#------------------------------------------------------------------------------
#$Date: 2017-03-04 16:01:41 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125525.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_4125525
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         'C9 H13 B O2, C8 H6 N2'
_chemical_formula_sum            'C17 H19 B N2 O2'
_chemical_formula_weight         294.15
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.292(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6712(4)
_cell_length_b                   19.9377(13)
_cell_length_c                   10.8372(6)
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3142
_cell_measurement_theta_min      3.3723
_cell_volume                     1635.76(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5806
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plaquet
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0522
_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)+(0.0452P)²+0.1807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                1853
_reflns_number_total             2861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_009.cif
_cod_data_source_block           co-mesface
_cod_depositor_comments
'Adding full bibliography for 4125513--4125529.cif.'
_cod_original_cell_volume        1635.76(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4125525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.6496(3) 0.15477(10) 1.03338(17) 0.0527(5) Uani 1 1 d .
C2 C 0.6942(3) 0.20985(10) 0.96438(18) 0.0555(5) Uani 1 1 d .
C3 C 0.5676(3) 0.24123(11) 0.87766(19) 0.0628(6) Uani 1 1 d .
H3 H 0.6000 0.2776 0.8326 0.075 Uiso 1 1 calc R
C4 C 0.3939(3) 0.21955(11) 0.85680(19) 0.0637(6) Uani 1 1 d .
C5 C 0.3500(3) 0.16590(12) 0.9250(2) 0.0690(6) Uani 1 1 d .
H5 H 0.2337 0.1509 0.9121 0.083 Uiso 1 1 calc R
C6 C 0.4735(3) 0.13305(11) 1.01297(18) 0.0607(6) Uani 1 1 d .
C7 C 0.8816(3) 0.23536(12) 0.9826(2) 0.0849(8) Uani 1 1 d .
H7A H 0.8951 0.2662 0.9167 0.127 Uiso 1 1 calc R
H7B H 0.9612 0.1983 0.9810 0.127 Uiso 1 1 calc R
H7C H 0.9080 0.2579 1.0618 0.127 Uiso 1 1 calc R
C8 C 0.2579(3) 0.25369(14) 0.7601(2) 0.0948(9) Uani 1 1 d .
H8A H 0.1495 0.2287 0.7498 0.142 Uiso 1 1 calc R
H8B H 0.3009 0.2557 0.6817 0.142 Uiso 1 1 calc R
H8C H 0.2370 0.2984 0.7874 0.142 Uiso 1 1 calc R
C9 C 0.4147(3) 0.07535(14) 1.0865(2) 0.0937(9) Uani 1 1 d .
H9A H 0.3898 0.0915 1.1653 0.140 Uiso 1 1 calc R
H9B H 0.5069 0.0423 1.1009 0.140 Uiso 1 1 calc R
H9C H 0.3102 0.0555 1.0402 0.140 Uiso 1 1 calc R
C10 C 0.8372(3) 0.06731(13) 0.7662(2) 0.0773(7) Uani 1 1 d .
H10 H 0.8693 0.0811 0.8487 0.093 Uiso 1 1 calc R
C11 C 0.7457(3) 0.11259(13) 0.6816(3) 0.0888(8) Uani 1 1 d .
H11 H 0.7184 0.1553 0.7074 0.107 Uiso 1 1 calc R
C12 C 0.6975(3) 0.09349(13) 0.5616(3) 0.0839(7) Uani 1 1 d .
H12 H 0.6381 0.1232 0.5033 0.101 Uiso 1 1 calc R
C13 C 0.7374(3) 0.02853(12) 0.52529(19) 0.0618(6) Uani 1 1 d .
C14 C 0.6899(3) 0.00209(15) 0.4035(2) 0.0816(8) Uani 1 1 d .
H14 H 0.6287 0.0284 0.3399 0.098 Uiso 1 1 calc R
C15 C 0.7342(3) -0.06174(16) 0.3803(2) 0.0867(8) Uani 1 1 d .
H15 H 0.7022 -0.0805 0.3013 0.104 Uiso 1 1 calc R
C16 C 0.8285(3) -0.09861(14) 0.4771(2) 0.0830(8) Uani 1 1 d .
H16 H 0.8593 -0.1423 0.4597 0.100 Uiso 1 1 calc R
C17 C 0.8304(2) -0.01317(11) 0.61630(18) 0.0548(5) Uani 1 1 d .
N1 N 0.8808(2) 0.00655(10) 0.73706(15) 0.0647(5) Uani 1 1 d .
N2 N 0.8776(2) -0.07668(9) 0.59092(17) 0.0710(5) Uani 1 1 d .
O1 O 0.8832(3) 0.06665(10) 1.08334(15) 0.0975(7) Uani 1 1 d .
O2 O 0.8338(2) 0.13844(9) 1.24578(14) 0.0856(6) Uani 1 1 d .
B1 B 0.7976(3) 0.11755(12) 1.1271(2) 0.0557(6) Uani 1 1 d .
