#------------------------------------------------------------------------------
#$Date: 2017-03-04 16:01:41 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125513.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4125513
loop_
_publ_author_name
'Georgiou, Irene'
'Kervyn, Simon'
'Rossignon, Alexandre'
'De Leo, Federica'
'Wouters, Johan'
'Bruylants, Gilles'
'Bonifazi, Davide'
_publ_section_title
;
 Versatile Self-Adapting Boronic Acids for H-Bond Recognition: From
 Discrete to Polymeric Supramolecules.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2710
_journal_page_last               2727
_journal_paper_doi               10.1021/jacs.6b11362
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C14 H8 N4, 2(C6 H7 B O2)'
_chemical_formula_sum            'C26 H22 B2 N4 O4'
_chemical_formula_weight         476.11
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.785(9)
_cell_angle_beta                 103.104(9)
_cell_angle_gamma                114.473(11)
_cell_formula_units_Z            1
_cell_length_a                   7.4283(8)
_cell_length_b                   8.3837(9)
_cell_length_c                   10.8769(12)
_cell_measurement_reflns_used    1947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7270
_cell_measurement_theta_min      4.2850
_cell_volume                     585.80(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Shelxs86
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4490
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.28
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.8557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.359
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.359
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0655
_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/[σ²(Fo²)+(0.0277P)²+0.7454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1889
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                1450
_reflns_number_total             2045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_033.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4125513--4125529.cif.'
_cod_original_cell_volume        585.80(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4125513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C7 C 0.2624(6) 0.4049(5) 0.7865(4) 0.0420(9) Uani 1 1 d .
C8 C 0.1395(6) 0.3846(5) 0.6591(4) 0.0490(10) Uani 1 1 d .
H8 H 0.1604 0.4847 0.6233 0.059 Uiso 1 1 calc R
C9 C -0.0069(6) 0.2207(6) 0.5904(4) 0.0520(10) Uani 1 1 d .
H9 H -0.0867 0.2087 0.5075 0.062 Uiso 1 1 calc R
C10 C -0.0408(7) 0.0655(6) 0.6432(4) 0.0554(11) Uani 1 1 d .
H10 H -0.1432 -0.0462 0.5942 0.067 Uiso 1 1 calc R
C11 C 0.0722(6) 0.0772(5) 0.7628(4) 0.0517(10) Uani 1 1 d .
H11 H 0.0482 -0.0260 0.7950 0.062 Uiso 1 1 calc R
C12 C 0.2280(6) 0.2469(5) 0.8396(4) 0.0432(9) Uani 1 1 d .
C13 C 0.4838(6) 0.4216(5) 1.0259(4) 0.0416(9) Uani 1 1 d .
N1 N 0.4048(5) 0.5675(4) 0.8542(3) 0.0443(8) Uani 1 1 d .
N2 N 0.3385(5) 0.2574(4) 0.9578(3) 0.0455(8) Uani 1 1 d .
C1 C 0.3525(6) 0.7857(5) 0.2333(4) 0.0428(9) Uani 1 1 d .
C2 C 0.4453(6) 0.7925(6) 0.3611(4) 0.0504(10) Uani 1 1 d .
H2 H 0.5426 0.9028 0.4149 0.060 Uiso 1 1 calc R
C3 C 0.3962(7) 0.6388(6) 0.4103(4) 0.0595(12) Uani 1 1 d .
H3 H 0.4594 0.6465 0.4964 0.071 Uiso 1 1 calc R
C4 C 0.2535(7) 0.4748(6) 0.3315(5) 0.0611(12) Uani 1 1 d .
H4 H 0.2204 0.3714 0.3643 0.073 Uiso 1 1 calc R
C5 C 0.1599(7) 0.4635(6) 0.2042(5) 0.0601(12) Uani 1 1 d .
H5 H 0.0641 0.3525 0.1507 0.072 Uiso 1 1 calc R
C6 C 0.2089(7) 0.6176(5) 0.1563(4) 0.0517(10) Uani 1 1 d .
H6 H 0.1441 0.6089 0.0703 0.062 Uiso 1 1 calc R
B1 B 0.3967(7) 0.9584(6) 0.1772(5) 0.0481(11) Uani 1 1 d .
O1 O 0.5425(6) 1.1184(4) 0.2542(3) 0.0758(11) Uani 1 1 d .
O2 O 0.2829(5) 0.9390(4) 0.0562(3) 0.0682(10) Uani 1 1 d .
H2O H 0.305(8) 1.037(7) 0.026(5) 0.085(17) Uiso 1 1 d .
H1O H 0.565(9) 1.214(8) 0.218(5) 0.100(19) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C7 C8 119.7(3) . .
N1 C7 C12 121.4(3) . .
C8 C7 C12 118.9(3) . .
C9 C8 C7 120.1(4) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C10 120.8(4) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
C11 C10 C9 121.4(4) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C10 C11 C12 120.1(4) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
N2 C12 C11 119.8(3) . .
N2 C12 C7 121.5(3) . .
C11 C12 C7 118.7(3) . .
N2 C13 N1 117.1(3) . 2_667
N2 C13 C13 121.4(4) . 2_667
N1 C13 C13 121.5(4) 2_667 2_667
C7 N1 C13 117.0(3) . 2_667
C12 N2 C13 117.1(3) . .
C2 C1 C6 117.2(4) . .
C2 C1 B1 122.5(4) . .
C6 C1 B1 120.3(4) . .
C3 C2 C1 121.5(4) . .
C3 C2 H2 119.3 . .
C1 C2 H2 119.3 . .
C4 C3 C2 119.8(4) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 120.1(4) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 119.6(4) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C5 C6 C1 121.8(4) . .
C5 C6 H6 119.1 . .
C1 C6 H6 119.1 . .
O2 B1 O1 124.0(4) . .
O2 B1 C1 117.8(4) . .
O1 B1 C1 118.3(4) . .
B1 O1 H1O 115(4) . .
B1 O2 H2O 118(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 N1 1.330(5) .
C7 C8 1.426(5) .
C7 C12 1.447(5) .
C8 C9 1.348(6) .
C8 H8 0.9300 .
C9 C10 1.425(6) .
C9 H9 0.9300 .
C10 C11 1.348(6) .
C10 H10 0.9300 .
C11 C12 1.421(5) .
C11 H11 0.9300 .
C12 N2 1.332(5) .
C13 N2 1.346(5) .
C13 N1 1.348(5) 2_667
C13 C13 1.433(7) 2_667
N1 C13 1.348(5) 2_667
C1 C2 1.389(5) .
C1 C6 1.392(5) .
C1 B1 1.566(6) .
C2 C3 1.385(6) .
C2 H2 0.9300 .
C3 C4 1.375(6) .
C3 H3 0.9300 .
C4 C5 1.375(6) .
C4 H4 0.9300 .
C5 C6 1.380(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
B1 O2 1.346(5) .
B1 O1 1.354(6) .
O1 H1O 0.90(6) .
O2 H2O 0.88(5) .
