#------------------------------------------------------------------------------
#$Date: 2017-03-05 09:41:37 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/55/1545502.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_1545502
loop_
_publ_author_name
'Yadav, C. Suresh'
'Viswanathan, Vijayan'
'Kannadasan, Sathananthan'
'Velmurugan, Devadasan'
_publ_section_title
;
 N-[(3-Bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-4-fluoroaniline
;
_journal_coeditor_code           SU4110
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x170147
_journal_paper_doi               10.1107/S241431461700147X
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C21 H16 Br F N2 O2 S'
_chemical_formula_moiety         'C21 H16 Br F N2 O2 S'
_chemical_formula_sum            'C21 H16 Br F N2 O2 S'
_chemical_formula_weight         459.33
_chemical_name_systematic
;
N-[(3-Bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-4-fluoroaniline
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                113.6990(10)
_cell_angle_beta                 94.6170(10)
_cell_angle_gamma                99.2030(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1732(5)
_cell_length_b                   10.5828(7)
_cell_length_c                   12.1781(8)
_cell_measurement_reflns_used    4427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.263
_cell_measurement_theta_min      2.150
_cell_volume                     939.81(11)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
PLATON (Spek, 2009) and SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11107
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.263
_diffrn_reflns_theta_min         2.150
_exptl_absorpt_coefficient_mu    2.328
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+0.1305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                3778
_reflns_number_total             4427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4110sup1.cif
_cod_data_source_block           I
_cod_database_code               1545502
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.605
_shelx_estimated_absorpt_t_max   0.768
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
C C1 1.0439(3) 0.3846(2) 0.3063(2) 0.0524(5) Uani d 1
C C2 0.8963(3) 0.4075(2) 0.3480(2) 0.0510(5) Uani d 1
H H2 0.870710 0.391539 0.415005 0.061 Uiso calc 1
C C3 0.7849(3) 0.4548(2) 0.2890(2) 0.0466(4) Uani d 1
H H3 0.684493 0.471193 0.317208 0.056 Uiso calc 1
C C4 0.8213(3) 0.47778(19) 0.18896(17) 0.0433(4) Uani d 1
C C5 0.9754(3) 0.4538(3) 0.1506(2) 0.0599(6) Uani d 1
H H5 1.003760 0.470852 0.084643 0.072 Uiso calc 1
C C6 1.0853(3) 0.4057(3) 0.2082(2) 0.0613(6) Uani d 1
H H6 1.185730 0.387984 0.180567 0.074 Uiso calc 1
C C7 0.5735(3) 0.5820(2) 0.17222(19) 0.0491(5) Uani d 1
H H7A 0.507416 0.521160 0.201672 0.059 Uiso calc 1
H H7B 0.500965 0.587821 0.108060 0.059 Uiso calc 1
C C8 0.6282(2) 0.7267(2) 0.27416(17) 0.0395(4) Uani d 1
