#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220738.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_2220738
loop_
_publ_author_name
'Kavitha, T.'
'Thenmozhi, M.'
'Gobi Rajeshwaran, G.'
'Mohanakrishnan, A. K.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 (E)-Methyl
 3-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)but-2-enoate
;
_journal_coeditor_code           CI2752
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o431
_journal_paper_doi               10.1107/S1600536809002931
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H19 N O4 S'
_chemical_formula_moiety         'C20 H19 N O4 S'
_chemical_formula_sum            'C20 H19 N O4 S'
_chemical_formula_weight         369.42
_chemical_name_systematic
;(E)-Methyl
 3-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)but-2-enoate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9498(3)
_cell_length_b                   8.8427(2)
_cell_length_c                   23.2836(7)
_cell_measurement_reflns_used    5673
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.3
_cell_volume                     1828.60(9)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23203
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9684
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.288
_refine_ls_extinction_coef       0.0057(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0625P)²+0.402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                3833
_reflns_number_total             5673
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2752.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220738
_cod_database_fobs_code          2220738
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.71830(17) 0.73053(17) 0.13969(7) 0.0461(3) Uani d . 1 . .
C C3 0.85936(15) 0.68775(16) 0.13101(6) 0.0406(3) Uani d . 1 . .
C C4 0.89541(15) 0.54808(16) 0.16149(6) 0.0408(3) Uani d . 1 . .
C C5 0.77241(15) 0.50989(17) 0.19043(6) 0.0430(3) Uani d . 1 . .
C C6 0.77105(19) 0.3804(2) 0.22371(7) 0.0587(4) Uani d . 1 . .
H H6 0.6889 0.3562 0.2428 0.070 Uiso calc R 1 . .
C C7 0.8966(2) 0.2887(2) 0.22744(8) 0.0703(5) Uani d . 1 . .
H H7 0.8983 0.2001 0.2490 0.084 Uiso calc R 1 . .
C C8 1.0202(2) 0.3256(2) 0.19985(9) 0.0682(5) Uani d . 1 . .
H H8 1.1036 0.2621 0.2036 0.082 Uiso calc R 1 . .
C C9 1.02144(17) 0.45440(19) 0.16699(7) 0.0546(4) Uani d . 1 . .
H H9 1.1050 0.4786 0.1487 0.065 Uiso calc R 1 . .
C C10 0.42383(15) 0.44900(18) 0.13523(7) 0.0462(3) Uani d . 1 . .
C C11 0.38591(18) 0.4876(2) 0.07757(7) 0.0550(4) Uani d . 1 . .
H H11 0.3946 0.5871 0.0655 0.066 Uiso calc R 1 . .
C C12 0.3352(2) 0.3766(2) 0.03848(9) 0.0702(5) Uani d . 1 . .
H H12 0.3097 0.4009 -0.0003 0.084 Uiso calc R 1 . .
C C13 0.3223(2) 0.2295(2) 0.05676(10) 0.0739(6) Uani d . 1 . .
H H13 0.2870 0.1553 0.0302 0.089 Uiso calc R 1 . .
C C14 0.3607(2) 0.1917(2) 0.11349(11) 0.0720(5) Uani d . 1 . .
H H14 0.3524 0.0919 0.1253 0.086 Uiso calc R 1 . .
C C15 0.41202(19) 0.3013(2) 0.15350(9) 0.0598(4) Uani d . 1 . .
H H15 0.4382 0.2760 0.1922 0.072 Uiso calc R 1 . .
C C16 0.6333(2) 0.8675(2) 0.11697(10) 0.0724(5) Uani d . 1 . .
H H16A 0.6151 0.9315 0.1487 0.109 Uiso calc R 1 . .
H H16B 0.5389 0.8374 0.0960 0.109 Uiso calc R 1 . .
H H16C 0.6911 0.9218 0.0916 0.109 Uiso calc R 1 . .
C C17 0.96483(16) 0.77322(16) 0.09861(6) 0.0430(3) Uani d . 1 . .
C C18 1.0118(2) 0.92731(19) 0.12070(8) 0.0648(5) Uani d . 1 . .
H H18A 1.1128 0.9231 0.1400 0.097 Uiso calc R 1 . .
H H18B 0.9452 0.9609 0.1474 0.097 Uiso calc R 1 . .
H H18C 1.0074 0.9967 0.0888 0.097 Uiso calc R 1 . .
