Piperazine derivatives of boronic acids – potential bifunctional biologically active compounds
Adamczyk-Woźniak, Agnieszka; Czerwińska, Karolina; Madura, Izabela D.; Matuszewska, Alicja; Sporzyński, Andrzej; Żubrowska-Zembrzuska, Anna; New J. Chem. 39 (2015) 4308–; doi:10.1039/C5NJ00084J

data_7054751
_publ_section_title
;
 Piperazine derivatives of boronic acids -- potential bifunctional
 biologically active compounds
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              4308
_journal_paper_doi               10.1039/C5NJ00084J
_journal_volume                  39
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H19 B N2 O2, H2 O'
_chemical_formula_sum            'C12 H21 B N2 O3'
_chemical_formula_weight         252.12
_chemical_name_systematic
;
2-((4-methylpiperazin-1-yl)methyl)phenylboronic acid
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.87751(17)
_cell_length_b                   10.18562(12)
_cell_length_c                   10.36536(14)
_cell_measurement_reflns_used    7344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.1610
_cell_measurement_theta_min      4.2700
_cell_volume                     1359.58(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
 Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_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.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, 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 0.8732
_diffrn_measured_fraction_theta_max 0.8864
_diffrn_measurement_details
;
  1 omega   11.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498   45.0000  180.0000 53

  2 omega  -16.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   42.0000  286.0000 53

  3 omega   31.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   77.0000  210.0000 58

  4 omega  -15.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498  -45.0000   60.0000 53

  5 omega -140.00 -100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -90.0000  229.0000 40

  6 omega -138.00 -101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -99.0000  280.0000 37

  7 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  270.0000 58

  8 omega   60.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000    0.0000 62

  9 omega   69.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 58

 10 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 58

 11 omega  126.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   90.0000  130.0000 52

 12 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  240.0000 58

 13 omega   69.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  285.0000 64

 14 omega   79.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   99.0000   79.0000 51

 15 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  210.0000 58

 16 omega  115.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 53

 17 omega   89.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000   30.0000 89

 18 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  150.0000 177

 19 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  330.0000 177
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0321776000
_diffrn_orient_matrix_UB_12      0.1280510000
_diffrn_orient_matrix_UB_13      -0.0683472000
_diffrn_orient_matrix_UB_21      -0.1037735000
_diffrn_orient_matrix_UB_22      -0.0635309000
_diffrn_orient_matrix_UB_23      -0.0394988000
_diffrn_orient_matrix_UB_31      -0.0501154000
_diffrn_orient_matrix_UB_32      0.0494713000
_diffrn_orient_matrix_UB_33      0.1258872000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10784
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.21
_diffrn_reflns_theta_min         5.54
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water, methanol'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0762P)^2^+0.2887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                2143
_reflns_number_total             2186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj00084j2.cif
_cod_data_source_block           (5)
_cod_depositor_comments
'Adding full bibliography for 7054747--7054752.cif.'
_cod_database_code               7054751