#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017535.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_2017535
loop_
_publ_author_name
'Becerra, Diana'
'Insuasty, Braulio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Hydrogen-bonding patterns in 3-alkyl-3-hydroxyindolin-2-ones
;
_journal_coeditor_code           SQ3233
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o79
_journal_page_last               o86
_journal_paper_doi               10.1107/S0108270110001058
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 N O3 S'
_chemical_formula_moiety         'C14 H11 N O3 S'
_chemical_formula_sum            'C14 H11 N O3 S'
_chemical_formula_weight         273.30
_chemical_name_systematic
;
3-hydroxy-3-(2-thienylcarbonylmethyl)indolin-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                78.51(2)
_cell_angle_beta                 76.555(13)
_cell_angle_gamma                84.559(15)
_cell_formula_units_Z            2
_cell_length_a                   6.5958(7)
_cell_length_b                   7.9577(14)
_cell_length_c                   12.045(3)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.28
_cell_volume                     601.8(2)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14010
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0450
_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)+(0.0487P)²+0.4932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1798
_reflns_number_total             2355
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3233.cif
_cod_data_source_block           VII
_cod_database_code               2017535
_cod_database_fobs_code          2017535
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.0025(3) 0.3142(2) 0.42275(17) 0.0200(4) Uani d . 1 . .
H H1 1.1019 0.3477 0.4499 0.024 Uiso calc R 1 . .
C C2 0.8172(3) 0.3972(3) 0.4230(2) 0.0210(5) Uani d . 1 . .
C C3 0.6810(3) 0.2928(3) 0.3776(2) 0.0193(5) Uani d . 1 . .
C C3a 0.8353(3) 0.1527(3) 0.3393(2) 0.0193(5) Uani d . 1 . .
C C4 0.8135(4) 0.0171(3) 0.2889(2) 0.0244(5) Uani d . 1 . .
H H4 0.6880 0.0061 0.2657 0.029 Uiso calc R 1 . .
C C5 0.9794(4) -0.1041(3) 0.2727(2) 0.0257(6) Uani d . 1 . .
H H5 0.9691 -0.1970 0.2358 0.031 Uiso calc R 1 . .
C C6 1.1574(4) -0.0898(3) 0.3097(2) 0.0250(6) Uani d . 1 . .
H H6 1.2674 -0.1753 0.2995 0.030 Uiso calc R 1 . .
C C7 1.1820(4) 0.0461(3) 0.3616(2) 0.0222(5) Uani d . 1 . .
H H7 1.3054 0.0553 0.3874 0.027 Uiso calc R 1 . .
C C7a 1.0186(3) 0.1660(3) 0.3735(2) 0.0196(5) Uani d . 1 . .
O O2 0.7576(2) 0.5298(2) 0.46143(15) 0.0237(4) Uani d . 1 . .
O O3 0.5315(2) 0.21687(19) 0.47558(14) 0.0219(4) Uani d . 1 . .
H H3 0.4640 0.2931 0.5071 0.033 Uiso d R 1 . .
C C31 0.5704(3) 0.4007(3) 0.2889(2) 0.0210(5) Uani d . 1 . .
H H31A 0.4999 0.3233 0.2567 0.025 Uiso calc R 1 . .
H H31B 0.4609 0.4756 0.3290 0.025 Uiso calc R 1 . .
C C32 0.7085(4) 0.5113(3) 0.1902(2) 0.0210(5) Uani d . 1 . .
O O32 0.8952(2) 0.5129(2) 0.18401(15) 0.0269(4) Uani d . 1 . .
S S321 0.75166(10) 0.75473(8) -0.00821(6) 0.0300(2) Uani d . 1 . .
C C322 0.6065(4) 0.6202(3) 0.1052(2) 0.0213(5) Uani d . 1 . .
C C323 0.3989(4) 0.6329(3) 0.0999(2) 0.0227(5) Uani d . 1 . .
H H323 0.2941 0.5674 0.1545 0.027 Uiso calc R 1 . .
C C324 0.3607(4) 0.7549(3) 0.0035(2) 0.0269(6) Uani d . 1 . .
H H324 0.2270 0.7815 -0.0141 0.032 Uiso calc R 1 . .
C C325 0.5370(4) 0.8295(3) -0.0608(2) 0.0300(6) Uani d . 1 . .
H H325 0.5400 0.9151 -0.1285 0.036 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'
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
C2 N1 C7a . . 111.20(19) ?
C2 N1 H1 . . 124.4 ?
C7a N1 H1 . . 124.4 ?
O2 C2 N1 . . 126.0(2) ?
O2 C2 C3 . . 124.7(2) ?
N1 C2 C3 . . 109.14(19) ?
O3 C3 C3a . . 107.73(17) ?
O3 C3 C31 . . 109.67(17) ?
C3a C3 C31 . . 117.8(2) ?
O3 C3 C2 . . 106.60(18) ?
C3a C3 C2 . . 101.11(17) ?
C31 C3 C2 . . 113.09(18) ?
C4 C3a C7a . . 120.0(2) ?
C4 C3a C3 . . 131.0(2) ?
C7a C3a C3 . . 108.8(2) ?
C3a C4 C5 . . 118.6(2) ?
C3a C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 122.0(2) ?
C5 C6 H6 . . 119.0 ?
C7 C6 H6 . . 119.0 ?
C7a C7 C6 . . 116.5(2) ?
C7a C7 H7 . . 121.8 ?
C6 C7 H7 . . 121.8 ?