C C19 1.01726(16) 0.70573(17) 0.05409(7) 0.0466(3) Uani d . 1 . .
H H19 0.9820 0.6090 0.0444 0.056 Uiso calc R 1 . .
C C20 1.12631(18) 0.77169(18) 0.01894(7) 0.0497(4) Uani d . 1 . .
C C21 1.2556(2) 0.7283(2) -0.06194(8) 0.0670(5) Uani d . 1 . .
H H21A 1.2073 0.7956 -0.0909 0.101 Uiso calc R 1 . .
H H21B 1.2938 0.6419 -0.0804 0.101 Uiso calc R 1 . .
H H21C 1.3373 0.7801 -0.0395 0.101 Uiso calc R 1 . .
N N1 0.66229(13) 0.62376(15) 0.17753(5) 0.0465(3) Uani d . 1 . .
O O1 0.48023(16) 0.53321(19) 0.24184(5) 0.0801(4) Uani d . 1 . .
O O2 0.40094(14) 0.72716(15) 0.16816(7) 0.0756(4) Uani d . 1 . .
O O3 1.1914(2) 0.88897(17) 0.02638(7) 0.0984(6) Uani d . 1 . .
O O4 1.14823(13) 0.67953(13) -0.02447(5) 0.0583(3) Uani d . 1 . .
S S1 0.48136(4) 0.59233(5) 0.185184(18) 0.05532(15) Uani d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 N1 . . 108.20(13) ?
C3 C2 C16 . . 128.09(15) ?
N1 C2 C16 . . 123.67(14) ?
C2 C3 C4 . . 108.77(12) ?
C2 C3 C17 . . 126.51(13) ?
C4 C3 C17 . . 124.64(12) ?
C9 C4 C5 . . 119.20(14) ?
C9 C4 C3 . . 133.22(14) ?
C5 C4 C3 . . 107.57(13) ?
C6 C5 C4 . . 122.05(14) ?
C6 C5 N1 . . 130.83(13) ?
C4 C5 N1 . . 107.12(13) ?
C7 C6 C5 . . 117.28(15) ?
C7 C6 H6 . . 121.4 ?
C5 C6 H6 . . 121.4 ?
C6 C7 C8 . . 121.55(17) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C9 C8 C7 . . 121.06(17) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C4 . . 118.85(15) ?
C8 C9 H9 . . 120.6 ?
C4 C9 H9 . . 120.6 ?
C15 C10 C11 . . 120.80(16) ?
C15 C10 S1 . . 120.41(13) ?
C11 C10 S1 . . 118.76(12) ?
C12 C11 C10 . . 119.07(17) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C12 C13 . . 120.15(19) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.61(19) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 120.24(18) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C10 C15 C14 . . 119.12(18) ?
C10 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C2 C16 H16A . . 109.5 ?
C2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C19 C17 C3 . . 118.34(13) ?
C19 C17 C18 . . 124.36(14) ?
C3 C17 C18 . . 117.20(13) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 C20 . . 125.32(14) ?
C17 C19 H19 . . 117.3 ?
C20 C19 H19 . . 117.3 ?
O3 C20 O4 . . 121.87(14) ?
O3 C20 C19 . . 127.63(15) ?
O4 C20 C19 . . 110.48(13) ?
O4 C21 H21A . . 109.5 ?
O4 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O4 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C5 N1 C2 . . 108.30(11) ?
C5 N1 S1 . . 121.12(10) ?
C2 N1 S1 . . 126.50(11) ?
C20 O4 C21 . . 116.60(13) ?
O1 S1 O2 . . 120.37(9) ?
O1 S1 N1 . . 106.13(7) ?
O2 S1 N1 . . 107.09(8) ?
O1 S1 C10 . . 108.35(9) ?
O2 S1 C10 . . 108.88(8) ?
N1 S1 C10 . . 104.96(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 C3 . 1.357(2) ?
C2 N1 . 1.4241(19) ?
C2 C16 . 1.493(2) ?
C3 C4 . 1.441(2) ?
C3 C17 . 1.4857(19) ?
C4 C9 . 1.393(2) ?
C4 C5 . 1.4012(19) ?
C5 C6 . 1.383(2) ?
C5 N1 . 1.415(2) ?
C6 C7 . 1.380(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.385(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.373(2) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
C10 C15 . 1.381(2) ?
C10 C11 . 1.386(2) ?
