#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017534.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_2017534
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 N2 O5'
_chemical_formula_moiety         'C16 H12 N2 O5'
_chemical_formula_sum            'C16 H12 N2 O5'
_chemical_formula_weight         312.28
_chemical_name_systematic
;
3-hydroxy-3-[(4-nitrobenzoyl)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                97.54(3)
_cell_angle_beta                 102.67(2)
_cell_angle_gamma                96.46(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0260(10)
_cell_length_b                   7.598(3)
_cell_length_c                   13.365(4)
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.71
_cell_volume                     682.7(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0642
_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            19392
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0571
_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)+(0.0696P)²+0.3346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                1528
_reflns_number_total             2683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3233.cif
_cod_data_source_block           VI
_cod_original_cell_volume        682.7(3)
_cod_database_code               2017534
_cod_database_fobs_code          2017534
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 0.0655(3) 0.3211(3) 0.57180(18) 0.0253(6) Uani d . 1 . .
H H1 -0.0461 0.3633 0.5525 0.030 Uiso calc R 1 . .
C C2 0.2408(4) 0.4009(4) 0.5653(2) 0.0261(7) Uani d . 1 . .
C C3 0.3976(4) 0.2833(4) 0.6037(2) 0.0237(7) Uani d . 1 . .
C C3a 0.2778(4) 0.1366(4) 0.6373(2) 0.0251(7) Uani d . 1 . .
C C4 0.3303(4) -0.0124(4) 0.6790(2) 0.0293(7) Uani d . 1 . .
H H4 0.4642 -0.0312 0.6960 0.035 Uiso calc R 1 . .
C C5 0.1825(4) -0.1341(4) 0.6955(2) 0.0307(7) Uani d . 1 . .
H H5 0.2153 -0.2370 0.7251 0.037 Uiso calc R 1 . .
C C6 -0.0116(4) -0.1072(4) 0.6695(2) 0.0306(7) Uani d . 1 . .
H H6 -0.1106 -0.1931 0.6808 0.037 Uiso calc R 1 . .
C C7 -0.0659(4) 0.0408(4) 0.6277(2) 0.0266(7) Uani d . 1 . .
H H7 -0.2001 0.0585 0.6095 0.032 Uiso calc R 1 . .
C C7a 0.0817(4) 0.1612(4) 0.6134(2) 0.0243(7) Uani d . 1 . .
O O2 0.2716(3) 0.5375(3) 0.52828(15) 0.0277(5) Uani d . 1 . .
O O3 0.4593(3) 0.2086(3) 0.51530(15) 0.0272(5) Uani d . 1 . .
H H3 0.5378 0.2901 0.4996 0.041 Uiso d R 1 . .
C C31 0.5773(4) 0.3853(4) 0.6834(2) 0.0254(7) Uani d . 1 . .
H H31A 0.6677 0.2986 0.7044 0.030 Uiso calc R 1 . .
H H31B 0.6466 0.4714 0.6491 0.030 Uiso calc R 1 . .
C C32 0.5422(4) 0.4864(4) 0.7794(2) 0.0245(7) Uani d . 1 . .
O O32 0.3772(3) 0.4957(3) 0.79150(16) 0.0317(5) Uani d . 1 . .
C C321 0.7201(4) 0.5813(4) 0.8598(2) 0.0236(7) Uani d . 1 . .
C C322 0.9068(4) 0.5751(4) 0.8453(2) 0.0263(7) Uani d . 1 . .
H H322 0.9243 0.5075 0.7838 0.032 Uiso calc R 1 . .
C C323 1.0697(4) 0.6664(4) 0.9194(2) 0.0284(7) Uani d . 1 . .
H H323 1.1991 0.6630 0.9095 0.034 Uiso calc R 1 . .
C C324 1.0392(4) 0.7618(4) 1.0072(2) 0.0252(7) Uani d . 1 . .
C C325 0.8545(4) 0.7693(4) 1.0248(2) 0.0302(7) Uani d . 1 . .
H H325 0.8380 0.8353 1.0870 0.036 Uiso calc R 1 . .
C C326 0.6945(4) 0.6790(4) 0.9502(2) 0.0299(7) Uani d . 1 . .
