#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038288.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_4038288
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            'C14 H16 B F2 N3 O S'
_chemical_formula_weight         323.17
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   '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                 107.296(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6493(2)
_cell_length_b                   6.22270(10)
_cell_length_c                   19.5519(3)
_cell_measurement_reflns_used    7479
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.7190
_cell_measurement_theta_min      2.3770
_cell_volume                     1469.39(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12930
_diffrn_reflns_theta_full        70.52
_diffrn_reflns_theta_max         70.52
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68842
_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    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²+0.6871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                2700
_reflns_number_total             2794
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo0c00552_si_002.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 4038285--4038289.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4038288
_oxdiff_exptl_absorpt_empirical_full_min 0.648
_oxdiff_exptl_absorpt_empirical_full_max 1.630
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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 0.50245(13) -1.2787(3) 0.39662(9) 0.0351(4) Uani 1 1 d . . .
H1A H 0.4718 -1.3605 0.3537 0.053 Uiso 1 1 calc R . .
H1B H 0.5315 -1.3747 0.4362 0.053 Uiso 1 1 calc R . .
H1C H 0.5609 -1.1887 0.3909 0.053 Uiso 1 1 calc R . .
C2 C 0.37942(13) -1.2001(3) 0.47154(8) 0.0331(3) Uani 1 1 d . . .
H2A H 0.4167 -1.1107 0.5114 0.050 Uiso 1 1 calc R . .
H2B H 0.3962 -1.3482 0.4839 0.050 Uiso 1 1 calc R . .
H2C H 0.3010 -1.1780 0.4599 0.050 Uiso 1 1 calc R . .
C3 C 0.37467(11) -0.9734(2) 0.36801(7) 0.0239(3) Uani 1 1 d . . .
C4 C 0.40157(11) -0.9378(2) 0.30358(8) 0.0249(3) Uani 1 1 d . . .
H4 H 0.4484 -1.0332 0.2901 0.030 Uiso 1 1 calc R . .
C5 C 0.35961(11) -0.7646(2) 0.26078(7) 0.0234(3) Uani 1 1 d . . .
H5 H 0.3779 -0.7459 0.2185 0.028 Uiso 1 1 calc R . .
C6 C 0.28982(11) -0.6147(2) 0.27919(7) 0.0211(3) Uani 1 1 d . . .
C7 C 0.26258(11) -0.6488(2) 0.34287(7) 0.0231(3) Uani 1 1 d . . .
H7 H 0.2163 -0.5518 0.3562 0.028 Uiso 1 1 calc R . .
C8 C 0.30305(11) -0.8230(2) 0.38598(7) 0.0241(3) Uani 1 1 d . . .
H8 H 0.2831 -0.8425 0.4277 0.029 Uiso 1 1 calc R . .
C9 C 0.24721(11) -0.4315(2) 0.23322(7) 0.0214(3) Uani 1 1 d . . .
C10 C 0.14103(11) -0.1335(2) 0.20257(7) 0.0220(3) Uani 1 1 d . . .
C11 C 0.04305(12) 0.1792(2) 0.13589(7) 0.0269(3) Uani 1 1 d . . .
C12 C 0.11228(12) 0.0832(2) 0.10438(7) 0.0258(3) Uani 1 1 d . . .
C13 C -0.02927(14) 0.3725(2) 0.11189(8) 0.0346(4) Uani 1 1 d . . .
H13A H 0.0102 0.4993 0.1333 0.052 Uiso 1 1 calc R . .
H13B H -0.0951 0.3579 0.1264 0.052 Uiso 1 1 calc R . .
H13C H -0.0492 0.3842 0.0607 0.052 Uiso 1 1 calc R . .
C14 C 0.13499(15) 0.1470(3) 0.03632(8) 0.0345(4) Uani 1 1 d . . .
H14A H 0.0842 0.2579 0.0131 0.052 Uiso 1 1 calc R . .