H1A H 0.959(4) 0.0448(14) 1.141(2) 0.114(10) Uiso 1 1 d .
H2A H 0.929(4) 0.1169(14) 1.294(3) 0.122(10) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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
C2 C1 C6 118.02(18)
C2 C1 B1 119.94(18)
C6 C1 B1 122.01(19)
C3 C2 C1 120.69(19)
C3 C2 C7 119.0(2)
C1 C2 C7 120.27(18)
C4 C3 C2 121.3(2)
C4 C3 H3 119.3
C2 C3 H3 119.3
C5 C4 C3 117.94(19)
C5 C4 C8 121.4(2)
C3 C4 C8 120.6(2)
C4 C5 C6 122.4(2)
C4 C5 H5 118.8
C6 C5 H5 118.8
C5 C6 C1 119.6(2)
C5 C6 C9 119.4(2)
C1 C6 C9 120.98(19)
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C6 C9 H9A 109.5
C6 C9 H9B 109.5
H9A C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 C11 124.2(2)
N1 C10 H10 117.9
C11 C10 H10 117.9
C12 C11 C10 118.8(2)
C12 C11 H11 120.6
C10 C11 H11 120.6
C11 C12 C13 119.6(2)
C11 C12 H12 120.2
C13 C12 H12 120.2
C17 C13 C12 117.5(2)
C17 C13 C14 117.6(2)
C12 C13 C14 124.9(2)
C15 C14 C13 119.3(2)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 118.4(2)
C14 C15 H15 120.8
C16 C15 H15 120.8
N2 C16 C15 125.0(2)
N2 C16 H16 117.5
C15 C16 H16 117.5
N2 C17 N1 114.89(18)
N2 C17 C13 122.37(19)
N1 C17 C13 122.7(2)
C10 N1 C17 117.08(19)
C16 N2 C17 117.3(2)
B1 O1 H1A 115.0(17)
B1 O2 H2A 115.0(17)
O1 B1 O2 122.7(2)
O1 B1 C1 118.12(19)
O2 B1 C1 119.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.402(3)
C1 C6 1.402(3)
C1 B1 1.581(3)
C2 C3 1.387(3)
C2 C7 1.508(3)
C3 C4 1.384(3)
C3 H3 0.9300
C4 C5 1.373(3)
C4 C8 1.516(3)
C5 C6 1.394(3)
C5 H5 0.9300
C6 C9 1.509(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 N1 1.309(3)
C10 C11 1.393(3)
C10 H10 0.9300
C11 C12 1.348(3)
C11 H11 0.9300
C12 C13 1.402(3)
C12 H12 0.9300
C13 C17 1.395(3)
C13 C14 1.413(3)
C14 C15 1.351(3)
C14 H14 0.9300
C15 C16 1.385(3)
C15 H15 0.9300
C16 N2 1.305(3)
C16 H16 0.9300
C17 N2 1.357(3)
C17 N1 1.361(2)
O1 B1 1.337(3)
O1 H1A 0.90(3)
O2 B1 1.338(3)
O2 H2A 0.93(3)
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
C6 C1 C2 C3 -0.7(3)
B1 C1 C2 C3 177.12(19)
C6 C1 C2 C7 180.0(2)
B1 C1 C2 C7 -2.2(3)
C1 C2 C3 C4 0.3(3)
C7 C2 C3 C4 179.6(2)
C2 C3 C4 C5 0.2(3)
C2 C3 C4 C8 -178.9(2)
C3 C4 C5 C6 -0.2(3)
C8 C4 C5 C6 178.9(2)
C4 C5 C6 C1 -0.2(3)
C4 C5 C6 C9 178.7(2)
C2 C1 C6 C5 0.7(3)
B1 C1 C6 C5 -177.09(19)
C2 C1 C6 C9 -178.2(2)
B1 C1 C6 C9 4.0(3)
N1 C10 C11 C12 0.2(4)
C10 C11 C12 C13 1.1(4)
C11 C12 C13 C17 -1.5(4)
C11 C12 C13 C14 178.2(2)
C17 C13 C14 C15 0.5(3)
C12 C13 C14 C15 -179.2(2)
C13 C14 C15 C16 -1.3(4)
C14 C15 C16 N2 0.7(4)
C12 C13 C17 N2 -179.3(2)
C14 C13 C17 N2 1.0(3)
C12 C13 C17 N1 0.8(3)
C14 C13 C17 N1 -178.98(19)
C11 C10 N1 C17 -0.9(4)
N2 C17 N1 C10 -179.54(19)
C13 C17 N1 C10 0.4(3)
C15 C16 N2 C17 0.8(4)
N1 C17 N2 C16 178.34(19)
C13 C17 N2 C16 -1.6(3)
C2 C1 B1 O1 -89.5(3)
C6 C1 B1 O1 88.2(3)
C2 C1 B1 O2 89.6(3)
C6 C1 B1 O2 -92.7(3)
