#------------------------------------------------------------------------------
#$Date: 2017-03-04 16:01:41 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125526.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_4125526
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 H6 B Cl O2)'
_chemical_formula_sum            'C26 H20 B2 Cl2 N4 O4'
_chemical_formula_weight         544.98
_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                112.762(4)
_cell_angle_beta                 94.006(4)
_cell_angle_gamma                96.904(4)
_cell_formula_units_Z            1
_cell_length_a                   6.7570(3)
_cell_length_b                   9.7827(4)
_cell_length_c                   10.5456(5)
_cell_measurement_reflns_used    7520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0690
_cell_measurement_theta_min      5.2260
_cell_volume                     632.96(5)
_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    Sir2011
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10195
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         5.25
_exptl_absorpt_coefficient_mu    2.658
_exptl_absorpt_correction_T_max  0.5680
_exptl_absorpt_correction_T_min  0.3500
_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    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0381
_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)+(0.0929P)²+0.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                2045
_reflns_number_total             2175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_032.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4125513--4125529.cif.'
_cod_database_code               4125526
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 0.7560(2) 0.66557(15) 0.55953(14) 0.0413(3) Uani 1 1 d .
C8 C 0.5894(2) 0.74383(16) 0.56904(16) 0.0500(4) Uani 1 1 d .
H8 H 0.4853 0.7094 0.4962 0.060 Uiso 1 1 calc R
C9 C 0.5822(2) 0.86789(18) 0.68349(18) 0.0565(4) Uani 1 1 d .
H9 H 0.4715 0.9171 0.6893 0.068 Uiso 1 1 calc R
C10 C 0.7415(3) 0.92492(17) 0.79585(17) 0.0563(4) Uani 1 1 d .
H10 H 0.7338 1.0113 0.8731 0.068 Uiso 1 1 calc R
C11 C 0.9030(2) 0.85515(17) 0.79147(15) 0.0513(4) Uani 1 1 d .
H11 H 1.0058 0.8941 0.8653 0.062 Uiso 1 1 calc R
C12 C 0.9167(2) 0.72200(15) 0.67412(14) 0.0417(3) Uani 1 1 d .
C13 C 0.92132(19) 0.47264(14) 0.44295(13) 0.0394(3) Uani 1 1 d .
N1 N 0.76070(16) 0.54299(12) 0.44641(11) 0.0418(3) Uani 1 1 d .
N2 N 1.07402(16) 0.65116(12) 0.67177(11) 0.0424(3) Uani 1 1 d .
C1 C 0.3188(2) 0.30009(14) 0.96497(14) 0.0414(3) Uani 1 1 d .
C2 C 0.3648(2) 0.22427(16) 0.83138(15) 0.0471(3) Uani 1 1 d .
H2 H 0.4921 0.1979 0.8197 0.057 Uiso 1 1 calc R
C3 C 0.2264(2) 0.18706(17) 0.71563(14) 0.0511(4) Uani 1 1 d .
H3 H 0.2596 0.1365 0.6271 0.061 Uiso 1 1 calc R
C4 C 0.0385(2) 0.22647(16) 0.73433(14) 0.0461(3) Uani 1 1 d .
C5 C -0.0143(2) 0.30105(17) 0.86402(16) 0.0512(4) Uani 1 1 d .
H5 H -0.1421 0.3267 0.8749 0.061 Uiso 1 1 calc R
C6 C 0.1269(2) 0.33704(16) 0.97785(15) 0.0486(3) Uani 1 1 d .
H6 H 0.0924 0.3876 1.0660 0.058 Uiso 1 1 calc R
O1 O 0.43906(17) 0.44552(12) 1.21799(11) 0.0528(3) Uani 1 1 d .
O2 O 0.64366(16) 0.27617(14) 1.07938(11) 0.0605(3) Uani 1 1 d .
Cl1 Cl -0.13898(6) 0.18053(5) 0.58926(4) 0.0689(2) Uani 1 1 d .
B1 B 0.4783(2) 0.34402(17) 1.09609(15) 0.0431(3) Uani 1 1 d .
H1O H 0.523(3) 0.468(2) 1.273(2) 0.065(6) Uiso 1 1 d .
H2O H 0.718(3) 0.297(2) 1.148(3) 0.071(6) 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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 119.51(12) . .
N1 C7 C12 121.63(12) . .
