#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017533.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_2017533
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 Br N O3'
_chemical_formula_moiety         'C16 H12 Br N O3'
_chemical_formula_sum            'C16 H12 Br N O3'
_chemical_formula_weight         346.18
_chemical_name_systematic
;
3-[(4-bromobenzoyl)methyl]-3-hydroxyindolin-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                99.69(3)
_cell_angle_beta                 101.51(4)
_cell_angle_gamma                96.70(3)
_cell_formula_units_Z            2
_cell_length_a                   7.016(3)
_cell_length_b                   7.7349(12)
_cell_length_c                   13.052(6)
_cell_measurement_reflns_used    2800
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.70
_cell_volume                     675.8(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  0.0751
_diffrn_reflns_av_sigmaI/netI    0.0515
_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            18834
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_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    3.051
_exptl_absorpt_correction_T_max  0.553
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.728
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0399
_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)+(0.0368P)²+0.5649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                2215
_reflns_number_total             2800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3233.cif
_cod_data_source_block           V
_cod_original_cell_volume        675.8(4)
_cod_database_code               2017533
_cod_database_fobs_code          2017533
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 0.0634(4) 0.3254(3) 0.5748(2) 0.0164(6) Uani d . 1 . .
H H1 -0.0485 0.3656 0.5572 0.020 Uiso calc R 1 . .
C C2 0.2370(5) 0.4033(4) 0.5659(2) 0.0156(7) Uani d . 1 . .
C C3 0.3941(5) 0.2896(4) 0.6001(2) 0.0156(6) Uani d . 1 . .
C C3a 0.2761(5) 0.1450(4) 0.6348(2) 0.0162(7) Uani d . 1 . .
C C4 0.3294(5) -0.0031(4) 0.6718(2) 0.0175(7) Uani d . 1 . .
H H4 0.4619 -0.0243 0.6820 0.021 Uiso calc R 1 . .
C C5 0.1851(5) -0.1201(4) 0.6938(3) 0.0204(7) Uani d . 1 . .
H H5 0.2196 -0.2201 0.7225 0.025 Uiso calc R 1 . .
C C6 -0.0073(5) -0.0928(4) 0.6743(3) 0.0213(7) Uani d . 1 . .
H H6 -0.1044 -0.1755 0.6891 0.026 Uiso calc R 1 . .
C C7 -0.0637(5) 0.0520(4) 0.6337(2) 0.0190(7) Uani d . 1 . .
H H7 -0.1976 0.0691 0.6186 0.023 Uiso calc R 1 . .
C C7a 0.0825(4) 0.1698(4) 0.6163(2) 0.0152(6) Uani d . 1 . .
O O2 0.2665(3) 0.5371(3) 0.52888(17) 0.0188(5) Uani d . 1 . .
O O3 0.4545(3) 0.2144(3) 0.50721(16) 0.0172(5) Uani d . 1 . .
H H3 0.5298 0.2904 0.4862 0.026 Uiso d R 1 . .
C C31 0.5741(4) 0.3945(4) 0.6810(2) 0.0163(7) Uani d . 1 . .
H H31A 0.6667 0.3113 0.6992 0.020 Uiso calc R 1 . .
H H31B 0.6402 0.4810 0.6464 0.020 Uiso calc R 1 . .
C C32 0.5389(5) 0.4934(4) 0.7827(2) 0.0177(7) Uani d . 1 . .
O O32 0.3737(3) 0.5021(3) 0.79489(18) 0.0242(5) Uani d . 1 . .
C C321 0.7157(5) 0.5854(4) 0.8656(2) 0.0180(7) Uani d . 1 . .
C C322 0.9027(5) 0.5873(4) 0.8470(3) 0.0205(7) Uani d . 1 . .
H H322 0.9199 0.5252 0.7811 0.025 Uiso calc R 1 . .
C C323 1.0650(5) 0.6781(4) 0.9229(3) 0.0204(7) Uani d . 1 . .
H H323 1.1935 0.6796 0.9097 0.025 Uiso calc R 1 . .
C C324 1.0375(5) 0.7661(4) 1.0177(3) 0.0203(7) Uani d . 1 . .
Br Br34 1.26306(5) 0.88941(4) 1.11883(3) 0.02613(13) Uani d . 1 . .
C C325 0.8537(5) 0.7636(4) 1.0397(3) 0.0225(7) Uani d . 1 . .
H H325 0.8376 0.8232 1.1065 0.027 Uiso calc R 1 . .
C C326 0.6939(5) 0.6729(4) 0.9628(3) 0.0206(7) Uani d . 1 . .
H H326 0.5660 0.6704 0.9769 0.025 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'
Br Br -0.2901 2.4595 '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 . . 110.9(3) ?
C2 N1 H1 . . 124.5 ?
C7a N1 H1 . . 124.5 ?
O2 C2 N1 . . 126.1(3) ?
O2 C2 C3 . . 124.7(3) ?
N1 C2 C3 . . 109.0(2) ?
O3 C3 C3a . . 108.4(2) ?
O3 C3 C31 . . 108.5(2) ?
C3a C3 C31 . . 117.0(3) ?
O3 C3 C2 . . 107.4(2) ?
C3a C3 C2 . . 101.5(2) ?
C31 C3 C2 . . 113.4(2) ?
C7a C3a C4 . . 120.0(3) ?
C7a C3a C3 . . 108.8(3) ?
C4 C3a C3 . . 130.9(3) ?
C3a C4 C5 . . 118.4(3) ?
C3a C4 H4 . . 120.8 ?
C5 C4 H4 . . 120.8 ?
C6 C5 C4 . . 120.5(3) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 121.7(3) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C7a C7 C6 . . 116.9(3) ?
C7a C7 H7 . . 121.5 ?
