#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017532.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_2017532
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          'C16 H12 Cl N O3'
_chemical_formula_moiety         'C16 H12 Cl N O3'
_chemical_formula_sum            'C16 H12 Cl N O3'
_chemical_formula_weight         301.72
_chemical_name_systematic
;
3-hydroxy-3-[(4-chlorobenzoyl)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                99.30(3)
_cell_angle_beta                 101.82(4)
_cell_angle_gamma                96.33(3)
_cell_formula_units_Z            2
_cell_length_a                   6.987(2)
_cell_length_b                   7.689(4)
_cell_length_c                   12.907(4)
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.08
_cell_volume                     662.4(5)
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0404
_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       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2604
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.397
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0431
_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)+(0.0495P)²+0.4161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                2051
_reflns_number_total             2604
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3233.cif
_cod_data_source_block           IV
_cod_database_code               2017532
_cod_database_fobs_code          2017532
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 0.0637(3) 0.3242(2) 0.57555(15) 0.0198(4) Uani d . 1 . .
H H1 -0.0486 0.3652 0.5571 0.024 Uiso calc R 1 . .
C C2 0.2389(3) 0.4025(3) 0.56735(18) 0.0187(5) Uani d . 1 . .
C C3 0.3969(3) 0.2882(3) 0.60392(18) 0.0182(5) Uani d . 1 . .
C C3a 0.2787(3) 0.1435(3) 0.63915(18) 0.0195(5) Uani d . 1 . .
C C4 0.3314(4) -0.0039(3) 0.67840(18) 0.0219(5) Uani d . 1 . .
H H4 0.4654 -0.0236 0.6918 0.026 Uiso calc R 1 . .
C C5 0.1862(4) -0.1234(3) 0.69815(19) 0.0241(5) Uani d . 1 . .
H H5 0.2208 -0.2246 0.7272 0.029 Uiso calc R 1 . .
C C6 -0.0086(4) -0.0960(3) 0.67581(19) 0.0238(5) Uani d . 1 . .
H H6 -0.1066 -0.1792 0.6898 0.029 Uiso calc R 1 . .
C C7 -0.0648(3) 0.0495(3) 0.63360(18) 0.0218(5) Uani d . 1 . .
H H7 -0.1994 0.0665 0.6165 0.026 Uiso calc R 1 . .
C C7a 0.0821(3) 0.1679(3) 0.61746(17) 0.0191(5) Uani d . 1 . .
O O2 0.2681(2) 0.5370(2) 0.52970(13) 0.0219(4) Uani d . 1 . .
O O3 0.4575(2) 0.2122(2) 0.51023(12) 0.0210(4) Uani d . 1 . .
H H3 0.5498 0.2915 0.5020 0.032 Uiso d R 1 . .
C C31 0.5768(3) 0.3936(3) 0.68514(18) 0.0201(5) Uani d . 1 . .
H H31A 0.6705 0.3103 0.7047 0.024 Uiso calc R 1 . .
H H31B 0.6426 0.4799 0.6496 0.024 Uiso calc R 1 . .
C C32 0.5399(3) 0.4941(3) 0.78720(19) 0.0200(5) Uani d . 1 . .
O O32 0.3728(2) 0.5017(2) 0.79844(13) 0.0268(4) Uani d . 1 . .
C C321 0.7157(3) 0.5886(3) 0.87034(18) 0.0199(5) Uani d . 1 . .
C C322 0.9053(4) 0.5893(3) 0.85359(19) 0.0223(5) Uani d . 1 . .
H H322 0.9243 0.5245 0.7882 0.027 Uiso calc R 1 . .
C C323 1.0668(4) 0.6823(3) 0.9300(2) 0.0240(5) Uani d . 1 . .
H H323 1.1962 0.6835 0.9175 0.029 Uiso calc R 1 . .
C C324 1.0370(4) 0.7728(3) 1.02429(19) 0.0228(5) Uani d . 1 . .