H H326 0.5654 0.6833 0.9604 0.036 Uiso calc R 1 . .
N N34 1.2127(4) 0.8555(3) 1.08607(19) 0.0311(6) Uani d . 1 . .
O O33 1.3745(3) 0.8340(4) 1.07444(19) 0.0526(7) Uani d . 1 . .
O O34 1.1852(3) 0.9505(4) 1.16011(18) 0.0506(7) Uani d . 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 . . 111.5(2) ?
C2 N1 H1 . . 124.2 ?
C7a N1 H1 . . 124.2 ?
O2 C2 N1 . . 126.3(3) ?
O2 C2 C3 . . 125.1(3) ?
N1 C2 C3 . . 108.4(2) ?
O3 C3 C3a . . 108.2(2) ?
O3 C3 C31 . . 108.5(2) ?
C3a C3 C31 . . 117.1(2) ?
O3 C3 C2 . . 106.7(2) ?
C3a C3 C2 . . 101.7(2) ?
C31 C3 C2 . . 114.0(2) ?
C4 C3a C7a . . 119.8(3) ?
C4 C3a C3 . . 131.1(3) ?
C7a C3a C3 . . 108.9(2) ?
C3a C4 C5 . . 118.2(3) ?
C3a C4 H4 . . 120.9 ?
C5 C4 H4 . . 120.9 ?
C6 C5 C4 . . 120.6(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C7 C6 C5 . . 121.8(3) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C7a C7 C6 . . 117.0(3) ?
C7a C7 H7 . . 121.5 ?
C6 C7 H7 . . 121.5 ?
C7 C7a C3a . . 122.6(3) ?
C7 C7a N1 . . 128.2(3) ?
C3a C7a N1 . . 109.2(2) ?
C3 O3 H3 . . 108.3 ?
C32 C31 C3 . . 117.0(2) ?
C32 C31 H31A . . 108.0 ?
C3 C31 H31A . . 108.0 ?
C32 C31 H31B . . 108.0 ?
C3 C31 H31B . . 108.0 ?
H31A C31 H31B . . 107.3 ?
O32 C32 C31 . . 121.9(3) ?
O32 C32 C321 . . 121.0(3) ?
C31 C32 C321 . . 117.0(2) ?
C322 C321 C326 . . 119.7(3) ?
C322 C321 C32 . . 121.2(3) ?
C326 C321 C32 . . 119.1(2) ?
C321 C322 C323 . . 120.6(3) ?
C321 C322 H322 . . 119.7 ?
C323 C322 H322 . . 119.7 ?
C324 C323 C322 . . 118.2(3) ?
C324 C323 H323 . . 120.9 ?
C322 C323 H323 . . 120.9 ?
C323 C324 C325 . . 122.7(3) ?
C323 C324 N34 . . 117.8(3) ?
C325 C324 N34 . . 119.4(3) ?
C326 C325 C324 . . 118.3(3) ?
C326 C325 H325 . . 120.8 ?
C324 C325 H325 . . 120.8 ?
C325 C326 C321 . . 120.4(3) ?
C325 C326 H326 . . 119.8 ?
C321 C326 H326 . . 119.8 ?
O33 N34 O34 . . 123.4(3) ?
O33 N34 C324 . . 118.8(3) ?
O34 N34 C324 . . 117.7(2) ?
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(4) ?
N1 C7a . 1.406(4) ?
N1 H1 . 0.8800 ?
C2 O2 . 1.225(3) ?
C2 C3 . 1.539(4) ?
C3 O3 . 1.418(3) ?
C3 C3a . 1.496(4) ?
C3 C31 . 1.518(4) ?
C3a C4 . 1.378(4) ?
C3a C7a . 1.385(4) ?
C4 C5 . 1.385(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.377(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.375(4) ?
C6 H6 . 0.9500 ?
C7 C7a . 1.367(4) ?
C7 H7 . 0.9500 ?
O3 H3 . 0.8600 ?
C31 C32 . 1.490(4) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 O32 . 1.214(3) ?
C32 C321 . 1.497(4) ?