C10 S1 . 1.7540(16) ?
C11 C12 . 1.377(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.365(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 C19 . 1.331(2) ?
C17 C18 . 1.498(2) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 C20 . 1.470(2) ?
C19 H19 . 0.93 ?
C20 O3 . 1.1915(19) ?
C20 O4 . 1.3315(19) ?
C21 O4 . 1.4415(19) ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
N1 S1 . 1.6740(12) ?
O1 S1 . 1.4202(14) ?
O2 S1 . 1.4234(14) ?
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
C6 H6 O2 2_645 0.93 2.58 3.391(2) 146
C13 H13 O3 1_445 0.93 2.50 3.277(2) 141
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 C4 . . . . 2.26(16) ?
C16 C2 C3 C4 . . . . 179.74(16) ?
N1 C2 C3 C17 . . . . -174.38(13) ?
C16 C2 C3 C17 . . . . 3.1(3) ?
C2 C3 C4 C9 . . . . 179.15(16) ?
C17 C3 C4 C9 . . . . -4.1(3) ?
C2 C3 C4 C5 . . . . -1.70(16) ?
C17 C3 C4 C5 . . . . 175.01(13) ?
C9 C4 C5 C6 . . . . -1.0(2) ?
C3 C4 C5 C6 . . . . 179.68(14) ?
C9 C4 C5 N1 . . . . 179.72(13) ?
C3 C4 C5 N1 . . . . 0.44(15) ?
C4 C5 C6 C7 . . . . -0.1(2) ?
N1 C5 C6 C7 . . . . 178.98(16) ?
C5 C6 C7 C8 . . . . 1.0(3) ?
C6 C7 C8 C9 . . . . -0.9(3) ?
C7 C8 C9 C4 . . . . -0.3(3) ?
C5 C4 C9 C8 . . . . 1.2(2) ?
C3 C4 C9 C8 . . . . -179.75(17) ?
C15 C10 C11 C12 . . . . 0.4(2) ?
S1 C10 C11 C12 . . . . -177.57(14) ?
C10 C11 C12 C13 . . . . 0.2(3) ?
C11 C12 C13 C14 . . . . -0.6(3) ?
C12 C13 C14 C15 . . . . 0.6(3) ?
C11 C10 C15 C14 . . . . -0.4(2) ?
S1 C10 C15 C14 . . . . 177.49(13) ?
C13 C14 C15 C10 . . . . -0.1(3) ?
C2 C3 C17 C19 . . . . -122.74(17) ?
C4 C3 C17 C19 . . . . 61.1(2) ?
C2 C3 C17 C18 . . . . 60.7(2) ?
C4 C3 C17 C18 . . . . -115.44(17) ?
C3 C17 C19 C20 . . . . -177.59(14) ?
C18 C17 C19 C20 . . . . -1.3(3) ?
C17 C19 C20 O3 . . . . 5.1(3) ?
C17 C19 C20 O4 . . . . -176.02(15) ?
C6 C5 N1 C2 . . . . -178.24(16) ?
C4 C5 N1 C2 . . . . 0.92(15) ?
C6 C5 N1 S1 . . . . -19.6(2) ?
C4 C5 N1 S1 . . . . 159.59(10) ?
C3 C2 N1 C5 . . . . -2.00(16) ?
C16 C2 N1 C5 . . . . -179.62(15) ?
C3 C2 N1 S1 . . . . -159.21(11) ?
C16 C2 N1 S1 . . . . 23.2(2) ?
O3 C20 O4 C21 . . . . 0.4(3) ?
C19 C20 O4 C21 . . . . -178.62(15) ?
C5 N1 S1 O1 . . . . 50.95(13) ?
C2 N1 S1 O1 . . . . -154.49(13) ?
C5 N1 S1 O2 . . . . -179.29(11) ?
C2 N1 S1 O2 . . . . -24.73(14) ?
C5 N1 S1 C10 . . . . -63.66(12) ?
C2 N1 S1 C10 . . . . 90.89(13) ?
C15 C10 S1 O1 . . . . -11.22(15) ?
C11 C10 S1 O1 . . . . 166.71(12) ?
C15 C10 S1 O2 . . . . -143.79(13) ?
C11 C10 S1 O2 . . . . 34.14(14) ?
C15 C10 S1 N1 . . . . 101.83(13) ?
C11 C10 S1 N1 . . . . -80.24(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741651
