#------------------------------------------------------------------------------
#$Date: 2020-07-24 02:13:35 +0300 (Fri, 24 Jul 2020) $
#$Revision: 254520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038602.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_4038602
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            'C19 H16 B N3 O5'
_chemical_formula_weight         377.16
_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                100.7080(10)
_cell_angle_beta                 95.7670(10)
_cell_angle_gamma                97.2850(10)
_cell_formula_units_Z            4
_cell_length_a                   9.6949(9)
_cell_length_b                   12.4853(11)
_cell_length_c                   15.2894(14)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.37
_cell_volume                     1789.1(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 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0792
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19498
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.367
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0549P)²+0.2610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6129
_reflns_number_total             7272
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            CIF_OBn2.cif
_cod_data_source_block           pNO2Ph_azo_OBnPhB_100
_cod_database_code               4038602
_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   0.990
_shelx_estimated_absorpt_t_max   0.997
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 0.84379(15) 0.12330(12) 0.25280(9) 0.0327(3) Uani 1 1 d . . . . .
B2 B 0.17259(14) 0.94617(11) 0.24424(9) 0.0303(3) Uani 1 1 d . . . . .
C1 C 0.87859(14) 0.87807(11) 0.39903(11) 0.0468(4) Uani 1 1 d . . . . .
H1 H 0.896484 0.955809 0.404758 0.056 Uiso 1 1 calc R U . . .
C2 C 0.87312(16) 0.83293(12) 0.47389(10) 0.0490(4) Uani 1 1 d . . . . .
H2 H 0.885845 0.879713 0.531569 0.059 Uiso 1 1 calc R U . . .
C3 C 0.84915(15) 0.71937(12) 0.46622(9) 0.0436(3) Uani 1 1 d . . . . .
H3 H 0.845813 0.688730 0.518520 0.052 Uiso 1 1 calc R U . . .
C4 C 0.83006(12) 0.65059(10) 0.38207(8) 0.0341(3) Uani 1 1 d . . . . .
C5 C 0.83433(14) 0.69701(11) 0.30672(9) 0.0410(3) Uani 1 1 d . . . . .
H5 H 0.820912 0.650735 0.248802 0.049 Uiso 1 1 calc R U . . .
C6 C 0.85794(16) 0.80998(12) 0.31512(10) 0.0475(3) Uani 1 1 d . . . . .
H6 H 0.859996 0.841084 0.263000 0.057 Uiso 1 1 calc R U . . .
C7 C 0.81358(14) 0.52773(11) 0.37034(10) 0.0408(3) Uani 1 1 d . . . . .
H7A H 0.878389 0.498156 0.329125 0.049 Uiso 1 1 calc R U . . .
H7B H 0.836859 0.507059 0.428931 0.049 Uiso 1 1 calc R U . . .
C8 C 0.64729(13) 0.37239(10) 0.29510(8) 0.0316(3) Uani 1 1 d . . . . .
C9 C 0.74757(13) 0.30224(10) 0.29827(8) 0.0306(3) Uani 1 1 d . . . . .
H9 H 0.836786 0.329292 0.332255 0.037 Uiso 1 1 calc R U . . .
C10 C 0.71901(12) 0.19265(10) 0.25224(7) 0.0281(2) Uani 1 1 d . . . . .
C11 C 0.58453(12) 0.15392(10) 0.20465(7) 0.0279(2) Uani 1 1 d . . . . .
C12 C 0.48209(13) 0.22380(10) 0.20437(8) 0.0329(3) Uani 1 1 d . . . . .
H12 H 0.390779 0.196279 0.173562 0.039 Uiso 1 1 calc R U . . .
C13 C 0.51359(13) 0.33228(10) 0.24868(9) 0.0350(3) Uani 1 1 d . . . . .
H13 H 0.444479 0.379753 0.247677 0.042 Uiso 1 1 calc R U . . .
C14 C 0.41753(13) -0.10314(10) 0.06857(8) 0.0304(3) Uani 1 1 d . . . . .
C15 C 0.28596(13) -0.13769(10) 0.01910(8) 0.0325(3) Uani 1 1 d . . . . .
H15 H 0.218959 -0.088278 0.020484 0.039 Uiso 1 1 calc R U . . .
C16 C 0.25134(13) -0.24348(11) -0.03227(8) 0.0340(3) Uani 1 1 d . . . . .
H16 H 0.161423 -0.267467 -0.066078 0.041 Uiso 1 1 calc R U . . .
