# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ML0508

_audit_creation_method           'ct.exe (M. Köckerling, 1996)'

_chemical_name_systematic        
;
3-(4-Fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-1H-indole
;
_chemical_melting_point_lt       509
_chemical_melting_point_gt       507

_chemical_formula_moiety         'C21 H16 F N O2 S'
_chemical_formula_sum            'C21 H16 F N O2 S'
_chemical_formula_weight         365.41

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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'

_cell_length_a                   17.9195(8)
_cell_length_b                   5.9807(3)
_cell_length_c                   16.6142(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.089(2)
_cell_angle_gamma                90.00
_cell_volume                     1758.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8389
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-X8 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            26355
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4340
_reflns_number_gt                3667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement. R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.8475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0001(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4340
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.069

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.046054(19) 0.82051(6) 0.09650(2) 0.02361(11) Uani 1 1 d . . .
O1 O -0.02799(6) 0.7197(2) 0.08793(7) 0.0318(3) Uani 1 1 d . . .
O2 O 0.05122(7) 1.06045(19) 0.09448(7) 0.0367(3) Uani 1 1 d . . .
C1 C 0.09224(9) 0.7094(3) 0.02004(9) 0.0286(3) Uani 1 1 d . . .
H1A H 0.0656 0.7553 -0.0335 0.043 Uiso 1 1 calc R . .
H1B H 0.0926 0.5458 0.0237 0.043 Uiso 1 1 calc R . .
H1C H 0.1443 0.7649 0.0272 0.043 Uiso 1 1 calc R . .
C2 C 0.09824(7) 0.7267(2) 0.18903(8) 0.0219(3) Uani 1 1 d . . .
C3 C 0.08403(8) 0.5183(3) 0.21916(8) 0.0240(3) Uani 1 1 d . . .
H3A H 0.0462 0.4245 0.1903 0.029 Uiso 1 1 calc R . .
C4 C 0.12577(8) 0.4482(2) 0.29209(8) 0.0232(3) Uani 1 1 d . . .
H4A H 0.1169 0.3040 0.3126 0.028 Uiso 1 1 calc R . .
C5 C 0.18075(7) 0.5858(2) 0.33600(8) 0.0203(3) Uani 1 1 d . . .
C6 C 0.19404(8) 0.7955(2) 0.30400(9) 0.0270(3) Uani 1 1 d . . .
H6A H 0.2311 0.8913 0.3331 0.032 Uiso 1 1 calc R . .
C7 C 0.15373(8) 0.8651(3) 0.23031(9) 0.0278(3) Uani 1 1 d . . .
H7A H 0.1639 1.0063 0.2082 0.033 Uiso 1 1 calc R . .
C8 C 0.22188(7) 0.5138(2) 0.41503(8) 0.0203(3) Uani 1 1 d . . .
N1 N 0.18957(6) 0.3611(2) 0.46205(7) 0.0224(2) Uani 1 1 d . . .
H1D H 0.1458 0.2941 0.4475 0.027 Uiso 1 1 calc R . .
C9 C 0.23659(7) 0.3311(2) 0.53478(8) 0.0216(3) Uani 1 1 d . . .
C10 C 0.22833(8) 0.1988(3) 0.60168(9) 0.0280(3) Uani 1 1 d . . .
H10A H 0.1835 0.1151 0.6032 0.034 Uiso 1 1 calc R . .
C11 C 0.28749(9) 0.1934(3) 0.66562(9) 0.0335(4) Uani 1 1 d . . .
H11A H 0.2834 0.1039 0.7120 0.040 Uiso 1 1 calc R . .
C12 C 0.35362(9) 0.3173(3) 0.66370(10) 0.0347(4) Uani 1 1 d . . .
H12A H 0.3939 0.3075 0.7082 0.042 Uiso 1 1 calc R . .
C13 C 0.36135(8) 0.4528(3) 0.59859(9) 0.0292(3) Uani 1 1 d . . .
H13A H 0.4061 0.5378 0.5981 0.035 Uiso 1 1 calc R . .
C14 C 0.30171(7) 0.4624(2) 0.53302(8) 0.0216(3) Uani 1 1 d . . .
C15 C 0.29142(7) 0.5776(2) 0.45642(8) 0.0208(3) Uani 1 1 d . . .
C16 C 0.34771(7) 0.7264(2) 0.42798(8) 0.0213(3) Uani 1 1 d . . .
C17 C 0.38159(8) 0.6670(3) 0.36104(9) 0.0284(3) Uani 1 1 d . . .
H17A H 0.3691 0.5283 0.3344 0.034 Uiso 1 1 calc R . .
C18 C 0.43329(9) 0.8080(3) 0.33279(10) 0.0346(4) Uani 1 1 d . . .
H18A H 0.4561 0.7684 0.2869 0.041 Uiso 1 1 calc R . .
C19 C 0.45039(8) 1.0053(3) 0.37285(10) 0.0324(4) Uani 1 1 d . . .
C20 C 0.41966(9) 1.0696(3) 0.43974(10) 0.0320(3) Uani 1 1 d . . .
H20A H 0.4332 1.2077 0.4663 0.038 Uiso 1 1 calc R . .
C21 C 0.36812(8) 0.9269(3) 0.46749(9) 0.0261(3) Uani 1 1 d . . .
H21A H 0.3465 0.9671 0.5141 0.031 Uiso 1 1 calc R . .
F1 F 0.50041(6) 1.1465(2) 0.34500(7) 0.0514(3) Uani 1 1 d . . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4387(12) .
S1 O1 1.4439(11) .
S1 C1 1.7529(15) .
S1 C2 1.7602(14) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.382(2) .
C2 C7 1.389(2) .
C3 C4 1.3846(19) .
C3 H3A 0.9500 .
C4 C5 1.3976(19) .
C4 H4A 0.9500 .
C5 C6 1.397(2) .
C5 C8 1.4654(18) .
C6 C7 1.3836(19) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
C8 C15 1.3786(18) .
C8 N1 1.3864(17) .
N1 C9 1.3714(17) .
N1 H1D 0.8800 .
C9 C10 1.391(2) .
C9 C14 1.4106(18) .
C10 C11 1.377(2) .
C10 H10A 0.9500 .
C11 C12 1.402(2) .
C11 H11A 0.9500 .
C12 C13 1.376(2) .
C12 H12A 0.9500 .
C13 C14 1.4016(19) .
C13 H13A 0.9500 .
C14 C15 1.4334(18) .
C15 C16 1.4777(18) .
C16 C21 1.388(2) .
C16 C17 1.395(2) .
C17 C18 1.388(2) .
C17 H17A 0.9500 .
C18 C19 1.366(2) .
C18 H18A 0.9500 .
C19 F1 1.3643(17) .
C19 C20 1.371(2) .
C20 C21 1.388(2) .
C20 H20A 0.9500 .
C21 H21A 0.9500 .

