#------------------------------------------------------------------------------
#$Date: 2021-05-28 06:47:23 +0300 (Fri, 28 May 2021) $
#$Revision: 265576 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158101.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_7158101
loop_
_publ_author_name
'Puji Pamungkas, Khurnia Krisna'
'Maruyama, Toshifumi'
'Murai, Toshiaki'
_publ_section_title
;
 Boron complexes of thiazole-bridged 1,5-bidentate nitrogen ligands:
 synthesis and acid-responsive photophysical properties
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB00828E
_journal_year                    2021
_chemical_formula_moiety         'C20 H15 B F2 N4 S'
_chemical_formula_sum            'C20 H15 B F2 N4 S'
_chemical_formula_weight         392.23
_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-2014/7
_audit_update_record
;
2021-04-28 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                105.166(3)
_cell_angle_beta                 96.037(2)
_cell_angle_gamma                108.811(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9896(2)
_cell_length_b                   9.2646(3)
_cell_length_c                   13.4601(4)
_cell_measurement_reflns_used    2266
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.4
_cell_volume                     890.46(5)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       'profile data from φ-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8310
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.446
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       Block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0421
_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)+(0.0537P)²+0.1258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2984
_reflns_number_total             4063
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00828e2.cif
_cod_data_source_block           200715
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7158101
_shelx_shelxl_version_number     2014/7
_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   0.958
_shelx_estimated_absorpt_t_max   0.970
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
S1 S 0.96006(6) 0.71408(5) 0.45412(3) 0.05012(16) Uani 1 1 d . . . . .
F1 F 1.35970(15) 0.78966(14) 0.23464(10) 0.0707(4) Uani 1 1 d . . . . .
F2 F 1.19605(16) 0.89511(15) 0.14794(8) 0.0695(4) Uani 1 1 d . . . . .
N1 N 1.22514(18) 0.97442(17) 0.56698(11) 0.0450(3) Uani 1 1 d . . . . .
N2 N 1.07943(19) 0.79487(17) 0.28426(11) 0.0470(4) Uani 1 1 d . . . . .
N3 N 0.8999(2) 0.6959(2) 0.65808(13) 0.0608(4) Uani 1 1 d . . . . .
N4 N 1.35773(19) 1.04810(17) 0.32691(11) 0.0462(4) Uani 1 1 d . . . . .
C1 C 1.0931(2) 0.8545(2) 0.57422(13) 0.0444(4) Uani 1 1 d . . . . .
C2 C 1.0950(2) 0.82918(19) 0.38980(13) 0.0428(4) Uani 1 1 d . . . . .
C3 C 1.2298(2) 0.9622(2) 0.46302(13) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.9237(2) 0.6661(2) 0.21538(13) 0.0478(4) Uani 1 1 d . . . . .
C5 C 0.7508(2) 0.6570(2) 0.22743(14) 0.0518(5) Uani 1 1 d . . . . .
H5 H 0.7344 0.7370 0.2793 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6024(3) 0.5284(2) 0.16209(15) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.4869 0.5230 0.1710 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6223(3) 0.4072(2) 0.08364(15) 0.0603(5) Uani 1 1 d . . . . .
C8 C 0.7947(3) 0.4222(2) 0.07037(16) 0.0678(6) Uani 1 1 d . . . . .
H8 H 0.8109 0.3450 0.0163 0.081 Uiso 1 1 calc R U . . .
C9 C 0.9451(3) 0.5494(2) 0.13540(16) 0.0621(5) Uani 1 1 d . . . . .
H9 H 1.0603 0.5560 0.1251 0.075 Uiso 1 1 calc R U . . .
C10 C 0.4614(3) 0.2627(3) 0.01472(18) 0.0833(8) Uani 1 1 d . . . . .
H10 H 0.4942 0.2142 -0.0487 0.125 Uiso 1 1 calc R U . . .
H10A H 0.3633 0.2961 -0.0027 0.125 Uiso 1 1 calc R U . . .
H10B H 0.4247 0.1861 0.0519 0.125 Uiso 1 1 calc R U . . .
C11 C 1.0451(2) 0.8278(2) 0.67106(14) 0.0475(4) Uani 1 1 d . . . . .
