#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038285.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_4038285
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            'C12 H11 B F2 I N3 O S'
_chemical_formula_weight         421.01
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.888(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7049(5)
_cell_length_b                   12.0661(5)
_cell_length_c                   7.7020(3)
_cell_measurement_reflns_used    2972
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5050
_cell_measurement_theta_min      3.1290
_cell_volume                     1454.20(10)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6716
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.075
_diffrn_reflns_theta_min         2.603
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39319
_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    1.923
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.492
_refine_diff_density_min         -1.617
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0719P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3102
_reflns_number_total             3707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00552_si_002.cif
_cod_data_source_block           2c
_cod_depositor_comments
'Adding full bibliography for 4038285--4038289.cif.'
_cod_original_cell_volume        1454.19(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038285
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.631
_oxdiff_exptl_absorpt_empirical_full_max 2.174
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_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
I1 I 1.06162(2) 0.14491(2) 0.69472(3) 0.02379(12) Uani 1 1 d . . . . .
S1 S 0.86601(7) 0.13657(8) 0.49850(14) 0.0216(2) Uani 1 1 d . . . . .
F1 F 0.85321(15) 0.5259(2) 0.3551(3) 0.0282(5) Uani 1 1 d . . . . .
F2 F 0.80133(14) 0.5146(2) 0.6198(3) 0.0260(5) Uani 1 1 d . . . . .
O1 O 0.72033(18) 0.4410(2) 0.3802(4) 0.0244(6) Uani 1 1 d . . . . .
N1 N 0.3498(2) 0.3371(3) 0.0223(5) 0.0272(8) Uani 1 1 d . . . . .
N2 N 0.7296(2) 0.2487(3) 0.3614(4) 0.0219(7) Uani 1 1 d . . . . .
N3 N 0.8505(2) 0.3469(3) 0.4930(5) 0.0212(7) Uani 1 1 d . . . . .
C1 C 0.2957(3) 0.4351(4) 0.0244(6) 0.0286(9) Uani 1 1 d . . . . .
H1A H 0.2432 0.4219 -0.0458 0.043 Uiso 1 1 calc R U . . .
H1B H 0.3247 0.4971 -0.0216 0.043 Uiso 1 1 calc R U . . .
H1C H 0.2836 0.4507 0.1419 0.043 Uiso 1 1 calc R U . . .
C2 C 0.3081(3) 0.2312(4) -0.0224(6) 0.0334(10) Uani 1 1 d . . . . .
H2A H 0.3397 0.1925 -0.1047 0.050 Uiso 1 1 calc R U . . .
H2B H 0.2510 0.2445 -0.0727 0.050 Uiso 1 1 calc R U . . .
H2C H 0.3062 0.1872 0.0810 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4315(3) 0.3391(3) 0.0985(6) 0.0219(8) Uani 1 1 d . . . . .
C4 C 0.4673(3) 0.4370(3) 0.1748(5) 0.0248(8) Uani 1 1 d . . . . .
H4 H 0.4344 0.5011 0.1749 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5502(2) 0.4386(3) 0.2488(5) 0.0238(8) Uani 1 1 d . . . . .
H5 H 0.5729 0.5043 0.2958 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6009(3) 0.3431(3) 0.2548(5) 0.0202(8) Uani 1 1 d . . . . .
C7 C 0.5657(2) 0.2454(4) 0.1790(5) 0.0221(8) Uani 1 1 d . . . . .
H7 H 0.5988 0.1814 0.1801 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4835(3) 0.2430(3) 0.1037(5) 0.0218(8) Uani 1 1 d . . . . .
H8 H 0.4615 0.1773 0.0554 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6882(3) 0.3434(3) 0.3347(5) 0.0202(8) Uani 1 1 d . . . . .
C10 C 0.8080(2) 0.2550(3) 0.4428(5) 0.0196(8) Uani 1 1 d . . . . .
C11 C 0.9313(3) 0.3262(3) 0.5738(5) 0.0220(8) Uani 1 1 d . . . . .
H11 H 0.9688 0.3820 0.6140 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9503(2) 0.2164(3) 0.5886(5) 0.0217(8) Uani 1 1 d . . . . .
B1 B 0.8073(3) 0.4621(4) 0.4616(6) 0.0230(9) 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'
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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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
C10 S1 C12 90.49(19) . . ?
C9 O1 B1 125.9(3) . . ?
C3 N1 C1 120.6(4) . . ?
C3 N1 C2 120.1(4) . . ?
C1 N1 C2 117.4(4) . . ?
C9 N2 C10 116.5(3) . . ?
C10 N3 C11 113.4(3) . . ?
C10 N3 B1 119.8(4) . . ?
C11 N3 B1 126.8(3) . . ?
N1 C3 C4 121.3(4) . . ?
N1 C3 C8 121.1(4) . . ?
C4 C3 C8 117.6(4) . . ?
C5 C4 C3 120.8(4) . . ?
C4 C5 C6 121.2(4) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 C9 121.7(4) . . ?
C7 C6 C9 120.0(4) . . ?
C8 C7 C6 121.0(4) . . ?
C7 C8 C3 121.0(4) . . ?
O1 C9 N2 124.0(4) . . ?
O1 C9 C6 116.1(3) . . ?
N2 C9 C6 119.9(4) . . ?
N3 C10 N2 127.0(4) . . ?
N3 C10 S1 112.0(3) . . ?
N2 C10 S1 121.0(3) . . ?
C12 C11 N3 113.5(4) . . ?
C11 C12 S1 110.6(3) . . ?
C11 C12 I1 128.0(3) . . ?
S1 C12 I1 121.3(2) . . ?
F1 B1 F2 110.3(4) . . ?
F1 B1 O1 110.9(3) . . ?
F2 B1 O1 108.8(3) . . ?
F1 B1 N3 110.5(3) . . ?
F2 B1 N3 109.5(3) . . ?
O1 B1 N3 106.7(3) . . ?
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
I1 C12 2.055(4) . ?
S1 C10 1.729(4) . ?
S1 C12 1.734(4) . ?
F1 B1 1.373(5) . ?
F2 B1 1.384(5) . ?
O1 C9 1.318(5) . ?
O1 B1 1.476(5) . ?
N1 C3 1.364(6) . ?
N1 C1 1.456(6) . ?
N1 C2 1.464(6) . ?
N2 C9 1.322(5) . ?
N2 C10 1.335(5) . ?
N3 C10 1.334(5) . ?
N3 C11 1.388(5) . ?
N3 B1 1.556(6) . ?
C3 C4 1.415(6) . ?
C3 C8 1.418(6) . ?
C4 C5 1.376(5) . ?
C5 C6 1.399(6) . ?
C6 C7 1.408(6) . ?
C6 C9 1.454(6) . ?
C7 C8 1.370(5) . ?
C11 C12 1.360(6) . ?
