#------------------------------------------------------------------------------
#$Date: 2020-07-24 02:11:02 +0300 (Fri, 24 Jul 2020) $
#$Revision: 254516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038599.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_4038599
loop_
_publ_author_name
'Suzuki, Yota'
'Ikeda, Ayumi'
'Ohno, Keiji'
'Fujihara, Takashi'
'Sugaya, Tomoaki'
'Ishihara, Koji'
_publ_section_title
;
 o-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose:
 o-Azophenylboronic Acids with Inserted Protic Solvent Are the Key
 Species for a Large Color Change.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01011
_journal_year                    2020
_chemical_formula_sum            'C20 H19 B N2 O3'
_chemical_formula_weight         346.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                108.236(2)
_cell_angle_beta                 94.370(2)
_cell_angle_gamma                99.634(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5595(12)
_cell_length_b                   10.6346(19)
_cell_length_c                   13.940(3)
_cell_measurement_reflns_used    5618
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.96
_cell_volume                     901.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9612
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.359
_diffrn_reflns_theta_min         1.553
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1540P)²+0.0622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3170
_reflns_number_total             3651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            CIF_OBn1.cif
_cod_data_source_block           ptol_azo_OBnPhB_100
_cod_original_cell_volume        902.0(3)
_cod_database_code               4038599
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0622(2) 0.59370(14) 0.15245(11) 0.0334(3) Uani 1 1 d . . . . .
C1 C -0.5208(3) 0.66005(17) 0.76119(13) 0.0616(5) Uani 1 1 d . . . . .
H1 H -0.571129 0.656870 0.822672 0.074 Uiso 1 1 calc R U . . .
C2 C -0.6222(3) 0.71294(19) 0.69999(16) 0.0639(5) Uani 1 1 d . . . . .
H2 H -0.742611 0.747941 0.719221 0.077 Uiso 1 1 calc R U . . .
C3 C -0.5517(3) 0.71659(16) 0.60887(13) 0.0505(4) Uani 1 1 d . . . . .
H3 H -0.624138 0.753498 0.566035 0.061 Uiso 1 1 calc R U . . .
C4 C -0.3757(2) 0.66623(13) 0.58105(10) 0.0369(3) Uani 1 1 d . . . . .
C5 C -0.2748(3) 0.61394(17) 0.64530(12) 0.0514(4) Uani 1 1 d . . . . .
H5 H -0.153596 0.579039 0.627552 0.062 Uiso 1 1 calc R U . . .
C6 C -0.3472(4) 0.61154(19) 0.73496(13) 0.0658(6) Uani 1 1 d . . . . .
H6 H -0.275193 0.575677 0.778699 0.079 Uiso 1 1 calc R U . . .
C7 C -0.2999(3) 0.66773(18) 0.48240(12) 0.0570(5) Uani 1 1 d . . . . .
H7A H -0.258651 0.581086 0.447782 0.068 Uiso 1 1 calc R U . . .
H7B H -0.412085 0.680158 0.436627 0.068 Uiso 1 1 calc R U . . .
C8 C 0.0002(2) 0.78129(13) 0.43147(10) 0.0307(3) Uani 1 1 d . . . . .
C9 C -0.0317(2) 0.68843(13) 0.33310(10) 0.0326(3) Uani 1 1 d . . . . .
H9 H -0.152787 0.618276 0.311774 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1123(2) 0.69723(12) 0.26534(9) 0.0288(3) Uani 1 1 d . . . . .
C11 C 0.28938(19) 0.80265(12) 0.29897(9) 0.0267(3) Uani 1 1 d . . . . .
C12 C 0.3131(2) 0.90136(13) 0.39546(9) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.428058 0.975733 0.415500 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1705(2) 0.89074(13) 0.46093(9) 0.0304(3) Uani 1 1 d . . . . .
H13 H 0.187115 0.957611 0.526362 0.037 Uiso 1 1 calc R U . . .
C14 C 0.7562(2) 0.89169(13) 0.19809(10) 0.0309(3) Uani 1 1 d . . . . .
C15 C 0.9334(2) 0.99371(14) 0.23538(11) 0.0353(3) Uani 1 1 d . . . . .
H15 H 0.944905 1.058723 0.301302 0.042 Uiso 1 1 calc R U . . .
C16 C 1.0941(2) 1.00090(15) 0.17642(12) 0.0398(4) Uani 1 1 d . . . . .
H16 H 1.213929 1.071660 0.202104 0.048 Uiso 1 1 calc R U . . .
C17 C 1.0812(2) 0.90545(15) 0.08020(12) 0.0389(4) Uani 1 1 d . . . . .
C18 C 1.2572(3) 0.9105(2) 0.01742(14) 0.0528(4) Uani 1 1 d . . . . .
H18A H 1.327946 0.835529 0.014744 0.079 Uiso 1 1 calc R U . . .
H18B H 1.356990 0.996496 0.048505 0.079 Uiso 1 1 calc R U . . .
H18C H 1.201420 0.902848 -0.051865 0.079 Uiso 1 1 calc R U . . .
C19 C 0.9026(2) 0.80391(16) 0.04382(11) 0.0406(4) Uani 1 1 d . . . . .
H19 H 0.891338 0.738932 -0.022100 0.049 Uiso 1 1 calc R U . . .
C20 C 0.7414(2) 0.79536(14) 0.10131(10) 0.0369(3) Uani 1 1 d . . . . .
H20 H 0.621509 0.724699 0.075356 0.044 Uiso 1 1 calc R U . . .
N1 N 0.43964(16) 0.80429(11) 0.23048(8) 0.0286(3) Uani 1 1 d . . . . .
N2 N 0.60441(17) 0.89281(11) 0.26597(8) 0.0312(3) Uani 1 1 d . . . . .