C12 C 1.1428(3) 0.9313(2) 0.76985(15) 0.0579(5) Uani 1 1 d . . . . .
H12 H 1.2443 1.0207 0.7765 0.069 Uiso 1 1 calc R U . . .
C13 C 1.0872(3) 0.8995(3) 0.85734(17) 0.0698(6) Uani 1 1 d . . . . .
H13 H 1.1495 0.9681 0.9243 0.084 Uiso 1 1 calc R U . . .
C14 C 0.9380(3) 0.7651(3) 0.84490(18) 0.0726(6) Uani 1 1 d . . . . .
H14 H 0.8977 0.7405 0.9029 0.087 Uiso 1 1 calc R U . . .
C15 C 0.8504(3) 0.6681(3) 0.74441(18) 0.0738(6) Uani 1 1 d . . . . .
H15 H 0.7498 0.5771 0.7364 0.089 Uiso 1 1 calc R U . . .
C16 C 1.3576(2) 1.0810(2) 0.43157(13) 0.0429(4) Uani 1 1 d . . . . .
C17 C 1.4776(2) 1.2282(2) 0.50242(15) 0.0495(4) Uani 1 1 d . . . . .
H17 H 1.4795 1.2507 0.5741 0.059 Uiso 1 1 calc R U . . .
C18 C 1.5916(2) 1.3384(2) 0.46586(16) 0.0550(5) Uani 1 1 d . . . . .
H18 H 1.6717 1.4358 0.5126 0.066 Uiso 1 1 calc R U . . .
C19 C 1.5870(3) 1.3039(2) 0.35849(16) 0.0585(5) Uani 1 1 d . . . . .
H19 H 1.6621 1.3785 0.3324 0.070 Uiso 1 1 calc R U . . .
C20 C 1.4706(2) 1.1590(2) 0.29190(16) 0.0549(5) Uani 1 1 d . . . . .
H20 H 1.4687 1.1355 0.2202 0.066 Uiso 1 1 calc R U . . .
B1 B 1.2449(3) 0.8746(3) 0.24291(16) 0.0511(5) 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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
C2 S1 C1 88.61(8) . . ?
C1 N1 C3 110.78(14) . . ?
C2 N2 C4 119.55(15) . . ?
C2 N2 B1 118.04(14) . . ?
C4 N2 B1 121.44(14) . . ?
C15 N3 C11 117.15(17) . . ?
C20 N4 C16 119.73(15) . . ?
N1 C1 C11 126.37(15) . . ?
N1 C1 S1 115.54(14) . . ?
C11 C1 S1 118.09(12) . . ?
N2 C2 C3 123.95(16) . . ?
N2 C2 S1 126.24(12) . . ?
C3 C2 S1 109.77(13) . . ?
N1 C3 C2 115.28(15) . . ?
N1 C3 C16 122.92(14) . . ?
C2 C3 C16 121.72(16) . . ?
C9 C4 C5 119.22(16) . . ?
C9 C4 N2 119.85(17) . . ?
C5 C4 N2 120.93(16) . . ?
C4 C5 C6 119.88(19) . . ?
C5 C6 C7 121.5(2) . . ?
C8 C7 C6 117.62(17) . . ?
C8 C7 C10 120.5(2) . . ?
C6 C7 C10 121.9(2) . . ?
C7 C8 C9 121.8(2) . . ?
C4 C9 C8 120.0(2) . . ?
N3 C11 C12 122.36(18) . . ?
N3 C11 C1 115.24(16) . . ?
C12 C11 C1 122.40(17) . . ?
C13 C12 C11 118.96(19) . . ?
C12 C13 C14 119.1(2) . . ?
C15 C14 C13 118.2(2) . . ?
N3 C15 C14 124.2(2) . . ?
N4 C16 C17 119.59(16) . . ?
N4 C16 C3 117.05(14) . . ?
C17 C16 C3 123.35(17) . . ?
C18 C17 C16 119.95(18) . . ?
C17 C18 C19 119.57(17) . . ?
C20 C19 C18 119.04(18) . . ?
N4 C20 C19 122.11(19) . . ?
F2 B1 F1 110.26(17) . . ?
F2 B1 N2 111.68(16) . . ?
F1 B1 N2 111.77(17) . . ?
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
S1 C2 1.7283(18) . ?
