#------------------------------------------------------------------------------
#$Date: 2022-04-23 04:57:50 +0300 (Sat, 23 Apr 2022) $
#$Revision: 274655 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566848.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_1566848
loop_
_publ_author_name
'Pineda, Leslie W.'
'Ferllini, Natasha'
'Cabezas, Jorge A.'
_publ_section_title
;
 1-(Phenylsulfonyl)-1H-indole-2-carbaldehyde
;
_journal_coeditor_code           HB4405
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x220401
_journal_paper_doi               10.1107/S2414314622004011
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C15 H11 N O3 S'
_chemical_formula_moiety         'C15 H11 N O3 S'
_chemical_formula_sum            'C15 H11 N O3 S'
_chemical_formula_weight         285.31
_chemical_name_systematic
;
1-(Phenylsulfonyl)-1H-indole-2-carbaldehyde
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 105.374(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6886(7)
_cell_length_b                   9.2655(6)
_cell_length_c                   11.6024(7)
_cell_measurement_reflns_used    3972
_cell_measurement_temperature    273.(2)
_cell_measurement_theta_max      23.7525
_cell_measurement_theta_min      2.7577
_cell_volume                     1315.24(14)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      273.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18696
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.76
_diffrn_source                   'Incoatec Microsource'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0479
_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)+(0.0529P)²+0.1517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1791
_reflns_number_total             3032
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4405sup1.cif
_cod_data_source_block           I
_cod_database_code               1566848
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.26292(4) 0.67883(6) 0.70277(4) 0.0461(2) Uani d 1 . .
O O1 0.03455(14) 0.88036(19) 0.38393(17) 0.0771(5) Uani d 1 . .
O O2 0.23104(12) 0.82550(16) 0.70663(14) 0.0621(5) Uani d 1 . .
O O3 0.27691(13) 0.58878(18) 0.80466(12) 0.0645(5) Uani d 1 . .
N N1 0.16726(12) 0.60075(18) 0.59334(13) 0.0407(4) Uani d 1 . .
C C1 0.11260(15) 0.6739(2) 0.48512(18) 0.0421(5) Uani d 1 . .
C C2 0.08938(16) 0.5776(2) 0.39588(18) 0.0447(5) Uani d 1 . .
H H2 0.0523 0.5978 0.317 0.054 Uiso calc 1 . .
C C3 0.13005(15) 0.4395(2) 0.44002(17) 0.0400(5) Uani d 1 . .
C C4 0.12749(18) 0.3046(3) 0.3870(2) 0.0537(6) Uani d 1 . .
H H4 0.0946 0.2926 0.3058 0.064 Uiso calc 1 . .
C C5 0.17400(19) 0.1897(3) 0.4559(2) 0.0599(7) Uani d 1 . .
H H5 0.1735 0.0992 0.4211 0.072 Uiso calc 1 . .
C C6 0.2220(2) 0.2070(2) 0.5775(2) 0.0595(6) Uani d 1 . .
H H6 0.2527 0.1272 0.6226 0.071 Uiso calc 1 . .
C C7 0.22548(18) 0.3386(2) 0.63281(19) 0.0519(6) Uani d 1 . .
H H7 0.2578 0.3491 0.7142 0.062 Uiso calc 1 . .
C C8 0.17904(15) 0.4546(2) 0.56285(17) 0.0384(5) Uani d 1 . .
C C9 0.07306(18) 0.8234(3) 0.4781(2) 0.0586(6) Uani d 1 . .
H H9 0.0781 0.8747 0.5483 0.07 Uiso calc 1 . .
C C10 0.39626(19) 0.7687(2) 0.5702(2) 0.0523(6) Uani d 1 . .
H H10 0.3429 0.8375 0.5392 0.063 Uiso calc 1 . .
C C11 0.4910(2) 0.7626(3) 0.5327(2) 0.0670(7) Uani d 1 . .
H H11 0.5014 0.8276 0.4756 0.08 Uiso calc 1 . .
C C12 0.5693(2) 0.6617(3) 0.5788(2) 0.0704(8) Uani d 1 . .
H H12 0.633 0.6591 0.5537 0.084 Uiso calc 1 . .
C C13 0.55456(19) 0.5649(3) 0.6616(2) 0.0672(7) Uani d 1 . .
H H13 0.6078 0.4958 0.692 0.081 Uiso calc 1 . .
C C14 0.46101(18) 0.5694(2) 0.70013(19) 0.0538(6) Uani d 1 . .
H H14 0.451 0.5038 0.7569 0.065 Uiso calc 1 . .
C C15 0.38264(15) 0.6712(2) 0.65436(16) 0.0385(5) 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
O3 S1 O2 . . 120.63(10) n
O3 S1 N1 . . 106.48(9) n
O2 S1 N1 . . 106.40(9) n
O3 S1 C15 . . 108.37(10) n
O2 S1 C15 . . 109.04(10) n
N1 S1 C15 . . 104.80(8) n
C8 N1 C1 . . 106.96(15) n
C8 N1 S1 . . 119.99(13) n
C1 N1 S1 . . 123.09(14) n
C2 C1 N1 . . 108.53(18) ?
C2 C1 C9 . . 125.7(2) ?
N1 C1 C9 . . 125.00(19) ?
C1 C2 C3 . . 109.67(18) ?
