#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033376.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_4033376
loop_
_publ_author_name
'Potopnyk, Mykhaylo A.'
'Lytvyn, Roman'
'Danyliv, Yan'
'Ceborska, Magdalena'
'Bezvikonnyi, Oleksandr'
'Volyniuk, Dmytro'
'Gražulevičius, Juozas Vidas'
_publ_section_title
;
 N,O π-Conjugated 4-Substituted 1,3-Thiazole BF₂ Complexes:
 Synthesis and Photophysical Properties.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1095
_journal_page_last               1105
_journal_paper_doi               10.1021/acs.joc.7b02239
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C16 H18 B Cl2 F2 N3 O3 S'
_chemical_formula_weight         452.10
_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_Hall  '-P 2ybc'
_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                 99.231(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0645(3)
_cell_length_b                   21.7182(8)
_cell_length_c                   12.3999(5)
_cell_measurement_reflns_used    3670
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6320
_cell_measurement_theta_min      3.6083
_cell_volume                     1877.86(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2974
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6453
_diffrn_reflns_theta_full        71.78
_diffrn_reflns_theta_max         71.78
_diffrn_reflns_theta_min         4.15
_exptl_absorpt_coefficient_mu    4.552
_exptl_absorpt_correction_T_max  0.9145
_exptl_absorpt_correction_T_min  0.4630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.037
_refine_diff_density_min         -1.826
_refine_diff_density_rms         0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      2.011
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.1373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4048
_refine_ls_wR_factor_ref         0.4125
_reflns_number_gt                3324
_reflns_number_total             3557
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo7b02239_si_003.cif
_cod_data_source_block           mpc_2017_3
_cod_depositor_comments
'Adding full bibliography for 4033375--4033378.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4033376
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
Cl1 Cl 0.6134(4) 0.08413(11) 0.51620(18) 0.0719(8) Uani 1 1 d . A 2
Cl2 Cl 0.7406(7) 0.00942(12) 0.7094(2) 0.0982(13) Uani 1 1 d . A 2
C1S C 0.671(2) 0.0828(5) 0.6636(8) 0.078(3) Uani 1 1 d . A 2
H1S1 H 0.7765 0.1122 0.6879 0.093 Uiso 1 1 calc R A 2
H1S2 H 0.5579 0.0958 0.6956 0.093 Uiso 1 1 calc R A 2
C1 C 0.3782(8) 0.7550(2) 0.4186(5) 0.0311(12) Uani 1 1 d . . .
H1A H 0.2477 0.7676 0.4259 0.047 Uiso 1 1 calc R . .
H1B H 0.4487 0.7904 0.3965 0.047 Uiso 1 1 calc R . .
H1C H 0.4438 0.7392 0.4888 0.047 Uiso 1 1 calc R . .
C2 C 0.3589(8) 0.7262(3) 0.2240(5) 0.0321(12) Uani 1 1 d . . .
H2A H 0.4593 0.7054 0.1917 0.048 Uiso 1 1 calc R . .
H2B H 0.3770 0.7708 0.2209 0.048 Uiso 1 1 calc R . .
H2C H 0.2329 0.7152 0.1831 0.048 Uiso 1 1 calc R . .
C3 C 0.3328(7) 0.6471(2) 0.3618(4) 0.0203(10) Uani 1 1 d . . .
C4 C 0.3166(7) 0.6009(2) 0.2797(4) 0.0203(10) Uani 1 1 d . . .
H4 H 0.3308 0.6118 0.2072 0.024 Uiso 1 1 calc R . .
C5 C 0.2810(7) 0.5412(2) 0.3036(4) 0.0215(10) Uani 1 1 d . . .
H5 H 0.2708 0.5111 0.2474 0.026 Uiso 1 1 calc R . .
C6 C 0.2589(6) 0.5233(2) 0.4101(4) 0.0179(10) Uani 1 1 d . . .
C7 C 0.2773(7) 0.5687(2) 0.4917(4) 0.0208(10) Uani 1 1 d . . .
H7 H 0.2652 0.5575 0.5643 0.025 Uiso 1 1 calc R . .
C8 C 0.3126(7) 0.6295(2) 0.4681(4) 0.0216(10) Uani 1 1 d . . .
H8 H 0.3233 0.6595 0.5244 0.026 Uiso 1 1 calc R . .
C9 C 0.2227(6) 0.4594(2) 0.4360(4) 0.0183(10) Uani 1 1 d . . .
C10 C 0.1459(6) 0.2810(2) 0.5344(4) 0.0205(10) Uani 1 1 d . . .
C11 C 0.1416(7) 0.2855(2) 0.6419(4) 0.0222(10) Uani 1 1 d . . .
H11 H 0.1235 0.2516 0.6874 0.027 Uiso 1 1 calc R . .