Cl Cl34 1.24115(9) 0.88843(8) 1.11917(5) 0.03051(19) Uani d . 1 . .
C C325 0.8504(4) 0.7723(3) 1.0448(2) 0.0258(5) Uani d . 1 . .
H H325 0.8327 0.8346 1.1112 0.031 Uiso calc R 1 . .
C C326 0.6909(4) 0.6798(3) 0.96712(19) 0.0243(5) Uani d . 1 . .
H H326 0.5617 0.6784 0.9801 0.029 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'
Cl Cl 0.1484 0.1585 '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 . . 111.1(2) ?
C2 N1 H1 . . 124.4 ?
C7a N1 H1 . . 124.4 ?
O2 C2 N1 . . 126.0(2) ?
O2 C2 C3 . . 125.0(2) ?
N1 C2 C3 . . 108.88(19) ?
O3 C3 C3a . . 108.34(18) ?
O3 C3 C31 . . 108.62(18) ?
C3a C3 C31 . . 117.46(19) ?
O3 C3 C2 . . 106.75(18) ?
C3a C3 C2 . . 101.63(18) ?
C31 C3 C2 . . 113.39(19) ?
C4 C3a C7a . . 119.8(2) ?
C4 C3a C3 . . 131.3(2) ?
C7a C3a C3 . . 108.7(2) ?
C3a C4 C5 . . 118.9(2) ?
C3a C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C6 C5 C4 . . 120.1(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 121.6(2) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C7a C7 C6 . . 117.0(2) ?
C7a C7 H7 . . 121.5 ?
C6 C7 H7 . . 121.5 ?
C7 C7a C3a . . 122.4(2) ?
C7 C7a N1 . . 128.0(2) ?
C3a C7a N1 . . 109.5(2) ?
C3 O3 H3 . . 105.8 ?
C32 C31 C3 . . 116.39(19) ?
C32 C31 H31A . . 108.2 ?
C3 C31 H31A . . 108.2 ?
C32 C31 H31B . . 108.2 ?
C3 C31 H31B . . 108.2 ?
H31A C31 H31B . . 107.3 ?
O32 C32 C321 . . 122.2(2) ?
O32 C32 C31 . . 120.8(2) ?
C321 C32 C31 . . 117.0(2) ?
C326 C321 C322 . . 118.7(2) ?
C326 C321 C32 . . 119.6(2) ?
C322 C321 C32 . . 121.7(2) ?
C323 C322 C321 . . 121.2(2) ?
C323 C322 H322 . . 119.4 ?
C321 C322 H322 . . 119.4 ?
C324 C323 C322 . . 118.6(2) ?
C324 C323 H323 . . 120.7 ?
C322 C323 H323 . . 120.7 ?
C323 C324 C325 . . 121.9(2) ?
C323 C324 Cl34 . . 118.0(2) ?
C325 C324 Cl34 . . 120.2(2) ?
C326 C325 C324 . . 118.6(2) ?
C326 C325 H325 . . 120.7 ?
C324 C325 H325 . . 120.7 ?
C325 C326 C321 . . 121.0(2) ?
C325 C326 H326 . . 119.5 ?
C321 C326 H326 . . 119.5 ?
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 . 1.336(3) ?
N1 C7a . 1.403(3) ?
N1 H1 . 0.8800 ?
C2 O2 . 1.227(3) ?
C2 C3 . 1.532(3) ?
C3 O3 . 1.421(3) ?
C3 C3a . 1.497(3) ?
C3 C31 . 1.516(3) ?
C3a C4 . 1.370(3) ?
C3a C7a . 1.384(3) ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.381(3) ?
C6 H6 . 0.9500 ?
C7 C7a . 1.367(3) ?
C7 H7 . 0.9500 ?
O3 H3 . 0.8726 ?
C31 C32 . 1.501(3) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 O32 . 1.212(3) ?
