#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017530.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_2017530
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          'C17 H15 N O3'
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_chemical_name_systematic
;
3-hydroxy-3-[(4-methylbenzoyl)methyl]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                99.48(2)
_cell_angle_beta                 101.68(3)
_cell_angle_gamma                96.33(2)
_cell_formula_units_Z            2
_cell_length_a                   6.873(2)
_cell_length_b                   7.6700(17)
_cell_length_c                   13.394(5)
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.72
_cell_volume                     674.4(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0881
_diffrn_reflns_av_sigmaI/netI    0.0609
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15497
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0620
_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)+(0.0779P)²+0.3503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                1783
_reflns_number_total             2520
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3233.cif
_cod_data_source_block           II
_cod_database_code               2017530
_cod_database_fobs_code          2017530
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 0.0627(3) 0.3203(3) 0.57141(17) 0.0215(5) Uani d . 1 . .
H H1 -0.0521 0.3582 0.5504 0.026 Uiso calc R 1 . .
C C2 0.2392(4) 0.4009(3) 0.5669(2) 0.0199(6) Uani d . 1 . .
C C3 0.4019(4) 0.2903(3) 0.6046(2) 0.0195(6) Uani d . 1 . .
C C3a 0.2815(4) 0.1467(3) 0.6389(2) 0.0199(6) Uani d . 1 . .
C C4 0.3367(4) 0.0028(3) 0.6808(2) 0.0232(6) Uani d . 1 . .
H H4 0.4739 -0.0132 0.6973 0.028 Uiso calc R 1 . .
C C5 0.1888(4) -0.1184(4) 0.6983(2) 0.0266(7) Uani d . 1 . .
H H5 0.2246 -0.2167 0.7292 0.032 Uiso calc R 1 . .
C C6 -0.0094(4) -0.0972(3) 0.6714(2) 0.0256(7) Uani d . 1 . .
H H6 -0.1092 -0.1828 0.6830 0.031 Uiso calc R 1 . .
C C7 -0.0681(4) 0.0460(3) 0.6277(2) 0.0229(6) Uani d . 1 . .
H H7 -0.2055 0.0597 0.6083 0.028 Uiso calc R 1 . .
C C7a 0.0811(4) 0.1661(3) 0.6141(2) 0.0199(6) Uani d . 1 . .
O O2 0.2693(3) 0.5361(2) 0.52997(14) 0.0237(5) Uani d . 1 . .
O O3 0.4674(3) 0.2124(2) 0.51594(14) 0.0235(5) Uani d . 1 . .
H H3 0.5354 0.2918 0.4957 0.035 Uiso d R 1 . .
C C31 0.5790(4) 0.4009(3) 0.6840(2) 0.0222(6) Uani d . 1 . .
H H31A 0.6779 0.3210 0.7035 0.027 Uiso calc R 1 . .
H H31B 0.6435 0.4898 0.6503 0.027 Uiso calc R 1 . .
C C32 0.5359(4) 0.4987(3) 0.7816(2) 0.0205(6) Uani d . 1 . .
O O32 0.3636(3) 0.5034(2) 0.78916(15) 0.0285(5) Uani d . 1 . .
C C321 0.7069(4) 0.5905(3) 0.8661(2) 0.0216(6) Uani d . 1 . .
C C322 0.9024(4) 0.6020(3) 0.8533(2) 0.0239(6) Uani d . 1 . .
H H322 0.9289 0.5461 0.7897 0.029 Uiso calc R 1 . .
C C323 1.0577(4) 0.6935(4) 0.9317(2) 0.0263(7) Uani d . 1 . .
H H323 1.1908 0.7013 0.9213 0.032 Uiso calc R 1 . .
C C324 1.0251(4) 0.7747(3) 1.0259(2) 0.0244(7) Uani d . 1 . .
C C325 0.8302(4) 0.7590(4) 1.0393(2) 0.0275(7) Uani d . 1 . .
H H325 0.8042 0.8112 1.1038 0.033 Uiso calc R 1 . .