C8 C7 C12 118.86(12) . .
C9 C8 C7 120.12(14) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C10 121.18(14) . .
C8 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C11 C10 C9 120.92(14) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C10 C11 C12 120.28(14) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
N2 C12 C11 120.10(12) . .
N2 C12 C7 121.27(12) . .
C11 C12 C7 118.62(12) . .
N2 C13 N1 117.03(11) 2_766 .
N2 C13 C13 121.81(15) 2_766 2_766
N1 C13 C13 121.15(15) . 2_766
C7 N1 C13 117.14(11) . .
C12 N2 C13 116.97(11) . 2_766
C6 C1 C2 117.26(12) . .
C6 C1 B1 121.27(12) . .
C2 C1 B1 121.47(12) . .
C3 C2 C1 121.82(13) . .
C3 C2 H2 119.1 . .
C1 C2 H2 119.1 . .
C4 C3 C2 118.52(13) . .
C4 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
C5 C4 C3 121.86(12) . .
C5 C4 Cl1 118.85(11) . .
C3 C4 Cl1 119.29(11) . .
C4 C5 C6 118.41(13) . .
C4 C5 H5 120.8 . .
C6 C5 H5 120.8 . .
C5 C6 C1 122.12(13) . .
C5 C6 H6 118.9 . .
C1 C6 H6 118.9 . .
B1 O1 H1O 112.8(17) . .
B1 O2 H2O 115.7(15) . .
O1 B1 O2 124.64(13) . .
O1 B1 C1 117.59(12) . .
O2 B1 C1 117.76(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 N1 1.3302(18) .
C7 C8 1.424(2) .
C7 C12 1.4495(19) .
C8 C9 1.349(2) .
C8 H8 0.9300 .
C9 C10 1.428(2) .
C9 H9 0.9300 .
C10 C11 1.350(2) .
C10 H10 0.9300 .
C11 C12 1.426(2) .
C11 H11 0.9300 .
C12 N2 1.3332(17) .
C13 N2 1.3461(18) 2_766
C13 N1 1.3485(17) .
C13 C13 1.432(2) 2_766
N2 C13 1.3461(18) 2_766
C1 C6 1.389(2) .
C1 C2 1.393(2) .
C1 B1 1.5745(19) .
C2 C3 1.382(2) .
C2 H2 0.9300 .
C3 C4 1.376(2) .
C3 H3 0.9300 .
C4 C5 1.374(2) .
C4 Cl1 1.7499(13) .
C5 C6 1.381(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
O1 B1 1.3536(19) .
O1 H1O 0.73(2) .
O2 B1 1.3546(19) .
O2 H2O 0.79(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C7 C8 C9 179.65(13) . .
C12 C7 C8 C9 -0.3(2) . .
C7 C8 C9 C10 1.1(2) . .
C8 C9 C10 C11 -0.8(3) . .
C9 C10 C11 C12 -0.4(2) . .
C10 C11 C12 N2 -178.21(13) . .
C10 C11 C12 C7 1.1(2) . .
N1 C7 C12 N2 -1.4(2) . .
C8 C7 C12 N2 178.54(12) . .
N1 C7 C12 C11 179.22(12) . .
C8 C7 C12 C11 -0.82(19) . .
C8 C7 N1 C13 -179.66(12) . .
C12 C7 N1 C13 0.31(18) . .
N2 C13 N1 C7 -179.83(10) 2_766 .
C13 C13 N1 C7 0.6(2) 2_766 .
C11 C12 N2 C13 -179.13(12) . 2_766
C7 C12 N2 C13 1.53(19) . 2_766
C6 C1 C2 C3 0.1(2) . .
B1 C1 C2 C3 -179.13(13) . .
C1 C2 C3 C4 -0.1(2) . .
C2 C3 C4 C5 -0.1(2) . .
C2 C3 C4 Cl1 179.98(11) . .
C3 C4 C5 C6 0.1(2) . .
Cl1 C4 C5 C6 -179.89(11) . .
C4 C5 C6 C1 -0.1(2) . .
C2 C1 C6 C5 0.0(2) . .
B1 C1 C6 C5 179.22(13) . .
C6 C1 B1 O1 -13.9(2) . .
C2 C1 B1 O1 165.38(13) . .
C6 C1 B1 O2 165.27(13) . .
C2 C1 B1 O2 -15.5(2) . .
