Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues
Adamczyk-Woźniak, Agnieszka; Borys, Krzysztof M.; Madura, Izabela D.; Pawełko, Alicja; Tomecka, Ewelina; Żukowski, Kamil; New Journal of Chemistry 37 (2013) 188–; doi:10.1039/c2nj40687j

data_7052996
_publ_section_title
;
 Lewis acidity and sugar receptor activity of 3-amino-substituted
 benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              188
_journal_paper_doi               10.1039/c2nj40687j
_journal_volume                  37
_journal_year                    2013
_chemical_formula_moiety         'C18 H22 B N O4, C H4 O'
_chemical_formula_sum            'C19 H26 B N O5'
_chemical_formula_weight         359.22
_chemical_name_systematic
;
(Benzene-1,2-diolato)(methanolato)(2-(morpholinomethyl)phenyl)boron
methanol solvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.016(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1083(3)
_cell_length_b                   9.45522(19)
_cell_length_c                   15.1358(4)
_cell_measurement_reflns_used    12845
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      67.0887
_cell_measurement_theta_min      3.4137
_cell_volume                     1852.78(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega -53.00 -25.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -41.0113 125.0000 -30.0000 28

2 omega -58.00 -20.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -41.0113 125.0000 -119.0000 38

3 omega 8.00 120.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 41.0113 77.0000 90.0000 112

4 omega 42.00 96.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 41.0113 -125.0000 -150.0000 54

5 omega 19.00 112.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 41.0113 37.0000 -30.0000 93

6 omega -121.00 -62.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 125.0000 60.0000 59

7 omega -120.00 -91.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 125.0000 -90.0000 29

8 omega 87.00 126.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -90.0000 -34.0000 39

9 omega 15.00 41.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -90.0000 -34.0000 26

10 omega 104.00 131.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -90.0000 123.0000 27

11 omega 93.00 119.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -83.0000 59.0000 26

12 omega 62.00 88.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 15.0000 -60.0000 26

13 omega 110.00 145.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 15.0000 -60.0000 35

14 omega 71.00 97.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 45.0000 -180.0000 26

15 omega 89.00 115.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -71.0000 -54.0000 26

16 omega 90.00 116.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -71.0000 44.0000 26

17 omega 81.00 119.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -92.0000 76.0000 38

18 omega 20.00 76.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -45.0000 -150.0000 56

19 omega 20.00 76.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -45.0000 -60.0000 56

20 omega 20.00 76.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -45.0000 90.0000 56

21 omega 98.00 124.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 125.0000 90.0000 26

22 omega 20.00 76.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -45.0000 30.0000 56

23 omega 69.00 135.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 77.0000 120.0000 66

24 omega 144.00 169.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 77.0000 120.0000 25

25 omega 29.00 62.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -146.0000 -46.0000 33

26 omega 68.00 98.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 45.0000 -30.0000 30

27 omega 20.00 105.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -146.0000 -4.0000 85

28 omega 61.00 119.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 77.0000 -60.0000 58

29 omega 33.00 74.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -15.0000 30.0000 41

30 omega 96.00 154.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -15.0000 30.0000 58

31 omega 20.00 62.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -71.0000 44.0000 42

32 omega 83.00 140.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 45.0000 60.0000 57

33 omega 77.00 116.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 125.0000 -180.0000 39

34 omega 96.00 122.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -89.0000 -129.0000 26

35 omega 29.00 57.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -89.0000 -129.0000 28

36 omega 131.00 157.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 45.0000 -180.0000 26

37 omega 112.00 138.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 45.0000 -30.0000 26

38 omega 69.00 94.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 77.0000 -180.0000 25

39 omega 44.00 74.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -77.0000 -120.0000 30

40 omega 95.00 121.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -77.0000 -120.0000 26

41 omega 24.00 62.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -77.0000 150.0000 38

42 omega 141.00 166.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 125.0000 -150.0000 25

43 omega 33.00 123.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -67.0000 -64.0000 90

44 omega 9.00 35.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -92.0000 76.0000 26

45 omega 48.00 75.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -90.0000 123.0000 27

46 omega 83.00 108.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 77.0000 0.0000 25

47 omega 119.00 155.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -15.0000 -180.0000 36

48 omega 39.00 109.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 93.5000 -92.0000 -172.0000 70
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23639
_diffrn_reflns_theta_full        67.20
_diffrn_reflns_theta_max         67.20
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.5541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                2894
_reflns_number_total             3316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2nj40687j.txt
_cod_data_source_block           5a
_cod_original_cell_volume        1852.80(7)
_cod_database_code               7052996