#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/11/2211165.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_2211165
loop_
_publ_author_name
'G. Senthil Kumar'
'K. Chinnakali'
'N. Ramesh'
'A. K. Mohanakrishnan'
'Hoong-Kun Fun'
_publ_section_title
;
 Methyl 2-bromomethyl-1-phenylsulfonyl-1H-indole-3-carboxylate
;
_journal_coeditor_code           OM2060
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5155
_journal_page_last               o5157
_journal_paper_doi               10.1107/S1600536806043339
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H14 Br N O4 S'
_chemical_formula_moiety         'C17 H14 Br N O4 S'
_chemical_formula_sum            'C17 H14 Br N O4 S'
_chemical_formula_weight         408.26
_chemical_name_systematic
;
Methyl 2-bromomethyl-1-phenylsulfonyl-1H-indole-3-carboxylate
;
_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                 91.4450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.22240(10)
_cell_length_b                   8.50860(10)
_cell_length_c                   19.1733(3)
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.23
_cell_volume                     1667.13(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area-detector'
_diffrn_measurement_method       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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24996
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  0.6479
_exptl_absorpt_correction_T_min  0.4183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.760
_refine_diff_density_min         -1.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0404
_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)+(0.0416P)²+1.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                3364
_reflns_number_total             4829
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2060.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211165
_cod_database_fobs_code          2211165
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
Br Br1 0.43367(3) 0.78735(5) 0.216437(15) 0.06933(13) Uani d . 1
S S1 0.77971(6) 0.96597(7) 0.12722(3) 0.04220(15) Uani d . 1
O O1 0.71352(18) 1.0338(2) 0.18415(10) 0.0604(5) Uani d . 1
O O2 0.86962(18) 1.0560(2) 0.08847(12) 0.0594(5) Uani d . 1
O O3 0.25951(19) 0.7708(3) 0.06201(11) 0.0633(5) Uani d . 1
O O4 0.32183(18) 0.6407(2) -0.03219(11) 0.0576(5) Uani d . 1
N N1 0.66307(17) 0.9055(2) 0.06938(9) 0.0355(4) Uani d . 1
C C1 0.5303(2) 0.8728(3) 0.08205(11) 0.0344(5) Uani d . 1
C C2 0.4811(2) 0.7838(3) 0.02826(12) 0.0360(5) Uani d . 1
C C3 0.5841(2) 0.7555(3) -0.02068(12) 0.0373(5) Uani d . 1
