#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/61/4506180.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_4506180
loop_
_publ_author_name
'Terada, Sho'
'Katagiri, Kosuke'
'Masu, Hyuma'
'Danjo, Hiroshi'
'Sei, Yoshihisa'
'Kawahata, Masatoshi'
'Tominaga, Masahide'
'Yamaguchi, Kentaro'
'Azumaya, Isao'
_publ_section_title
;
 Polymorphism of Aromatic Sulfonamides with Fluorine Groups
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2908
_journal_paper_doi               10.1021/cg300098q
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C18 H14 F N O3 S'
_chemical_formula_weight         343.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.139(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4890(19)
_cell_length_b                   12.364(3)
_cell_length_c                   13.425(3)
_cell_measurement_reflns_used    3401
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.88
_cell_measurement_theta_min      2.24
_cell_volume                     1574.7(6)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7457
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.23
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9549
_exptl_absorpt_correction_T_min  0.9335
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.7406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                2675
_reflns_number_total             3126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300098q_si_001.cif
_cod_data_source_block           compound3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1574.8(5)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4506180
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.10221(4) 0.83795(3) 0.47548(3) 0.01937(12) Uani 1 1 d .
O3 O 0.07102(11) 1.06203(9) 0.22896(8) 0.0235(3) Uani 1 1 d .
O1 O -0.00209(12) 0.88383(9) 0.53910(8) 0.0255(3) Uani 1 1 d .
O2 O 0.09675(12) 0.72546(9) 0.45216(8) 0.0254(3) Uani 1 1 d .
N1 N 0.08731(14) 0.90750(11) 0.37276(9) 0.0214(3) Uani 1 1 d .
H1 H 0.0240 0.9595 0.3712 0.026 Uiso 1 1 calc R
F1 F 0.45244(13) 1.08272(10) 0.65435(9) 0.0492(3) Uani 1 1 d .
C1 C 0.27019(16) 0.86526(13) 0.52902(11) 0.0215(3) Uani 1 1 d .
C13 C -0.07115(16) 1.05699(13) 0.19998(11) 0.0218(3) Uani 1 1 d .
C11 C 0.32811(16) 0.79646(14) 0.18032(12) 0.0242(3) Uani 1 1 d .
H11 H 0.3872 0.7358 0.1691 0.029 Uiso 1 1 calc R
C12 C 0.25346(16) 0.80302(13) 0.26826(12) 0.0217(3) Uani 1 1 d .
H12 H 0.2614 0.7471 0.3165 0.026 Uiso 1 1 calc R
C16 C -0.35553(18) 1.06112(16) 0.14880(13) 0.0315(4) Uani 1 1 d .
H16 H -0.4532 1.0625 0.1318 0.038 Uiso 1 1 calc R
C2 C 0.29456(18) 0.96686(14) 0.57106(12) 0.0267(4) Uani 1 1 d .
H2 H 0.2242 1.0215 0.5698 0.032 Uiso 1 1 calc R
C7 C 0.16706(15) 0.89195(12) 0.28524(11) 0.0190(3) Uani 1 1 d .
C14 C -0.14213(19) 1.15512(14) 0.19741(13) 0.0292(4) Uani 1 1 d .
H14 H -0.0940 1.2206 0.2128 0.035 Uiso 1 1 calc R
C3 C 0.4251(2) 0.98435(15) 0.61435(13) 0.0335(4) Uani 1 1 d .
C10 C 0.31768(17) 0.87697(14) 0.10880(12) 0.0270(4) Uani 1 1 d .
H10 H 0.3704 0.8722 0.0495 0.032 Uiso 1 1 calc R
C8 C 0.15487(16) 0.97126(12) 0.21148(12) 0.0206(3) Uani 1 1 d .
C17 C -0.28250(18) 0.96414(15) 0.15072(13) 0.0297(4) Uani 1 1 d .
H17 H -0.3303 0.8989 0.1340 0.036 Uiso 1 1 calc R
C9 C 0.22954(17) 0.96479(14) 0.12451(12) 0.0265(4) Uani 1 1 d .
H9 H 0.2207 1.0201 0.0757 0.032 Uiso 1 1 calc R
C15 C -0.2846(2) 1.15605(15) 0.17198(13) 0.0334(4) Uani 1 1 d .
H15 H -0.3342 1.2228 0.1704 0.040 Uiso 1 1 calc R
C18 C -0.13980(17) 0.96107(13) 0.17692(12) 0.0257(4) Uani 1 1 d .
