#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017531.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_2017531
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 F N O3'
_chemical_formula_moiety         'C16 H12 F N O3'
_chemical_formula_sum            'C16 H12 F N O3'
_chemical_formula_weight         285.27
_chemical_name_systematic
;
3-hydroxy-3-[(4-fluorobenzoyl)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                98.229(7)
_cell_angle_beta                 103.667(7)
_cell_angle_gamma                96.034(9)
_cell_formula_units_Z            2
_cell_length_a                   6.8858(7)
_cell_length_b                   7.7074(8)
_cell_length_c                   12.7010(9)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.70
_cell_volume                     641.43(11)
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0412
_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            15674
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0533
_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)+(0.0718P)²+0.3321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                1664
_reflns_number_total             2528
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3233.cif
_cod_data_source_block           III
_cod_original_cell_volume        641.43(10)
_cod_database_code               2017531
_cod_database_fobs_code          2017531
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 0.0665(3) 0.3209(2) 0.57578(16) 0.0224(5) Uani d . 1 . .
H H1 -0.0489 0.3608 0.5540 0.027 Uiso calc R 1 . .
C C2 0.2446(4) 0.4007(3) 0.57078(19) 0.0222(5) Uani d . 1 . .
C C3 0.4086(3) 0.2876(3) 0.61206(19) 0.0228(5) Uani d . 1 . .
C C3a 0.2888(4) 0.1426(3) 0.64738(19) 0.0229(5) Uani d . 1 . .
C C4 0.3438(4) -0.0031(3) 0.6909(2) 0.0263(6) Uani d . 1 . .
H H4 0.4815 -0.0205 0.7098 0.032 Uiso calc R 1 . .
C C5 0.1951(4) -0.1246(3) 0.7069(2) 0.0285(6) Uani d . 1 . .
H H5 0.2310 -0.2254 0.7379 0.034 Uiso calc R 1 . .
C C6 -0.0051(4) -0.1001(3) 0.6779(2) 0.0267(6) Uani d . 1 . .
H H6 -0.1050 -0.1856 0.6889 0.032 Uiso calc R 1 . .
C C7 -0.0643(4) 0.0454(3) 0.63341(19) 0.0246(6) Uani d . 1 . .
H H7 -0.2022 0.0615 0.6131 0.030 Uiso calc R 1 . .
C C7a 0.0861(4) 0.1654(3) 0.62006(18) 0.0219(5) Uani d . 1 . .
O O2 0.2742(2) 0.5356(2) 0.53256(13) 0.0266(4) Uani d . 1 . .
O O3 0.4692(2) 0.2111(2) 0.51872(13) 0.0241(4) Uani d . 1 . .
H H3 0.5364 0.2907 0.5008 0.036 Uiso d R 1 . .
C C31 0.5908(3) 0.3927(3) 0.69646(19) 0.0231(5) Uani d . 1 . .
H H31A 0.6845 0.3096 0.7220 0.028 Uiso calc R 1 . .
H H31B 0.6612 0.4749 0.6597 0.028 Uiso calc R 1 . .
C C32 0.5497(3) 0.4983(3) 0.7951(2) 0.0222(5) Uani d . 1 . .
O O32 0.3775(2) 0.5030(2) 0.80313(14) 0.0295(4) Uani d . 1 . .
C C321 0.7247(4) 0.5995(3) 0.88164(19) 0.0232(5) Uani d . 1 . .
C C322 0.9199(4) 0.6077(3) 0.8692(2) 0.0251(6) Uani d . 1 . .
H H322 0.9440 0.5450 0.8046 0.030 Uiso calc R 1 . .
C C323 1.0783(4) 0.7057(3) 0.9494(2) 0.0281(6) Uani d . 1 . .
H H323 1.2120 0.7133 0.9407 0.034 Uiso calc R 1 . .
C C324 1.0393(4) 0.7919(3) 1.0418(2) 0.0296(6) Uani d . 1 . .
F F34 1.1973(2) 0.8857(2) 1.12187(12) 0.0411(4) Uani d . 1 . .
C C325 0.8506(4) 0.7859(3) 1.0593(2) 0.0324(6) Uani d . 1 . .
H H325 0.8291 0.8462 1.1253 0.039 Uiso calc R 1 . .
C C326 0.6933(4) 0.6889(3) 0.9776(2) 0.0291(6) Uani d . 1 . .
H H326 0.5601 0.6830 0.9870 0.035 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'
F F 0.0171 0.0103 '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 . . 111.5(2) ?
C2 N1 H1 . . 124.3 ?
C7a N1 H1 . . 124.3 ?
O2 C2 N1 . . 126.4(2) ?
O2 C2 C3 . . 124.5(2) ?
N1 C2 C3 . . 108.9(2) ?
O3 C3 C3a . . 107.67(18) ?
O3 C3 C31 . . 109.31(18) ?
C3a C3 C31 . . 117.5(2) ?
O3 C3 C2 . . 106.85(18) ?
C3a C3 C2 . . 101.44(18) ?
C31 C3 C2 . . 113.37(19) ?
C4 C3a C7a . . 119.7(2) ?
C4 C3a C3 . . 131.6(2) ?
C7a C3a C3 . . 108.5(2) ?
C3a C4 C5 . . 118.8(2) ?
C3a C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C6 C5 C4 . . 120.4(2) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 121.8(2) ?
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 . . 122.5(2) ?
C7 C7a N1 . . 128.0(2) ?
C3a C7a N1 . . 109.4(2) ?
C3 O3 H3 . . 107.0 ?
