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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_p

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
N-(4-acetyl-5-methyl-3-phenyl-1H-pyrrol-2-yl)-N-phenylmethanesulfonamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O3 S'
_chemical_formula_weight         368.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.5572(6)
_cell_length_b                   15.5085(8)
_cell_length_c                   20.8957(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.733(5)
_cell_angle_gamma                90.00
_cell_volume                     3732.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8449
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3649
_reflns_number_gt                3086
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.1169P)²+11.4622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   0.704
_refine_ls_restrained_S_all      0.704
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.71312(4) 1.02727(3) 0.72977(2) 0.02064(17) Uani 1 1 d . . .
O1 O 0.70184(14) 1.11873(10) 0.72741(8) 0.0311(4) Uani 1 1 d . . .
N2 N 0.51338(14) 0.88046(11) 0.67030(8) 0.0214(4) Uani 1 1 d . . .
H2A H 0.4626 0.9166 0.6819 0.026 Uiso 1 1 calc R . .
N1 N 0.66094(15) 0.98907(11) 0.65968(8) 0.0207(4) Uani 1 1 d . . .
C4 C 0.49637(17) 0.79480(13) 0.66424(9) 0.0212(4) Uani 1 1 d . . .
C2 C 0.68025(17) 0.82866(13) 0.63930(9) 0.0189(4) Uani 1 1 d . . .
C1 C 0.62349(17) 0.90201(13) 0.65528(9) 0.0193(4) Uani 1 1 d . . .
C6 C 0.60666(19) 0.66761(14) 0.62723(10) 0.0253(5) Uani 1 1 d . . .
C3 C 0.59848(17) 0.75893(13) 0.64385(9) 0.0202(4) Uani 1 1 d . . .
C41 C 0.64284(19) 1.04582(13) 0.60481(10) 0.0236(4) Uani 1 1 d . . .
C21 C 0.80504(17) 0.82614(13) 0.62671(9) 0.0205(4) Uani 1 1 d . . .
C22 C 0.84673(19) 0.87648(15) 0.57855(11) 0.0297(5) Uani 1 1 d . . .
H22A H 0.7952 0.9087 0.5516 0.036 Uiso 1 1 calc R . .
C46 C 0.7366(2) 1.08139(16) 0.57744(12) 0.0340(5) Uani 1 1 d . . .
H46A H 0.8121 1.0698 0.5941 0.041 Uiso 1 1 calc R . .
C23 C 0.9647(2) 0.87900(19) 0.57041(14) 0.0437(7) Uani 1 1 d . . .
H23A H 0.9917 0.9133 0.5383 0.052 Uiso 1 1 calc R . .
C42 C 0.5303(2) 1.06293(15) 0.57977(12) 0.0344(5) Uani 1 1 d . . .
H42A H 0.4677 1.0392 0.5988 0.041 Uiso 1 1 calc R . .
C45 C 0.7155(3) 1.13509(18) 0.52422(13) 0.0472(7) Uani 1 1 d . . .
H45A H 0.7777 1.1598 0.5054 0.057 Uiso 1 1 calc R . .
C43 C 0.5116(3) 1.11559(18) 0.52624(13) 0.0499(8) Uani 1 1 d . . .
H43A H 0.4363 1.1262 0.5087 0.060 Uiso 1 1 calc R . .
C44 C 0.6040(3) 1.15189(18) 0.49925(12) 0.0513(8) Uani 1 1 d . . .
H44A H 0.5913 1.1881 0.4639 0.062 Uiso 1 1 calc R . .
C25 C 1.0016(2) 0.77912(18) 0.65685(12) 0.0373(6) Uani 1 1 d . . .
H25A H 1.0533 0.7455 0.6826 0.045 Uiso 1 1 calc R . .
O2 O 0.65962(15) 0.98081(11) 0.77873(7) 0.0356(4) Uani 1 1 d . . .
O3 O 0.52939(15) 0.61692(10) 0.63809(9) 0.0394(4) Uani 1 1 d . . .
C26 C 0.88410(19) 0.77745(15) 0.66571(10) 0.0279(5) Uani 1 1 d . . .
H26A H 0.8576 0.7434 0.6981 0.034 Uiso 1 1 calc R . .
C5 C 0.38297(19) 0.75608(15) 0.67825(11) 0.0292(5) Uani 1 1 d . . .
H5A H 0.3322 0.8006 0.6913 0.044 Uiso 1 1 calc R . .