C17 C 0.35162(13) -0.31296(10) -0.03280(8) 0.0322(3) Uani 1 1 d . . . . .
C18 C 0.48227(15) -0.28175(12) 0.01695(10) 0.0450(3) Uani 1 1 d . . . . .
H18 H 0.548272 -0.331921 0.016180 0.054 Uiso 1 1 calc R U . . .
C19 C 0.51519(14) -0.17607(11) 0.06789(10) 0.0423(3) Uani 1 1 d . . . . .
H19 H 0.604607 -0.153089 0.102536 0.051 Uiso 1 1 calc R U . . .
C20 C 0.12139(15) 0.17991(12) 0.03187(11) 0.0490(4) Uani 1 1 d . . . . .
H20 H 0.116274 0.103493 0.007726 0.059 Uiso 1 1 calc R U . . .
C21 C 0.12084(14) 0.21622(11) 0.12295(10) 0.0444(3) Uani 1 1 d . . . . .
H21 H 0.115379 0.164599 0.161408 0.053 Uiso 1 1 calc R U . . .
C22 C 0.12824(14) 0.32792(11) 0.15840(9) 0.0384(3) Uani 1 1 d . . . . .
H22 H 0.127211 0.352478 0.220949 0.046 Uiso 1 1 calc R U . . .
C23 C 0.13711(12) 0.40353(10) 0.10264(8) 0.0333(3) Uani 1 1 d . . . . .
C24 C 0.13754(14) 0.36570(12) 0.01137(9) 0.0419(3) Uani 1 1 d . . . . .
H24 H 0.143525 0.416788 -0.027527 0.050 Uiso 1 1 calc R U . . .
C25 C 0.12934(16) 0.25449(13) -0.02335(10) 0.0493(4) Uani 1 1 d . . . . .
H25 H 0.129214 0.229573 -0.085975 0.059 Uiso 1 1 calc R U . . .
C26 C 0.14738(14) 0.52481(11) 0.13906(10) 0.0410(3) Uani 1 1 d . . . . .
H26A H 0.127117 0.564068 0.089714 0.049 Uiso 1 1 calc R U . . .
H26B H 0.078974 0.538582 0.182244 0.049 Uiso 1 1 calc R U . . .
C27 C 0.32151(13) 0.67201(10) 0.22152(8) 0.0309(3) Uani 1 1 d . . . . .
C28 C 0.23446(12) 0.75128(10) 0.21308(8) 0.0294(3) Uani 1 1 d . . . . .
H28 H 0.145940 0.730499 0.177057 0.035 Uiso 1 1 calc R U . . .
C29 C 0.27619(12) 0.86118(10) 0.25716(7) 0.0271(2) Uani 1 1 d . . . . .
C30 C 0.40685(12) 0.88900(10) 0.31076(7) 0.0273(2) Uani 1 1 d . . . . .
C31 C 0.49564(13) 0.80941(10) 0.31709(8) 0.0326(3) Uani 1 1 d . . . . .
H31 H 0.584982 0.829702 0.352164 0.039 Uiso 1 1 calc R U . . .
C32 C 0.45337(13) 0.70232(10) 0.27262(9) 0.0346(3) Uani 1 1 d . . . . .
H32 H 0.513833 0.648716 0.276574 0.042 Uiso 1 1 calc R U . . .
C33 C 0.59534(13) 1.13576(10) 0.45038(8) 0.0302(3) Uani 1 1 d . . . . .
C34 C 0.72777(13) 1.16114(11) 0.49930(8) 0.0353(3) Uani 1 1 d . . . . .
H34 H 0.785392 1.105144 0.500353 0.042 Uiso 1 1 calc R U . . .
C35 C 0.77701(13) 1.26723(11) 0.54666(8) 0.0354(3) Uani 1 1 d . . . . .
H35 H 0.867968 1.285003 0.579810 0.043 Uiso 1 1 calc R U . . .
C36 C 0.69000(13) 1.34641(10) 0.54429(8) 0.0325(3) Uani 1 1 d . . . . .
C37 C 0.55690(14) 1.32353(11) 0.49694(9) 0.0374(3) Uani 1 1 d . . . . .
H37 H 0.499293 1.379672 0.496981 0.045 Uiso 1 1 calc R U . . .
C38 C 0.50920(14) 1.21772(11) 0.44963(9) 0.0369(3) Uani 1 1 d . . . . .
H38 H 0.418137 1.200479 0.416609 0.044 Uiso 1 1 calc R U . . .