C32 C31 C3 . . 116.11(19) ?
C32 C31 H31A . . 108.3 ?
C3 C31 H31A . . 108.3 ?
C32 C31 H31B . . 108.3 ?
C3 C31 H31B . . 108.3 ?
H31A C31 H31B . . 107.4 ?
O32 C32 C321 . . 121.2(2) ?
O32 C32 C31 . . 120.9(2) ?
C321 C32 C31 . . 118.0(2) ?
C322 C321 C326 . . 118.8(2) ?
C322 C321 C32 . . 121.7(2) ?
C326 C321 C32 . . 119.5(2) ?
C323 C322 C321 . . 120.5(2) ?
C323 C322 H322 . . 119.8 ?
C321 C322 H322 . . 119.8 ?
C324 C323 C322 . . 118.4(2) ?
C324 C323 H323 . . 120.8 ?
C322 C323 H323 . . 120.8 ?
F34 C324 C323 . . 118.1(2) ?
F34 C324 C325 . . 118.3(2) ?
C323 C324 C325 . . 123.6(2) ?
C324 C325 C326 . . 117.3(2) ?
C324 C325 H325 . . 121.4 ?
C326 C325 H325 . . 121.4 ?
C325 C326 C321 . . 121.4(2) ?
C325 C326 H326 . . 119.3 ?
C321 C326 H326 . . 119.3 ?
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 . 1.400(3) ?
N1 H1 . 0.8800 ?
C2 O2 . 1.227(3) ?
C2 C3 . 1.539(3) ?
C3 O3 . 1.419(3) ?
C3 C3a . 1.501(3) ?
C3 C31 . 1.511(3) ?
C3a C4 . 1.371(3) ?
C3a C7a . 1.393(3) ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.381(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.383(3) ?
C6 H6 . 0.9500 ?
C7 C7a . 1.372(3) ?
C7 H7 . 0.9500 ?
O3 H3 . 0.8203 ?
C31 C32 . 1.495(3) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 O32 . 1.217(3) ?
C32 C321 . 1.483(3) ?
C321 C322 . 1.386(3) ?
C321 C326 . 1.387(3) ?
C322 C323 . 1.371(4) ?
C322 H322 . 0.9500 ?
C323 C324 . 1.362(4) ?
C323 H323 . 0.9500 ?
C324 F34 . 1.357(3) ?
C324 C325 . 1.366(4) ?
C325 C326 . 1.373(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 1.99 2.842(2) 163 no
O3 H3 O2 2_666 0.82 1.93 2.746(2) 172 no
C325 H325 Cg1 2_677 0.95 2.69 3.614(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 . . . . 177.4(2) ?
C7a N1 C2 C3 . . . . 2.2(3) ?
O2 C2 C3 O3 . . . . -66.8(3) ?
N1 C2 C3 O3 . . . . 108.6(2) ?
O2 C2 C3 C3a . . . . -179.4(2) ?
N1 C2 C3 C3a . . . . -4.1(2) ?
O2 C2 C3 C31 . . . . 53.7(3) ?
N1 C2 C3 C31 . . . . -131.0(2) ?
O3 C3 C3a C4 . . . . 67.2(3) ?
C31 C3 C3a C4 . . . . -56.6(3) ?
C2 C3 C3a C4 . . . . 179.2(2) ?
O3 C3 C3a C7a . . . . -107.4(2) ?
C31 C3 C3a C7a . . . . 128.7(2) ?
C2 C3 C3a C7a . . . . 4.6(2) ?
C7a C3a C4 C5 . . . . -0.1(3) ?
C3 C3a C4 C5 . . . . -174.3(2) ?
C3a C4 C5 C6 . . . . 0.9(3) ?
C4 C5 C6 C7 . . . . -0.6(4) ?
C5 C6 C7 C7a . . . . -0.5(3) ?
C6 C7 C7a C3a . . . . 1.3(3) ?
C6 C7 C7a N1 . . . . 179.0(2) ?
C4 C3a C7a C7 . . . . -1.0(4) ?
C3 C3a C7a C7 . . . . 174.4(2) ?
C4 C3a C7a N1 . . . . -179.1(2) ?
C3 C3a C7a N1 . . . . -3.7(3) ?
C2 N1 C7a C7 . . . . -177.0(2) ?
C2 N1 C7a C3a . . . . 0.9(3) ?
O3 C3 C31 C32 . . . . 173.64(18) ?
C3a C3 C31 C32 . . . . -63.4(3) ?
C2 C3 C31 C32 . . . . 54.6(3) ?
C3 C31 C32 O32 . . . . -2.9(3) ?
C3 C31 C32 C321 . . . . 178.3(2) ?
O32 C32 C321 C322 . . . . -174.3(2) ?
C31 C32 C321 C322 . . . . 4.6(3) ?
O32 C32 C321 C326 . . . . 5.5(3) ?
C31 C32 C321 C326 . . . . -175.6(2) ?
C326 C321 C322 C323 . . . . -1.4(4) ?
C32 C321 C322 C323 . . . . 178.5(2) ?
C321 C322 C323 C324 . . . . 1.0(4) ?
C322 C323 C324 F34 . . . . 178.7(2) ?
C322 C323 C324 C325 . . . . 0.2(4) ?
F34 C324 C325 C326 . . . . -179.5(2) ?
C323 C324 C325 C326 . . . . -0.9(4) ?
C324 C325 C326 C321 . . . . 0.6(4) ?
C322 C321 C326 C325 . . . . 0.6(4) ?
C32 C321 C326 C325 . . . . -179.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 319350
