#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038287.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_4038287
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            'C18 H16 B F2 N3 O3 S2'
_chemical_formula_weight         435.27
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 110.0670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.87160(10)
_cell_length_b                   12.50580(10)
_cell_length_c                   17.17690(10)
_cell_measurement_reflns_used    21053
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.0120
_cell_measurement_theta_min      4.3100
_cell_volume                     3807.73(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33583
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         4.33
_exptl_absorpt_coefficient_mu    2.949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66845
_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    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0309
_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)+(0.0408P)²+4.4338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                3511
_reflns_number_total             3607
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo0c00552_si_002.cif
_cod_data_source_block           2j
_cod_depositor_comments
'Adding full bibliography for 4038285--4038289.cif.'
_cod_original_cell_volume        3807.72(4)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4038287
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 -0.26965(9) 0.63585(13) -0.39822(10) 0.0288(3) Uani 1 1 d . . .
H1A H -0.3154 0.6347 -0.4475 0.043 Uiso 1 1 calc R . .
H1B H -0.2315 0.6811 -0.4088 0.043 Uiso 1 1 calc R . .
H1C H -0.2817 0.6646 -0.3512 0.043 Uiso 1 1 calc R . .
C2 C -0.28722(8) 0.43992(13) -0.42471(9) 0.0264(3) Uani 1 1 d . . .
H2A H -0.2563 0.3906 -0.4439 0.040 Uiso 1 1 calc R . .
H2B H -0.3280 0.4683 -0.4726 0.040 Uiso 1 1 calc R . .
H2C H -0.3088 0.4017 -0.3883 0.040 Uiso 1 1 calc R . .
C3 C -0.17825(7) 0.50850(12) -0.31156(9) 0.0207(3) Uani 1 1 d . . .
C4 C -0.15161(8) 0.40287(11) -0.28949(9) 0.0218(3) Uani 1 1 d . . .
H4 H -0.1786 0.3444 -0.3214 0.026 Uiso 1 1 calc R . .
C5 C -0.08757(8) 0.38382(11) -0.22281(9) 0.0213(3) Uani 1 1 d . . .
H5 H -0.0708 0.3123 -0.2095 0.026 Uiso 1 1 calc R . .
C6 C -0.04614(8) 0.46821(11) -0.17366(8) 0.0192(3) Uani 1 1 d . . .
C7 C -0.07327(8) 0.57277(11) -0.19442(9) 0.0216(3) Uani 1 1 d . . .
H7 H -0.0465 0.6309 -0.1618 0.026 Uiso 1 1 calc R . .
C8 C -0.13742(8) 0.59292(11) -0.26067(9) 0.0228(3) Uani 1 1 d . . .
H8 H -0.1548 0.6644 -0.2727 0.027 Uiso 1 1 calc R . .
C9 C 0.02152(8) 0.44779(11) -0.10436(9) 0.0195(3) Uani 1 1 d . . .
C10 C 0.12314(8) 0.50463(12) 0.00215(8) 0.0205(3) Uani 1 1 d . . .
C11 C 0.21458(8) 0.40540(13) 0.09493(9) 0.0256(3) Uani 1 1 d . . .
H11 H 0.2397 0.3417 0.1198 0.031 Uiso 1 1 calc R . .
C12 C 0.23934(8) 0.50393(13) 0.12280(9) 0.0243(3) Uani 1 1 d . . .
C13 C 0.39306(8) 0.54248(13) 0.16300(9) 0.0238(3) Uani 1 1 d . . .
C14 C 0.40981(9) 0.64233(13) 0.13828(10) 0.0282(3) Uani 1 1 d . . .
H14 H 0.3836 0.7043 0.1455 0.034 Uiso 1 1 calc R . .
C15 C 0.46559(9) 0.64969(13) 0.10285(10) 0.0296(3) Uani 1 1 d . . .
H15 H 0.4776 0.7171 0.0851 0.035 Uiso 1 1 calc R . .
C16 C 0.50373(8) 0.55853(13) 0.09343(9) 0.0273(3) Uani 1 1 d . . .
H16 H 0.5423 0.5641 0.0698 0.033 Uiso 1 1 calc R . .
C17 C 0.48615(9) 0.45927(13) 0.11813(9) 0.0273(3) Uani 1 1 d . . .
H17 H 0.5123 0.3973 0.1109 0.033 Uiso 1 1 calc R . .
C18 C 0.43035(8) 0.45068(13) 0.15326(9) 0.0265(3) Uani 1 1 d . . .
H18 H 0.4179 0.3831 0.1704 0.032 Uiso 1 1 calc R . .
B1 B 0.10629(9) 0.30632(13) -0.02113(10) 0.0222(3) Uani 1 1 d . . .
N1 N -0.24052(7) 0.52771(10) -0.37928(8) 0.0248(3) Uani 1 1 d . . .