S1 C1 1.7557(17) . ?
F1 B1 1.384(3) . ?
F2 B1 1.375(2) . ?
N1 C1 1.296(2) . ?
N1 C3 1.379(2) . ?
N2 C2 1.355(2) . ?
N2 C4 1.433(2) . ?
N2 B1 1.531(3) . ?
N3 C15 1.327(3) . ?
N3 C11 1.342(2) . ?
N4 C20 1.355(2) . ?
N4 C16 1.361(2) . ?
C1 C11 1.456(3) . ?
C2 C3 1.391(2) . ?
C3 C16 1.430(2) . ?
C4 C9 1.381(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.386(2) . ?
C6 C7 1.389(3) . ?
C7 C8 1.374(3) . ?
C7 C10 1.515(3) . ?
C8 C9 1.387(3) . ?
C11 C12 1.389(2) . ?
C12 C13 1.370(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.373(3) . ?
C16 C17 1.404(2) . ?
C17 C18 1.368(3) . ?
C18 C19 1.390(3) . ?
C19 C20 1.364(3) . ?
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
C3 N1 C1 C11 -179.31(17) . . . . ?
C3 N1 C1 S1 -0.2(2) . . . . ?
C2 S1 C1 N1 -0.32(15) . . . . ?
C2 S1 C1 C11 178.91(15) . . . . ?
C4 N2 C2 C3 -172.50(17) . . . . ?
B1 N2 C2 C3 18.6(3) . . . . ?
C4 N2 C2 S1 10.2(2) . . . . ?
B1 N2 C2 S1 -158.69(14) . . . . ?
C1 S1 C2 N2 178.31(16) . . . . ?
C1 S1 C2 C3 0.69(14) . . . . ?
C1 N1 C3 C2 0.7(2) . . . . ?
C1 N1 C3 C16 177.69(16) . . . . ?
N2 C2 C3 N1 -178.65(16) . . . . ?
S1 C2 C3 N1 -1.0(2) . . . . ?
N2 C2 C3 C16 4.4(3) . . . . ?
S1 C2 C3 C16 -177.96(14) . . . . ?
C2 N2 C4 C9 -128.9(2) . . . . ?
B1 N2 C4 C9 39.6(3) . . . . ?
C2 N2 C4 C5 51.4(2) . . . . ?
B1 N2 C4 C5 -140.14(19) . . . . ?
C9 C4 C5 C6 2.4(3) . . . . ?
N2 C4 C5 C6 -177.83(17) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -2.3(3) . . . . ?
C5 C6 C7 C10 177.44(18) . . . . ?
C6 C7 C8 C9 2.8(3) . . . . ?
C10 C7 C8 C9 -177.0(2) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
N2 C4 C9 C8 178.27(18) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C15 N3 C11 C12 0.9(3) . . . . ?
C15 N3 C11 C1 -179.25(18) . . . . ?
N1 C1 C11 N3 178.75(18) . . . . ?
S1 C1 C11 N3 -0.4(2) . . . . ?
N1 C1 C11 C12 -1.4(3) . . . . ?
S1 C1 C11 C12 179.47(15) . . . . ?
N3 C11 C12 C13 -1.3(3) . . . . ?
C1 C11 C12 C13 178.84(19) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C11 N3 C15 C14 -0.1(4) . . . . ?
C13 C14 C15 N3 -0.2(4) . . . . ?
C20 N4 C16 C17 -1.5(3) . . . . ?
C20 N4 C16 C3 177.24(16) . . . . ?
N1 C3 C16 N4 174.60(15) . . . . ?
C2 C3 C16 N4 -8.6(3) . . . . ?
N1 C3 C16 C17 -6.7(3) . . . . ?
C2 C3 C16 C17 170.02(17) . . . . ?
N4 C16 C17 C18 1.0(3) . . . . ?
C3 C16 C17 C18 -177.62(17) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C16 N4 C20 C19 0.6(3) . . . . ?
C18 C19 C20 N4 0.7(3) . . . . ?
C2 N2 B1 F2 -151.04(16) . . . . ?
C4 N2 B1 F2 40.3(2) . . . . ?
C2 N2 B1 F1 84.90(19) . . . . ?
C4 N2 B1 F1 -83.8(2) . . . . ?
