#------------------------------------------------------------------------------
#$Date: 2017-03-04 16:01:41 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125521.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_4125521
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         'C6 H4 B F3 O2, C8 H6 N2'
_chemical_formula_sum            'C14 H10 B F3 N2 O2'
_chemical_formula_weight         306.05
_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                 93.811(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8701(4)
_cell_length_b                   12.5606(14)
_cell_length_c                   28.597(2)
_cell_measurement_reflns_used    1865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4808
_cell_measurement_theta_min      3.2777
_cell_volume                     1387.0(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    shelx86
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            5977
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
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    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0501
_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)+(0.0147P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                1137
_reflns_number_total             2454
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b11362_si_017.cif
_cod_data_source_block           faces
_cod_depositor_comments
'Adding full bibliography for 4125513--4125529.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4125521
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 0.4298(7) 0.2478(3) 0.10969(9) 0.0488(8) Uani 1 1 d .
C2 C 0.5819(7) 0.1592(3) 0.09058(10) 0.0574(9) Uani 1 1 d .
H2 H 0.6577 0.1031 0.1099 0.069 Uiso 1 1 calc R
C3 C 0.6208(8) 0.1542(3) 0.04321(13) 0.0694(11) Uani 1 1 d .
C4 C 0.5113(9) 0.2340(4) 0.01421(12) 0.0787(12) Uani 1 1 d .
C5 C 0.3574(9) 0.3210(4) 0.03201(12) 0.0748(12) Uani 1 1 d .
C6 C 0.3175(7) 0.3295(3) 0.07928(10) 0.0599(9) Uani 1 1 d .
H6 H 0.2152 0.3899 0.0911 0.072 Uiso 1 1 calc R
C7 C 0.3425(7) 0.0810(3) 0.30911(12) 0.0661(10) Uani 1 1 d .
H7 H 0.4329 0.0214 0.2949 0.079 Uiso 1 1 calc R
C8 C 0.2537(8) 0.0708(3) 0.35569(12) 0.0702(10) Uani 1 1 d .
H8 H 0.2821 0.0065 0.3716 0.084 Uiso 1 1 calc R
C9 C 0.1255(8) 0.1574(3) 0.37674(11) 0.0658(10) Uani 1 1 d .
H9 H 0.0658 0.1535 0.4077 0.079 Uiso 1 1 calc R
C10 C 0.0830(7) 0.2530(3) 0.35181(9) 0.0493(8) Uani 1 1 d .
C11 C -0.0469(7) 0.3475(3) 0.37056(10) 0.0608(9) Uani 1 1 d .
H11 H -0.1106 0.3494 0.4013 0.073 Uiso 1 1 calc R
C12 C -0.0779(7) 0.4355(3) 0.34333(11) 0.0635(9) Uani 1 1 d .
H12 H -0.1635 0.4986 0.3550 0.076 Uiso 1 1 calc R
C13 C 0.0211(7) 0.4298(3) 0.29731(11) 0.0618(9) Uani 1 1 d .
H13 H -0.0007 0.4911 0.2791 0.074 Uiso 1 1 calc R
C14 C 0.1769(7) 0.2549(3) 0.30525(9) 0.0465(8) Uani 1 1 d .
B1 B 0.3788(9) 0.2539(3) 0.16368(12) 0.0509(9) Uani 1 1 d .
N1 N 0.3075(6) 0.1681(2) 0.28410(8) 0.0562(7) Uani 1 1 d .
N2 N 0.1430(6) 0.3438(2) 0.27794(8) 0.0552(7) Uani 1 1 d .
O1 O 0.2354(5) 0.34343(18) 0.18065(8) 0.0649(7) Uani 1 1 d .
O2 O 0.4764(6) 0.16832(18) 0.18967(8) 0.0679(7) Uani 1 1 d .
F1 F 0.7753(5) 0.06805(19) 0.02512(7) 0.1102(8) Uani 1 1 d .
F2 F 0.5498(6) 0.2270(2) -0.03238(6) 0.1252(10) Uani 1 1 d .
F3 F 0.2432(6) 0.3989(2) 0.00218(7) 0.1155(9) Uani 1 1 d .
H1A H 0.208(9) 0.339(3) 0.2117(13) 0.130(16) Uiso 1 1 d .