C12 C 0.1899(6) 0.3839(2) 0.5566(4) 0.0179(9) Uani 1 1 d . . .
C13 C 0.1354(7) 0.2229(2) 0.4729(5) 0.0257(11) Uani 1 1 d . . .
C14 C 0.1034(15) 0.1152(4) 0.4841(7) 0.0564(19) Uani 1 1 d DU . .
H14A H -0.0202 0.1071 0.4360 0.068 Uiso 1 1 calc R . .
H14B H 0.2073 0.1133 0.4393 0.068 Uiso 1 1 calc R . .
C15 C 0.136(3) 0.0697(8) 0.5704(14) 0.112(5) Uani 1 1 d DU . .
H15A H 0.2238 0.0864 0.6326 0.168 Uiso 1 1 calc R . .
H15B H 0.1918 0.0326 0.5434 0.168 Uiso 1 1 calc R . .
H15C H 0.0134 0.0592 0.5936 0.168 Uiso 1 1 calc R . .
B1 B 0.1762(8) 0.3536(2) 0.3611(5) 0.0204(11) Uani 1 1 d . . .
N1 N 0.3697(7) 0.7071(2) 0.3366(4) 0.0272(10) Uani 1 1 d . . .
N2 N 0.2186(6) 0.44409(18) 0.5381(3) 0.0196(9) Uani 1 1 d . . .
N3 N 0.1731(5) 0.33775(18) 0.4848(3) 0.0175(9) Uani 1 1 d . . .
O1 O 0.1956(6) 0.42079(16) 0.3531(3) 0.0246(9) Uani 1 1 d . . .
O2 O 0.1605(7) 0.21683(19) 0.3796(3) 0.0363(10) Uani 1 1 d . . .
O3 O 0.0998(9) 0.1759(2) 0.5354(4) 0.0460(12) Uani 1 1 d . . .
F1 F 0.0074(4) 0.33548(14) 0.2976(2) 0.0268(8) Uani 1 1 d . . .
F2 F 0.3334(5) 0.32764(15) 0.3243(3) 0.0303(8) Uani 1 1 d . . .
S1 S 0.17268(15) 0.35987(5) 0.68697(9) 0.0187(5) 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'
Cl Cl 0.3639 0.7018 '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
Cl2 C1S Cl1 110.6(6)
N1 C3 C8 121.6(5)
N1 C3 C4 120.3(5)
C8 C3 C4 118.1(4)
C5 C4 C3 120.9(5)
C4 C5 C6 121.3(5)
C7 C6 C5 118.0(4)
C7 C6 C9 120.7(4)
C5 C6 C9 121.3(4)
C8 C7 C6 121.1(5)
C7 C8 C3 120.6(5)
N2 C9 O1 124.7(4)
N2 C9 C6 119.0(4)
O1 C9 C6 116.4(4)
C11 C10 N3 113.3(4)
C11 C10 C13 124.9(5)
N3 C10 C13 121.7(4)
C10 C11 S1 111.9(4)
N3 C12 N2 128.0(4)
N3 C12 S1 112.8(3)
N2 C12 S1 119.2(4)
O2 C13 O3 123.1(5)
O2 C13 C10 126.1(5)
O3 C13 C10 110.8(5)
C15 C14 O3 107.8(10)
F1 B1 F2 111.2(4)
F1 B1 O1 109.1(4)
F2 B1 O1 107.1(4)
F1 B1 N3 110.4(4)
F2 B1 N3 111.6(4)
O1 B1 N3 107.4(4)
C3 N1 C2 120.5(5)
C3 N1 C1 120.6(5)
C2 N1 C1 117.5(5)
C9 N2 C12 115.8(4)
C12 N3 C10 111.8(4)
C12 N3 B1 118.2(4)
C10 N3 B1 130.0(4)
C9 O1 B1 125.7(4)
C13 O3 C14 114.9(6)
C11 S1 C12 90.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1S 1.808(10)
Cl2 C1S 1.736(12)
C1 N1 1.448(7)
C2 N1 1.447(8)
C3 N1 1.374(6)
C3 C8 1.402(7)
C3 C4 1.421(7)
C4 C5 1.362(7)
C5 C6 1.410(6)
C6 C7 1.404(7)
C6 C9 1.456(6)
C7 C8 1.384(7)
C9 N2 1.315(6)
C9 O1 1.315(6)
C10 C11 1.342(7)
C10 N3 1.405(6)
C10 C13 1.469(7)
C11 S1 1.711(5)
C12 N3 1.333(6)
C12 N2 1.348(6)
C12 S1 1.722(5)
C13 O2 1.205(7)
C13 O3 1.330(7)
C14 C15 1.447(15)
C14 O3 1.466(8)
B1 F1 1.376(6)
B1 F2 1.387(6)
B1 O1 1.470(6)
B1 N3 1.575(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327654
