#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/78/7227882.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_7227882
loop_
_publ_author_name
'Abdel-Mohsen, H. T.'
'Conrad, J.'
'Harms, K.'
'Nohr, D.'
'Beifuss, U.'
_publ_section_title
;
 Laccase-catalyzed green synthesis and cytotoxic activity of novel
 pyrimidobenzothiazoles and catechol thioethers
;
_journal_issue                   28
_journal_name_full               'RSC Adv.'
_journal_page_first              17427
_journal_paper_doi               10.1039/C6RA28102H
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C11 H5 F3 N2 O3 S'
_chemical_formula_sum            'C11 H5 F3 N2 O3 S'
_chemical_formula_weight         302.23
_chemical_name_common            HAMH205
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-03 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.862(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5438(4)
_cell_length_b                   13.1859(7)
_cell_length_c                   12.5014(7)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.2028
_cell_measurement_theta_min      2.2476
_cell_volume                     1076.24(11)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.294
_diffrn_reflns_theta_min         2.248
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' '
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0280
_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)+(0.0305P)²+1.1028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1760
_reflns_number_total             1953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra28102h2.cif
_cod_data_source_block           HAMH205_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7227882
_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_min   0.871
_shelx_estimated_absorpt_t_max   0.986
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
F1 F 0.78608(16) 0.65192(8) 0.86814(9) 0.0199(3) Uani 1 1 d . .
O1 O 0.23096(17) 0.53534(9) 0.60531(9) 0.0111(3) Uani 1 1 d . .
C1 C 0.3956(2) 0.50284(12) 0.64513(13) 0.0091(3) Uani 1 1 d . .
C2 C 0.5208(3) 0.54876(13) 0.72984(13) 0.0103(4) Uani 1 1 d . .
H2 H 0.4753 0.6085 0.7634 0.012 Uiso 1 1 calc R U
F2 F 0.79903(18) 0.50637(9) 0.94638(8) 0.0260(3) Uani 1 1 d . .
F3 F 1.03202(15) 0.54882(8) 0.84132(8) 0.0171(2) Uani 1 1 d . .
C3 C 0.7034(3) 0.50762(13) 0.76242(13) 0.0099(3) Uani 1 1 d . .
N4 N 0.7843(2) 0.42160(11) 0.72207(11) 0.0101(3) Uani 1 1 d . .
C5 C 0.6681(2) 0.37833(12) 0.64534(13) 0.0088(3) Uani 1 1 d . .
S6 S 0.74119(6) 0.26897(3) 0.58172(3) 0.01109(13) Uani 1 1 d . .
C7 C 0.5157(3) 0.27104(13) 0.49852(13) 0.0096(3) Uani 1 1 d . .
C8 C 0.4574(3) 0.20102(13) 0.41909(13) 0.0108(3) Uani 1 1 d . .
H8 H 0.5471 0.1478 0.4016 0.013 Uiso 1 1 calc R U
O9 O 0.2100(2) 0.14335(9) 0.28729(10) 0.0134(3) Uani 1 1 d . .
H9 H 0.086(4) 0.1426(17) 0.2747(18) 0.024(6) Uiso 1 1 d . .
C9 C 0.2659(3) 0.21057(13) 0.36611(13) 0.0099(3) Uani 1 1 d . .
O10 O -0.05252(18) 0.29090(10) 0.33795(10) 0.0123(3) Uani 1 1 d . .
H10 H -0.114(4) 0.3434(19) 0.3529(19) 0.029(6) Uiso 1 1 d . .
C10 C 0.1337(3) 0.28956(13) 0.39319(13) 0.0093(3) Uani 1 1 d . .
C11 C 0.1931(3) 0.36061(12) 0.47093(13) 0.0088(3) Uani 1 1 d . .
H11 H 0.1044 0.4143 0.4882 0.011 Uiso 1 1 calc R U
C12 C 0.3873(3) 0.35064(12) 0.52288(13) 0.0085(3) Uani 1 1 d . .
N13 N 0.4795(2) 0.41299(10) 0.60534(11) 0.0077(3) Uani 1 1 d . .
