#------------------------------------------------------------------------------
#$Date: 2023-02-20 14:32:37 +0100 (Mon 20 de Feb de 2023) $
#$Revision: 281043 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/62/7246295.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_7246295
loop_
_publ_author_name
'Taylor, Dominic'
'Malcomson, Thomas'
'Zhakeyev, Adilet'
'Rosair, Georgina M.'
'Paterson, Martin J.'
'Marques-Hueso, Jose'
'Dalgarno, Scott J.'
'Vilela, Filipe'
_publ_section_title
;
 Regioselective electrophilic aromatic borylation as a method for
 synthesising sterically hindered benzothiadiazole fluorophores
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              5826
_journal_page_last               5832
_journal_paper_doi               10.1039/D2RA08319A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C24 H16 N2 S'
_chemical_formula_sum            'C24 H16 N2 S'
_chemical_formula_weight         364.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-09-21 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.199(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4393(6)
_cell_length_b                   10.3703(5)
_cell_length_c                   17.1418(12)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.19
_cell_measurement_theta_min      5.40
_cell_volume                     1772.77(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex 4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22077
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.151
_diffrn_reflns_theta_min         5.403
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.689
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0701 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8632.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0351
_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)+(0.0367P)²+1.3907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3345
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra08319a2.cif
_cod_data_source_block           cu_8v00698_0m_a
_cod_database_code               7246295
_shelx_shelxl_version_number     2014/7
_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_max   0.751
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
S1 S 0.63133(3) 0.34349(3) 0.58338(2) 0.01604(11) Uani 1 1 d . . . . .
N1 N 0.66333(11) 0.49301(11) 0.60728(7) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.47401(12) 0.33464(11) 0.57734(7) 0.0156(2) Uani 1 1 d . . . . .
C1 C 0.54732(13) 0.54491(13) 0.61193(8) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.52749(14) 0.67689(13) 0.62941(8) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.40118(14) 0.70922(13) 0.63206(8) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.3844 0.7959 0.6441 0.020 Uiso 1 1 calc R U . . .
C4 C 0.29466(14) 0.61854(14) 0.61762(8) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.2105 0.6468 0.6219 0.020 Uiso 1 1 calc R U . . .
C5 C 0.30764(13) 0.49190(13) 0.59771(8) 0.0148(3) Uani 1 1 d . . . . .
C6 C 0.43781(13) 0.45393(13) 0.59464(8) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.63609(14) 0.77403(13) 0.64158(8) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.76209(15) 0.75343(14) 0.69739(9) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.7802 0.6749 0.7272 0.023 Uiso 1 1 calc R U . . .
C9 C 0.86112(16) 0.84691(16) 0.70969(9) 0.0236(3) Uani 1 1 d . . . . .
H9 H 0.9462 0.8323 0.7483 0.028 Uiso 1 1 calc R U . . .
C10 C 0.83690(16) 0.96165(15) 0.66610(10) 0.0252(3) Uani 1 1 d . . . . .
H10 H 0.9045 1.0259 0.6753 0.030 Uiso 1 1 calc R U . . .
C11 C 0.71278(17) 0.98160(15) 0.60894(11) 0.0285(4) Uani 1 1 d . . . . .
H11 H 0.6963 1.0589 0.5779 0.034 Uiso 1 1 calc R U . . .
C12 C 0.61282(16) 0.88899(15) 0.59705(10) 0.0237(3) Uani 1 1 d . . . . .
H12 H 0.5279 0.9039 0.5583 0.028 Uiso 1 1 calc R U . . .
C13 C 0.19264(13) 0.40003(13) 0.57830(8) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.11392(14) 0.38101(13) 0.63153(9) 0.0160(3) Uani 1 1 d . . . . .
C15 C 0.00248(14) 0.29929(14) 0.60713(9) 0.0189(3) Uani 1 1 d . . . . .
H15 H -0.0511 0.2863 0.6426 0.023 Uiso 1 1 calc R U . . .
C16 C -0.03134(14) 0.23690(15) 0.53231(9) 0.0209(3) Uani 1 1 d . . . . .
H16 H -0.1072 0.1816 0.5168 0.025 Uiso 1 1 calc R U . . .
C17 C 0.04669(14) 0.25589(15) 0.48002(9) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.0242 0.2135 0.4286 0.025 Uiso 1 1 calc R U . . .
C18 C 0.15719(14) 0.33667(14) 0.50294(9) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.2098 0.3492 0.4668 0.022 Uiso 1 1 calc R U . . .
C19 C 0.14515(14) 0.44412(14) 0.71315(9) 0.0173(3) Uani 1 1 d . . . . .
C20 C 0.27197(15) 0.43296(14) 0.77032(9) 0.0198(3) Uani 1 1 d . . . . .
H20 H 0.3392 0.3834 0.7571 0.024 Uiso 1 1 calc R U . . .
C21 C 0.30119(15) 0.49244(14) 0.84549(9) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.3881 0.4847 0.8833 0.026 Uiso 1 1 calc R U . . .
C22 C 0.20147(16) 0.56479(14) 0.86595(9) 0.0227(3) Uani 1 1 d . . . . .
H22 H 0.2203 0.6063 0.9175 0.027 Uiso 1 1 calc R U . . .
C23 C 0.07356(15) 0.57462(14) 0.80884(9) 0.0204(3) Uani 1 1 d . . . . .
H23 H 0.0055 0.6232 0.8219 0.025 Uiso 1 1 calc R U . . .