C C326 0.6748(4) 0.6695(3) 0.9611(2) 0.0263(7) Uani d . 1 . .
H H326 0.5419 0.6610 0.9719 0.032 Uiso calc R 1 . .
C C327 1.1965(4) 0.8748(4) 1.1100(2) 0.0320(7) Uani d . 1 . .
H H32A 1.3216 0.8330 1.0991 0.048 Uiso calc R 1 . .
H H32B 1.1745 0.8543 1.1775 0.048 Uiso calc R 1 . .
H H32C 1.2059 1.0028 1.1088 0.048 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'
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 . . 111.3(2) ?
C2 N1 H1 . . 124.3 ?
C7a N1 H1 . . 124.3 ?
O2 C2 N1 . . 125.9(2) ?
O2 C2 C3 . . 124.4(2) ?
N1 C2 C3 . . 109.4(2) ?
O3 C3 C3a . . 108.5(2) ?
O3 C3 C31 . . 109.6(2) ?
C3a C3 C31 . . 117.3(2) ?
O3 C3 C2 . . 107.0(2) ?
C3a C3 C2 . . 101.0(2) ?
C31 C3 C2 . . 112.9(2) ?
C4 C3a C7a . . 119.7(2) ?
C4 C3a C3 . . 131.1(2) ?
C7a C3a C3 . . 109.0(2) ?
C3a C4 C5 . . 118.7(3) ?
C3a C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C6 C5 C4 . . 120.3(3) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 121.7(3) ?
C5 C6 H6 . . 119.1 ?
C7 C6 H6 . . 119.1 ?
C7a C7 C6 . . 116.7(2) ?
C7a C7 H7 . . 121.6 ?
C6 C7 H7 . . 121.6 ?
C7 C7a C3a . . 122.8(2) ?
C7 C7a N1 . . 128.1(2) ?
C3a C7a N1 . . 109.1(2) ?
C3 O3 H3 . . 109.5 ?
C32 C31 C3 . . 116.8(2) ?
C32 C31 H31A . . 108.1 ?
C3 C31 H31A . . 108.1 ?
C32 C31 H31B . . 108.1 ?
C3 C31 H31B . . 108.1 ?
H31A C31 H31B . . 107.3 ?
O32 C32 C321 . . 121.6(3) ?
O32 C32 C31 . . 120.0(2) ?
C321 C32 C31 . . 118.4(2) ?
C322 C321 C326 . . 118.1(3) ?
C322 C321 C32 . . 121.6(2) ?
C326 C321 C32 . . 120.3(2) ?
C323 C322 C321 . . 120.4(3) ?
C323 C322 H322 . . 119.8 ?
C321 C322 H322 . . 119.8 ?
C322 C323 C324 . . 121.4(3) ?
C322 C323 H323 . . 119.3 ?
C324 C323 H323 . . 119.3 ?
C325 C324 C323 . . 118.0(3) ?
C325 C324 C327 . . 121.5(3) ?
C323 C324 C327 . . 120.5(3) ?
C326 C325 C324 . . 120.7(3) ?
C326 C325 H325 . . 119.6 ?
C324 C325 H325 . . 119.6 ?
C325 C326 C321 . . 121.3(3) ?
C325 C326 H326 . . 119.4 ?
C321 C326 H326 . . 119.4 ?
C324 C327 H32A . . 109.5 ?
C324 C327 H32B . . 109.5 ?
H32A C327 H32B . . 109.5 ?
C324 C327 H32C . . 109.5 ?
H32A C327 H32C . . 109.5 ?
H32B C327 H32C . . 109.5 ?
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 . 1.317(3) ?
N1 C7a . 1.402(3) ?
N1 H1 . 0.8800 ?
C2 O2 . 1.235(3) ?
C2 C3 . 1.532(4) ?
C3 O3 . 1.418(3) ?
C3 C3a . 1.493(4) ?
C3 C31 . 1.511(4) ?
C3a C4 . 1.374(3) ?
C3a C7a . 1.380(4) ?
C4 C5 . 1.384(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.372(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.388(4) ?