C14 C 0.8325(3) 0.55413(14) 0.85443(14) 0.0131(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 0.0033 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N13 120.01(15)
O1 C1 C2 126.41(15)
N13 C1 C2 113.56(14)
C3 C2 C1 120.32(16)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 N4 125.51(16)
C2 C3 C14 120.33(15)
N4 C3 C14 114.10(15)
C5 N4 C3 114.31(14)
N4 C5 N13 125.52(15)
N4 C5 S6 122.25(13)
N13 C5 S6 112.23(12)
C5 S6 C7 90.69(8)
C8 C7 C12 121.11(16)
C8 C7 S6 126.51(13)
C12 C7 S6 112.32(13)
C9 C8 C7 118.55(15)
C9 C8 H8 120.7
C7 C8 H8 120.7
C9 O9 H9 111.3(16)
O9 C9 C8 118.66(15)
O9 C9 C10 121.12(15)
C8 C9 C10 120.21(15)
C10 O10 H10 109.1(17)
O10 C10 C11 123.16(15)
O10 C10 C9 115.54(15)
C11 C10 C9 121.30(15)
C10 C11 C12 117.83(15)
C10 C11 H11 121.1
C12 C11 H11 121.1
C7 C12 C11 120.95(15)
C7 C12 N13 111.24(14)
C11 C12 N13 127.78(15)
C5 N13 C1 120.74(14)
C5 N13 C12 113.42(14)
C1 N13 C12 125.83(14)
F3 C14 F1 107.47(14)
F3 C14 F2 107.43(14)
F1 C14 F2 106.91(14)
F3 C14 C3 112.87(14)
F1 C14 C3 111.61(14)
F2 C14 C3 110.27(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.338(2)
O1 C1 1.233(2)
C1 N13 1.411(2)
C1 C2 1.429(2)
C2 C3 1.350(2)
C2 H2 0.9500
F2 C14 1.342(2)
F3 C14 1.328(2)
C3 N4 1.363(2)
C3 C14 1.511(2)
N4 C5 1.314(2)
C5 N13 1.378(2)
C5 S6 1.7298(17)
S6 C7 1.7473(17)
C7 C8 1.390(2)
C7 C12 1.391(2)
C8 C9 1.383(2)
C8 H8 0.9500
O9 C9 1.357(2)
O9 H9 0.82(2)
C9 C10 1.410(2)
O10 C10 1.359(2)
O10 H10 0.83(3)
C10 C11 1.387(2)
C11 C12 1.394(2)
C11 H11 0.9500
C12 N13 1.421(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 N4 0.82(2) 2.21(2) 2.9755(19) 157(2) 4_465
O10 H10 O1 0.83(3) 1.86(3) 2.6884(17) 175(2) 3_566
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
O1 C1 C2 C3 -176.67(16)
N13 C1 C2 C3 1.9(2)
C1 C2 C3 N4 -1.0(3)
C1 C2 C3 C14 -177.95(15)
C2 C3 N4 C5 0.0(2)
C14 C3 N4 C5 177.04(14)
C3 N4 C5 N13 0.1(2)
C3 N4 C5 S6 179.43(12)
N4 C5 S6 C7 -178.61(14)
N13 C5 S6 C7 0.83(13)
C5 S6 C7 C8 -179.59(16)
C5 S6 C7 C12 -2.47(13)
C12 C7 C8 C9 -1.6(2)
S6 C7 C8 C9 175.34(13)
C7 C8 C9 O9 178.89(15)
C7 C8 C9 C10 -0.4(2)
O9 C9 C10 O10 2.1(2)
C8 C9 C10 O10 -178.64(15)
O9 C9 C10 C11 -177.59(15)
C8 C9 C10 C11 1.6(2)
O10 C10 C11 C12 179.35(15)
C9 C10 C11 C12 -1.0(2)
C8 C7 C12 C11 2.3(2)
S6 C7 C12 C11 -175.04(13)
C8 C7 C12 N13 -179.27(15)
S6 C7 C12 N13 3.43(17)
C10 C11 C12 C7 -1.0(2)
C10 C11 C12 N13 -179.15(15)
N4 C5 N13 C1 1.0(2)
S6 C5 N13 C1 -178.42(11)
N4 C5 N13 C12 -179.61(15)
S6 C5 N13 C12 0.97(17)
O1 C1 N13 C5 176.78(15)
C2 C1 N13 C5 -1.9(2)
O1 C1 N13 C12 -2.5(2)
C2 C1 N13 C12 178.79(14)
C7 C12 N13 C5 -2.84(19)
C11 C12 N13 C5 175.50(16)
C7 C12 N13 C1 176.51(14)
C11 C12 N13 C1 -5.1(3)
C2 C3 C14 F3 -144.19(16)
N4 C3 C14 F3 38.6(2)
C2 C3 C14 F1 -23.0(2)
N4 C3 C14 F1 159.73(14)
C2 C3 C14 F2 95.66(19)
N4 C3 C14 F2 -81.60(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203361