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
O2 S1 O1 118.42(7) . .
O2 S1 C1 108.77(8) . .
O1 S1 C1 107.57(7) . .
O2 S1 C2 108.13(7) . .
O1 S1 C2 107.82(7) . .
C1 S1 C2 105.40(7) . .
S1 C1 H1A 109.5 . .
S1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
S1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 121.15(13) . .
C3 C2 S1 120.07(10) . .
C7 C2 S1 118.78(11) . .
C2 C3 C4 119.03(13) . .
C2 C3 H3A 120.5 . .
C4 C3 H3A 120.5 . .
C3 C4 C5 121.15(13) . .
C3 C4 H4A 119.4 . .
C5 C4 H4A 119.4 . .
C6 C5 C4 118.59(12) . .
C6 C5 C8 120.86(12) . .
C4 C5 C8 120.53(13) . .
C7 C6 C5 120.67(13) . .
C7 C6 H6A 119.7 . .
C5 C6 H6A 119.7 . .
C6 C7 C2 119.38(14) . .
C6 C7 H7A 120.3 . .
C2 C7 H7A 120.3 . .
C15 C8 N1 109.04(11) . .
C15 C8 C5 130.75(13) . .
N1 C8 C5 120.18(11) . .
C9 N1 C8 109.24(11) . .
C9 N1 H1D 125.4 . .
C8 N1 H1D 125.4 . .
N1 C9 C10 130.57(13) . .
N1 C9 C14 107.70(12) . .
C10 C9 C14 121.73(12) . .
C11 C10 C9 117.61(13) . .
C11 C10 H10A 121.2 . .
C9 C10 H10A 121.2 . .
C10 C11 C12 121.35(14) . .
C10 C11 H11A 119.3 . .
C12 C11 H11A 119.3 . .
C13 C12 C11 121.29(14) . .
C13 C12 H12A 119.4 . .
C11 C12 H12A 119.4 . .
C12 C13 C14 118.43(13) . .
C12 C13 H13A 120.8 . .
C14 C13 H13A 120.8 . .
C13 C14 C9 119.53(13) . .
C13 C14 C15 133.25(13) . .
C9 C14 C15 107.17(11) . .
C8 C15 C14 106.81(12) . .
C8 C15 C16 128.03(12) . .
C14 C15 C16 125.10(12) . .
C21 C16 C17 118.80(13) . .
C21 C16 C15 120.76(12) . .
C17 C16 C15 120.44(13) . .
C18 C17 C16 120.84(15) . .
C18 C17 H17A 119.6 . .
C16 C17 H17A 119.6 . .
C19 C18 C17 118.07(14) . .
C19 C18 H18A 121.0 . .
C17 C18 H18A 121.0 . .
F1 C19 C18 118.57(15) . .
F1 C19 C20 118.11(15) . .
C18 C19 C20 123.32(14) . .
C19 C20 C21 118.06(15) . .
C19 C20 H20A 121.0 . .
C21 C20 H20A 121.0 . .
C16 C21 C20 120.88(14) . .
C16 C21 H21A 119.6 . .
C20 C21 H21A 119.6 . .