C1 C2 H2 . . 125.2 ?
C3 C2 H2 . . 125.2 ?
C4 C3 C8 . . 119.5(2) ?
C4 C3 C2 . . 133.3(2) ?
C8 C3 C2 . . 107.27(18) ?
C5 C4 C3 . . 119.0(2) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
C4 C5 C6 . . 120.6(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C7 C6 C5 . . 121.9(2) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 117.4(2) ?
C6 C7 H7 . . 121.3 ?
C8 C7 H7 . . 121.3 ?
C7 C8 C3 . . 121.63(19) ?
C7 C8 N1 . . 130.82(18) ?
C3 C8 N1 . . 107.53(17) ?
O1 C9 C1 . . 121.2(2) ?
O1 C9 H9 . . 119.4 ?
C1 C9 H9 . . 119.4 ?
C15 C10 C11 . . 118.7(2) ?
C15 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
C12 C11 C10 . . 120.5(2) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C13 C12 C11 . . 120.4(2) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 119.6(2) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C10 . . 120.8(2) ?
C14 C15 S1 . . 120.28(17) ?
C10 C15 S1 . . 118.89(16) ?
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
S1 O3 . 1.4191(15) n
S1 O2 . 1.4220(16) n
S1 N1 . 1.6708(16) n
S1 C15 . 1.755(2) n
O1 C9 . 1.195(3) ?
N1 C8 . 1.417(2) ?
N1 C1 . 1.434(2) ?
C1 C2 . 1.339(3) ?
C1 C9 . 1.468(3) ?
C2 C3 . 1.423(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.390(3) ?
C3 C8 . 1.403(3) ?
C4 C5 . 1.367(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.373(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.382(3) ?
C7 H7 . 0.93 ?
C9 H9 . 0.93 ?
C10 C15 . 1.375(3) ?
C10 C11 . 1.384(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.366(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.362(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.376(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.371(3) ?
C14 H14 . 0.93 ?
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
_geom_hbond_publ_flag
C7 H7 O3 . 0.93 2.44 3.014(3) 120 y
C9 H9 O2 . 0.93 2.34 2.869(3) 116 y
C4 H4 O1 2_545 0.93 2.51 3.343(3) 150 y
C12 H12 Cg2 3_666 0.93 2.71 3.638(3) 174 y
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
O3 S1 N1 C8 . . . . -53.53(16) ?
O2 S1 N1 C8 . . . . 176.62(14) ?
C15 S1 N1 C8 . . . . 61.18(16) ?
O3 S1 N1 C1 . . . . 165.38(15) ?
O2 S1 N1 C1 . . . . 35.52(17) ?
C15 S1 N1 C1 . . . . -79.91(16) ?
C8 N1 C1 C2 . . . . 2.0(2) ?
S1 N1 C1 C2 . . . . 147.38(14) ?
C8 N1 C1 C9 . . . . 172.76(18) ?
S1 N1 C1 C9 . . . . -41.9(3) ?
N1 C1 C2 C3 . . . . -1.7(2) ?
C9 C1 C2 C3 . . . . -172.36(19) ?
C1 C2 C3 C4 . . . . 179.4(2) ?
C1 C2 C3 C8 . . . . 0.7(2) ?
C8 C3 C4 C5 . . . . -0.7(3) ?
C2 C3 C4 C5 . . . . -179.1(2) ?
C3 C4 C5 C6 . . . . 0.7(3) ?
C4 C5 C6 C7 . . . . -0.4(4) ?
C5 C6 C7 C8 . . . . 0.0(3) ?
C6 C7 C8 C3 . . . . 0.1(3) ?
C6 C7 C8 N1 . . . . 178.25(19) ?
C4 C3 C8 C7 . . . . 0.3(3) ?
C2 C3 C8 C7 . . . . 179.11(18) ?
C4 C3 C8 N1 . . . . -178.29(17) ?
C2 C3 C8 N1 . . . . 0.5(2) ?
C1 N1 C8 C7 . . . . -179.9(2) ?
S1 N1 C8 C7 . . . . 33.4(3) ?
C1 N1 C8 C3 . . . . -1.55(19) ?
S1 N1 C8 C3 . . . . -148.17(13) ?
C2 C1 C9 O1 . . . . -15.8(3) ?
N1 C1 C9 O1 . . . . 175.04(19) ?
C15 C10 C11 C12 . . . . -0.2(4) ?
C10 C11 C12 C13 . . . . 0.7(4) ?
C11 C12 C13 C14 . . . . -0.7(4) ?
C12 C13 C14 C15 . . . . 0.4(4) ?
C13 C14 C15 C10 . . . . 0.1(3) ?
C13 C14 C15 S1 . . . . -179.84(17) ?
C11 C10 C15 C14 . . . . -0.2(3) ?
C11 C10 C15 S1 . . . . 179.77(17) ?
O3 S1 C15 C14 . . . . 11.35(19) ?
O2 S1 C15 C14 . . . . 144.39(17) ?
N1 S1 C15 C14 . . . . -102.03(17) ?
O3 S1 C15 C10 . . . . -168.59(16) ?
O2 S1 C15 C10 . . . . -35.55(19) ?
N1 S1 C15 C10 . . . . 78.03(18) ?

_cod_database_fobs_code 1566848
