21.468 (3)
C1—O11.349 (3)C13—C141.380 (3)
C1—C21.380 (3)C13—H130.9300
C2—C151.447 (3)C14—H140.9300
C2—C31.453 (3)C15—O61.216 (2)
C3—C81.397 (3)C15—O51.341 (2)
C3—C41.409 (3)C16—O51.448 (3)
C4—C51.397 (3)C16—C171.486 (4)
C4—C91.487 (3)C16—H15A0.9700
C5—O21.375 (2)C16—H15B0.9700
C5—C61.393 (3)C17—O71.408 (3)
C6—C71.378 (3)C17—H17A0.9700
C6—H60.9300C17—H17B0.9700
C7—C81.361 (3)C18—O71.424 (3)
C7—H70.9300C18—H18A0.9600
C8—O11.394 (2)C18—H18B0.9600
C9—C141.384 (3)C18—H18C0.9600
C9—C101.392 (3)N1—H1A0.89 (3)
C10—C111.375 (3)N1—H1B0.83 (3)
C10—H100.9300N2—O41.212 (3)
C11—C121.370 (3)N2—O31.218 (3)
C11—H110.9300O2—H2O0.88 (3)
C12—C131.376 (3)
N1—C1—O1116.06 (19)C12—C13—H13120.8
N1—C1—C2131.5 (2)C14—C13—H13120.8
O1—C1—C2112.45 (17)C13—C14—C9121.09 (19)
C1—C2—C15119.26 (18)C13—C14—H14119.5
C1—C2—C3105.70 (17)C9—C14—H14119.5
C15—C2—C3134.37 (17)O6—C15—O5122.9 (2)
C8—C3—C4118.08 (17)O6—C15—C2123.5 (2)
C8—C3—C2105.17 (16)O5—C15—C2113.51 (17)
C4—C3—C2136.74 (17)O5—C16—C17109.8 (2)
C5—C4—C3116.75 (17)O5—C16—H15A109.7
C5—C4—C9119.87 (17)C17—C16—H15A109.7
C3—C4—C9123.23 (17)O5—C16—H15B109.7
O2—C5—C6120.48 (18)C17—C16—H15B109.7
O2—C5—C4116.78 (18)H15A—C16—H15B108.2
C6—C5—C4122.66 (18)O7—C17—C16110.3 (2)
C7—C6—C5120.60 (19)O7—C17—H17A109.6
C7—C6—H6119.7C16—C17—H17A109.6
C5—C6—H6119.7O7—C17—H17B109.6
C8—C7—C6116.59 (19)C16—C17—H17B109.6
C8—C7—H7121.7H17A—C17—H17B108.1
C6—C7—H7121.7O7—C18—H18A109.5
C7—C8—O1124.28 (18)O7—C18—H18B109.5
C7—C8—C3125.21 (18)H18A—C18—H18B109.5
O1—C8—C3110.50 (17)O7—C18—H18C109.5
C14—C9—C10118.59 (18)H18A—C18—H18C109.5
C14—C9—C4120.45 (17)H18B—C18—H18C109.5
C10—C9—C4120.95 (17)C1—N1—H1A115.4 (19)
C11—C10—C9120.97 (19)C1—N1—H1B114 (2)
C11—C10—H10119.5H1A—N1—H1B122 (3)
C9—C10—H10119.5O4—N2—O3123.5 (2)
C12—C11—C10118.8 (2)O4—N2—C12118.3 (2)
C12—C11—H11120.6O3—N2—C12118.1 (2)
C10—C11—H11120.6C1—O1—C8106.12 (15)
C11—C12—C13122.05 (19)C5—O2—H2O109.6 (17)
C11—C12—N2118.8 (2)C15—O5—C16116.75 (18)
C13—C12—N2119.2 (2)C17—O7—C18113.83 (19)
C12—C13—C14118.5 (2)
N1—C1—C2—C1511.7 (4)C3—C4—C9—C10124.6 (2)
O1—C1—C2—C15169.66 (17)C14—C9—C10—C111.2 (3)
N1—C1—C2—C3176.4 (2)C4—C9—C10—C11179.96 (18)
O1—C1—C2—C32.2 (2)C9—C10—C11—C120.2 (3)
C1—C2—C3—C82.4 (2)C10—C11—C12—C131.0 (3)
C15—C2—C3—C8167.7 (2)C10—C11—C12—N2179.02 (19)
C1—C2—C3—C4176.8 (2)C11—C12—C13—C141.2 (3)
C15—C2—C3—C413.2 (4)N2—C12—C13—C14178.81 (19)
C8—C3—C4—C53.6 (3)C12—C13—C14—C90.2 (3)
C2—C3—C4—C5177.3 (2)C10—C9—C14—C130.9 (3)
C8—C3—C4—C9171.97 (18)C4—C9—C14—C13179.83 (19)
C2—C3—C4—C97.1 (3)C1—C2—C15—O622.3 (3)
C3—C4—C5—O2178.79 (17)C3—C2—C15—O6168.7 (2)
C9—C4—C5—O23.0 (3)C1—C2—C15—O5155.14 (19)