# eof
_database_code_depnum_ccdc_archive 'CCDC 963572'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ML1510

_audit_creation_method           'ct.exe (M. Köckerling, 1996)'

_chemical_name_systematic        
;
N-(2-(4-Fluorobenzoyl)-4-methylphenyl)-4-(methylsulfonyl)benzamide
;
_chemical_melting_point          468-470
_chemical_formula_moiety         'C22 H18 F N O4 S'
_chemical_formula_sum            'C22 H18 F N O4 S'
_chemical_formula_weight         411.43

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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'

_cell_length_a                   13.4778(7)
_cell_length_b                   5.3885(3)
_cell_length_c                   26.674(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.875(3)
_cell_angle_gamma                90.00
_cell_volume                     1930.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5798
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      31.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9127
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'


_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-X8 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            25185
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         32.64
_reflns_number_total             6986
_reflns_number_gt                4820
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc.
and is
  not relevant to the choice of reflections for refinement.  R-factors
based
  on F² are statistically about twice as large as those based on F,
and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.1280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6986
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        32.64
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.055


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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34621(2) -0.00237(6) 0.216427(13) 0.02982(10) Uani 1 1 d . . .
O1 O 0.36571(8) 0.25272(19) 0.22943(5) 0.0456(3) Uani 1 1 d . . .
O2 O 0.39314(7) -0.1063(2) 0.17476(4) 0.0434(3) Uani 1 1 d . . .
C1 C 0.37608(11) -0.1866(3) 0.26960(6) 0.0378(3) Uani 1 1 d . . .
H1A H 0.4478 -0.1770 0.2791 0.057 Uiso 1 1 calc R . .
H1B H 0.3574 -0.3592 0.2620 0.057 Uiso 1 1 calc R . .
H1C H 0.3397 -0.1267 0.2975 0.057 Uiso 1 1 calc R . .
C2 C 0.21630(9) -0.0361(2) 0.20346(5) 0.0262(2) Uani 1 1 d . . .
C3 C 0.15269(10) 0.1433(2) 0.21972(5) 0.0299(3) Uani 1 1 d . . .
H3A H 0.1783 0.2800 0.2393 0.036 Uiso 1 1 calc R . .
C4 C 0.05152(10) 0.1210(2) 0.20716(5) 0.0288(3) Uani 1 1 d . . .
H4A H 0.0074 0.2433 0.2181 0.035 Uiso 1 1 calc R . .
C5 C 0.01353(9) -0.0795(2) 0.17853(4) 0.0251(2) Uani 1 1 d . . .
C6 C 0.07863(10) -0.2585(2) 0.16285(5) 0.0292(3) Uani 1 1 d . . .
H6A H 0.0533 -0.3959 0.1435 0.035 Uiso 1 1 calc R . .
C7 C 0.18014(10) -0.2375(2) 0.17535(5) 0.0305(3) Uani 1 1 d . . .
H7A H 0.2245 -0.3601 0.1647 0.037 Uiso 1 1 calc R . .
C8 C -0.09763(9) -0.0868(2) 0.16723(5) 0.0266(2) Uani 1 1 d . . .
O3 O -0.15085(7) 0.06915(19) 0.18416(4) 0.0362(2) Uani 1 1 d . . .
N1 N -0.13133(8) -0.2803(2) 0.13764(4) 0.0286(2) Uani 1 1 d . . .
H1D H -0.0849 -0.3772 0.1271 0.034 Uiso 1 1 calc R . .
C9 C -0.22935(9) -0.3472(2) 0.12164(4) 0.0260(2) Uani 1 1 d . . .
C10 C -0.24491(9) -0.5524(2) 0.08880(5) 0.0265(2) Uani 1 1 d . . .
C11 C -0.34271(9) -0.6353(3) 0.07729(5) 0.0304(3) Uani 1 1 d . . .
H11A H -0.3535 -0.7792 0.0570 0.037 Uiso 1 1 calc R . .
C12 C -0.42448(10) -0.5149(3) 0.09445(5) 0.0342(3) Uani 1 1 d . . .
C13 C -0.40670(10) -0.3044(3) 0.12333(6) 0.0371(3) Uani 1 1 d . . .
H13A H -0.4617 -0.2142 0.1339 0.045 Uiso 1 1 calc R . .
C14 C -0.31141(10) -0.2206(3) 0.13730(5) 0.0328(3) Uani 1 1 d . . .
H14A H -0.3019 -0.0764 0.1576 0.039 Uiso 1 1 calc R . .
C15 C -0.52788(11) -0.6158(4) 0.08257(7) 0.0515(4) Uani 1 1 d . . .
H15A H -0.5760 -0.5076 0.0974 0.077 Uiso 1 1 calc R . .
H15B H -0.5320 -0.7832 0.0966 0.077 Uiso 1 1 calc R . .
H15C H -0.5430 -0.6223 0.0460 0.077 Uiso 1 1 calc R . .
C16 C -0.16132(9) -0.6841(2) 0.06778(5) 0.0270(2) Uani 1 1 d . . .
O4 O -0.07465(7) -0.66123(19) 0.08572(4) 0.0347(2) Uani 1 1 d . . .
C17 C -0.17935(9) -0.8487(2) 0.02278(5) 0.0265(2) Uani 1 1 d . . .
C18 C -0.11686(9) -1.0539(2) 0.01959(5) 0.0300(3) Uani 1 1 d . . .
H18A H -0.0673 -1.0874 0.0462 0.036 Uiso 1 1 calc R . .
C19 C -0.12641(11) -1.2086(3) -0.02184(5) 0.0352(3) Uani 1 1 d . . .
H19A H -0.0850 -1.3502 -0.0238 0.042 Uiso 1 1 calc R . .
C20 C -0.19748(11) -1.1519(3) -0.06010(5) 0.0366(3) Uani 1 1 d . . .
C21 C -0.25886(11) -0.9483(3) -0.05936(5) 0.0361(3) Uani 1 1 d . . .
H21A H -0.3065 -0.9134 -0.0868 0.043 Uiso 1 1 calc R . .
C22 C -0.24909(10) -0.7957(3) -0.01753(5) 0.0320(3) Uani 1 1 d . . .
H22A H -0.2903 -0.6533 -0.0162 0.038 Uiso 1 1 calc R . .
F1 F -0.20718(8) -1.30316(18) -0.10066(3) 0.0541(3) Uani 1 1 d . . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4364(10) .
S1 O2 1.4380(11) .
S1 C1 1.7498(15) .
S1 C2 1.7651(13) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C7 1.3842(17) .
C2 C3 1.3859(17) .
C3 C4 1.3814(18) .
C3 H3A 0.9500 .
C4 C5 1.3949(17) .
C4 H4A 0.9500 .
C5 C6 1.3920(17) .
C5 C8 1.5035(17) .
C6 C7 1.3850(18) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
C8 O3 1.2165(15) .
C8 N1 1.3620(16) .
N1 C9 1.4006(16) .
N1 H1D 0.8800 .
C9 C14 1.3934(17) .
C9 C10 1.4154(18) .
C10 C11 1.4009(17) .
C10 C16 1.4814(17) .
C11 C12 1.3895(18) .
C11 H11A 0.9500 .
C12 C13 1.380(2) .
C12 C15 1.504(2) .
C13 C14 1.382(2) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 O4 1.2304(15) .
C16 C17 1.4955(17) .
C17 C22 1.3961(18) .
C17 C18 1.3969(18) .
C18 C19 1.3813(19) .
C18 H18A 0.9500 .
C19 C20 1.373(2) .
C19 H19A 0.9500 .
C20 F1 1.3518(15) .
C20 C21 1.375(2) .
C21 C22 1.3832(19) .
C21 H21A 0.9500 .
C22 H22A 0.9500 .

