#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:07:14 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 234777 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/72/7157219.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_7157219
loop_
_publ_author_name
'Shimomura, N.'
'Egawa, Y.'
'Miki, R.'
'Fujihara, T.'
'Ishimaru, Y.'
'Seki, T.'
_publ_section_title
;
 A red fluorophore comprising a borinate-containing xanthene analogue as a
 polyol sensor.
;
_journal_issue                   42
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10031
_journal_page_last               10036
_journal_paper_doi               10.1039/c6ob01695b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C23 H23 B N2 O2'
_chemical_formula_weight         370.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-06-16 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2732(9)
_cell_length_b                   18.924(2)
_cell_length_c                   31.436(4)
_cell_measurement_reflns_used    6731
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.25
_cell_volume                     4326.8(9)
_computing_cell_refinement       'Bruker SAINT (Bruker 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker 2014)'
_computing_data_reduction        'Bruker SAINT and XPREP (Bruker 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'XCIF (Bruker, 2014)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            23868
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_min         1.295
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/2 - Bruker 2014'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.8621
_exptl_transmission_factor_min   0.7992
_platon_squeeze_details
;
The chloroform solvent molecule could not be resolved due
to extensive disorder and their assumed presence was removed from
the overall scattering by the PLATON SQUEEZE procedure [Spek (2009).
Acta Cryst. D65, 148-155].
A total of 56 e was found in each cavity (estimated volume 131 ?%A³),
corresponding to approximately one chloroform molecule per cavity.
;
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0655
_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)+(0.0742P)²+6.3230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1889
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2071
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob01695b2.cif
_cod_data_source_block           fuji_maru_jsd_150716_01
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7157219
_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   0.988
_shelx_estimated_absorpt_t_max   0.997
_platon_squeeze_void_probe_radius 1.20
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, -z'
'-x+1/2, y, -z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z+1/2'
'-x+1, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, z'
'x-1/2, -y, z-1/2'
'x-1/2, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z-1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
B1 B 0.0000 0.34252(17) 0.11829(10) 0.0346(7) Uani 1 2 d S T P
C1 C 0.0000 0.27413(19) -0.00115(10) 0.0500(8) Uani 1 2 d S T P
C2 C 0.0000 0.31771(18) 0.03613(10) 0.0501(8) Uani 1 2 d S T P
H2 H 0.0000 0.3675 0.0324 0.060 Uiso 1 2 calc R U P
C3 C 0.0000 0.29204(15) 0.07650(9) 0.0387(7) Uani 1 2 d S T P
C4 C 0.0000 0.29759(14) 0.16215(9) 0.0321(6) Uani 1 2 d S T P
C5 C 0.0000 0.32982(15) 0.20133(9) 0.0383(7) Uani 1 2 d S T P
H5 H 0.0000 0.3800 0.2022 0.046 Uiso 1 2 calc R U P
C6 C 0.0000 0.29248(16) 0.24082(9) 0.0359(6) Uani 1 2 d S T P
C7 C 0.0000 0.21778(17) 0.23869(10) 0.0464(8) Uani 1 2 d S T P
H7 H 0.0000 0.1907 0.2641 0.056 Uiso 1 2 calc R U P
C8 C 0.0000 0.18466(17) 0.20007(11) 0.0535(9) Uani 1 2 d S T P
H8 H 0.0000 0.1345 0.1992 0.064 Uiso 1 2 calc R U P
C9 C 0.0000 0.22237(16) 0.16137(10) 0.0403(7) Uani 1 2 d S T P
C10 C 0.0000 0.18664(17) 0.12203(11) 0.0570(10) Uani 1 2 d S T P
H10 H 0.0000 0.1365 0.1231 0.068 Uiso 1 2 calc R U P
C11 C 0.0000 0.21719(17) 0.08164(11) 0.0485(8) Uani 1 2 d S T P
C12 C 0.0000 0.1737(2) 0.04484(13) 0.0731(13) Uani 1 2 d S T P
H12 H 0.0000 0.1238 0.0482 0.088 Uiso 1 2 calc R U P
C13 C 0.0000 0.2015(2) 0.00449(12) 0.0609(10) Uani 1 2 d S T P
H13 H 0.0000 0.1710 -0.0195 0.073 Uiso 1 2 calc R U P
C14 C 0.0000 0.3759(3) -0.04816(13) 0.129(3) Uani 1 2 d S T P
H14A H 0.0662 0.3999 -0.0252 0.193 Uiso 0.5 1 calc R U P
H14B H -0.1270 0.3931 -0.0492 0.193 Uiso 0.5 1 calc R U P
H14C H 0.0608 0.3857 -0.0753 0.193 Uiso 0.5 1 calc R U P
C15 C 0.0000 0.2565(3) -0.07846(12) 0.0728(13) Uani 1 2 d S T P
H15A H -0.0493 0.2835 -0.1025 0.109 Uiso 0.5 1 calc R U P
H15B H -0.0768 0.2148 -0.0735 0.109 Uiso 0.5 1 calc R U P
H15C H 0.1260 0.2416 -0.0849 0.109 Uiso 0.5 1 calc R U P
C16 C 0.0000 0.4022(2) 0.28168(12) 0.0872(17) Uani 1 2 d S T P
H16A H 0.1261 0.4198 0.2789 0.131 Uiso 0.5 1 calc R U P
H16B H -0.0499 0.4164 0.3093 0.131 Uiso 0.5 1 calc R U P
H16C H -0.0762 0.4220 0.2589 0.131 Uiso 0.5 1 calc R U P
C17 C 0.0000 0.2881(2) 0.31873(10) 0.0540(9) Uani 1 2 d S T P
H17A H 0.1211 0.2667 0.3233 0.081 Uiso 0.5 1 calc R U P
H17B H -0.0939 0.2510 0.3179 0.081 Uiso 0.5 1 calc R U P
H17C H -0.0272 0.3209 0.3420 0.081 Uiso 0.5 1 calc R U P
C18 C 0.0958(3) 0.45604(10) 0.13177(6) 0.0375(5) Uani 1 1 d . . .