C6 H6 . 0.9500 ?
C7 C7a . 1.363(4) ?
C7 H7 . 0.9500 ?
O3 H3 . 0.8400 ?
C31 C32 . 1.498(4) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 O32 . 1.212(3) ?
C32 C321 . 1.475(4) ?
C321 C322 . 1.384(4) ?
C321 C326 . 1.387(4) ?
C322 C323 . 1.368(4) ?
C322 H322 . 0.9500 ?
C323 C324 . 1.384(4) ?
C323 H323 . 0.9500 ?
C324 C325 . 1.383(4) ?
C324 C327 . 1.492(4) ?
C325 C326 . 1.363(4) ?
C325 H325 . 0.9500 ?
C326 H326 . 0.9500 ?
C327 H32A . 0.9800 ?
C327 H32B . 0.9800 ?
C327 H32C . 0.9800 ?
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_566 0.88 1.99 2.838(3) 162 no
O3 H3 O2 2_666 0.84 1.90 2.729(3) 169 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 . . . . 177.5(2) ?
C7a N1 C2 C3 . . . . 3.2(3) ?
O2 C2 C3 O3 . . . . -66.1(3) ?
N1 C2 C3 O3 . . . . 108.3(2) ?
O2 C2 C3 C3a . . . . -179.4(2) ?
N1 C2 C3 C3a . . . . -5.1(3) ?
O2 C2 C3 C31 . . . . 54.5(3) ?
N1 C2 C3 C31 . . . . -131.1(2) ?
O3 C3 C3a C4 . . . . 67.6(4) ?
C31 C3 C3a C4 . . . . -57.1(4) ?
C2 C3 C3a C4 . . . . 179.8(3) ?
O3 C3 C3a C7a . . . . -107.1(2) ?
C31 C3 C3a C7a . . . . 128.2(2) ?
C2 C3 C3a C7a . . . . 5.2(3) ?
C7a C3a C4 C5 . . . . -0.9(4) ?
C3 C3a C4 C5 . . . . -175.1(3) ?
C3a C4 C5 C6 . . . . 1.9(4) ?
C4 C5 C6 C7 . . . . -1.1(4) ?
C5 C6 C7 C7a . . . . -0.8(4) ?
C6 C7 C7a C3a . . . . 1.9(4) ?
C6 C7 C7a N1 . . . . 179.5(3) ?
C4 C3a C7a C7 . . . . -1.1(4) ?
C3 C3a C7a C7 . . . . 174.3(2) ?
C4 C3a C7a N1 . . . . -179.1(2) ?
C3 C3a C7a N1 . . . . -3.7(3) ?
C2 N1 C7a C7 . . . . -177.6(3) ?
C2 N1 C7a C3a . . . . 0.3(3) ?
O3 C3 C31 C32 . . . . 178.0(2) ?
C3a C3 C31 C32 . . . . -57.9(3) ?
C2 C3 C31 C32 . . . . 58.9(3) ?
C3 C31 C32 O32 . . . . -8.3(3) ?
C3 C31 C32 C321 . . . . 172.9(2) ?
O32 C32 C321 C322 . . . . -172.7(2) ?
C31 C32 C321 C322 . . . . 6.1(3) ?
O32 C32 C321 C326 . . . . 6.8(4) ?
C31 C32 C321 C326 . . . . -174.4(2) ?
C326 C321 C322 C323 . . . . -1.8(4) ?
C32 C321 C322 C323 . . . . 177.7(2) ?
C321 C322 C323 C324 . . . . 0.8(4) ?
C322 C323 C324 C325 . . . . 0.9(4) ?
C322 C323 C324 C327 . . . . -179.6(2) ?
C323 C324 C325 C326 . . . . -1.5(4) ?
C327 C324 C325 C326 . . . . 179.0(2) ?
C324 C325 C326 C321 . . . . 0.4(4) ?
C322 C321 C326 C325 . . . . 1.2(4) ?
C32 C321 C326 C325 . . . . -178.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 289032
2 PubChem 680788
