#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/30/2213079.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_2213079
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-[2-(Hydroxymethyl)anilino]isobenzofuran-1(3H)-one
;
_journal_coeditor_code           AT2248
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2159
_journal_page_last               o2161
_journal_paper_doi               10.1107/S1600536807014481
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H13 N O3'
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_name_systematic
;
3-[2-(Hydroxymethyl)anilino]isobenzofuran-1(3H)-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
_audit_creation_method           SHELXL97
_cell_angle_alpha                83.926(12)
_cell_angle_beta                 87.035(12)
_cell_angle_gamma                64.626(11)
_cell_formula_units_Z            2
_cell_length_a                   8.0032(12)
_cell_length_b                   8.4448(13)
_cell_length_c                   9.8464(14)
_cell_measurement_reflns_used    10249
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.95
_cell_volume                     597.88(16)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10249
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9506
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.044P)²+0.1187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2036
_reflns_number_total             2340
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2248.cif
_cod_data_source_block           I
_cod_original_cell_volume        597.88(15)
_cod_database_code               2213079
_cod_database_fobs_code          2213079
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
C C1 0.26426(19) 0.75153(17) 0.52545(12) 0.0406(3) Uani d . 1
C C2 0.08286(18) 0.75436(16) 0.50282(12) 0.0379(3) Uani d . 1
C C3 -0.0718(2) 0.8018(2) 0.58652(14) 0.0493(3) Uani d . 1
H H3 -0.0729 0.8407 0.6716 0.059 Uiso calc R 1
C C4 -0.2239(2) 0.7892(2) 0.53909(16) 0.0547(4) Uani d . 1
H H4 -0.3303 0.8203 0.5928 0.066 Uiso calc R 1
C C5 -0.2207(2) 0.7307(2) 0.41245(16) 0.0515(4) Uani d . 1
H H5 -0.3251 0.7227 0.3829 0.062 Uiso calc R 1
C C6 -0.06629(19) 0.68383(18) 0.32913(14) 0.0428(3) Uani d . 1
H H6 -0.0648 0.6442 0.2443 0.051 Uiso calc R 1
C C7 0.08574(17) 0.69781(16) 0.37605(12) 0.0356(3) Uani d . 1
C C8 0.27082(17) 0.65621(17) 0.31006(12) 0.0366(3) Uani d . 1
H H8 0.3328 0.5303 0.2978 0.044 Uiso calc R 1
C C9 0.41894(16) 0.72023(16) 0.10080(11) 0.0338(3) Uani d . 1
C C10 0.40824(17) 0.83155(16) -0.01810(12) 0.0358(3) Uani d . 1
C C11 0.56383(19) 0.79231(19) -0.10051(14) 0.0446(3) Uani d . 1
H H11 0.5575 0.8672 -0.1784 0.054 Uiso calc R 1
C C12 0.72715(19) 0.6469(2) -0.07142(15) 0.0491(3) Uani d . 1
H H12 0.8291 0.6227 -0.1292 0.059 Uiso calc R 1
C C13 0.73685(18) 0.53790(19) 0.04499(15) 0.0467(3) Uani d . 1
H H13 0.8459 0.4381 0.0656 0.056 Uiso calc R 1
C C14 0.58629(17) 0.57529(18) 0.13134(13) 0.0417(3) Uani d . 1
H H14 0.5966 0.5026 0.2113 0.050 Uiso calc R 1
C C15 0.23395(18) 0.98719(18) -0.06359(13) 0.0418(3) Uani d . 1
H H15A 0.1664 1.0423 0.0160 0.050 Uiso calc R 1
H H15B 0.2655 1.0725 -0.1191 0.050 Uiso calc R 1
N N1 0.26374(15) 0.75382(15) 0.18468(10) 0.0384(3) Uani d . 1
O O1 0.32095(15) 0.78683(15) 0.62372(10) 0.0563(3) Uani d . 1
O O2 0.37114(12) 0.69750(13) 0.41497(9) 0.0446(2) Uani d . 1
O O3 0.11771(13) 0.94078(14) -0.14028(10) 0.0500(3) Uani d . 1
H H1 0.165(2) 0.848(2) 0.1662(15) 0.044(4) Uiso d . 1
H H3A 0.186(3) 0.887(3) -0.218(2) 0.088(6) Uiso 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
_geom_angle_publ_flag
O1 C1 O2 121.47(13) y
O1 C1 C2 129.63(13) y
O2 C1 C2 108.89(11) ?
C7 C2 C3 121.83(13) ?
C7 C2 C1 108.18(11) ?
C3 C2 C1 130.00(12) ?
C4 C3 C2 117.42(13) ?
C4 C3 H3 121.3 ?
C2 C3 H3 121.3 ?
C3 C4 C5 120.86(13) ?
C3 C4 H4 119.6 ?
C5 C4 H4 119.6 ?
C6 C5 C4 121.55(13) ?
C6 C5 H5 119.2 ?
C4 C5 H5 119.2 ?
C7 C6 C5 117.65(13) ?
C7 C6 H6 121.2 ?
