#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:25:50 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226713 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/52/4035247.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_4035247
loop_
_publ_author_name
'Potopnyk, Mykhaylo A.'
'Volyniuk, Dmytro'
'Ceborska, Magdalena'
'Cmoch, Piotr'
'Hladka, Iryna'
'Danyliv, Yan'
'Gražulevičius, Juozas Vidas'
_publ_section_title
;
 Benzo[4,5]thiazolo[3,2- c][1,3,5,2]oxadiazaborinines: Synthesis,
 Structural, and Photophysical Properties.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12129
_journal_page_last               12142
_journal_paper_doi               10.1021/acs.joc.8b02098
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C16 H13 B F3 N3 O S'
_chemical_formula_weight         363.16
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.90800(10)
_cell_length_b                   7.90800(10)
_cell_length_c                   25.1636(5)
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5268
_cell_measurement_theta_min      3.5099
_cell_volume                     1573.64(4)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3004
_diffrn_reflns_point_group_measured_fraction_full 0.694
_diffrn_reflns_point_group_measured_fraction_max 0.679
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.655
_diffrn_reflns_theta_min         5.594
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.231
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_correction_T_min  0.6396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0560
_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)+(0.0522P)²+4.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.393
_reflns_Friedel_fraction_max     0.378
_reflns_number_gt                1953
_reflns_number_total             2018
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02098_si_004.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1573.64(5)
_cod_database_code               4035247
_shelx_shelxl_version_number     2018/1
_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   0.640
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
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
C2 C 0.8362(9) 1.8821(9) 0.2273(3) 0.0339(18) Uani 1 1 d . .
H2A H 0.736220 1.862197 0.248013 0.051 Uiso 1 1 calc R U
H2B H 0.866967 1.999323 0.229687 0.051 Uiso 1 1 calc R U
H2C H 0.926966 1.813611 0.240617 0.051 Uiso 1 1 calc R U
C1 C 0.8494(10) 1.9559(9) 0.1303(3) 0.0349(18) Uani 1 1 d . U
H1A H 0.935898 1.906949 0.108456 0.052 Uiso 1 1 calc R U
H1B H 0.891007 2.058244 0.146159 0.052 Uiso 1 1 calc R U
H1C H 0.752016 1.981000 0.108957 0.052 Uiso 1 1 calc R U
F3 F 0.0378(6) 0.2910(6) 0.10998(19) 0.0465(13) Uani 1 1 d D .
C15 C 0.1120(9) 0.4520(9) 0.1063(3) 0.0312(16) Uani 1 1 d D .
C3 C 0.7310(8) 1.6872(8) 0.1596(3) 0.0218(13) Uani 1 1 d . .
C4 C 0.6942(8) 1.5676(7) 0.1998(3) 0.0232(13) Uani 1 1 d . .
H4 H 0.724582 1.591669 0.234734 0.028 Uiso 1 1 calc R U
C5 C 0.6152(8) 1.4176(8) 0.1888(3) 0.0223(14) Uani 1 1 d . .
H5 H 0.590325 1.343140 0.216371 0.027 Uiso 1 1 calc R U
C6 C 0.5713(8) 1.3747(8) 0.1364(3) 0.0209(14) Uani 1 1 d . U
C7 C 0.6113(8) 1.4921(8) 0.0951(3) 0.0233(14) Uani 1 1 d . .
H7 H 0.584053 1.466072 0.060130 0.028 Uiso 1 1 calc R U
C8 C 0.6885(8) 1.6412(9) 0.1063(3) 0.0268(15) Uani 1 1 d . .
H8 H 0.714212 1.715014 0.078732 0.032 Uiso 1 1 calc R U
C9 C 0.4861(7) 1.2179(8) 0.1249(3) 0.0193(13) Uani 1 1 d . .
C10 C 0.3655(8) 0.9690(8) 0.1493(3) 0.0208(13) Uani 1 1 d . U
C11 C 0.2293(9) 0.6872(9) 0.1474(3) 0.0262(15) Uani 1 1 d . U
C12 C 0.2579(7) 0.7593(8) 0.0973(3) 0.0206(13) Uani 1 1 d . .
C13 C 0.2122(8) 0.6704(9) 0.0509(3) 0.0275(15) Uani 1 1 d . .