H18 H -0.0903 0.8943 0.1789 0.031 Uiso 1 1 calc R
C6 C 0.37252(18) 0.78584(15) 0.52956(13) 0.0298(4) Uani 1 1 d .
H6 H 0.3543 0.7174 0.4997 0.036 Uiso 1 1 calc R
C4 C 0.5294(2) 0.90718(17) 0.61805(14) 0.0385(5) Uani 1 1 d .
H4 H 0.6177 0.9219 0.6498 0.046 Uiso 1 1 calc R
C5 C 0.5030(2) 0.80778(17) 0.57461(15) 0.0388(5) Uani 1 1 d .
H5 H 0.5744 0.7539 0.5754 0.047 Uiso 1 1 calc R
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
O2 S1 O1 119.54(7)
O2 S1 N1 109.07(7)
O1 S1 N1 104.22(7)
O2 S1 C1 107.70(7)
O1 S1 C1 108.00(7)
N1 S1 C1 107.80(7)
C13 O3 C8 117.82(12)
C7 N1 S1 126.09(11)
C7 N1 H1 117.0
S1 N1 H1 117.0
C6 C1 C2 121.84(15)
C6 C1 S1 119.63(13)
C2 C1 S1 118.52(13)
C18 C13 C14 121.14(15)
C18 C13 O3 123.18(14)
C14 C13 O3 115.67(14)
C10 C11 C12 121.04(15)
C10 C11 H11 119.5
C12 C11 H11 119.5
C11 C12 C7 119.75(15)
C11 C12 H12 120.1
C7 C12 H12 120.1
C17 C16 C15 119.24(16)
C17 C16 H16 120.4
C15 C16 H16 120.4
C3 C2 C1 116.97(16)
C3 C2 H2 121.5
C1 C2 H2 121.5
C12 C7 C8 118.61(14)
C12 C7 N1 124.47(14)
C8 C7 N1 116.91(13)
C15 C14 C13 118.90(16)
C15 C14 H14 120.6
C13 C14 H14 120.6
F1 C3 C4 118.51(16)
F1 C3 C2 118.26(17)
C4 C3 C2 123.22(17)
C11 C10 C9 119.43(15)
C11 C10 H10 120.3
C9 C10 H10 120.3
C9 C8 C7 121.49(14)
C9 C8 O3 119.47(14)
C7 C8 O3 118.94(14)
C16 C17 C18 120.79(17)
C16 C17 H17 119.6
C18 C17 H17 119.6
C8 C9 C10 119.64(15)
C8 C9 H9 120.2
C10 C9 H9 120.2
C16 C15 C14 121.00(16)
C16 C15 H15 119.5
C14 C15 H15 119.5
C13 C18 C17 118.93(16)
C13 C18 H18 120.5
C17 C18 H18 120.5
C1 C6 C5 118.83(17)
C1 C6 H6 120.6
C5 C6 H6 120.6
C3 C4 C5 118.55(17)
C3 C4 H4 120.7
C5 C4 H4 120.7
C4 C5 C6 120.57(18)
C4 C5 H5 119.7
C6 C5 H5 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4263(12)
S1 O1 1.4369(11)
S1 N1 1.6289(13)
S1 C1 1.7680(16)
O3 C13 1.3979(19)
O3 C8 1.3982(18)
N1 C7 1.4233(19)
N1 H1 0.8800
F1 C3 1.353(2)
C1 C6 1.381(2)
C1 C2 1.395(2)
C13 C18 1.385(2)
C13 C14 1.388(2)
C11 C10 1.385(2)
C11 C12 1.391(2)
C11 H11 0.9500
C12 C7 1.393(2)
C12 H12 0.9500
C16 C17 1.385(3)
C16 C15 1.386(3)
C16 H16 0.9500
C2 C3 1.375(2)
C2 H2 0.9500
C7 C8 1.397(2)
C14 C15 1.387(3)
C14 H14 0.9500
C3 C4 1.375(3)
C10 C9 1.389(2)
C10 H10 0.9500
C8 C9 1.380(2)
C17 C18 1.393(2)
C17 H17 0.9500
C9 H9 0.9500
C15 H15 0.9500
C18 H18 0.9500
C6 C5 1.394(3)
C6 H6 0.9500
C4 C5 1.381(3)
C4 H4 0.9500
C5 H5 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652443
2 PubChem 102487713