N1 N 0.56173(10) 0.04316(8) 0.15547(6) 0.0288(2) Uani 1 1 d . . . . .
N2 N 0.43852(11) 0.00737(8) 0.11853(7) 0.0319(2) Uani 1 1 d . . . . .
N3 N 0.31653(13) -0.42478(9) -0.08822(7) 0.0393(3) Uani 1 1 d . . . . .
N4 N 0.44172(10) 1.00026(8) 0.35778(6) 0.0289(2) Uani 1 1 d . . . . .
N5 N 0.56047(11) 1.02431(9) 0.40354(7) 0.0330(2) Uani 1 1 d . . . . .
N6 N 0.74132(12) 1.45930(10) 0.59343(7) 0.0401(3) Uani 1 1 d . . . . .
O1 O 0.67096(9) 0.48179(7) 0.33404(6) 0.0398(2) Uani 1 1 d . . . . .
O2 O 0.96011(10) 0.16543(8) 0.31131(6) 0.0444(2) Uani 1 1 d . . . . .
H2O H 1.021818 0.124488 0.302476 0.067 Uiso 1 1 calc R U . . .
O3 O 0.83818(10) 0.02570(8) 0.19344(7) 0.0454(2) Uani 1 1 d . . . . .
H3O H 0.756653 0.006363 0.166078 0.068 Uiso 1 1 calc R U . . .
O4 O 0.19797(11) -0.45312(8) -0.12884(7) 0.0489(3) Uani 1 1 d . . . . .
O5 O 0.40686(12) -0.48477(9) -0.09126(8) 0.0601(3) Uani 1 1 d . . . . .
O6 O 0.28814(9) 0.56299(7) 0.18313(7) 0.0404(2) Uani 1 1 d . . . . .
O7 O 0.06383(9) 0.91405(7) 0.17829(6) 0.0390(2) Uani 1 1 d . . . . .
H7O H 0.007497 0.960023 0.183765 0.058 Uiso 1 1 calc R U . . .
O8 O 0.18780(10) 1.04877(7) 0.29785(6) 0.0430(2) Uani 1 1 d . . . . .
H8O H 0.265811 1.061563 0.330084 0.065 Uiso 1 1 calc R U . . .
O9 O 0.86153(12) 1.47989(10) 0.63139(9) 0.0676(4) Uani 1 1 d . . . . .
O10 O 0.66304(12) 1.52852(9) 0.59487(8) 0.0589(3) Uani 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'
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
O2 B1 O3 120.50(12) . . ?
O2 B1 C10 117.86(11) . . ?
O3 B1 C10 121.58(11) . . ?
O7 B2 O8 119.70(12) . . ?
O7 B2 C29 117.62(10) . . ?
O8 B2 C29 122.67(11) . . ?
C2 C1 C6 119.66(13) . . ?
C1 C2 C3 120.56(13) . . ?
C2 C3 C4 119.97(14) . . ?
C5 C4 C3 119.06(12) . . ?
C5 C4 C7 118.73(12) . . ?
C3 C4 C7 122.11(13) . . ?
C6 C5 C4 120.48(12) . . ?
C5 C6 C1 120.27(14) . . ?
O1 C7 C4 109.18(11) . . ?
O1 C8 C9 123.98(11) . . ?
O1 C8 C13 115.97(11) . . ?
C9 C8 C13 120.04(11) . . ?
C8 C9 C10 120.99(11) . . ?
C9 C10 C11 118.26(11) . . ?
C9 C10 B1 116.98(10) . . ?
C11 C10 B1 124.65(10) . . ?
C12 C11 C10 120.55(10) . . ?
C12 C11 N1 122.98(10) . . ?
C10 C11 N1 116.43(10) . . ?
C13 C12 C11 120.16(11) . . ?
C12 C13 C8 119.94(12) . . ?
C15 C14 C19 119.75(11) . . ?
C15 C14 N2 114.75(11) . . ?
C19 C14 N2 125.49(11) . . ?
C16 C15 C14 120.75(12) . . ?
C17 C16 C15 117.99(11) . . ?
C16 C17 C18 122.61(11) . . ?
C16 C17 N3 118.35(11) . . ?
C18 C17 N3 119.04(12) . . ?
C17 C18 C19 118.72(13) . . ?
C18 C19 C14 120.17(12) . . ?
C25 C20 C21 119.74(13) . . ?
C20 C21 C22 120.23(14) . . ?
C23 C22 C21 120.07(13) . . ?
C22 C23 C24 118.96(12) . . ?