H13 H 0.233084 0.716037 0.017485 0.033 Uiso 1 1 calc R U
C14 C 0.1369(9) 0.5160(10) 0.0560(3) 0.0297(16) Uani 1 1 d . .
H14 H 0.103017 0.455388 0.026210 0.036 Uiso 1 1 calc R U
C16 C 0.1533(9) 0.5287(9) 0.1529(3) 0.0268(15) Uani 1 1 d . .
H16 H 0.132587 0.479435 0.185842 0.032 Uiso 1 1 calc R U
B1 B 0.3951(10) 1.0254(10) 0.0517(3) 0.0247(16) Uani 1 1 d . .
N1 N 0.8031(8) 1.8382(7) 0.1715(3) 0.0325(15) Uani 1 1 d . .
N2 N 0.4421(7) 1.1136(7) 0.1638(2) 0.0215(12) Uani 1 1 d . .
N3 N 0.3375(6) 0.9168(7) 0.0998(2) 0.0196(11) Uani 1 1 d . .
O1 O 0.4596(6) 1.1845(6) 0.07368(18) 0.0268(11) Uani 1 1 d . .
F1 F 0.5262(5) 0.9405(5) 0.02618(15) 0.0285(9) Uani 1 1 d . .
F2 F 0.2657(5) 1.0540(5) 0.01724(17) 0.0349(10) Uani 1 1 d . .
S1 S 0.2982(2) 0.8248(2) 0.19733(6) 0.0246(4) 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'
Br Br -0.6763 1.2805 '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
C16 C15 C14 126.4(6)
C16 C15 F3 116.5(6)
C14 C15 F3 117.0(6)
N1 C3 C4 121.0(7)
N1 C3 C8 122.1(6)
C4 C3 C8 116.9(6)
C5 C4 C3 121.8(6)
C4 C5 C6 120.7(6)
C5 C6 C7 118.1(6)
C5 C6 C9 120.8(6)
C7 C6 C9 121.2(6)
C8 C7 C6 120.9(6)
C7 C8 C3 121.5(6)
N2 C9 O1 123.4(6)
N2 C9 C6 120.6(6)
O1 C9 C6 116.0(6)
N3 C10 N2 126.3(6)
N3 C10 S1 113.3(5)
N2 C10 S1 120.4(5)
C16 C11 C12 121.6(6)
C16 C11 S1 128.4(6)
C12 C11 S1 110.0(5)
N3 C12 C11 113.3(6)
N3 C12 C13 126.6(6)
C11 C12 C13 120.0(6)
C14 C13 C12 118.7(7)
C13 C14 C15 118.6(7)
C15 C16 C11 114.7(6)
F2 B1 F1 110.2(6)
F2 B1 O1 111.1(6)
F1 B1 O1 109.2(6)
F2 B1 N3 111.6(6)
F1 B1 N3 108.2(6)
O1 B1 N3 106.5(5)
C3 N1 C1 121.0(6)
C3 N1 C2 119.7(6)
C1 N1 C2 119.3(6)
C9 N2 C10 116.5(6)
C10 N3 C12 113.1(6)
C10 N3 B1 120.6(5)
C12 N3 B1 126.2(5)
C9 O1 B1 126.1(6)
C10 S1 C11 90.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N1 1.469(9)
C1 N1 1.440(9)
F3 C15 1.405(7)
C15 C16 1.361(10)
C15 C14 1.376(10)
C3 N1 1.358(9)
C3 C4 1.417(9)
C3 C8 1.428(10)
C4 C5 1.369(8)
C5 C6 1.407(9)
C6 C7 1.428(9)
C6 C9 1.440(9)
C7 C8 1.357(9)
C9 N2 1.327(8)
C9 O1 1.331(8)
C10 N3 1.331(8)
C10 N2 1.345(8)
C10 S1 1.745(7)
C11 C16 1.397(10)
C11 C12 1.402(9)
C11 S1 1.749(8)
C12 N3 1.397(8)
C12 C13 1.410(9)
C13 C14 1.365(10)
B1 F2 1.361(8)
B1 F1 1.393(9)
B1 O1 1.466(9)
B1 N3 1.551(9)