C C4 0.5902(3) 0.6749(3) -0.08410(13) 0.0484(6) Uani d . 1
H H4 0.5178 0.6212 -0.1022 0.058 Uiso calc R 1
C C5 0.7069(3) 0.6773(4) -0.11911(14) 0.0581(7) Uani d . 1
H H5 0.7127 0.6242 -0.1613 0.070 Uiso calc R 1
C C6 0.8153(3) 0.7572(4) -0.09268(15) 0.0562(7) Uani d . 1
H H6 0.8917 0.7576 -0.1180 0.067 Uiso calc R 1
C C7 0.8133(2) 0.8359(3) -0.03018(14) 0.0473(6) Uani d . 1
H H7 0.8866 0.8886 -0.0124 0.057 Uiso calc R 1
C C8 0.6954(2) 0.8330(3) 0.00557(12) 0.0366(5) Uani d . 1
C C9 0.8574(2) 0.7929(3) 0.15563(11) 0.0372(5) Uani d . 1
C C10 0.7934(3) 0.6924(4) 0.19928(14) 0.0539(7) Uani d . 1
H H10 0.7075 0.7123 0.2115 0.065 Uiso calc R 1
C C11 0.8585(3) 0.5614(4) 0.22483(16) 0.0653(9) Uani d . 1
H H11 0.8160 0.4919 0.2541 0.078 Uiso calc R 1
C C12 0.9861(3) 0.5334(4) 0.20708(14) 0.0583(7) Uani d . 1
H H12 1.0296 0.4452 0.2245 0.070 Uiso calc R 1
C C13 1.0491(3) 0.6346(4) 0.16417(15) 0.0559(7) Uani d . 1
H H13 1.1354 0.6149 0.1527 0.067 Uiso calc R 1
C C14 0.9861(2) 0.7657(3) 0.13754(14) 0.0455(6) Uani d . 1
H H14 1.0290 0.8344 0.1081 0.055 Uiso calc R 1
C C15 0.4569(2) 0.9399(3) 0.14088(12) 0.0420(5) Uani d . 1
H H15A 0.3717 0.9749 0.1238 0.050 Uiso calc R 1
H H15B 0.5036 1.0308 0.1592 0.050 Uiso calc R 1
C C16 0.3430(2) 0.7333(3) 0.02245(13) 0.0429(5) Uani d . 1
C C17 0.1896(3) 0.5808(4) -0.04044(19) 0.0713(9) Uani d . 1
H H17A 0.1827 0.5188 -0.0822 0.107 Uiso calc R 1
H H17B 0.1294 0.6672 -0.0437 0.107 Uiso calc R 1
H H17C 0.1693 0.5168 -0.0009 0.107 Uiso calc R 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'
Br Br -0.2901 2.4595 '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 120.64(13)
O2 S1 N1 106.04(11)
O1 S1 N1 106.64(10)
O2 S1 C9 108.76(11)
O1 S1 C9 108.85(12)
N1 S1 C9 104.75(10)
C16 O4 C17 115.4(2)
C1 N1 C8 108.00(18)
C1 N1 S1 127.81(15)
C8 N1 S1 121.57(14)
C2 C1 N1 108.45(19)
C2 C1 C15 127.2(2)
N1 C1 C15 124.1(2)
C1 C2 C3 108.8(2)
C1 C2 C16 123.5(2)
C3 C2 C16 127.7(2)
C8 C3 C4 119.4(2)
C8 C3 C2 106.7(2)
C4 C3 C2 133.9(2)
C5 C4 C3 118.2(3)
C5 C4 H4 120.9
C3 C4 H4 120.9
C4 C5 C6 121.4(3)
C4 C5 H5 119.3
C6 C5 H5 119.3
C7 C6 C5 121.9(3)
C7 C6 H6 119.0
C5 C6 H6 119.0
C6 C7 C8 116.7(2)
C6 C7 H7 121.6
C8 C7 H7 121.6
C3 C8 C7 122.3(2)
C3 C8 N1 108.08(19)
C7 C8 N1 129.6(2)
C10 C9 C14 121.1(2)
C10 C9 S1 119.58(18)
C14 C9 S1 119.13(19)
C9 C10 C11 119.1(2)
C9 C10 H10 120.5
C11 C10 H10 120.5
C12 C11 C10 120.1(3)
C12 C11 H11 119.9
C10 C11 H11 119.9
C13 C12 C11 120.3(3)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C14 120.7(2)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C9 118.6(2)
C13 C14 H14 120.7
C9 C14 H14 120.7
C1 C15 Br1 112.27(16)