C5 C6 H6 121.2 ?
C2 C7 C6 120.68(12) ?
C2 C7 C8 109.51(11) ?
C6 C7 C8 129.80(12) ?
N1 C8 O2 111.53(10) y
N1 C8 C7 114.14(11) ?
O2 C8 C7 102.53(9) ?
N1 C8 H8 109.5 ?
O2 C8 H8 109.5 ?
C7 C8 H8 109.5 ?
C14 C9 N1 121.23(11) ?
C14 C9 C10 118.53(11) ?
N1 C9 C10 120.23(11) ?
C11 C10 C9 118.72(12) ?
C11 C10 C15 118.11(11) ?
C9 C10 C15 123.11(11) ?
C12 C11 C10 122.44(13) ?
C12 C11 H11 118.8 ?
C10 C11 H11 118.8 ?
C11 C12 C13 118.64(12) ?
C11 C12 H12 120.7 ?
C13 C12 H12 120.7 ?
C12 C13 C14 120.55(13) ?
C12 C13 H13 119.7 ?
C14 C13 H13 119.7 ?
C13 C14 C9 121.08(13) ?
C13 C14 H14 119.5 ?
C9 C14 H14 119.5 ?
O3 C15 C10 112.58(11) ?
O3 C15 H15A 109.1 ?
C10 C15 H15A 109.1 ?
O3 C15 H15B 109.1 ?
C10 C15 H15B 109.1 ?
H15A C15 H15B 107.8 ?
C9 N1 C8 122.50(11) ?
C9 N1 H1 119.1(10) ?
C8 N1 H1 117.6(10) ?
C1 O2 C8 110.88(10) ?
C15 O3 H3A 107.9(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.2056(16) y
C1 O2 1.3407(16) y
C1 C2 1.4699(19) ?
C2 C7 1.3785(17) y
C2 C3 1.3824(19) ?
C3 C4 1.375(2) ?
C3 H3 0.9300 ?
C4 C5 1.384(2) ?
C4 H4 0.9300 ?
C5 C6 1.379(2) ?
C5 H5 0.9300 ?
C6 C7 1.3787(18) ?
C6 H6 0.9300 ?
C7 C8 1.4974(17) ?
C8 N1 1.3996(16) ?
C8 O2 1.4951(15) ?
C8 H8 0.9800 ?
C9 C14 1.3933(18) ?
C9 N1 1.3953(16) y
C9 C10 1.4036(17) ?
C10 C11 1.3847(18) ?
C10 C15 1.4975(18) ?
C11 C12 1.374(2) ?
C11 H11 0.9300 ?
C12 C13 1.375(2) ?
C12 H12 0.9300 ?
C13 C14 1.3782(19) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 O3 1.4273(17) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
N1 H1 0.859(16) ?
O3 H3A 0.95(2) ?
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
N1 H1 O3 2_575 0.859(16) 2.205(17) 3.0519(16) 168.6(14)
O3 H3A O1 1_554 0.95(2) 1.91(2) 2.8586(16) 178.1(19)
C5 H5 O2 1_455 0.93 2.53 3.3949(17) 154.6
C15 H15A O3 2_575 0.97 2.48 3.2445(18) 135.4
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
O1 C1 C2 C7 -178.08(14)
O2 C1 C2 C7 0.86(14)
O1 C1 C2 C3 1.6(2)
O2 C1 C2 C3 -179.44(13)
C7 C2 C3 C4 0.5(2)
C1 C2 C3 C4 -179.14(14)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 -0.3(2)
C4 C5 C6 C7 -0.2(2)
C3 C2 C7 C6 -1.09(19)
C1 C2 C7 C6 178.64(11)
C3 C2 C7 C8 -179.98(12)
C1 C2 C7 C8 -0.25(14)
C5 C6 C7 C2 0.91(19)
C5 C6 C7 C8 179.55(13)
C2 C7 C8 N1 -121.13(12)
C6 C7 C8 N1 60.11(18)
C2 C7 C8 O2 -0.37(13)
C6 C7 C8 O2 -179.13(12)
C14 C9 C10 C11 0.37(17)
N1 C9 C10 C11 -178.68(11)
C14 C9 C10 C15 177.74(11)
N1 C9 C10 C15 -1.31(18)
C9 C10 C11 C12 1.15(19)
C15 C10 C11 C12 -176.35(12)
C10 C11 C12 C13 -1.0(2)
C11 C12 C13 C14 -0.8(2)
C12 C13 C14 C9 2.3(2)
N1 C9 C14 C13 176.96(12)
C10 C9 C14 C13 -2.08(18)
C11 C10 C15 O3 93.02(14)
C9 C10 C15 O3 -84.37(14)
C14 C9 N1 C8 6.58(18)
C10 C9 N1 C8 -174.39(11)
O2 C8 N1 C9 71.65(15)
C7 C8 N1 C9 -172.73(11)
O1 C1 O2 C8 177.92(12)
C2 C1 O2 C8 -1.12(14)
N1 C8 O2 C1 123.48(12)
C7 C8 O2 C1 0.93(13)