C24 C 0.04635(15) 0.51437(14) 0.73422(9) 0.0205(3) Uani 1 1 d . . . . .
H24 H -0.0409 0.5207 0.6966 0.025 Uiso 1 1 calc R U . . .
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'
N N 0.0311 0.0180 '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 S1 N2 101.59(6) . . ?
C1 N1 S1 106.04(9) . . ?
C6 N2 S1 106.17(9) . . ?
N1 C1 C2 125.64(12) . . ?
N1 C1 C6 113.41(12) . . ?
C2 C1 C6 120.93(12) . . ?
C1 C2 C7 121.83(12) . . ?
C3 C2 C1 116.13(12) . . ?
C3 C2 C7 122.02(13) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.81(13) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 118.4 . . ?
C5 C4 C3 123.12(13) . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 115.90(12) . . ?
C4 C5 C13 122.29(12) . . ?
C6 C5 C13 121.79(12) . . ?
N2 C6 C1 112.79(12) . . ?
N2 C6 C5 126.17(12) . . ?
C5 C6 C1 121.04(12) . . ?
C8 C7 C2 121.22(13) . . ?
C8 C7 C12 118.78(13) . . ?
C12 C7 C2 119.99(13) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.42(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.56(15) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.39(14) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.28(15) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.54(15) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C5 121.98(12) . . ?
C18 C13 C5 118.82(12) . . ?
C18 C13 C14 119.09(13) . . ?
C13 C14 C19 122.55(12) . . ?
C15 C14 C13 118.89(13) . . ?
C15 C14 C19 118.56(12) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.41(13) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.50(13) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.98(13) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.13(13) . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C14 121.32(13) . . ?
C24 C19 C14 119.94(13) . . ?
C24 C19 C20 118.73(14) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.29(14) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.68(14) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.98(14) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.45(14) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.86(14) . . ?
C23 C24 H24 119.6 . . ?
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
S1 N1 1.6133(12) . ?
S1 N2 1.6174(12) . ?
N1 C1 1.3490(18) . ?
N2 C6 1.3517(18) . ?
C1 C2 1.4291(19) . ?
C1 C6 1.4438(19) . ?
C2 C3 1.3743(19) . ?
C2 C7 1.4845(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.421(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(2) . ?
C5 C6 1.4306(19) . ?
C5 C13 1.4912(19) . ?
C7 C8 1.395(2) . ?
C7 C12 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.411(2) . ?
C13 C18 1.398(2) . ?
C14 C15 1.400(2) . ?
C14 C19 1.491(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(2) . ?
C19 C24 1.395(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.409(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.407(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(2) . ?
C24 H24 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -178.22(11) . . . . ?
S1 N1 C1 C6 -0.12(14) . . . . ?
S1 N2 C6 C1 -0.01(14) . . . . ?
S1 N2 C6 C5 -179.12(11) . . . . ?
N1 S1 N2 C6 -0.05(10) . . . . ?
N1 C1 C2 C3 -179.35(13) . . . . ?
N1 C1 C2 C7 2.4(2) . . . . ?
N1 C1 C6 N2 0.09(17) . . . . ?
N1 C1 C6 C5 179.25(12) . . . . ?
N2 S1 N1 C1 0.10(10) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C7 C8 -52.54(19) . . . . ?
C1 C2 C7 C12 127.83(15) . . . . ?
C2 C1 C6 N2 178.30(12) . . . . ?
C2 C1 C6 C5 -2.54(19) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C2 C7 C8 C9 -178.10(13) . . . . ?
C2 C7 C12 C11 178.83(14) . . . . ?
C3 C2 C7 C8 129.28(15) . . . . ?
C3 C2 C7 C12 -50.3(2) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C3 C4 C5 C13 -176.55(13) . . . . ?
C4 C5 C6 N2 179.24(13) . . . . ?
C4 C5 C6 C1 0.19(19) . . . . ?
C4 C5 C13 C14 -53.24(19) . . . . ?
C4 C5 C13 C18 122.94(15) . . . . ?
C5 C13 C14 C15 176.09(13) . . . . ?
C5 C13 C14 C19 -4.2(2) . . . . ?
C5 C13 C18 C17 -176.39(13) . . . . ?
C6 C1 C2 C3 2.67(19) . . . . ?
C6 C1 C2 C7 -175.61(12) . . . . ?
C6 C5 C13 C14 128.38(14) . . . . ?
C6 C5 C13 C18 -55.44(18) . . . . ?
C7 C2 C3 C4 177.65(13) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C8 C7 C12 C11 -0.8(2) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
C10 C11 C12 C7 -0.8(2) . . . . ?
C12 C7 C8 C9 1.5(2) . . . . ?
C13 C5 C6 N2 -2.3(2) . . . . ?
C13 C5 C6 C1 178.67(12) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C13 C14 C19 C20 -53.7(2) . . . . ?
C13 C14 C19 C24 127.31(15) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C14 C19 C20 C21 179.33(13) . . . . ?
C14 C19 C24 C23 -179.21(13) . . . . ?
C15 C14 C19 C20 126.02(15) . . . . ?
C15 C14 C19 C24 -53.01(19) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C13 0.1(2) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C18 C13 C14 C19 179.59(13) . . . . ?
C19 C14 C15 C16 -179.47(13) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C19 C24 C23 1.7(2) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C19 -1.0(2) . . . . ?
C24 C19 C20 C21 -1.6(2) . . . . ?
