#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/34/2213476.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_2213476
loop_
_publ_author_name
'B. Thimme Gowda'
'Sabine Foro'
'Hartmut Fuess '
_publ_section_title
;
 N-(4-Fluorophenyl)methanesulfonamide
;
_journal_coeditor_code           LW2011
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2570
_journal_page_last               o2570
_journal_paper_doi               10.1107/S1600536807018491
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H8 F N O2 S'
_chemical_formula_moiety         'C7 H8 F N O2 S'
_chemical_formula_sum            'C7 H8 F N O2 S'
_chemical_formula_weight         189.20
_chemical_name_common            Methanesulfon-4-fluoroanilide
_chemical_name_systematic
;
N-(4-Fluorophenyl)methanesulfonamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.272(3)
_cell_length_b                   5.0590(10)
_cell_length_c                   10.140(2)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      3.63
_cell_volume                     867.8(3)
_computing_cell_refinement
;
CrysAlis CCD
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur Diffractometer with
Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4986
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.8522
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.539
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1757
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0975
_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)+(0.1115P)²+1.0115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2477
_refine_ls_wR_factor_ref         0.2618
_reflns_number_gt                1471
_reflns_number_total             1757
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lw2011.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213476
_cod_database_fobs_code          2213476
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
C C1 0.5825(4) 0.0142(13) 0.4135(6) 0.0720(16) Uani d . 1
H H1A 0.5800 -0.1721 0.4302 0.086 Uiso calc R 1
H H1B 0.5303 0.0880 0.3990 0.086 Uiso calc R 1
H H1C 0.6152 0.0981 0.4898 0.086 Uiso calc R 1
C C6 0.7729(3) -0.0529(9) 0.3838(5) 0.0558(13) Uani d . 1
C C7 0.7940(4) -0.1872(12) 0.5050(6) 0.0697(15) Uani d . 1
H H7 0.7612 -0.3199 0.5258 0.084 Uiso calc R 1
C C8 0.8630(4) -0.1275(15) 0.5955(7) 0.0833(19) Uani d . 1
H H8 0.8784 -0.2233 0.6748 0.100 Uiso calc R 1
C C9 0.9079(4) 0.0773(16) 0.5645(8) 0.084(2) Uani d . 1
C C10 0.8894(4) 0.2161(14) 0.4461(8) 0.0833(19) Uani d . 1
H H10 0.9224 0.3510 0.4283 0.100 Uiso calc R 1
C C11 0.8209(4) 0.1538(12) 0.3523(7) 0.0716(16) Uani d . 1
H H11 0.8073 0.2459 0.2716 0.086 Uiso calc R 1
N N5 0.7032(3) -0.1189(9) 0.2855(5) 0.0605(12) Uani d D 1
H H5N 0.683(3) -0.271(6) 0.294(6) 0.073 Uiso d D 1
O O3 0.6484(3) 0.3356(7) 0.2684(4) 0.0803(13) Uani d . 1
O O4 0.5695(3) -0.0318(8) 0.1535(4) 0.0776(13) Uani d . 1
F F12 0.9756(3) 0.1488(12) 0.6532(6) 0.1259(18) Uani d . 1
S S2 0.62315(9) 0.0664(2) 0.26953(12) 0.0555(5) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.082(4) 0.076(4) 0.063(3) 0.015(3) 0.029(3) 0.007(3)
C6 0.070(3) 0.040(3) 0.064(3) -0.002(2) 0.032(3) -0.009(2)
C7 0.079(4) 0.061(4) 0.073(4) 0.000(3) 0.026(3) 0.004(3)
C8 0.089(5) 0.089(5) 0.073(4) 0.013(4) 0.019(4) 0.002(3)
C9 0.062(4) 0.096(5) 0.094(5) 0.010(3) 0.017(3) -0.030(4)
C10 0.068(4) 0.077(4) 0.113(5) -0.011(3) 0.036(4) -0.018(4)
C11 0.076(4) 0.063(4) 0.083(4) -0.014(3) 0.034(3) -0.002(3)
N5 0.079(3) 0.041(2) 0.069(3) -0.008(2) 0.031(2) -0.010(2)
O3 0.107(3) 0.0325(19) 0.096(3) -0.012(2) 0.008(3) 0.0096(19)
O4 0.112(3) 0.063(3) 0.049(2) -0.018(2) -0.004(2) -0.0031(17)
F12 0.077(3) 0.160(5) 0.132(4) 0.001(3) 0.002(3) -0.043(3)
S2 0.0833(10) 0.0364(7) 0.0463(7) -0.0082(6) 0.0115(6) 0.0026(5)
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
S2 C1 H1A 109.5
S2 C1 H1B 109.5
H1A C1 H1B 109.5
S2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C6 C11 120.2(6)
C7 C6 N5 122.3(5)
C11 C6 N5 117.6(5)
C8 C7 C6 121.2(6)
C8 C7 H7 119.4
C6 C7 H7 119.4
C9 C8 C7 117.7(7)
C9 C8 H8 121.1
C7 C8 H8 121.1
C8 C9 C10 123.2(7)
C8 C9 F12 119.7(8)
C10 C9 F12 117.1(7)
C9 C10 C11 119.7(6)
C9 C10 H10 120.1
C11 C10 H10 120.1
C10 C11 C6 118.0(6)
C10 C11 H11 121.0
C6 C11 H11 121.0
C6 N5 S2 120.2(3)
C6 N5 H5N 116(4)
S2 N5 H5N 100(4)
O3 S2 O4 118.2(3)
O3 S2 N5 106.9(3)
O4 S2 N5 105.9(3)
O3 S2 C1 108.8(3)
O4 S2 C1 109.2(3)
N5 S2 C1 107.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 S2 1.763(5)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C6 C7 1.387(8)
C6 C11 1.410(7)
C6 N5 1.439(7)
C7 C8 1.383(9)
C7 H7 0.9300
C8 C9 1.368(10)
C8 H8 0.9300
C9 C10 1.371(10)
C9 F12 1.372(8)
C10 C11 1.397(9)
C10 H10 0.9300
C11 H11 0.9300
N5 S2 1.651(5)
N5 H5N 0.859(10)
O3 S2 1.431(4)
O4 S2 1.432(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N5 H5N O3 1_545 0.859(10) 2.08(2) 2.911(6) 164(6)
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
C11 C6 C7 C8 -1.8(9)
N5 C6 C7 C8 177.3(5)
C6 C7 C8 C9 3.1(9)
C7 C8 C9 C10 -3.1(10)
C7 C8 C9 F12 178.0(5)
C8 C9 C10 C11 1.6(10)
F12 C9 C10 C11 -179.4(5)
C9 C10 C11 C6 -0.1(9)
C7 C6 C11 C10 0.2(8)
N5 C6 C11 C10 -178.8(5)
C7 C6 N5 S2 102.8(5)
C11 C6 N5 S2 -78.1(6)
C6 N5 S2 O3 45.9(4)
C6 N5 S2 O4 172.7(4)
C6 N5 S2 C1 -70.7(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 676075