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
O1 S1 O2 118.41(7) . .
O1 S1 C1 108.80(7) . .
O2 S1 C1 108.64(7) . .
O1 S1 C2 107.69(6) . .
O2 S1 C2 107.61(6) . .
C1 S1 C2 104.87(7) . .
S1 C1 H1A 109.5 . .
S1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
S1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C7 C2 C3 121.19(12) . .
C7 C2 S1 118.98(9) . .
C3 C2 S1 119.78(9) . .
C4 C3 C2 119.16(11) . .
C4 C3 H3A 120.4 . .
C2 C3 H3A 120.4 . .
C3 C4 C5 120.61(11) . .
C3 C4 H4A 119.7 . .
C5 C4 H4A 119.7 . .
C6 C5 C4 119.32(11) . .
C6 C5 C8 124.36(11) . .
C4 C5 C8 116.31(11) . .
C7 C6 C5 120.39(11) . .
C7 C6 H6A 119.8 . .
C5 C6 H6A 119.8 . .
C2 C7 C6 119.32(11) . .
C2 C7 H7A 120.3 . .
C6 C7 H7A 120.3 . .
O3 C8 N1 124.47(12) . .
O3 C8 C5 121.09(12) . .
N1 C8 C5 114.44(10) . .
C8 N1 C9 129.26(11) . .
C8 N1 H1D 115.4 . .
C9 N1 H1D 115.4 . .
C14 C9 N1 122.34(12) . .
C14 C9 C10 119.23(11) . .
N1 C9 C10 118.42(11) . .
C11 C10 C9 118.15(11) . .
C11 C10 C16 119.74(12) . .
C9 C10 C16 122.08(11) . .
C12 C11 C10 122.47(13) . .
C12 C11 H11A 118.8 . .
C10 C11 H11A 118.8 . .
C13 C12 C11 117.55(12) . .
C13 C12 C15 121.89(13) . .
C11 C12 C15 120.54(14) . .
C12 C13 C14 122.14(12) . .
C12 C13 H13A 118.9 . .
C14 C13 H13A 118.9 . .
C13 C14 C9 120.15(13) . .
C13 C14 H14A 119.9 . .
C9 C14 H14A 119.9 . .
C12 C15 H15A 109.5 . .
C12 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C12 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O4 C16 C10 122.16(11) . .
O4 C16 C17 117.11(11) . .
C10 C16 C17 120.73(11) . .
C22 C17 C18 119.00(12) . .
C22 C17 C16 123.35(11) . .
C18 C17 C16 117.42(11) . .
C19 C18 C17 120.71(13) . .
C19 C18 H18A 119.6 . .
C17 C18 H18A 119.6 . .
C20 C19 C18 118.18(13) . .
C20 C19 H19A 120.9 . .
C18 C19 H19A 120.9 . .
F1 C20 C19 118.35(13) . .
F1 C20 C21 118.36(13) . .
C19 C20 C21 123.29(12) . .
C20 C21 C22 118.01(13) . .
C20 C21 H21A 121.0 . .
C22 C21 H21A 121.0 . .
C21 C22 C17 120.76(13) . .
C21 C22 H22A 119.6 . .
C17 C22 H22A 119.6 . .