C22 C23 C26 121.34(12) . . ?
C24 C23 C26 119.69(12) . . ?
C25 C24 C23 120.58(13) . . ?
C20 C25 C24 120.41(13) . . ?
O6 C26 C23 107.31(10) . . ?
O6 C27 C28 124.72(11) . . ?
O6 C27 C32 115.21(11) . . ?
C28 C27 C32 120.07(11) . . ?
C27 C28 C29 120.69(11) . . ?
C28 C29 C30 118.28(11) . . ?
C28 C29 B2 117.84(10) . . ?
C30 C29 B2 123.88(10) . . ?
C31 C30 C29 120.74(10) . . ?
C31 C30 N4 122.95(10) . . ?
C29 C30 N4 116.30(10) . . ?
C32 C31 C30 120.04(11) . . ?
C31 C32 C27 120.11(12) . . ?
C34 C33 C38 119.83(11) . . ?
C34 C33 N5 114.45(11) . . ?
C38 C33 N5 125.72(11) . . ?
C35 C34 C33 120.77(12) . . ?
C36 C35 C34 118.09(11) . . ?
C35 C36 C37 122.57(11) . . ?
C35 C36 N6 118.65(11) . . ?
C37 C36 N6 118.78(12) . . ?
C36 C37 C38 118.86(12) . . ?
C37 C38 C33 119.89(12) . . ?
N2 N1 C11 115.62(10) . . ?
N1 N2 C14 115.04(10) . . ?
O5 N3 O4 123.32(11) . . ?
O5 N3 C17 118.34(11) . . ?
O4 N3 C17 118.35(11) . . ?
N5 N4 C30 115.40(10) . . ?
N4 N5 C33 115.32(11) . . ?
O10 N6 O9 122.70(11) . . ?
O10 N6 C36 119.04(11) . . ?
O9 N6 C36 118.26(12) . . ?
C8 O1 C7 116.42(10) . . ?
C27 O6 C26 117.50(10) . . ?
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 1.3493(16) . ?
B1 O3 1.3689(17) . ?
B1 C10 1.5747(19) . ?
B2 O7 1.3484(16) . ?
B2 O8 1.3682(16) . ?
B2 C29 1.5754(18) . ?
C1 C2 1.369(2) . ?
C1 C6 1.381(2) . ?
C2 C3 1.388(2) . ?
C3 C4 1.3887(18) . ?
C4 C5 1.3844(19) . ?
C4 C7 1.4968(18) . ?
C5 C6 1.380(2) . ?
C7 O1 1.4406(15) . ?
C8 O1 1.3652(14) . ?
C8 C9 1.3918(18) . ?
C8 C13 1.3975(17) . ?
C9 C10 1.3968(16) . ?
C10 C11 1.4078(16) . ?
C11 C12 1.4028(18) . ?
C11 N1 1.4245(14) . ?
C12 C13 1.3781(17) . ?
C14 C15 1.3894(17) . ?
C14 C19 1.3938(19) . ?
C14 N2 1.4264(15) . ?
C15 C16 1.3868(17) . ?
C16 C17 1.3823(19) . ?
C17 C18 1.3805(18) . ?
C17 N3 1.4713(16) . ?
C18 C19 1.3823(19) . ?
C20 C25 1.368(2) . ?
C20 C21 1.383(2) . ?
C21 C22 1.3892(19) . ?
C22 C23 1.3851(19) . ?
C23 C24 1.3881(18) . ?
C23 C26 1.5001(17) . ?
C24 C25 1.380(2) . ?
C26 O6 1.4402(15) . ?
C27 O6 1.3621(14) . ?
C27 C28 1.3949(18) . ?
C27 C32 1.3981(17) . ?
C28 C29 1.4006(16) . ?
C29 C30 1.4039(16) . ?
C30 C31 1.4049(18) . ?
C30 N4 1.4219(15) . ?
C31 C32 1.3731(17) . ?
C33 C34 1.3872(17) . ?
C33 C38 1.4013(19) . ?
C33 N5 1.4231(15) . ?
C34 C35 1.3858(18) . ?
C35 C36 1.3816(19) . ?
C36 C37 1.3830(18) . ?
C36 N6 1.4669(15) . ?
C37 C38 1.3803(18) . ?
N1 N2 1.2573(14) . ?
N3 O5 1.2213(16) . ?
N3 O4 1.2263(15) . ?
N4 N5 1.2560(14) . ?
N6 O10 1.2190(16) . ?
N6 O9 1.2222(15) . ?