C1 C15 H15A 109.2
Br1 C15 H15A 109.2
C1 C15 H15B 109.2
Br1 C15 H15B 109.2
H15A C15 H15B 107.9
O3 C16 O4 123.6(2)
O3 C16 C2 124.7(2)
O4 C16 C2 111.7(2)
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.964(2)
S1 O2 1.420(2)
S1 O1 1.4211(19)
S1 N1 1.6881(18)
S1 C9 1.753(2)
O3 C16 1.200(3)
O4 C16 1.325(3)
O4 C17 1.449(3)
N1 C1 1.413(3)
N1 C8 1.417(3)
C1 C2 1.365(3)
C1 C15 1.485(3)
C2 C3 1.448(3)
C2 C16 1.477(3)
C3 C8 1.398(3)
C3 C4 1.399(3)
C4 C5 1.383(4)
C4 H4 0.93
C5 C6 1.385(4)
C5 H5 0.93
C6 C7 1.373(4)
C6 H6 0.93
C7 C8 1.401(3)
C7 H7 0.93
C9 C10 1.373(4)
C9 C14 1.389(3)
C10 C11 1.381(4)
C10 H10 0.93
C11 C12 1.378(4)
C11 H11 0.93
C12 C13 1.363(4)
C12 H12 0.93
C13 C14 1.379(4)
C13 H13 0.93
C14 H14 0.93
C15 H15A 0.97
C15 H15B 0.97
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
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
C4 H4 O4 . 0.93 2.45 2.956(4) 115
C7 H7 O2 . 0.93 2.41 2.991(3) 120
C10 H10 Br1 . 0.93 2.87 3.787(3) 167
C13 H13 O3 1_655 0.93 2.55 3.165(4) 124
C14 H14 O2 . 0.93 2.51 2.889(3) 104
C15 H15A O3 . 0.97 2.38 2.877(3) 111
C15 H15B O1 . 0.97 2.19 2.846(3) 124
C17 H17B O2 3_675 0.96 2.51 3.277(4) 137
C15 H15A Cg1 3_675 0.97 2.72 3.432(3) 131
C17 H17A Cg3 3_665 0.96 2.66 3.573(4) 160
C17 H17C Cg1 3_665 0.96 2.88 3.581(4) 131
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
O2 S1 N1 C1 -150.96(19)
O1 S1 N1 C1 -21.2(2)
C9 S1 N1 C1 94.1(2)
O2 S1 N1 C8 49.7(2)
O1 S1 N1 C8 179.40(18)
C9 S1 N1 C8 -65.29(19)
C8 N1 C1 C2 -0.2(2)
S1 N1 C1 C2 -161.79(17)
C8 N1 C1 C15 -174.6(2)
S1 N1 C1 C15 23.8(3)
N1 C1 C2 C3 0.6(3)
C15 C1 C2 C3 174.8(2)
N1 C1 C2 C16 -177.2(2)
C15 C1 C2 C16 -3.0(4)
C1 C2 C3 C8 -0.9(3)
C16 C2 C3 C8 176.9(2)
C1 C2 C3 C4 -179.4(3)
C16 C2 C3 C4 -1.7(4)
C8 C3 C4 C5 -1.0(4)
C2 C3 C4 C5 177.4(3)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 C7 1.0(5)
C5 C6 C7 C8 -0.6(4)
C4 C3 C8 C7 1.4(4)
C2 C3 C8 C7 -177.4(2)
C4 C3 C8 N1 179.5(2)
C2 C3 C8 N1 0.7(2)
C6 C7 C8 C3 -0.6(4)
C6 C7 C8 N1 -178.3(2)
C1 N1 C8 C3 -0.4(2)
S1 N1 C8 C3 162.62(16)
C1 N1 C8 C7 177.6(2)
S1 N1 C8 C7 -19.4(3)
O2 S1 C9 C10 174.6(2)
O1 S1 C9 C10 41.4(2)
N1 S1 C9 C10 -72.4(2)
O2 S1 C9 C14 -0.8(2)
O1 S1 C9 C14 -134.0(2)
N1 S1 C9 C14 112.2(2)
C14 C9 C10 C11 -0.7(4)
S1 C9 C10 C11 -176.0(2)
C9 C10 C11 C12 0.6(5)
C10 C11 C12 C13 -0.1(5)
C11 C12 C13 C14 -0.4(5)
C12 C13 C14 C9 0.3(4)
C10 C9 C14 C13 0.2(4)
S1 C9 C14 C13 175.6(2)
C2 C1 C15 Br1 83.2(3)
N1 C1 C15 Br1 -103.5(2)
C17 O4 C16 O3 -2.2(4)
C17 O4 C16 C2 177.8(2)
C1 C2 C16 O3 3.6(4)
C3 C2 C16 O3 -173.8(3)
C1 C2 C16 O4 -176.3(2)
C3 C2 C16 O4 6.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9878917