C C9 0.6028(2) 0.7717(2) 0.39091(18) 0.0401(4) Uani d 1
C C10 0.6911(2) 0.9145(2) 0.46065(17) 0.0396(4) Uani d 1
C C11 0.7743(2) 0.9561(2) 0.38144(16) 0.0378(4) Uani d 1
C C12 0.8800(3) 1.0883(2) 0.4218(2) 0.0476(5) Uani d 1
H H12 0.936670 1.115759 0.369150 0.057 Uiso calc 1
C C13 0.8966(3) 1.1766(2) 0.5435(2) 0.0562(5) Uani d 1
H H13 0.966282 1.265694 0.572957 0.067 Uiso calc 1
C C14 0.8138(3) 1.1379(2) 0.6233(2) 0.0559(5) Uani d 1
H H14 0.827849 1.201048 0.704601 0.067 Uiso calc 1
C C15 0.7107(3) 1.0068(2) 0.58341(18) 0.0488(5) Uani d 1
H H15 0.655233 0.980097 0.636937 0.059 Uiso calc 1
C C16 0.5460(2) 0.9385(2) 0.13481(16) 0.0372(4) Uani d 1
C C17 0.5621(3) 1.0827(2) 0.1861(2) 0.0470(4) Uani d 1
H H17 0.667034 1.142071 0.220819 0.056 Uiso calc 1
C C18 0.4198(3) 1.1384(2) 0.1854(2) 0.0524(5) Uani d 1
H H18 0.428905 1.235653 0.220589 0.063 Uiso calc 1
C C19 0.2653(3) 1.0502(2) 0.1329(2) 0.0493(5) Uani d 1
H H19 0.170302 1.088132 0.132396 0.059 Uiso calc 1
C C20 0.2503(3) 0.9069(3) 0.0815(2) 0.0528(5) Uani d 1
H H20 0.145091 0.848001 0.046733 0.063 Uiso calc 1
C C21 0.3913(3) 0.8489(2) 0.08082(19) 0.0476(4) Uani d 1
H H21 0.381825 0.751566 0.044744 0.057 Uiso calc 1
N N1 0.7090(2) 0.51720(19) 0.12096(15) 0.0522(4) Uani d 1
H H1 0.721138 0.502532 0.047600 0.063 Uiso calc 1
N N2 0.73770(19) 0.83989(17) 0.26447(13) 0.0383(3) Uani d 1
O O1 0.87084(18) 0.9732(2) 0.15578(15) 0.0572(4) Uani d 1
O O2 0.6999(2) 0.73241(18) 0.03837(13) 0.0560(4) Uani d 1
F F1 1.1535(2) 0.33908(19) 0.36508(16) 0.0767(4) Uani d 1
S S1 0.72622(6) 0.86853(6) 0.13829(4) 0.04184(12) Uani d 1
Br BR1 0.47945(3) 0.66201(3) 0.45649(2) 0.05848(10) 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'
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'
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
C6 C1 F1 118.9(2)
C6 C1 C2 122.2(2)
F1 C1 C2 118.9(2)
C1 C2 C3 119.1(2)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 120.8(2)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 117.71(19)
C3 C4 N1 123.4(2)
C5 C4 N1 118.8(2)
C6 C5 C4 121.6(2)
C6 C5 H5 119.2
C4 C5 H5 119.2
C1 C6 C5 118.5(2)
C1 C6 H6 120.7
C5 C6 H6 120.7
N1 C7 C8 114.88(17)
N1 C7 H7A 108.5
C8 C7 H7A 108.5
N1 C7 H7B 108.5
C8 C7 H7B 108.5
H7A C7 H7B 107.5
C9 C8 N2 107.46(17)
C9 C8 C7 128.96(19)
N2 C8 C7 123.22(18)
C8 C9 C10 110.49(17)
C8 C9 BR1 125.55(16)
C10 C9 BR1 123.88(14)
C11 C10 C15 120.12(19)
C11 C10 C9 106.54(16)
C15 C10 C9 133.28(19)
C12 C11 C10 121.47(18)
C12 C11 N2 130.41(18)
C10 C11 N2 108.01(16)
C13 C12 C11 116.9(2)
C13 C12 H12 121.6
C11 C12 H12 121.6
C14 C13 C12 122.5(2)
C14 C13 H13 118.7
C12 C13 H13 118.7
C15 C14 C13 120.5(2)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C10 118.5(2)
C14 C15 H15 120.7
C10 C15 H15 120.7
C17 C16 C21 121.15(18)
C17 C16 S1 118.91(15)
C21 C16 S1 119.94(15)
C16 C17 C18 119.11(19)
C16 C17 H17 120.4
C18 C17 H17 120.4
C19 C18 C17 120.2(2)
C19 C18 H18 119.9
C17 C18 H18 119.9
C20 C19 C18 120.40(19)