C321 C322 . 1.372(4) ?
C321 C326 . 1.390(4) ?
C322 C323 . 1.385(4) ?
C322 H322 . 0.9500 ?
C323 C324 . 1.367(4) ?
C323 H323 . 0.9500 ?
C324 C325 . 1.375(4) ?
C324 N34 . 1.466(4) ?
C325 C326 . 1.372(4) ?
C325 H325 . 0.9500 ?
C326 H326 . 0.9500 ?
N34 O33 . 1.206(3) ?
N34 O34 . 1.211(3) ?
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 2.848(3) 164 no
O3 H3 O2 2_666 0.86 1.90 2.756(3) 175 no
C31 H31B O2 2_666 0.99 2.55 3.330(4) 135 no
C323 H323 O32 1_655 0.95 2.52 3.308(4) 140 no
C326 H326 O33 1_455 0.95 2.49 3.304(4) 143 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 . . . . 176.7(3) ?
C7a N1 C2 C3 . . . . 1.6(3) ?
O2 C2 C3 O3 . . . . -65.4(4) ?
N1 C2 C3 O3 . . . . 109.8(2) ?
O2 C2 C3 C3a . . . . -178.7(3) ?
N1 C2 C3 C3a . . . . -3.5(3) ?
O2 C2 C3 C31 . . . . 54.4(4) ?
N1 C2 C3 C31 . . . . -130.4(2) ?
O3 C3 C3a C4 . . . . 67.6(4) ?
C31 C3 C3a C4 . . . . -55.3(4) ?
C2 C3 C3a C4 . . . . 179.8(3) ?
O3 C3 C3a C7a . . . . -108.0(3) ?
C31 C3 C3a C7a . . . . 129.1(3) ?
C2 C3 C3a C7a . . . . 4.2(3) ?
C7a C3a C4 C5 . . . . 0.1(4) ?
C3 C3a C4 C5 . . . . -175.1(3) ?
C3a C4 C5 C6 . . . . 0.8(4) ?
C4 C5 C6 C7 . . . . -0.7(5) ?
C5 C6 C7 C7a . . . . -0.3(4) ?
C6 C7 C7a C3a . . . . 1.3(4) ?
C6 C7 C7a N1 . . . . 179.5(3) ?
C4 C3a C7a C7 . . . . -1.2(4) ?
C3 C3a C7a C7 . . . . 175.0(3) ?
C4 C3a C7a N1 . . . . -179.8(3) ?
C3 C3a C7a N1 . . . . -3.6(3) ?
C2 N1 C7a C7 . . . . -177.2(3) ?
C2 N1 C7a C3a . . . . 1.2(3) ?
O3 C3 C31 C32 . . . . 175.4(2) ?
C3a C3 C31 C32 . . . . -61.8(3) ?
C2 C3 C31 C32 . . . . 56.7(3) ?
C3 C31 C32 O32 . . . . -4.0(4) ?
C3 C31 C32 C321 . . . . 177.7(2) ?
O32 C32 C321 C322 . . . . -178.2(3) ?
C31 C32 C321 C322 . . . . 0.1(4) ?
O32 C32 C321 C326 . . . . 1.0(4) ?
C31 C32 C321 C326 . . . . 179.3(3) ?
C326 C321 C322 C323 . . . . -0.5(4) ?
C32 C321 C322 C323 . . . . 178.7(3) ?
C321 C322 C323 C324 . . . . 0.3(4) ?
C322 C323 C324 C325 . . . . 0.4(4) ?
C322 C323 C324 N34 . . . . 178.9(2) ?
C323 C324 C325 C326 . . . . -0.9(4) ?
N34 C324 C325 C326 . . . . -179.4(3) ?
C324 C325 C326 C321 . . . . 0.6(5) ?
C322 C321 C326 C325 . . . . 0.0(4) ?
C32 C321 C326 C325 . . . . -179.2(3) ?
C323 C324 N34 O33 . . . . -5.6(4) ?
C325 C324 N34 O33 . . . . 173.0(3) ?
C323 C324 N34 O34 . . . . 174.6(3) ?
C325 C324 N34 O34 . . . . -6.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 318349