H5B H 0.3955 0.7144 0.7121 0.044 Uiso 1 1 calc R . .
H5C H 0.3482 0.7283 0.6404 0.044 Uiso 1 1 calc R . .
C31 C 0.86046(19) 1.00007(17) 0.73727(12) 0.0341(5) Uani 1 1 d . . .
H31A H 0.8954 1.0209 0.7776 0.051 Uiso 1 1 calc R . .
H31B H 0.8983 1.0258 0.7028 0.051 Uiso 1 1 calc R . .
H31C H 0.8685 0.9385 0.7355 0.051 Uiso 1 1 calc R . .
C7 C 0.7098(2) 0.63459(16) 0.59547(13) 0.0372(6) Uani 1 1 d . . .
H7A H 0.7014 0.5738 0.5879 0.056 Uiso 1 1 calc R . .
H7B H 0.7792 0.6451 0.6229 0.056 Uiso 1 1 calc R . .
H7C H 0.7149 0.6638 0.5553 0.056 Uiso 1 1 calc R . .
C24 C 1.0418(2) 0.83111(19) 0.60942(13) 0.0436(7) Uani 1 1 d . . .
H24A H 1.1208 0.8336 0.6040 0.052 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
_geom_bond_publ_flag
S1 O1 1.4248(16) . ?
S1 O2 1.4326(16) . ?
S1 N1 1.6473(17) . ?
S1 C31 1.749(2) . ?
N2 C4 1.347(3) . ?
N2 C1 1.377(2) . ?
N1 C1 1.418(3) . ?
N1 C41 1.447(3) . ?
C4 C3 1.402(3) . ?
C4 C5 1.492(3) . ?
C2 C1 1.368(3) . ?
C2 C3 1.444(3) . ?
C2 C21 1.488(3) . ?
C6 O3 1.225(3) . ?
C6 C3 1.463(3) . ?
C6 C7 1.502(3) . ?
C41 C46 1.381(3) . ?
C41 C42 1.387(3) . ?
C21 C22 1.391(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.388(3) . ?
C46 C45 1.394(4) . ?
C23 C24 1.375(4) . ?
C42 C43 1.387(4) . ?
C45 C44 1.375(5) . ?
C43 C44 1.370(5) . ?
C25 C26 1.386(3) . ?
C25 C24 1.387(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
O1 S1 O2 118.80(10) . . ?
O1 S1 N1 107.55(9) . . ?
O2 S1 N1 107.82(9) . . ?
O1 S1 C31 109.20(12) . . ?
O2 S1 C31 106.81(12) . . ?
N1 S1 C31 105.98(10) . . ?
C4 N2 C1 110.39(17) . . ?
C1 N1 C41 120.27(16) . . ?
C1 N1 S1 119.17(13) . . ?
C41 N1 S1 120.27(14) . . ?
N2 C4 C3 107.44(17) . . ?
N2 C4 C5 120.13(19) . . ?
C3 C4 C5 132.4(2) . . ?
C1 C2 C3 106.08(17) . . ?
C1 C2 C21 123.80(18) . . ?
C3 C2 C21 129.87(18) . . ?
C2 C1 N2 108.94(17) . . ?
C2 C1 N1 131.10(18) . . ?
N2 C1 N1 119.94(17) . . ?
O3 C6 C3 121.0(2) . . ?
O3 C6 C7 118.7(2) . . ?
C3 C6 C7 120.28(19) . . ?
C4 C3 C2 107.13(17) . . ?
C4 C3 C6 121.91(19) . . ?
C2 C3 C6 130.81(19) . . ?
C46 C41 C42 120.7(2) . . ?
C46 C41 N1 120.3(2) . . ?
C42 C41 N1 119.0(2) . . ?
C22 C21 C26 118.51(19) . . ?
C22 C21 C2 120.80(18) . . ?
C26 C21 C2 120.56(18) . . ?
C23 C22 C21 120.4(2) . . ?
C41 C46 C45 118.5(3) . . ?
C24 C23 C22 120.5(2) . . ?
C41 C42 C43 119.7(3) . . ?
C44 C45 C46 120.8(3) . . ?
C44 C43 C42 119.9(3) . . ?
C43 C44 C45 120.3(2) . . ?
C26 C25 C24 119.7(2) . . ?
C25 C26 C21 120.9(2) . . ?
C23 C24 C25 119.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.049
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane, ethyl acetate'
_database_code_depnum_ccdc_archive 'CCDC 1009902'