O1 O -0.12341(16) 0.77782(10) 0.50562(7) 0.0412(3) Uani 1 1 d . . . . .
O2 O -0.12139(16) 0.50470(10) 0.12458(7) 0.0454(3) Uani 1 1 d . . . . .
H2O H -0.138864 0.465472 0.061207 0.068 Uiso 1 1 calc R U . . .
O3 O 0.20188(15) 0.59398(10) 0.08434(7) 0.0402(3) Uani 1 1 d . . . . .
H3O H 0.305055 0.657544 0.111391 0.060 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B1 O3 120.38(11) . . ?
O2 B1 C10 118.59(11) . . ?
O3 B1 C10 121.04(11) . . ?
C2 C1 C6 120.08(15) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.57(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.75(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 118.34(14) . . ?
C5 C4 C7 121.38(15) . . ?
C3 C4 C7 120.27(15) . . ?
C4 C5 C6 120.88(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.37(17) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C4 107.80(11) . . ?
O1 C7 H7A 110.1 . . ?
C4 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C4 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
O1 C8 C9 125.70(12) . . ?
O1 C8 C13 114.45(11) . . ?
C9 C8 C13 119.84(12) . . ?
C8 C9 C10 120.77(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 118.27(11) . . ?
C9 C10 B1 118.64(11) . . ?
C11 C10 B1 122.99(11) . . ?
C12 C11 C10 120.62(11) . . ?
C12 C11 N1 122.37(11) . . ?
C10 C11 N1 117.01(10) . . ?
C13 C12 C11 120.10(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.09(11) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C20 119.57(12) . . ?
C15 C14 N2 115.17(11) . . ?
C20 C14 N2 125.22(12) . . ?
C14 C15 C16 120.19(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.68(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C19 C17 C16 118.49(12) . . ?
C19 C17 C18 120.64(14) . . ?
C16 C17 C18 120.86(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 121.59(13) . . ?
C20 C19 H19 119.2 . . ?
C17 C19 H19 119.2 . . ?
C19 C20 C14 119.47(13) . . ?
C19 C20 H20 120.3 . . ?
C14 C20 H20 120.3 . . ?
N2 N1 C11 115.44(10) . . ?
N1 N2 C14 115.19(10) . . ?
C8 O1 C7 118.15(10) . . ?
B1 O2 H2O 109.5 . . ?
B1 O3 H3O 109.5 . . ?
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
B1 O2 1.3467(17) . ?
B1 O3 1.3693(17) . ?
B1 C10 1.5851(18) . ?
C1 C2 1.351(3) . ?
C1 C6 1.356(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(2) . ?
C4 C7 1.5012(19) . ?
C5 C6 1.377(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.4379(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.3672(15) . ?
C8 C9 1.3925(18) . ?
C8 C13 1.4024(18) . ?
C9 C10 1.3983(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.4064(17) . ?
C11 C12 1.4019(17) . ?
C11 N1 1.4253(15) . ?
C12 C13 1.3709(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900(18) . ?
C14 C20 1.4003(19) . ?
C14 N2 1.4237(16) . ?
C15 C16 1.3918(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C19 1.392(2) . ?
C17 C18 1.5052(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3829(18) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 N2 1.2592(16) . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
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
_geom_hbond_publ_flag
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
O2 H2O O3 0.84 1.92 2.7441(14) 168.6 2_565 yes
O3 H3O N1 0.84 1.91 2.6611(14) 147.4 . yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C7 179.11(14) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C7 C4 C5 C6 -179.17(15) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C5 C4 C7 O1 -78.14(18) . . . . ?
C3 C4 C7 O1 102.60(17) . . . . ?
O1 C8 C9 C10 -176.04(12) . . . . ?
C13 C8 C9 C10 4.6(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C8 C9 C10 B1 -176.76(12) . . . . ?
O2 B1 C10 C9 2.8(2) . . . . ?
O3 B1 C10 C9 -177.10(12) . . . . ?
O2 B1 C10 C11 -173.45(12) . . . . ?
O3 B1 C10 C11 6.7(2) . . . . ?
C9 C10 C11 C12 -4.26(18) . . . . ?
B1 C10 C11 C12 171.99(12) . . . . ?
C9 C10 C11 N1 176.31(10) . . . . ?
B1 C10 C11 N1 -7.44(18) . . . . ?
C10 C11 C12 C13 4.57(19) . . . . ?
N1 C11 C12 C13 -176.03(10) . . . . ?
C11 C12 C13 C8 -0.19(19) . . . . ?
O1 C8 C13 C12 176.23(11) . . . . ?
C9 C8 C13 C12 -4.4(2) . . . . ?
C20 C14 C15 C16 0.7(2) . . . . ?
N2 C14 C15 C16 178.69(10) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C19 0.9(2) . . . . ?
C15 C16 C17 C18 -178.25(12) . . . . ?
C16 C17 C19 C20 -0.8(2) . . . . ?
C18 C17 C19 C20 178.33(12) . . . . ?
C17 C19 C20 C14 0.7(2) . . . . ?
C15 C14 C20 C19 -0.6(2) . . . . ?
N2 C14 C20 C19 -178.38(11) . . . . ?
C12 C11 N1 N2 6.43(17) . . . . ?
C10 C11 N1 N2 -174.15(10) . . . . ?
C11 N1 N2 C14 178.44(9) . . . . ?
C15 C14 N2 N1 176.84(11) . . . . ?
C20 C14 N2 N1 -5.30(19) . . . . ?
C9 C8 O1 C7 1.6(2) . . . . ?
C13 C8 O1 C7 -179.06(13) . . . . ?
C4 C7 O1 C8 165.63(13) . . . . ?