C19 C 0.1935(4) 0.51418(11) 0.14522(7) 0.0532(6) Uani 1 1 d . . .
H19 H 0.3241 0.5144 0.1447 0.064 Uiso 1 1 calc R U .
C20 C 0.0946(5) 0.57292(13) 0.15969(8) 0.0667(8) Uani 1 1 d . . .
H20 H 0.1590 0.6133 0.1696 0.080 Uiso 1 1 calc R U .
N1 N 0.0000 0.3007(2) -0.04044(9) 0.0709(10) Uani 1 2 d S T P
N2 N 0.0000 0.32629(15) 0.27859(8) 0.0451(7) Uani 1 2 d S T P
O1 O 0.1636(2) 0.39311(7) 0.11794(4) 0.0380(4) 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'
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
O1 B1 O1 102.3(2) 10 .
O1 B1 C4 109.59(15) 10 .
O1 B1 C4 109.59(15) . .
O1 B1 C3 111.27(15) 10 .
O1 B1 C3 111.27(15) . .
C4 B1 C3 112.3(2) . .
N1 C1 C13 119.5(3) . .
N1 C1 C2 122.7(3) . .
C13 C1 C2 117.8(3) . .
C3 C2 C1 123.9(3) . .
C3 C2 H2 118.0 . .
C1 C2 H2 118.0 . .
C2 C3 C11 117.5(3) . .
C2 C3 B1 123.0(3) . .
C11 C3 B1 119.5(3) . .
C5 C4 C9 117.3(3) . .
C5 C4 B1 122.0(2) . .
C9 C4 B1 120.7(2) . .
C4 C5 C6 124.0(3) . .
C4 C5 H5 118.0 . .
C6 C5 H5 118.0 . .
N2 C6 C7 121.0(3) . .
N2 C6 C5 122.0(3) . .
C7 C6 C5 116.9(3) . .
C8 C7 C6 120.0(3) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C7 C8 C9 122.3(3) . .
C7 C8 H8 118.8 . .
C9 C8 H8 118.8 . .
C10 C9 C8 120.9(3) . .
C10 C9 C4 119.7(3) . .
C8 C9 C4 119.4(3) . .
C11 C10 C9 126.8(3) . .
C11 C10 H10 116.6 . .
C9 C10 H10 116.6 . .
C10 C11 C12 120.1(3) . .
C10 C11 C3 121.0(3) . .
C12 C11 C3 118.9(3) . .
C13 C12 C11 122.0(3) . .
C13 C12 H12 119.0 . .
C11 C12 H12 119.0 . .
C12 C13 C1 119.9(3) . .
C12 C13 H13 120.1 . .
C1 C13 H13 120.1 . .
N1 C14 H14A 109.5 . .
N1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C15 H15A 109.5 . .
N1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N2 C16 H16A 109.5 . .
N2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
N2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N2 C17 H17A 109.5 . .
N2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O1 C18 C19 127.7(2) . .
O1 C18 C18 111.24(12) . 10
C19 C18 C18 121.09(15) . 10
C18 C19 C20 118.0(3) . .
C18 C19 H19 121.0 . .
C20 C19 H19 121.0 . .
C20 C20 C19 120.92(17) 10 .
C20 C20 H20 119.5 10 .
C19 C20 H20 119.5 . .
C1 N1 C14 121.8(3) . .
C1 N1 C15 122.9(4) . .