C7 C7a C3a . . 122.7(2) ?
C7 C7a N1 . . 128.1(2) ?
C3a C7a N1 . . 109.22(19) ?
C3 O3 H3 . . 108.9 ?
C32 C31 C3 . . 115.01(18) ?
C32 C31 H31A . . 108.5 ?
C3 C31 H31A . . 108.5 ?
C32 C31 H31B . . 108.5 ?
C3 C31 H31B . . 108.5 ?
H31A C31 H31B . . 107.5 ?
O32 C32 C322 . . 122.1(2) ?
O32 C32 C31 . . 121.5(2) ?
C322 C32 C31 . . 116.4(2) ?
C325 S321 C322 . . 91.38(12) ?
C323 C322 C32 . . 129.0(2) ?
C323 C322 S321 . . 111.50(18) ?
C32 C322 S321 . . 119.49(17) ?
C322 C323 C324 . . 111.9(2) ?
C322 C323 H323 . . 124.0 ?
C324 C323 H323 . . 124.0 ?
C325 C324 C323 . . 112.2(2) ?
C325 C324 H324 . . 123.9 ?
C323 C324 H324 . . 123.9 ?
C324 C325 S321 . . 113.1(2) ?
C324 C325 H325 . . 123.5 ?
S321 C325 H325 . . 123.5 ?
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
N1 C2 . 1.333(3) ?
N1 C7a . 1.407(3) ?
N1 H1 . 0.8800 ?
C2 O2 . 1.230(3) ?
C2 C3 . 1.533(3) ?
C3 O3 . 1.420(3) ?
C3 C3a . 1.504(3) ?
C3 C31 . 1.514(3) ?
C3a C4 . 1.372(3) ?
C3a C7a . 1.385(3) ?
C4 C5 . 1.393(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.371(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.9500 ?
C7 C7a . 1.371(3) ?
C7 H7 . 0.9500 ?
O3 H3 . 0.8202 ?
C31 C32 . 1.500(3) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 O32 . 1.218(3) ?
C32 C322 . 1.452(3) ?
S321 C325 . 1.693(3) ?
S321 C322 . 1.713(2) ?
C322 C323 . 1.379(3) ?
C323 C324 . 1.412(3) ?
C323 H323 . 0.9500 ?
C324 C325 . 1.354(4) ?
C324 H324 . 0.9500 ?
C325 H325 . 0.9500 ?
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
N1 H1 O2 2_766 0.88 2.00 2.843(3) 160 no
O3 H3 O2 2_666 0.82 1.96 2.736(2) 158 no
C7 H7 O3 1_655 0.95 2.58 3.443(3) 151 no
C31 H31B O2 2_666 0.99 2.59 3.382(3) 137 no
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
C7a N1 C2 O2 . . . . 179.3(2) ?
C7a N1 C2 C3 . . . . 4.4(3) ?
O2 C2 C3 O3 . . . . -69.5(3) ?
N1 C2 C3 O3 . . . . 105.6(2) ?
O2 C2 C3 C3a . . . . 178.1(2) ?
N1 C2 C3 C3a . . . . -6.9(2) ?
O2 C2 C3 C31 . . . . 51.1(3) ?
N1 C2 C3 C31 . . . . -133.8(2) ?
O3 C3 C3a C4 . . . . 69.3(3) ?
C31 C3 C3a C4 . . . . -55.3(3) ?
C2 C3 C3a C4 . . . . -179.1(2) ?
O3 C3 C3a C7a . . . . -104.5(2) ?
C31 C3 C3a C7a . . . . 130.8(2) ?
C2 C3 C3a C7a . . . . 7.1(2) ?
C7a C3a C4 C5 . . . . -0.5(3) ?
C3 C3a C4 C5 . . . . -173.8(2) ?
C3a C4 C5 C6 . . . . 1.9(4) ?
C4 C5 C6 C7 . . . . -1.6(4) ?
C5 C6 C7 C7a . . . . -0.3(3) ?
C6 C7 C7a C3a . . . . 1.8(3) ?
C6 C7 C7a N1 . . . . 179.8(2) ?
C4 C3a C7a C7 . . . . -1.4(4) ?
C3 C3a C7a C7 . . . . 173.2(2) ?
C4 C3a C7a N1 . . . . -179.7(2) ?
C3 C3a C7a N1 . . . . -5.1(3) ?
C2 N1 C7a C7 . . . . -177.8(2) ?
C2 N1 C7a C3a . . . . 0.4(3) ?
O3 C3 C31 C32 . . . . 170.28(18) ?
C3a C3 C31 C32 . . . . -66.1(3) ?
C2 C3 C31 C32 . . . . 51.5(3) ?
C3 C31 C32 O32 . . . . -0.5(3) ?
C3 C31 C32 C322 . . . . -178.3(2) ?
O32 C32 C322 C323 . . . . 179.8(2) ?
C31 C32 C322 C323 . . . . -2.4(4) ?
O32 C32 C322 S321 . . . . 0.5(3) ?
C31 C32 C322 S321 . . . . 178.26(16) ?
C325 S321 C322 C323 . . . . 0.89(19) ?
C325 S321 C322 C32 . . . . -179.7(2) ?
C32 C322 C323 C324 . . . . 179.8(2) ?
S321 C322 C323 C324 . . . . -0.8(3) ?
C322 C323 C324 C325 . . . . 0.3(3) ?
C323 C324 C325 S321 . . . . 0.4(3) ?
C322 S321 C325 C324 . . . . -0.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2119256