H2A H 0.427(9) 0.170(3) 0.2194(13) 0.133(17) 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 0.0030 0.0020 '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 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 '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 117.8(3)
C2 C1 B1 120.7(3)
C6 C1 B1 121.5(3)
C3 C2 C1 120.1(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 F1 119.1(3)
C4 C3 C2 121.4(3)
F1 C3 C2 119.5(4)
C3 C4 F2 120.3(4)
C3 C4 C5 119.6(3)
F2 C4 C5 120.1(4)
F3 C5 C4 118.6(3)
F3 C5 C6 120.7(4)
C4 C5 C6 120.7(4)
C5 C6 C1 120.3(3)
C5 C6 H6 119.8
C1 C6 H6 119.8
N1 C7 C8 124.9(3)
N1 C7 H7 117.6
C8 C7 H7 117.6
C9 C8 C7 118.0(3)
C9 C8 H8 121.0
C7 C8 H8 121.0
C8 C9 C10 119.8(3)
C8 C9 H9 120.1
C10 C9 H9 120.1
C9 C10 C14 117.9(3)
C9 C10 C11 124.2(3)
C14 C10 C11 117.9(3)
C12 C11 C10 119.3(3)
C12 C11 H11 120.3
C10 C11 H11 120.3
C11 C12 C13 118.7(3)
C11 C12 H12 120.6
C13 C12 H12 120.6
N2 C13 C12 124.6(3)
N2 C13 H13 117.7
C12 C13 H13 117.7
N1 C14 N2 115.2(3)
N1 C14 C10 122.4(3)
N2 C14 C10 122.4(3)
O2 B1 O1 124.8(3)
O2 B1 C1 117.0(3)
O1 B1 C1 118.2(3)
C7 N1 C14 117.1(3)
C13 N2 C14 117.0(3)
B1 O1 H1A 112(3)
B1 O2 H2A 116(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(4)
C1 C6 1.395(4)
C1 B1 1.571(4)
C2 C3 1.374(4)
C2 H2 0.9300
C3 C4 1.351(5)
C3 F1 1.355(4)
C4 F2 1.353(3)
C4 C5 1.360(5)
C5 F3 1.353(4)
C5 C6 1.375(4)
C6 H6 0.9300
C7 N1 1.309(4)
C7 C8 1.403(4)
C7 H7 0.9300
C8 C9 1.354(4)
C8 H8 0.9300
C9 C10 1.400(4)
C9 H9 0.9300
C10 C14 1.404(3)
C10 C11 1.409(4)
C11 C12 1.353(4)
C11 H11 0.9300
C12 C13 1.397(3)
C12 H12 0.9300
C13 N2 1.315(3)
C13 H13 0.9300
C14 N1 1.361(3)
C14 N2 1.364(3)
B1 O2 1.347(4)
B1 O1 1.358(4)
O1 H1A 0.90(4)
O2 H2A 0.88(4)
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 0.5(4)
B1 C1 C2 C3 179.1(3)
C1 C2 C3 C4 -0.4(5)
C1 C2 C3 F1 178.8(3)
F1 C3 C4 F2 1.2(5)
C2 C3 C4 F2 -179.5(3)
F1 C3 C4 C5 -179.7(3)
C2 C3 C4 C5 -0.4(5)
C3 C4 C5 F3 -178.6(3)
F2 C4 C5 F3 0.4(5)
C3 C4 C5 C6 1.2(6)
F2 C4 C5 C6 -179.8(3)
F3 C5 C6 C1 178.7(3)
C4 C5 C6 C1 -1.1(5)
C2 C1 C6 C5 0.2(4)
B1 C1 C6 C5 -178.4(3)
N1 C7 C8 C9 -0.7(5)
C7 C8 C9 C10 0.5(5)
C8 C9 C10 C14 0.0(4)
C8 C9 C10 C11 -179.8(3)
C9 C10 C11 C12 -179.9(3)
C14 C10 C11 C12 0.4(4)
C10 C11 C12 C13 -0.1(4)
C11 C12 C13 N2 0.3(5)
C9 C10 C14 N1 -0.3(4)
C11 C10 C14 N1 179.4(3)
C9 C10 C14 N2 179.5(3)
C11 C10 C14 N2 -0.8(4)
C2 C1 B1 O2 -2.5(4)
C6 C1 B1 O2 176.0(3)
C2 C1 B1 O1 178.6(3)
C6 C1 B1 O1 -2.9(4)
C8 C7 N1 C14 0.4(4)
N2 C14 N1 C7 -179.7(2)
C10 C14 N1 C7 0.1(4)
C12 C13 N2 C14 -0.7(4)
N1 C14 N2 C13 -179.3(3)
C10 C14 N2 C13 0.9(4)
