#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/10/7051015.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_7051015
loop_
_publ_author_name
'Steiner, Thomas'
'Schreurs, Antoine M. M.'
'Lutz, Martin'
'Kroon, Jan'
_publ_section_title
;
 Making very short O--H···Ph hydrogen bonds: the
 example of tetraphenylborate salts
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              174
_journal_paper_doi               10.1039/b004932h
_journal_volume                  25
_journal_year                    2001
_chemical_formula_sum            'C29 H34 B N O'
_chemical_formula_weight         423.38
_chemical_name_systematic
;
 choline tetraphenylborate
;
_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                 107.08(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.743(2)
_cell_length_b                   13.474(7)
_cell_length_c                   18.902(11)
_cell_measurement_temperature    125(2)
_cell_volume                     2372(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44261
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         44261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0871
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+5.4720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.2231
_reflns_number_gt                28347
_reflns_number_total             44261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b004932h.txt
_cod_data_source_block           (I)
_cod_original_cell_volume        2372.0(19)
_cod_original_sg_symbol_H-M      'P 21 /c'
_cod_database_code               7051015
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.22763(15) 0.43157(9) 0.45942(8) 0.0407(4) Uani 1 1 d . . .
H1O H 0.231(3) 0.4815(19) 0.4277(15) 0.126(11) Uiso 1 1 d . . .
N N 0.17471(14) 0.21749(8) 0.40237(7) 0.0198(3) Uani 1 1 d . . .
C1 C 0.0893(2) 0.39307(11) 0.42377(10) 0.0321(5) Uani 1 1 d . . .
H1A H 0.0648 0.4055 0.3699 0.038 Uiso 1 1 calc R . .
H1B H 0.0171 0.4271 0.4427 0.038 Uiso 1 1 calc R . .
C2 C 0.08584(19) 0.28268(10) 0.43788(10) 0.0265(4) Uani 1 1 d . . .
H2A H -0.0152 0.2602 0.4201 0.032 Uiso 1 1 calc R . .
H2B H 0.1193 0.2717 0.4920 0.032 Uiso 1 1 calc R . .
C3 C 0.33148(18) 0.23127(13) 0.43789(11) 0.0397(5) Uani 1 1 d . . .
H3A H 0.3543 0.2179 0.4911 0.060 Uiso 1 1 calc R . .
H3B H 0.3583 0.2997 0.4303 0.060 Uiso 1 1 calc R . .
H3C H 0.3851 0.1853 0.4157 0.060 Uiso 1 1 calc R . .
C4 C 0.1410(2) 0.23744(12) 0.32137(9) 0.0335(5) Uani 1 1 d . . .
H4A H 0.0380 0.2281 0.2976 0.050 Uiso 1 1 calc R . .
H4B H 0.1953 0.1914 0.2996 0.050 Uiso 1 1 calc R . .
H4C H 0.1677 0.3058 0.3137 0.050 Uiso 1 1 calc R . .
C5 C 0.1354(2) 0.11194(10) 0.41409(11) 0.0399(5) Uani 1 1 d . . .
H5A H 0.0326 0.1018 0.3902 0.060 Uiso 1 1 calc R . .
H5B H 0.1575 0.0987 0.4672 0.060 Uiso 1 1 calc R . .
H5C H 0.1906 0.0666 0.3924 0.060 Uiso 1 1 calc R . .
B B 0.8201(2) 0.25524(13) 0.08768(10) 0.0171(4) Uani 1 1 d . . .
C11 C 0.99548(16) 0.25472(11) 0.11148(8) 0.0172(4) Uani 1 1 d . . .
C12 C 1.07565(18) 0.16659(11) 0.11654(9) 0.0206(4) Uani 1 1 d . . .
H12 H 1.0256 0.1052 0.1083 0.025 Uiso 1 1 calc R . .
C13 C 1.22361(18) 0.16501(12) 0.13288(9) 0.0255(4) Uani 1 1 d . . .
H13 H 1.2724 0.1033 0.1364 0.031 Uiso 1 1 calc R . .
C14 C 1.30109(17) 0.25250(13) 0.14404(9) 0.0262(4) Uani 1 1 d . . .
H14 H 1.4028 0.2518 0.1556 0.031 Uiso 1 1 calc R . .