C32 C321 . 1.483(3) ?
C321 C326 . 1.384(3) ?
C321 C322 . 1.385(3) ?
C322 C323 . 1.376(3) ?
C322 H322 . 0.9500 ?
C323 C324 . 1.368(4) ?
C323 H323 . 0.9500 ?
C324 C325 . 1.382(4) ?
C324 Cl34 . 1.726(3) ?
C325 C326 . 1.375(4) ?
C325 H325 . 0.9500 ?
C326 H326 . 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_566 0.88 2.00 2.843(3) 160 no
O3 H3 O2 2_666 0.87 1.88 2.752(3) 174 no
C31 H31B O2 2_666 0.99 2.50 3.276(3) 135 no
C323 H323 O32 1_655 0.95 2.51 3.281(4) 138 no
C325 H325 Cg1 2_667 0.95 2.97 3.890(3) 164 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 . . . . 177.1(2) ?
C7a N1 C2 C3 . . . . 1.8(3) ?
O2 C2 C3 O3 . . . . -65.3(3) ?
N1 C2 C3 O3 . . . . 110.0(2) ?
O2 C2 C3 C3a . . . . -178.7(2) ?
N1 C2 C3 C3a . . . . -3.4(2) ?
O2 C2 C3 C31 . . . . 54.3(3) ?
N1 C2 C3 C31 . . . . -130.4(2) ?
O3 C3 C3a C4 . . . . 66.2(3) ?
C31 C3 C3a C4 . . . . -57.3(3) ?
C2 C3 C3a C4 . . . . 178.4(2) ?
O3 C3 C3a C7a . . . . -108.4(2) ?
C31 C3 C3a C7a . . . . 128.2(2) ?
C2 C3 C3a C7a . . . . 3.8(2) ?
C7a C3a C4 C5 . . . . -1.6(3) ?
C3 C3a C4 C5 . . . . -175.7(2) ?
C3a C4 C5 C6 . . . . 1.7(4) ?
C4 C5 C6 C7 . . . . 0.0(4) ?
C5 C6 C7 C7a . . . . -1.6(3) ?
C6 C7 C7a C3a . . . . 1.7(3) ?
C6 C7 C7a N1 . . . . 179.7(2) ?
C4 C3a C7a C7 . . . . -0.1(4) ?
C3 C3a C7a C7 . . . . 175.2(2) ?
C4 C3a C7a N1 . . . . -178.4(2) ?
C3 C3a C7a N1 . . . . -3.1(3) ?
C2 N1 C7a C7 . . . . -177.4(2) ?
C2 N1 C7a C3a . . . . 0.8(3) ?
O3 C3 C31 C32 . . . . 176.17(17) ?
C3a C3 C31 C32 . . . . -60.5(3) ?
C2 C3 C31 C32 . . . . 57.7(3) ?
C3 C31 C32 O32 . . . . -6.3(3) ?
C3 C31 C32 C321 . . . . 176.27(19) ?
O32 C32 C321 C326 . . . . 4.1(3) ?
C31 C32 C321 C326 . . . . -178.5(2) ?
O32 C32 C321 C322 . . . . -175.4(2) ?
C31 C32 C321 C322 . . . . 2.0(3) ?
C326 C321 C322 C323 . . . . -1.6(3) ?
C32 C321 C322 C323 . . . . 177.9(2) ?
C321 C322 C323 C324 . . . . 0.9(4) ?
C322 C323 C324 C325 . . . . 0.4(4) ?
C322 C323 C324 Cl34 . . . . 179.96(18) ?
C323 C324 C325 C326 . . . . -0.9(4) ?
Cl34 C324 C325 C326 . . . . 179.56(18) ?
C324 C325 C326 C321 . . . . 0.1(4) ?
C322 C321 C326 C325 . . . . 1.1(3) ?
C32 C321 C326 C325 . . . . -178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 289030