C6 C7 H7 . . 121.5 ?
C7 C7a C3a . . 122.4(3) ?
C7 C7a N1 . . 127.9(3) ?
C3a C7a N1 . . 109.7(3) ?
C3 O3 H3 . . 112.4 ?
C32 C31 C3 . . 116.6(3) ?
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 . . 121.9(3) ?
O32 C32 C31 . . 121.1(3) ?
C321 C32 C31 . . 117.0(3) ?
C322 C321 C326 . . 118.8(3) ?
C322 C321 C32 . . 121.3(3) ?
C326 C321 C32 . . 119.9(3) ?
C323 C322 C321 . . 120.9(3) ?
C323 C322 H322 . . 119.6 ?
C321 C322 H322 . . 119.6 ?
C324 C323 C322 . . 118.7(3) ?
C324 C323 H323 . . 120.6 ?
C322 C323 H323 . . 120.6 ?
C323 C324 C325 . . 121.9(3) ?
C323 C324 Br34 . . 117.3(3) ?
C325 C324 Br34 . . 120.8(3) ?
C326 C325 C324 . . 118.5(3) ?
C326 C325 H325 . . 120.8 ?
C324 C325 H325 . . 120.8 ?
C325 C326 C321 . . 121.3(3) ?
C325 C326 H326 . . 119.4 ?
C321 C326 H326 . . 119.4 ?
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 . 1.330(4) ?
N1 C7a . 1.409(4) ?
N1 H1 . 0.8800 ?
C2 O2 . 1.227(3) ?
C2 C3 . 1.532(4) ?
C3 O3 . 1.419(4) ?
C3 C3a . 1.498(4) ?
C3 C31 . 1.519(4) ?
C3a C7a . 1.373(4) ?
C3a C4 . 1.378(4) ?
C4 C5 . 1.384(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.371(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.383(4) ?
C6 H6 . 0.9500 ?
C7 C7a . 1.371(4) ?
C7 H7 . 0.9500 ?
O3 H3 . 0.8599 ?
C31 C32 . 1.497(4) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 O32 . 1.209(4) ?
C32 C321 . 1.488(4) ?
C321 C322 . 1.380(5) ?
C321 C326 . 1.380(4) ?
C322 C323 . 1.378(5) ?
C322 H322 . 0.9500 ?
C323 C324 . 1.368(5) ?
C323 H323 . 0.9500 ?
C324 C325 . 1.375(5) ?
C324 Br34 . 1.883(3) ?
C325 C326 . 1.373(5) ?
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 2.01 2.851(4) 160 no
O3 H3 O2 2_666 0.86 1.90 2.746(3) 167 no
C31 H31B O2 2_666 0.99 2.49 3.257(4) 134 no
C323 H323 O32 1_655 0.95 2.49 3.271(4) 140 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 . . . . 177.3(3) ?
C7a N1 C2 C3 . . . . 2.3(3) ?
O2 C2 C3 O3 . . . . -64.7(4) ?
N1 C2 C3 O3 . . . . 110.4(3) ?
O2 C2 C3 C3a . . . . -178.4(3) ?
N1 C2 C3 C3a . . . . -3.3(3) ?
O2 C2 C3 C31 . . . . 55.2(4) ?
N1 C2 C3 C31 . . . . -129.7(3) ?
O3 C3 C3a C7a . . . . -109.7(3) ?
C31 C3 C3a C7a . . . . 127.2(3) ?
C2 C3 C3a C7a . . . . 3.2(3) ?
O3 C3 C3a C4 . . . . 65.1(4) ?
C31 C3 C3a C4 . . . . -58.0(4) ?
C2 C3 C3a C4 . . . . 178.0(3) ?
C7a C3a C4 C5 . . . . -2.7(4) ?
C3 C3a C4 C5 . . . . -177.0(3) ?
C3a C4 C5 C6 . . . . 2.9(5) ?
C4 C5 C6 C7 . . . . -0.7(5) ?
C5 C6 C7 C7a . . . . -1.6(5) ?
C6 C7 C7a C3a . . . . 1.8(5) ?
C6 C7 C7a N1 . . . . 179.3(3) ?
C4 C3a C7a C7 . . . . 0.4(5) ?
C3 C3a C7a C7 . . . . 175.8(3) ?
C4 C3a C7a N1 . . . . -177.5(3) ?
C3 C3a C7a N1 . . . . -2.1(3) ?
C2 N1 C7a C7 . . . . -177.9(3) ?
C2 N1 C7a C3a . . . . -0.2(3) ?
O3 C3 C31 C32 . . . . 176.6(2) ?
C3a C3 C31 C32 . . . . -60.4(4) ?
C2 C3 C31 C32 . . . . 57.3(3) ?
C3 C31 C32 O32 . . . . -6.7(4) ?
C3 C31 C32 C321 . . . . 175.6(2) ?
O32 C32 C321 C322 . . . . -174.2(3) ?
C31 C32 C321 C322 . . . . 3.5(4) ?
O32 C32 C321 C326 . . . . 4.9(5) ?
C31 C32 C321 C326 . . . . -177.4(3) ?
C326 C321 C322 C323 . . . . -1.4(4) ?
C32 C321 C322 C323 . . . . 177.7(3) ?
C321 C322 C323 C324 . . . . 0.3(5) ?
C322 C323 C324 C325 . . . . 1.2(5) ?
C322 C323 C324 Br34 . . . . -179.7(2) ?
C323 C324 C325 C326 . . . . -1.4(5) ?
Br34 C324 C325 C326 . . . . 179.5(2) ?
C324 C325 C326 C321 . . . . 0.2(5) ?
C322 C321 C326 C325 . . . . 1.2(5) ?
C32 C321 C326 C325 . . . . -178.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 318339