C15 C 1.22669(18) 0.34105(12) 0.13798(9) 0.0253(4) Uani 1 1 d . . .
H15 H 1.2777 0.4021 0.1448 0.030 Uiso 1 1 calc R . .
C16 C 1.07899(18) 0.34166(11) 0.12218(9) 0.0207(4) Uani 1 1 d . . .
H16 H 1.0315 0.4039 0.1184 0.025 Uiso 1 1 calc R . .
C21 C 0.75602(17) 0.35116(10) 0.12306(9) 0.0161(4) Uani 1 1 d . . .
C22 C 0.62296(17) 0.39391(10) 0.08662(9) 0.0195(4) Uani 1 1 d . . .
H22 H 0.5733 0.3714 0.0382 0.023 Uiso 1 1 calc R . .
C23 C 0.56019(18) 0.46805(11) 0.11828(10) 0.0230(4) Uani 1 1 d . . .
H23 H 0.4698 0.4950 0.0914 0.028 Uiso 1 1 calc R . .
C24 C 0.6294(2) 0.50234(11) 0.18872(10) 0.0240(4) Uani 1 1 d . . .
H24 H 0.5863 0.5517 0.2111 0.029 Uiso 1 1 calc R . .
C25 C 0.76154(19) 0.46389(11) 0.22580(10) 0.0236(4) Uani 1 1 d . . .
H25 H 0.8117 0.4884 0.2735 0.028 Uiso 1 1 calc R . .
C26 C 0.82250(18) 0.38897(11) 0.19367(9) 0.0207(4) Uani 1 1 d . . .
H26 H 0.9130 0.3626 0.2210 0.025 Uiso 1 1 calc R . .
C31 C 0.75448(17) 0.15744(10) 0.12028(9) 0.0161(4) Uani 1 1 d . . .
C32 C 0.83059(18) 0.10498(11) 0.18384(9) 0.0201(4) Uani 1 1 d . . .
H32 H 0.9270 0.1238 0.2080 0.024 Uiso 1 1 calc R . .
C33 C 0.77099(19) 0.02603(11) 0.21332(9) 0.0231(4) Uani 1 1 d . . .
H33 H 0.8269 -0.0073 0.2565 0.028 Uiso 1 1 calc R . .
C34 C 0.6327(2) -0.00290(11) 0.18001(10) 0.0247(4) Uani 1 1 d . . .
H34 H 0.5920 -0.0564 0.1998 0.030 Uiso 1 1 calc R . .
C35 C 0.55237(18) 0.04625(11) 0.11730(10) 0.0232(4) Uani 1 1 d . . .
H35 H 0.4562 0.0265 0.0936 0.028 Uiso 1 1 calc R . .
C36 C 0.61294(17) 0.12507(11) 0.08876(9) 0.0203(4) Uani 1 1 d . . .
H36 H 0.5554 0.1583 0.0460 0.024 Uiso 1 1 calc R . .
C41 C 0.76760(16) 0.25864(11) -0.00360(8) 0.0171(4) Uani 1 1 d . . .
C42 C 0.73237(18) 0.17454(11) -0.04886(9) 0.0223(4) Uani 1 1 d . . .
H42 H 0.7330 0.1117 -0.0259 0.027 Uiso 1 1 calc R . .
C43 C 0.69655(18) 0.17828(13) -0.12568(10) 0.0276(4) Uani 1 1 d . . .
H43 H 0.6716 0.1191 -0.1538 0.033 Uiso 1 1 calc R . .
C44 C 0.69718(18) 0.26768(13) -0.16115(10) 0.0305(4) Uani 1 1 d . . .
H44 H 0.6738 0.2707 -0.2136 0.037 Uiso 1 1 calc R . .
C45 C 0.73270(18) 0.35299(12) -0.11866(10) 0.0270(4) Uani 1 1 d . . .
H45 H 0.7336 0.4152 -0.1421 0.032 Uiso 1 1 calc R . .
C46 C 0.76674(17) 0.34802(11) -0.04254(9) 0.0219(4) Uani 1 1 d . . .
H46 H 0.7908 0.4078 -0.0150 0.026 Uiso 1 1 calc R . .