N2 N 0.14940(7) 0.40586(10) 0.02689(7) 0.0212(3) Uani 1 1 d . . .
N3 N 0.06116(7) 0.52951(9) -0.06089(7) 0.0211(3) Uani 1 1 d . . .
O1 O 0.04023(6) 0.34676(8) -0.08825(6) 0.0240(2) Uani 1 1 d . . .
O2 O 0.31074(6) 0.63517(11) 0.23797(7) 0.0343(3) Uani 1 1 d . . .
O3 O 0.33596(6) 0.43914(11) 0.25862(7) 0.0369(3) Uani 1 1 d . . .
F1 F 0.08374(5) 0.24284(7) 0.03142(6) 0.0294(2) Uani 1 1 d . . .
F2 F 0.15285(5) 0.25022(7) -0.05347(5) 0.0261(2) Uani 1 1 d . . .
S1 S 0.180050(19) 0.60244(3) 0.06420(2) 0.02454(11) Uani 1 1 d . . .
S2 S 0.32148(2) 0.53209(3) 0.20690(2) 0.02703(11) 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 C8 121.50(13) . . ?
N1 C3 C4 121.04(13) . . ?
C8 C3 C4 117.46(13) . . ?
C5 C4 C3 121.02(13) . . ?
C4 C5 C6 121.29(13) . . ?
C7 C6 C5 117.78(13) . . ?
C7 C6 C9 121.19(12) . . ?
C5 C6 C9 121.03(13) . . ?
C8 C7 C6 121.52(13) . . ?
C7 C8 C3 120.89(13) . . ?
O1 C9 N3 124.04(13) . . ?
O1 C9 C6 116.27(12) . . ?
N3 C9 C6 119.70(13) . . ?
N3 C10 N2 126.74(13) . . ?
N3 C10 S1 121.49(11) . . ?
N2 C10 S1 111.77(10) . . ?
C12 C11 N2 113.48(14) . . ?
C11 C12 S1 111.56(11) . . ?
C11 C12 S2 125.27(13) . . ?
S1 C12 S2 123.16(9) . . ?
C18 C13 C14 121.94(14) . . ?
C18 C13 S2 119.05(11) . . ?
C14 C13 S2 119.00(12) . . ?
C15 C14 C13 118.67(15) . . ?
C16 C15 C14 119.91(15) . . ?
C15 C16 C17 120.74(14) . . ?
C18 C17 C16 119.96(15) . . ?
C17 C18 C13 118.77(14) . . ?
F1 B1 F2 110.71(13) . . ?
F1 B1 O1 110.13(12) . . ?
F2 B1 O1 110.20(12) . . ?
F1 B1 N2 109.67(12) . . ?
F2 B1 N2 109.25(12) . . ?
O1 B1 N2 106.80(12) . . ?
C3 N1 C1 120.30(13) . . ?
C3 N1 C2 120.74(13) . . ?
C1 N1 C2 117.94(12) . . ?
C10 N2 C11 113.42(12) . . ?
C10 N2 B1 119.83(12) . . ?
C11 N2 B1 126.75(12) . . ?
C10 N3 C9 116.38(12) . . ?
C9 O1 B1 126.21(11) . . ?
C10 S1 C12 89.76(7) . . ?
O3 S2 O2 121.31(7) . . ?
O3 S2 C12 105.95(7) . . ?
O2 S2 C12 106.79(7) . . ?
O3 S2 C13 108.31(7) . . ?
O2 S2 C13 108.62(7) . . ?
C12 S2 C13 104.64(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 1.454(2) . ?
C2 N1 1.4557(19) . ?
C3 N1 1.3615(19) . ?
C3 C8 1.418(2) . ?
C3 C4 1.418(2) . ?
C4 C5 1.371(2) . ?
C5 C6 1.4088(19) . ?
C6 C7 1.405(2) . ?
C6 C9 1.439(2) . ?
C7 C8 1.371(2) . ?
C9 O1 1.3155(18) . ?
C9 N3 1.3335(18) . ?
C10 N3 1.3299(19) . ?
C10 N2 1.3445(19) . ?
C10 S1 1.7320(14) . ?
C11 C12 1.346(2) . ?
C11 N2 1.3756(19) . ?
C12 S1 1.7350(16) . ?
C12 S2 1.7541(14) . ?
C13 C18 1.386(2) . ?
C13 C14 1.390(2) . ?
C13 S2 1.7634(14) . ?
C14 C15 1.388(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.386(2) . ?
B1 F1 1.3746(18) . ?
B1 F2 1.3812(19) . ?
B1 O1 1.4672(19) . ?
B1 N2 1.5593(19) . ?
O2 S2 1.4359(13) . ?
O3 S2 1.4312(13) . ?
