#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038286.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_4038286
loop_
_publ_author_name
'Potopnyk, Mykhaylo A.'
'Volyniuk, Dmytro'
'Luboradzki, Roman'
'Ceborska, Magdalena'
'Hladka, Iryna'
'Danyliv, Yan'
'Grazulevicius, Juozas V.'
_publ_section_title
;
 Organolithium-Mediated Postfunctionalization of
 Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6060
_journal_page_last               6072
_journal_paper_doi               10.1021/acs.joc.0c00552
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C13 H14 B F2 N3 O S'
_chemical_formula_weight         309.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        '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                 94.7240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5882(2)
_cell_length_b                   11.6785(2)
_cell_length_c                   7.53310(10)
_cell_measurement_reflns_used    12476
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.0380
_cell_measurement_theta_min      6.8290
_cell_volume                     1366.72(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24025
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0302
_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)+(0.0483P)²+0.6135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2482
_reflns_number_total             2573
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo0c00552_si_002.cif
_cod_data_source_block           2d
_cod_depositor_comments
'Adding full bibliography for 4038285--4038289.cif.'
_cod_database_code               4038286
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
C1 C 1.18375(9) 0.71743(14) 0.5567(2) 0.0307(3) Uani 1 1 d . . .
H1A H 1.1883 0.7838 0.4829 0.046 Uiso 1 1 calc R . .
H1B H 1.2401 0.6953 0.6061 0.046 Uiso 1 1 calc R . .
H1C H 1.1483 0.7349 0.6515 0.046 Uiso 1 1 calc R . .
C2 C 1.20145(9) 0.53137(13) 0.4002(2) 0.0283(3) Uani 1 1 d . . .
H2A H 1.1786 0.4593 0.4355 0.042 Uiso 1 1 calc R . .
H2B H 1.2580 0.5420 0.4587 0.042 Uiso 1 1 calc R . .
H2C H 1.2047 0.5320 0.2735 0.042 Uiso 1 1 calc R . .
C3 C 1.06140(9) 0.62715(12) 0.38481(18) 0.0201(3) Uani 1 1 d . . .
C4 C 1.02368(9) 0.53499(12) 0.28333(19) 0.0226(3) Uani 1 1 d . . .
H4 H 1.0573 0.4722 0.2582 0.027 Uiso 1 1 calc R . .
C5 C 0.93823(9) 0.53696(12) 0.22163(18) 0.0219(3) Uani 1 1 d . . .
H5 H 0.9146 0.4742 0.1594 0.026 Uiso 1 1 calc R . .
C6 C 0.88587(9) 0.63196(11) 0.25067(17) 0.0194(3) Uani 1 1 d . . .
C7 C 0.92333(9) 0.72439(11) 0.34822(17) 0.0199(3) Uani 1 1 d . . .
H7 H 0.8900 0.7885 0.3675 0.024 Uiso 1 1 calc R . .
C8 C 1.00773(9) 0.72247(12) 0.41568(18) 0.0207(3) Uani 1 1 d . . .
H8 H 1.0302 0.7842 0.4824 0.025 Uiso 1 1 calc R . .
C9 C 0.79618(9) 0.63519(11) 0.18326(17) 0.0197(3) Uani 1 1 d . . .
C10 C 0.67211(9) 0.73001(12) 0.10762(17) 0.0202(3) Uani 1 1 d . . .
C11 C 0.54418(9) 0.66147(12) -0.01354(18) 0.0230(3) Uani 1 1 d . . .
H11 H 0.5054 0.6049 -0.0541 0.028 Uiso 1 1 calc R . .
C12 C 0.52380(9) 0.77314(13) -0.01739(18) 0.0230(3) Uani 1 1 d . . .
C13 C 0.44013(10) 0.82829(14) -0.0800(2) 0.0294(3) Uani 1 1 d . . .
H13A H 0.4176 0.8683 0.0173 0.044 Uiso 1 1 calc R . .