# eof

_database_code_depnum_ccdc_archive 'CCDC 963601'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_AP-ML-2010

_audit_creation_method           'ct.exe (M. Köckerling, 1996)'

_chemical_name_systematic        
;
1-(4-Fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-ethanone
;

_chemical_melting_point_gt       455
_chemical_melting_point_lt       458
_chemical_formula_moiety         'C15 H13 F O3 S'
_chemical_formula_sum            'C15 H13 F O3 S'
_chemical_formula_weight         292.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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'
S S 0.1265 0.1256 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5241(2)
_cell_length_b                   8.5534(2)
_cell_length_c                   14.6136(4)
_cell_angle_alpha                82.578(1)
_cell_angle_beta                 88.938(1)
_cell_angle_gamma                72.577(1)
_cell_volume                     653.14(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      34.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'


_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_reflns_number            33122
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         38.33
_reflns_number_total             7225
_reflns_number_gt                5510
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7225
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        38.33
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.064

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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.22961(13) 1.45906(8) 0.49046(6) 0.04010(17) Uani 1 1 d . . .
C1 C -0.18224(19) 1.32160(12) 0.44872(7) 0.02564(17) Uani 1 1 d . . .
C2 C -0.33777(19) 1.22212(12) 0.46729(7) 0.02530(17) Uani 1 1 d . . .
H2 H -0.4755 1.2496 0.5081 0.030 Uiso 1 1 calc R . .
C3 C -0.28612(17) 1.08035(11) 0.42419(6) 0.02163(15) Uani 1 1 d . . .
H3 H -0.3914 1.0104 0.4353 0.026 Uiso 1 1 calc R . .
C4 C -0.08229(16) 1.03909(10) 0.36494(5) 0.01849(14) Uani 1 1 d . . .
C5 C 0.06916(17) 1.14395(11) 0.34764(6) 0.02204(15) Uani 1 1 d . . .
H5 H 0.2075 1.1171 0.3070 0.026 Uiso 1 1 calc R . .
C6 C 0.01922(18) 1.28741(12) 0.38937(7) 0.02537(17) Uani 1 1 d . . .
H6 H 0.1206 1.3597 0.3774 0.030 Uiso 1 1 calc R . .
C7 C -0.03572(17) 0.88200(11) 0.32366(6) 0.01936(14) Uani 1 1 d . . .
O1 O -0.16650(15) 0.79099(9) 0.34292(5) 0.02794(15) Uani 1 1 d . . .
C8 C 0.18085(18) 0.84305(11) 0.25653(6) 0.02368(17) Uani 1 1 d . . .
H8A H 0.1419 0.9303 0.2027 0.028 Uiso 1 1 calc R . .
H8B H 0.3371 0.8469 0.2871 0.028 Uiso 1 1 calc R . .
C9 C 0.23217(17) 0.67779(11) 0.22243(6) 0.02057(15) Uani 1 1 d . . .
C10 C 0.46313(18) 0.55697(12) 0.24311(6) 0.02339(16) Uani 1 1 d . . .
H10 H 0.5841 0.5772 0.2817 0.028 Uiso 1 1 calc R . .
C11 C 0.51959(18) 0.40664(11) 0.20804(6) 0.02366(16) Uani 1 1 d . . .
H11 H 0.6776 0.3243 0.2225 0.028 Uiso 1 1 calc R . .
C12 C 0.34131(16) 0.37889(11) 0.15160(5) 0.01889(14) Uani 1 1 d . . .
C13 C 0.10714(17) 0.49740(12) 0.13099(6) 0.02203(15) Uani 1 1 d . . .
H13 H -0.0142 0.4764 0.0930 0.026 Uiso 1 1 calc R . .
C14 C 0.05336(17) 0.64667(12) 0.16675(6) 0.02305(16) Uani 1 1 d . . .
H14 H -0.1060 0.7281 0.1532 0.028 Uiso 1 1 calc R . .
S1 S 0.41777(4) 0.19231(3) 0.102666(14) 0.02033(6) Uani 1 1 d . . .
O2 O 0.57726(16) 0.06222(9) 0.16687(5) 0.03111(16) Uani 1 1 d . . .
O3 O 0.18518(14) 0.17128(10) 0.07094(6) 0.03173(16) Uani 1 1 d . . .
C16 C 0.5979(2) 0.22548(13) 0.00553(7) 0.02769(19) Uani 1 1 d . . .
H16A H 0.6427 0.1277 -0.0269 0.042 Uiso 1 1 calc R . .
H16B H 0.7532 0.2456 0.0255 0.042 Uiso 1 1 calc R . .
H16C H 0.4982 0.3216 -0.0360 0.042 Uiso 1 1 calc R . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.3484(11) .
C1 C2 1.3803(14) .
C1 C6 1.3824(14) .
C2 C3 1.3899(12) .
C2 H2 0.9500 .
C3 C4 1.3953(12) .
C3 H3 0.9500 .
C4 C5 1.3969(12) .
C4 C7 1.4940(11) .
C5 C6 1.3922(13) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O1 1.2164(11) .
C7 C8 1.5188(12) .
C8 C9 1.5045(12) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.3896(13) .
C9 C14 1.3971(13) .
C10 C11 1.3919(13) .
C10 H10 0.9500 .
C11 C12 1.3883(12) .
C11 H11 0.9500 .
C12 C13 1.3935(13) .
C12 S1 1.7654(9) .
C13 C14 1.3896(13) .
C13 H13 0.9500 .
C14 H14 0.9500 .
S1 O2 1.4382(8) .
S1 O3 1.4422(8) .
S1 C16 1.7602(9) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .

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
F1 C1 C2 118.31(9) . .
F1 C1 C6 118.43(9) . .
C2 C1 C6 123.26(8) . .
C1 C2 C3 117.75(8) . .
C1 C2 H2 121.1 . .
C3 C2 H2 121.1 . .
C2 C3 C4 121.12(8) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C4 C5 119.20(8) . .
C3 C4 C7 117.64(7) . .
C5 C4 C7 123.16(7) . .
C6 C5 C4 120.61(8) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C1 C6 C5 118.06(8) . .
C1 C6 H6 121.0 . .
C5 C6 H6 121.0 . .
O1 C7 C4 121.23(8) . .
O1 C7 C8 122.11(8) . .
C4 C7 C8 116.66(7) . .
C9 C8 C7 114.53(7) . .
C9 C8 H8A 108.6 . .
C7 C8 H8A 108.6 . .
C9 C8 H8B 108.6 . .
C7 C8 H8B 108.6 . .
H8A C8 H8B 107.6 . .
C10 C9 C14 119.42(8) . .
C10 C9 C8 120.00(8) . .
C14 C9 C8 120.53(8) . .
C9 C10 C11 120.85(8) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C12 C11 C10 118.94(8) . .
C12 C11 H11 120.5 . .
C10 C11 H11 120.5 . .
C11 C12 C13 121.17(8) . .
C11 C12 S1 119.10(7) . .
C13 C12 S1 119.71(7) . .
C14 C13 C12 119.19(8) . .
C14 C13 H13 120.4 . .
C12 C13 H13 120.4 . .
C13 C14 C9 120.41(8) . .
C13 C14 H14 119.8 . .
C9 C14 H14 119.8 . .
O2 S1 O3 117.92(5) . .
O2 S1 C16 108.30(5) . .
O3 S1 C16 108.20(5) . .
O2 S1 C12 108.85(4) . .
O3 S1 C12 108.14(4) . .
C16 S1 C12 104.63(4) . .
S1 C16 H16A 109.5 . .
S1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
S1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .


# eof

_database_code_depnum_ccdc_archive 'CCDC 963602'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ML51/12

_audit_creation_method           'ct.exe (M. Köckerling, 1996)'


_chemical_name_systematic        
;
2-(4-Methoxyphenyl)-3-[4-(methylsulfonyl)phenyl]-1H-indole
;

_chemical_melting_point_lt       516
_chemical_melting_point_gt       514


_chemical_formula_moiety         'C22 H19 N O3 S'
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1265 0.1256 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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'

_cell_length_a                   11.6987(6)
_cell_length_b                   18.059(1)
_cell_length_c                   9.5364(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.647(2)
_cell_angle_gamma                90.00
_cell_volume                     1885.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      39.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9352
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'


_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_number            54915
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         39.46
_reflns_number_total             11261
_reflns_number_gt                8816
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.2893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11261
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        39.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.066


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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.19540(5) 0.31735(3) 0.62651(8) 0.01966(10) Uani 1 1 d . . .
H1 H 0.1238 0.2984 0.6174 0.024 Uiso 1 1 calc R . .
C1 C 0.22125(5) 0.39153(4) 0.63041(8) 0.01818(11) Uani 1 1 d . . .
C2 C 0.14503(6) 0.45240(4) 0.62135(9) 0.02338(13) Uani 1 1 d . . .
H2 H 0.0606 0.4462 0.6048 0.028 Uiso 1 1 calc R . .
C3 C 0.19756(7) 0.52210(4) 0.63743(10) 0.02529(14) Uani 1 1 d . . .
H3 H 0.1483 0.5647 0.6307 0.030 Uiso 1 1 calc R . .
C4 C 0.32308(7) 0.53059(4) 0.66367(9) 0.02369(13) Uani 1 1 d . . .
H4 H 0.3576 0.5789 0.6788 0.028 Uiso 1 1 calc R . .
C5 C 0.39746(6) 0.47034(4) 0.66803(8) 0.01982(11) Uani 1 1 d . . .
H5 H 0.4817 0.4770 0.6842 0.024 Uiso 1 1 calc R . .
C6 C 0.34577(5) 0.39901(4) 0.64808(8) 0.01627(10) Uani 1 1 d . . .
C7 C 0.39366(5) 0.32510(3) 0.65129(7) 0.01566(10) Uani 1 1 d . . .
C8 C 0.29853(5) 0.27682(4) 0.63897(8) 0.01674(10) Uani 1 1 d . . .
C9 C 0.29324(5) 0.19547(4) 0.63707(8) 0.01749(10) Uani 1 1 d . . .
C10 C 0.24417(7) 0.15791(4) 0.73150(9) 0.02285(12) Uani 1 1 d . . .
H10 H 0.2171 0.1852 0.7991 0.027 Uiso 1 1 calc R . .
C11 C 0.23463(8) 0.08152(4) 0.72744(10) 0.02750(14) Uani 1 1 d . . .
H11 H 0.2019 0.0566 0.7926 0.033 Uiso 1 1 calc R . .
C12 C 0.27318(8) 0.04097(4) 0.62731(9) 0.02416(13) Uani 1 1 d . . .
C13 C 0.32260(7) 0.07722(4) 0.53274(9) 0.02319(12) Uani 1 1 d . . .
H13 H 0.3492 0.0498 0.4650 0.028 Uiso 1 1 calc R . .
C14 C 0.33249(6) 0.15423(4) 0.53875(9) 0.02052(11) Uani 1 1 d . . .
H14 H 0.3665 0.1790 0.4748 0.025 Uiso 1 1 calc R . .
O1 O 0.25835(8) -0.03384(3) 0.63090(8) 0.03597(15) Uani 1 1 d . . .
C15 C 0.29138(13) -0.07777(5) 0.52721(12) 0.0405(2) Uani 1 1 d . . .
H15A H 0.2764 -0.1301 0.5417 0.061 Uiso 1 1 calc R . .
H15B H 0.3782 -0.0705 0.5437 0.061 Uiso 1 1 calc R . .
H15C H 0.2423 -0.0629 0.4248 0.061 Uiso 1 1 calc R . .
C16 C 0.51985(5) 0.30745(3) 0.66779(7) 0.01503(9) Uani 1 1 d . . .
C17 C 0.58430(5) 0.24864(4) 0.75735(8) 0.01878(11) Uani 1 1 d . . .
H17 H 0.5437 0.2166 0.8037 0.023 Uiso 1 1 calc R . .
C18 C 0.70686(6) 0.23664(4) 0.77914(8) 0.01905(11) Uani 1 1 d . . .
H18 H 0.7499 0.1967 0.8396 0.023 Uiso 1 1 calc R . .
C19 C 0.76540(5) 0.28402(4) 0.71111(8) 0.01702(10) Uani 1 1 d . . .
C20 C 0.70341(5) 0.34229(4) 0.62070(8) 0.01794(10) Uani 1 1 d . . .
H20 H 0.7446 0.3743 0.5751 0.022 Uiso 1 1 calc R . .
C21 C 0.58097(5) 0.35309(4) 0.59801(8) 0.01719(10) Uani 1 1 d . . .
H21 H 0.5377 0.3920 0.5342 0.021 Uiso 1 1 calc R . .
C22 C 0.98944(8) 0.33987(6) 0.88995(11) 0.03419(18) Uani 1 1 d . . .
H22A H 0.9739 0.3252 0.9805 0.051 Uiso 1 1 calc R . .
H22B H 0.9540 0.3889 0.8576 0.051 Uiso 1 1 calc R . .
H22C H 1.0777 0.3417 0.9115 0.051 Uiso 1 1 calc R . .
S1 S 0.922391(14) 0.275045(12) 0.74680(2) 0.02302(5) Uani 1 1 d . . .
O2 O 0.96216(6) 0.20174(4) 0.80116(9) 0.03584(15) Uani 1 1 d . . .
O3 O 0.94476(5) 0.30012(5) 0.61442(8) 0.03666(16) Uani 1 1 d . . .