C14 N1 C15 115.3(3) . .
C6 N2 C16 122.2(3) . .
C6 N2 C17 121.9(3) . .
C16 N2 C17 115.9(3) . .
C18 O1 B1 105.33(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O1 1.527(2) 10
B1 O1 1.527(2) .
B1 C4 1.620(4) .
B1 C3 1.624(4) .
C1 N1 1.334(5) .
C1 C13 1.386(5) .
C1 C2 1.433(4) .
C2 C3 1.359(4) .
C2 H2 0.9500 .
C3 C11 1.426(4) .
C4 C5 1.374(4) .
C4 C9 1.424(4) .
C5 C6 1.428(4) .
C5 H5 0.9500 .
C6 N2 1.349(4) .
C6 C7 1.415(4) .
C7 C8 1.366(5) .
C7 H7 0.9500 .
C8 C9 1.410(4) .
C8 H8 0.9500 .
C9 C10 1.409(4) .
C10 C11 1.395(5) .
C10 H10 0.9500 .
C11 C12 1.420(5) .
C12 C13 1.373(6) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 N1 1.443(6) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 N1 1.458(4) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 N2 1.439(5) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 N2 1.454(4) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 O1 1.360(2) .
C18 C19 1.376(3) .
C18 C18 1.394(5) 10
C19 C20 1.400(4) .
C19 H19 0.9500 .
C20 C20 1.377(7) 10
C20 H20 0.9500 .
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_4
N1 C1 C2 C3 180.000(0) . .
C13 C1 C2 C3 0.000(0) . .
C1 C2 C3 C11 0.000(0) . .
C1 C2 C3 B1 180.000(0) . .
O1 B1 C3 C2 56.72(16) 10 .
O1 B1 C3 C2 -56.72(16) . .
C4 B1 C3 C2 180.000(0) . .
O1 B1 C3 C11 -123.28(16) 10 .
O1 B1 C3 C11 123.28(16) . .
C4 B1 C3 C11 0.000(0) . .
O1 B1 C4 C5 -55.78(15) 10 .
O1 B1 C4 C5 55.78(15) . .
C3 B1 C4 C5 180.000(0) . .
O1 B1 C4 C9 124.22(15) 10 .
O1 B1 C4 C9 -124.22(15) . .
C3 B1 C4 C9 0.000(0) . .
C9 C4 C5 C6 0.000(1) . .
B1 C4 C5 C6 180.000(0) . .
C4 C5 C6 N2 180.000(1) . .
C4 C5 C6 C7 0.000(1) . .
N2 C6 C7 C8 180.000(1) . .
C5 C6 C7 C8 0.000(1) . .
C6 C7 C8 C9 0.000(1) . .
C7 C8 C9 C10 180.000(0) . .
C7 C8 C9 C4 0.000(1) . .
C5 C4 C9 C10 180.000(0) . .
B1 C4 C9 C10 0.000(0) . .
C5 C4 C9 C8 0.000(1) . .
B1 C4 C9 C8 180.000(0) . .
C8 C9 C10 C11 180.000(0) . .
C4 C9 C10 C11 0.000(1) . .
C9 C10 C11 C12 180.000(0) . .
C9 C10 C11 C3 0.000(0) . .
C2 C3 C11 C10 180.000(0) . .
B1 C3 C11 C10 0.000(0) . .
C2 C3 C11 C12 0.000(0) . .
B1 C3 C11 C12 180.000(0) . .
C10 C11 C12 C13 180.000(0) . .
C3 C11 C12 C13 0.000(0) . .
C11 C12 C13 C1 0.000(0) . .
N1 C1 C13 C12 180.000(0) . .
C2 C1 C13 C12 0.000(0) . .
O1 C18 C19 C20 -177.67(19) . .
C18 C18 C19 C20 1.2(3) 10 .
C18 C19 C20 C20 -1.2(3) . 10
C13 C1 N1 C14 180.000(0) . .
C2 C1 N1 C14 0.000(0) . .
C13 C1 N1 C15 0.000(0) . .
C2 C1 N1 C15 180.000(0) . .
C7 C6 N2 C16 180.000(1) . .
C5 C6 N2 C16 0.000(1) . .
C7 C6 N2 C17 0.000(1) . .
C5 C6 N2 C17 180.000(1) . .
C19 C18 O1 B1 165.7(2) . .
C18 C18 O1 B1 -13.30(15) 10 .
O1 B1 O1 C18 20.0(2) 10 .
C4 B1 O1 C18 -96.24(19) . .
C3 B1 O1 C18 138.93(18) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 131 56 ' '
2 0.000 0.500 0.500 131 56 ' '
3 0.500 0.500 0.000 131 56 ' '
4 0.500 1.000 0.500 131 56 ' '