H13B H 0.3999 0.7706 -0.1236 0.044 Uiso 1 1 calc R . .
H13C H 0.4492 0.8814 -0.1739 0.044 Uiso 1 1 calc R . .
B1 B 0.67054(10) 0.51707(13) 0.0789(2) 0.0216(3) Uani 1 1 d . . .
N1 N 1.14534(8) 0.62385(10) 0.45015(16) 0.0234(3) Uani 1 1 d . . .
N2 N 0.62716(8) 0.63686(10) 0.05532(15) 0.0206(3) Uani 1 1 d . . .
N3 N 0.75370(7) 0.73302(10) 0.17983(15) 0.0209(2) Uani 1 1 d . . .
O1 O 0.76289(6) 0.53683(8) 0.12347(14) 0.0250(2) Uani 1 1 d . . .
F1 F 0.63537(5) 0.45871(7) 0.21616(11) 0.0277(2) Uani 1 1 d . . .
F2 F 0.65821(5) 0.45494(7) -0.07647(11) 0.0270(2) Uani 1 1 d . . .
S1 S 0.61222(2) 0.85287(3) 0.06801(4) 0.02280(12) 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 C3 C4 121.13(12) . . ?
N1 C3 C8 121.60(13) . . ?
C4 C3 C8 117.27(12) . . ?
C5 C4 C3 121.09(13) . . ?
C4 C5 C6 121.32(13) . . ?
C5 C6 C7 117.78(13) . . ?
C5 C6 C9 121.50(12) . . ?
C7 C6 C9 120.72(12) . . ?
C8 C7 C6 121.73(13) . . ?
C7 C8 C3 120.75(13) . . ?
N3 C9 O1 124.22(13) . . ?
N3 C9 C6 119.86(12) . . ?
O1 C9 C6 115.89(12) . . ?
N2 C10 N3 126.69(13) . . ?
N2 C10 S1 111.31(10) . . ?
N3 C10 S1 121.99(10) . . ?
C12 C11 N2 114.98(13) . . ?
C11 C12 C13 128.61(14) . . ?
C11 C12 S1 109.44(11) . . ?
C13 C12 S1 121.95(12) . . ?
F2 B1 F1 109.78(12) . . ?
F2 B1 O1 110.02(12) . . ?
F1 B1 O1 110.28(12) . . ?
F2 B1 N2 110.32(12) . . ?
F1 B1 N2 109.37(12) . . ?
O1 B1 N2 107.03(11) . . ?
C3 N1 C1 121.22(12) . . ?
C3 N1 C2 120.46(12) . . ?
C1 N1 C2 118.04(12) . . ?
C10 N2 C11 113.13(12) . . ?
C10 N2 B1 119.05(12) . . ?
C11 N2 B1 127.81(11) . . ?
C9 N3 C10 116.26(12) . . ?
C9 O1 B1 124.28(11) . . ?
C10 S1 C12 91.13(7) . . ?
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
C1 N1 1.4553(19) . ?
C2 N1 1.4586(18) . ?
C3 N1 1.3601(18) . ?
C3 C4 1.419(2) . ?
C3 C8 1.4231(19) . ?
C4 C5 1.374(2) . ?
C5 C6 1.4052(19) . ?
C6 C7 1.4056(19) . ?
C6 C9 1.448(2) . ?
C7 C8 1.3710(19) . ?
C9 N3 1.3197(18) . ?
C9 O1 1.3241(16) . ?
C10 N2 1.3357(18) . ?
C10 N3 1.3419(18) . ?
C10 S1 1.7244(14) . ?
C11 C12 1.342(2) . ?
C11 N2 1.3837(18) . ?
C12 C13 1.496(2) . ?
C12 S1 1.7421(14) . ?
B1 F2 1.3771(18) . ?
B1 F1 1.3882(18) . ?
B1 O1 1.4693(18) . ?
B1 N2 1.5575(19) . ?
