#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/84/2018494.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018494
loop_
_publ_author_name
'Urdaneta, Neudo'
'Nuñez, Jesús'
'González, Teresa'
'Briceño, Alexander'
_publ_section_title
;
 1-[5-(4,5-Dimethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]ethanone and
 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
;
_journal_coeditor_code           FG3242
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o213
_journal_page_last               o215
_journal_paper_doi               10.1107/S0108270112018598
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H13 B O3 S'
_chemical_formula_moiety         'C10 H13 B O3 S'
_chemical_formula_sum            'C10 H13 B O3 S'
_chemical_formula_weight         224.07
_chemical_name_systematic
;
1-[5-(4,5-Dimethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]ethanone
;
_space_group_IT_number           14
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.390(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.038(3)
_cell_length_b                   10.286(4)
_cell_length_c                   20.096(8)
_cell_measurement_reflns_used    836
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      1.97
_cell_volume                     1214.2(9)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution
;
CrystalStructure (Rigaku/MSC, 2005) and SHELXTL  (Sheldrick,
2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku AFC-7S Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13808
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0638
_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)+(0.0619P)²+0.3633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                1479
_reflns_number_total             2365
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3242.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018494
_cod_database_fobs_code          2018494
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 -0.08116(13) -0.06102(8) 0.41076(4) 0.0722(3) Uani d . 1 1
O O1 -0.2449(4) 0.2032(3) 0.33680(13) 0.0985(9) Uani d . 1 1
O O2 0.1025(4) 0.2696(2) 0.32444(14) 0.0980(8) Uani d . 1 1
O O3 -0.0798(5) -0.3107(3) 0.48410(19) 0.1243(11) Uani d . 1 1
B B1 -0.0174(7) 0.1781(4) 0.3488(2) 0.0738(10) Uani d . 1 1
C C1 -0.0545(8) 0.3691(4) 0.2914(2) 0.1065(14) Uani d . 1 1
H H1 -0.0580 0.3696 0.2424 0.128 Uiso calc R 1 1
C C2 -0.2886(8) 0.3259(5) 0.3013(2) 0.1107(15) Uani d . 1 1
H H2 -0.3437 0.3890 0.3303 0.133 Uiso calc R 1 1
C C3 0.0868(5) 0.0540(3) 0.38535(15) 0.0630(8) Uani d . 1 1
C C4 0.3103(5) 0.0150(3) 0.40285(16) 0.0702(9) Uani d . 1 1
H H4 0.4287 0.0644 0.3936 0.084 Uiso calc R 1 1
C C5 0.3439(5) -0.1055(3) 0.43578(16) 0.0675(8) Uani d . 1 1
H H5 0.4856 -0.1448 0.4502 0.081 Uiso calc R 1 1
C C6 0.1463(5) -0.1590(3) 0.44453(15) 0.0625(8) Uani d . 1 1
C C7 0.1096(7) -0.2809(3) 0.4785(2) 0.0847(11) Uani d . 1 1
C C8 0.3125(7) -0.3645(4) 0.5073(2) 0.1080(14) Uani d . 1 1
H H8A 0.2626 -0.4502 0.5158 0.162 Uiso calc R 1 1
H H8B 0.3975 -0.3274 0.5493 0.162 Uiso calc R 1 1
H H8C 0.4074 -0.3695 0.4751 0.162 Uiso calc R 1 1
C C9 -0.4652(8) 0.3080(7) 0.2357(3) 0.170(3) Uani d . 1 1
H H9A -0.5990 0.2692 0.2453 0.255 Uiso calc R 1 1
H H9B -0.4059 0.2523 0.2056 0.255 Uiso calc R 1 1
H H9C -0.5035 0.3909 0.2142 0.255 Uiso calc R 1 1
C C10 0.0263(12) 0.4987(5) 0.3210(4) 0.187(3) Uani d . 1 1
H H10A 0.1768 0.5148 0.3147 0.280 Uiso calc R 1 1
H H10B 0.0290 0.4994 0.3689 0.280 Uiso calc R 1 1
H H10C -0.0750 0.5652 0.2983 0.280 Uiso calc R 1 1
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 S1 C6 92.80(15)
B1 O1 C2 108.4(3)
B1 O2 C1 108.1(3)
O2 B1 O1 114.0(3)
O2 B1 C3 124.1(3)
O1 B1 C3 121.9(3)
O2 C1 C10 109.3(4)
O2 C1 C2 105.1(3)
C10 C1 C2 115.6(5)
O2 C1 H1 108.9
C10 C1 H1 108.9
C2 C1 H1 108.9
O1 C2 C9 109.8(4)
O1 C2 C1 104.3(3)
C9 C2 C1 114.1(4)
O1 C2 H2 109.5
C9 C2 H2 109.5
C1 C2 H2 109.5
C4 C3 B1 129.5(3)
C4 C3 S1 109.7(2)
B1 C3 S1 120.8(2)
C3 C4 C5 114.0(3)
C3 C4 H4 123.0
C5 C4 H4 123.0
C6 C5 C4 112.6(3)
C6 C5 H5 123.7
C4 C5 H5 123.7
C5 C6 C7 129.5(3)
C5 C6 S1 110.9(2)
C7 C6 S1 119.6(2)
O3 C7 C6 120.3(4)
O3 C7 C8 121.5(3)
C6 C7 C8 118.1(3)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 C9 H9A 109.5
C2 C9 H9B 109.5
H9A C9 H9B 109.5
C2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 C10 H10A 109.5
C1 C10 H10B 109.5
H10A C10 H10B 109.5
C1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.711(3)
S1 C6 1.712(3)
O1 B1 1.363(4)
O1 C2 1.443(4)
O2 B1 1.347(5)
O2 C1 1.447(4)
O3 C7 1.214(4)
B1 C3 1.533(5)
C1 C10 1.495(7)
C1 C2 1.538(6)
C1 H1 0.9800
C2 C9 1.503(6)
C2 H2 0.9800
C3 C4 1.373(4)
C4 C5 1.397(4)
C4 H4 0.9300
C5 C6 1.362(4)
C5 H5 0.9300
C6 C7 1.469(5)
C7 C8 1.499(5)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 O2 B1 O1 -0.5(5)
C1 O2 B1 C3 178.0(3)
C2 O1 B1 O2 -1.0(5)
C2 O1 B1 C3 -179.5(3)
B1 O2 C1 C10 126.2(4)
B1 O2 C1 C2 1.6(5)
B1 O1 C2 C9 124.6(4)
B1 O1 C2 C1 1.9(5)
O2 C1 C2 O1 -2.1(5)
C10 C1 C2 O1 -122.6(5)
O2 C1 C2 C9 -121.9(4)
C10 C1 C2 C9 117.6(5)
O2 B1 C3 C4 3.3(6)
O1 B1 C3 C4 -178.3(3)
O2 B1 C3 S1 -176.6(3)
O1 B1 C3 S1 1.7(5)
C6 S1 C3 C4 0.2(2)
C6 S1 C3 B1 -179.8(3)
B1 C3 C4 C5 -179.7(3)
S1 C3 C4 C5 0.2(4)
C3 C4 C5 C6 -0.8(4)
C4 C5 C6 C7 -177.6(3)
C4 C5 C6 S1 0.9(4)
C3 S1 C6 C5 -0.7(3)
C3 S1 C6 C7 178.0(3)
C5 C6 C7 O3 176.8(4)
S1 C6 C7 O3 -1.7(5)
C5 C6 C7 C8 -1.8(6)
S1 C6 C7 C8 179.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061324