_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3710(9) .
N1 C8 1.3801(8) .
N1 H1 0.8800 .
C1 C2 1.3986(9) .
C1 C6 1.4127(8) .
C2 C3 1.3853(11) .
C2 H2 0.9500 .
C3 C4 1.4083(11) .
C3 H3 0.9500 .
C4 C5 1.3847(10) .
C4 H4 0.9500 .
C5 C6 1.4071(9) .
C5 H5 0.9500 .
C6 C7 1.4437(9) .
C7 C8 1.3858(8) .
C7 C16 1.4635(8) .
C8 C9 1.4703(9) .
C9 C14 1.3957(10) .
C9 C10 1.4018(10) .
C10 C11 1.3835(11) .
C10 H10 0.9500 .
C11 C12 1.3983(12) .
C11 H11 0.9500 .
C12 O1 1.3639(10) .
C12 C13 1.3943(11) .
C13 C14 1.3949(10) .
C13 H13 0.9500 .
C14 H14 0.9500 .
O1 C15 1.4233(13) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C21 1.4032(9) .
C16 C17 1.4042(9) .
C17 C18 1.3913(9) .
C17 H17 0.9500 .
C18 C19 1.3913(9) .
C18 H18 0.9500 .
C19 C20 1.3912(9) .
C19 S1 1.7534(6) .
C20 C21 1.3850(8) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 S1 1.7590(10) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
S1 O2 1.4380(7) .
S1 O3 1.4492(7) .

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
C1 N1 C8 109.76(5) . .
C1 N1 H1 125.1 . .
C8 N1 H1 125.1 . .
N1 C1 C2 129.53(6) . .
N1 C1 C6 107.76(5) . .
C2 C1 C6 122.71(6) . .
C3 C2 C1 117.32(6) . .
C3 C2 H2 121.3 . .
C1 C2 H2 121.3 . .
C2 C3 C4 120.84(7) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C5 C4 C3 121.64(7) . .
C5 C4 H4 119.2 . .
C3 C4 H4 119.2 . .
C4 C5 C6 118.67(6) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
C5 C6 C1 118.65(6) . .
C5 C6 C7 134.30(5) . .
C1 C6 C7 106.88(5) . .
C8 C7 C6 106.61(5) . .
C8 C7 C16 128.43(6) . .
C6 C7 C16 124.95(5) . .
N1 C8 C7 108.98(6) . .
N1 C8 C9 119.81(5) . .
C7 C8 C9 131.21(5) . .
C14 C9 C10 118.67(6) . .
C14 C9 C8 121.27(6) . .
C10 C9 C8 120.03(6) . .
C11 C10 C9 120.77(7) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C10 C11 C12 119.94(7) . .
C10 C11 H11 120.0 . .
C12 C11 H11 120.0 . .
O1 C12 C13 124.52(7) . .
O1 C12 C11 115.28(7) . .
C13 C12 C11 120.20(7) . .
C12 C13 C14 119.26(7) . .
C12 C13 H13 120.4 . .
C14 C13 H13 120.4 . .
C13 C14 C9 121.16(7) . .
C13 C14 H14 119.4 . .
C9 C14 H14 119.4 . .
C12 O1 C15 117.81(7) . .
O1 C15 H15A 109.5 . .
O1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C21 C16 C17 118.59(5) . .
C21 C16 C7 118.98(5) . .
C17 C16 C7 122.35(5) . .
C18 C17 C16 120.85(6) . .
C18 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C19 C18 C17 119.03(6) . .
C19 C18 H18 120.5 . .
C17 C18 H18 120.5 . .
C20 C19 C18 121.30(5) . .
C20 C19 S1 118.14(5) . .
C18 C19 S1 120.45(5) . .
C21 C20 C19 119.20(6) . .
C21 C20 H20 120.4 . .
C19 C20 H20 120.4 . .
C20 C21 C16 121.00(6) . .
C20 C21 H21 119.5 . .
C16 C21 H21 119.5 . .
S1 C22 H22A 109.5 . .
S1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
S1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
O2 S1 O3 117.83(5) . .
O2 S1 C19 109.80(4) . .
O3 S1 C19 107.49(3) . .
O2 S1 C22 109.50(5) . .
O3 S1 C22 107.46(5) . .
C19 S1 C22 103.83(4) . .

# eof

_database_code_depnum_ccdc_archive 'CCDC 963609'