C3—C4—C5—C62.0 (3)C3—C2—C15—O513.9 (3)
C9—C4—C5—C6173.74 (19)O5—C16—C17—O783.6 (2)
O2—C5—C6—C7176.1 (2)C11—C12—N2—O4173.8 (2)
C4—C5—C6—C70.5 (3)C13—C12—N2—O46.2 (3)
C5—C6—C7—C81.4 (3)C11—C12—N2—O35.4 (3)
C6—C7—C8—O1179.86 (19)C13—C12—N2—O3174.5 (2)
C6—C7—C8—C30.5 (3)N1—C1—O1—C8177.8 (2)
C4—C3—C8—C73.0 (3)C2—C1—O1—C81.1 (2)
C2—C3—C8—C7177.62 (19)C7—C8—O1—C1178.9 (2)
C4—C3—C8—O1177.49 (16)C3—C8—O1—C10.6 (2)
C2—C3—C8—O11.8 (2)O6—C15—O5—C169.3 (3)
C5—C4—C9—C14118.9 (2)C2—C15—O5—C16173.19 (18)
C3—C4—C9—C1456.5 (3)C17—C16—O5—C15157.75 (19)
C5—C4—C9—C1059.9 (3)C16—C17—O7—C18170.9 (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···AD—HH···AD···AD—H···A
C17—H17A···O3i0.972.493.366 (3)150
N1—H1A···O2ii0.89 (3)2.14 (3)3.013 (3)165 (3)
N1—H1B···O60.83 (3)2.22 (3)2.819 (3)129 (3)
O2—H2O···O7iii0.88 (3)1.81 (3)2.691 (2)176 (3)
C10—H10···Cg1iii0.932.763.521 (3)139
C11—H11···Cg2iii0.932.803.601 (3)145
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, 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).
NsymopREelecEpolEdispErepEtotalinteraction
2x, y, z12.04-9.1-2.5-14.19.1-18.1C7—H7···O4i
1-x, -y, -z10.51-8.2-3.0-11.713.1-12.9C11—H11···O3ii
1-x, -y, -z11.10-3.2-1.9-12.22.8-13.6
2x, y, z12.43-3.3-1.4-5.41.0-8.6
1-x, -y, -z12.978.5-1.0-2.30.56.5N2—O4···O4iii
1-x, -y, -z5.99-27.6-3.7-67.735.8-68.8N1—H1A···O4iv
1-x, -y, -z6.67-8.0-3.0-43.422.8-34.4
2x, y, z9.44-42.2-10.7-27.752.0-44.5O2—H2···O6v
1-x, -y, -z5.08-13.2-1.5-76.136.5-58.7C10—H10···O6vi
1-x, -y, -z9.631.5-1.2-14.83.4-10.1
1-x, -y, -z11.07-0.5-1.9-14.64.5-11.9
Notes: (a) Energy Model: CE_B3LYP···B3LYP/6-31G(d,p) electron densities. Scale factors for benchmarked energy model (Mackenzie et al. 2017): kele = 1.057; kpol = 0.740; kdisp = 0.871; krep= 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
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).
NsymopREelecEpolEdispErepEtotalinteraction
1-x, -y, -z10.65-2.1-0.6-21.212.0-13.7
2-x, y + 1/2, -z + 1/26.41-70.6-16.2-59.898.4-77.9O2—H2O···O7i
2x, -y + 1/2, z + 1/211.49-4.5-1.4-6.24.1-8.6
2x, y, z9.09-23.5-7.2-29.935.7-34.2N1—H1A···O2ii
1-x, -y, -z12.21-1.4-0.1-2.20.2-3.3
2x, -y + 1/2, z + 1/210.11-1.4-0.4-13.65.3-10.4
2-x, y + 1/2, -zz + 1/27.42-8.0-2.5-26.413.6-25.0
1-x, -y, -z9.34-6.5-0.8-22.812.2-19.9
2x, -y + 1/2, z + 1/212.672.2-0.3-3.10.6-0.2
1-x, -y, -z10.57-17.3-6.8-22.226.4-26.3C17—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): kele = 1.057; kpol = 0.740; kdisp = 0.871; krep= 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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