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'
B B 0.0013 0.0007 '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'
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
_geom_angle_publ_flag
C1 O H1O 100.0(17) . . ?
C3 N C4 109.11(13) . . ?
C3 N C5 108.84(13) . . ?
C4 N C5 109.40(13) . . ?
C3 N C2 111.76(13) . . ?
C4 N C2 111.50(13) . . ?
C5 N C2 106.15(12) . . ?
O C1 C2 110.09(14) . . ?
O C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C1 C2 N 116.41(13) . . ?
C1 C2 H2A 108.2 . . ?
N C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
N C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
N C3 H3A 109.5 . . ?
N C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N C4 H4A 109.5 . . ?
N C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N C5 H5A 109.5 . . ?
N C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 B C41 105.42(12) . . ?
C11 B C21 112.29(13) . . ?
C41 B C21 111.23(14) . . ?
C11 B C31 112.33(13) . . ?
C41 B C31 112.04(13) . . ?
C21 B C31 103.72(11) . . ?
C16 C11 C12 113.98(14) . . ?
C16 C11 B 123.36(13) . . ?
C12 C11 B 122.43(14) . . ?
C13 C12 C11 123.29(15) . . ?
C13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C14 C13 C12 120.51(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 118.27(15) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 120.69(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 123.24(15) . . ?
C15 C16 H16 118.4 . . ?
C11 C16 H16 118.4 . . ?
C26 C21 C22 114.96(14) . . ?
C26 C21 B 123.04(15) . . ?
C22 C21 B 121.72(15) . . ?
C23 C22 C21 122.87(16) . . ?
C23 C22 H22 118.6 . . ?
C21 C22 H22 118.6 . . ?
C24 C23 C22 120.06(17) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 118.97(15) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 120.32(17) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 122.80(17) . . ?
C21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
C36 C31 C32 114.44(14) . . ?
C36 C31 B 121.83(15) . . ?
C32 C31 B 123.59(15) . . ?
C33 C32 C31 123.06(16) . . ?
C33 C32 H32 118.5 . . ?
C31 C32 H32 118.5 . . ?
C34 C33 C32 120.03(17) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 119.47(15) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C36 119.87(16) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C31 123.14(16) . . ?
C35 C36 H36 118.4 . . ?
C31 C36 H36 118.4 . . ?
C42 C41 C46 114.16(15) . . ?
C42 C41 B 124.16(14) . . ?
C46 C41 B 121.47(14) . . ?
C43 C42 C41 123.35(15) . . ?
C43 C42 H42 118.3 . . ?
C41 C42 H42 118.3 . . ?
C44 C43 C42 120.23(16) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 118.58(16) . . ?
C43 C44 H44 120.7 . . ?
C45 C44 H44 120.7 . . ?
C46 C45 C44 120.42(16) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C45 C46 C41 123.26(15) . . ?
C45 C46 H46 118.4 . . ?
C41 C46 H46 118.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.416(2) . ?
O H1O 0.91(3) . ?
N C3 1.489(2) . ?
N C4 1.493(2) . ?
N C5 1.5060(19) . ?
N C2 1.5209(18) . ?
C1 C2 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
B C11 1.634(2) . ?
B C41 1.650(3) . ?
B C21 1.659(2) . ?
B C31 1.660(2) . ?
C11 C16 1.407(2) . ?
C11 C12 1.409(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.397(2) . ?
C21 C22 1.401(2) . ?
C22 C23 1.395(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.397(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.402(2) . ?
C31 C32 1.404(2) . ?
C32 C33 1.403(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.366(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.398(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.401(2) . ?
C41 C46 1.410(2) . ?
C42 C43 1.391(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.379(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.387(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.380(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O H1O C31 0.91(3) 2.56(3) 3.423(2) 160(2) 2_655
O H1O C32 0.91(3) 2.61(3) 3.494(2) 164(2) 2_655
O H1O C33 0.91(3) 2.73(3) 3.508(3) 145(2) 2_655
O H1O C34 0.91(3) 2.74(3) 3.418(3) 132(2) 2_655
O H1O C35 0.91(3) 2.64(3) 3.303(2) 130(2) 2_655
O H1O C36 0.91(3) 2.53(3) 3.297(2) 142(2) 2_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21142419