C20 C19 H19 119.8
C18 C19 H19 119.8
C19 C20 C21 120.4(2)
C19 C20 H20 119.8
C21 C20 H20 119.8
C16 C21 C20 118.8(2)
C16 C21 H21 120.6
C20 C21 H21 120.6
C4 N1 C7 121.22(18)
C4 N1 H1 119.4
C7 N1 H1 119.4
C11 N2 C8 107.49(15)
C11 N2 S1 120.22(13)
C8 N2 S1 122.79(13)
O1 S1 O2 119.87(10)
O1 S1 N2 106.12(9)
O2 S1 N2 106.04(9)
O1 S1 C16 109.28(10)
O2 S1 C16 109.01(9)
N2 S1 C16 105.53(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.360(4)
C1 F1 1.363(3)
C1 C2 1.366(3)
C2 C3 1.387(3)
C2 H2 0.9300
C3 C4 1.380(3)
C3 H3 0.9300
C4 C5 1.403(3)
C4 N1 1.407(3)
C5 C6 1.374(3)
C5 H5 0.9300
C6 H6 0.9300
C7 N1 1.449(3)
C7 C8 1.500(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.351(3)
C8 N2 1.427(3)
C9 C10 1.431(3)
C9 BR1 1.8712(19)
C10 C11 1.392(3)
C10 C15 1.397(3)
C11 C12 1.392(3)
C11 N2 1.427(2)
C12 C13 1.379(3)
C12 H12 0.9300
C13 C14 1.381(4)
C13 H13 0.9300
C14 C15 1.375(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.376(3)
C16 C21 1.383(3)
C16 S1 1.7562(18)
C17 C18 1.386(3)
C17 H17 0.9300
C18 C19 1.374(3)
C18 H18 0.9300
C19 C20 1.368(3)
C19 H19 0.9300
C20 C21 1.389(3)
C20 H20 0.9300
C21 H21 0.9300
N1 H1 0.8600
N2 S1 1.6799(15)
O1 S1 1.4215(17)
O2 S1 1.4324(17)
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
C3 H3 Br1 . 0.93 2.92 3.765(2) 151
C12 H12 O1 . 0.93 2.38 2.957(3) 120
C13 H13 Cg2 2_776 0.93 2.90 3.8382(3) 151
C15 H15 Cg4 2_676 0.93 2.72 3.6522(2) 154
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
C6 C1 C2 C3 -0.5(3)
F1 C1 C2 C3 179.51(19)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 -1.0(3)
C2 C3 C4 N1 175.91(18)
C3 C4 C5 C6 1.6(3)
N1 C4 C5 C6 -175.4(2)
F1 C1 C6 C5 -178.9(2)
C2 C1 C6 C5 1.0(4)
C4 C5 C6 C1 -1.6(4)
N1 C7 C8 C9 -118.5(2)
N1 C7 C8 N2 53.7(3)
N2 C8 C9 C10 0.9(2)
C7 C8 C9 C10 174.02(18)
N2 C8 C9 BR1 -176.08(12)
C7 C8 C9 BR1 -3.0(3)
C8 C9 C10 C11 -0.5(2)
BR1 C9 C10 C11 176.56(13)
C8 C9 C10 C15 -177.6(2)
BR1 C9 C10 C15 -0.6(3)
C15 C10 C11 C12 0.9(3)
C9 C10 C11 C12 -176.67(17)
C15 C10 C11 N2 177.44(16)
C9 C10 C11 N2 -0.15(19)
C10 C11 C12 C13 -0.8(3)
N2 C11 C12 C13 -176.45(18)
C11 C12 C13 C14 0.1(3)
C12 C13 C14 C15 0.5(3)
C13 C14 C15 C10 -0.4(3)
C11 C10 C15 C14 -0.3(3)
C9 C10 C15 C14 176.5(2)
C21 C16 C17 C18 1.2(3)
S1 C16 C17 C18 -178.91(17)
C16 C17 C18 C19 -0.7(3)
C17 C18 C19 C20 0.3(3)
C18 C19 C20 C21 -0.5(4)
C17 C16 C21 C20 -1.4(3)
S1 C16 C21 C20 178.72(17)
C19 C20 C21 C16 1.1(3)
C3 C4 N1 C7 21.2(3)
C5 C4 N1 C7 -162.0(2)
C8 C7 N1 C4 66.9(3)
C12 C11 N2 C8 176.79(19)
C10 C11 N2 C8 0.68(19)
C12 C11 N2 S1 -36.0(3)
C10 C11 N2 S1 147.90(13)
C9 C8 N2 C11 -0.97(19)
C7 C8 N2 C11 -174.58(16)
C9 C8 N2 S1 -147.16(14)
C7 C8 N2 S1 39.2(2)
C11 N2 S1 O1 47.52(16)
C8 N2 S1 O1 -170.39(15)
C11 N2 S1 O2 176.02(14)
C8 N2 S1 O2 -41.89(17)
C11 N2 S1 C16 -68.41(15)
C8 N2 S1 C16 73.69(16)
C17 C16 S1 O1 -20.95(18)
C21 C16 S1 O1 158.89(16)
C17 C16 S1 O2 -153.69(16)
C21 C16 S1 O2 26.15(18)
C17 C16 S1 N2 92.79(16)
C21 C16 S1 N2 -87.37(17)

_cod_database_fobs_code 1545502