H14B H 0.1259 0.0246 0.0052 0.052 Uiso 1 1 calc R . .
H14C H 0.2095 0.1996 0.0470 0.052 Uiso 1 1 calc R . .
B1 B 0.24930(13) -0.2483(3) 0.12082(8) 0.0245(3) Uani 1 1 d . . .
N1 N 0.41621(11) -1.1453(2) 0.41039(7) 0.0324(3) Uani 1 1 d . . .
N2 N 0.17784(9) -0.29634(18) 0.24914(6) 0.0217(2) Uani 1 1 d . . .
N3 N 0.16702(9) -0.09510(18) 0.14245(6) 0.0221(2) Uani 1 1 d . . .
O1 O 0.28286(8) -0.41387(16) 0.17652(5) 0.0272(2) Uani 1 1 d . . .
F1 F 0.34047(7) -0.13660(14) 0.11600(5) 0.0327(2) Uani 1 1 d . . .
F2 F 0.19530(8) -0.34609(14) 0.05605(4) 0.0330(2) Uani 1 1 d . . .
S1 S 0.04584(3) 0.04711(5) 0.214783(17) 0.02507(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 120.91(13) . . ?
N1 C3 C8 121.88(13) . . ?
C4 C3 C8 117.21(12) . . ?
C5 C4 C3 120.93(13) . . ?
C4 C5 C6 121.67(12) . . ?
C5 C6 C7 117.83(12) . . ?
C5 C6 C9 120.60(12) . . ?
C7 C6 C9 121.57(12) . . ?
C8 C7 C6 121.20(13) . . ?
C7 C8 C3 121.16(13) . . ?
N2 C9 O1 124.27(12) . . ?
N2 C9 C6 120.36(12) . . ?
O1 C9 C6 115.37(12) . . ?
N3 C10 N2 127.12(13) . . ?
N3 C10 S1 111.90(10) . . ?
N2 C10 S1 120.92(10) . . ?
C12 C11 C13 129.05(14) . . ?
C12 C11 S1 110.53(11) . . ?
C13 C11 S1 120.42(12) . . ?
C11 C12 N3 113.16(13) . . ?
C11 C12 C14 127.61(14) . . ?
N3 C12 C14 119.23(13) . . ?
F1 B1 F2 110.78(12) . . ?
F1 B1 O1 110.04(12) . . ?
F2 B1 O1 108.92(12) . . ?
F1 B1 N3 110.56(12) . . ?
F2 B1 N3 109.17(12) . . ?
O1 B1 N3 107.28(11) . . ?
C3 N1 C2 121.88(12) . . ?
C3 N1 C1 120.69(12) . . ?
C2 N1 C1 117.41(12) . . ?
C9 N2 C10 116.13(12) . . ?
C10 N3 C12 113.48(12) . . ?
C10 N3 B1 119.29(11) . . ?
C12 N3 B1 127.21(11) . . ?
C9 O1 B1 125.88(11) . . ?
C10 S1 C11 90.92(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 1.4580(19) . ?
C2 N1 1.4470(19) . ?
C3 N1 1.3594(18) . ?
C3 C4 1.4167(19) . ?
C3 C8 1.418(2) . ?
C4 C5 1.371(2) . ?
C5 C6 1.4024(19) . ?
C6 C7 1.4032(19) . ?
C6 C9 1.4527(19) . ?
C7 C8 1.3752(19) . ?
C9 N2 1.3179(18) . ?
C9 O1 1.3197(16) . ?
C10 N3 1.3327(17) . ?
C10 N2 1.3495(17) . ?
C10 S1 1.7148(14) . ?
C11 C12 1.351(2) . ?
C11 C13 1.500(2) . ?
C11 S1 1.7388(15) . ?
C12 N3 1.3992(18) . ?
C12 C14 1.496(2) . ?
B1 F1 1.3734(18) . ?
B1 F2 1.3880(17) . ?
B1 O1 1.4674(18) . ?
B1 N3 1.5595(19) . ?
