#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/51/2235187.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_2235187
loop_
_publ_author_name
'Wang, Hong-Yao'
'Yang, Jing-Kui'
_publ_section_title
;
 2-Benzyl-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one
;
_journal_coeditor_code           NR2026
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1795
_journal_paper_doi               10.1107/S1600536812021575
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H15 N O2'
_chemical_formula_moiety         'C16 H15 N O2'
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29
_chemical_name_systematic
;
2-Benzyl-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.777(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.093(4)
_cell_length_b                   11.604(4)
_cell_length_c                   21.226(7)
_cell_measurement_reflns_used    4918
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.124
_cell_measurement_theta_min      2.569
_cell_volume                     2674.8(16)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11602
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0419
_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)+(0.0560P)²+0.0264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2673
_reflns_number_total             3479
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nr2026.cif
_cod_data_source_block           I
_cod_original_cell_volume        2674.7(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235187
_cod_database_fobs_code          2235187
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
O O1 0.48310(7) 0.73617(7) 0.04556(4) 0.0310(2) Uani d . 1 1
O O2 0.49294(7) 0.35635(7) 0.07278(4) 0.0321(2) Uani d . 1 1
N N1 0.46720(9) 0.54981(8) 0.09038(4) 0.0256(2) Uani d . 1 1
C C1 0.53806(10) 0.65930(9) 0.09452(5) 0.0263(2) Uani d . 1 1
C C2 0.66237(10) 0.61485(9) 0.08633(5) 0.0242(2) Uani d . 1 1
C C3 0.76900(10) 0.67523(10) 0.08427(5) 0.0300(3) Uani d . 1 1
H H3 0.7719 0.7568 0.0880 0.036 Uiso calc R 1 1
C C4 0.87197(11) 0.61253(10) 0.07655(6) 0.0314(3) Uani d . 1 1
H H4 0.9459 0.6525 0.0746 0.038 Uiso calc R 1 1
C C5 0.86960(11) 0.49285(10) 0.07166(5) 0.0290(3) Uani d . 1 1
H H5 0.9418 0.4523 0.0672 0.035 Uiso calc R 1 1
C C6 0.76204(10) 0.43254(9) 0.07334(5) 0.0257(3) Uani d . 1 1
H H6 0.7589 0.3509 0.0699 0.031 Uiso calc R 1 1
C C7 0.65951(10) 0.49583(9) 0.08021(5) 0.0227(2) Uani d . 1 1
C C8 0.53351(11) 0.45578(9) 0.08088(5) 0.0247(2) Uani d . 1 1
C C9 0.33419(10) 0.54720(10) 0.08518(5) 0.0295(3) Uani d . 1 1
H H9A 0.3006 0.4809 0.0578 0.035 Uiso calc R 1 1
H H9B 0.2989 0.6181 0.0628 0.035 Uiso calc R 1 1
C C10 0.29071(10) 0.53813(10) 0.14795(5) 0.0283(3) Uani d . 1 1
C C11 0.33512(12) 0.45438(11) 0.19347(6) 0.0352(3) Uani d . 1 1
H H11 0.4002 0.4052 0.1873 0.042 Uiso calc R 1 1
C C12 0.28499(13) 0.44209(12) 0.24794(6) 0.0409(3) Uani d . 1 1
H H12 0.3159 0.3844 0.2788 0.049 Uiso calc R 1 1
C C13 0.19061(13) 0.51312(13) 0.25754(6) 0.0433(3) Uani d . 1 1
H H13 0.1557 0.5037 0.2945 0.052 Uiso calc R 1 1
C C14 0.14733(12) 0.59773(14) 0.21325(7) 0.0470(4) Uani d . 1 1
H H14 0.0832 0.6475 0.2200 0.056 Uiso calc R 1 1
C C15 0.19722(11) 0.61047(12) 0.15877(6) 0.0391(3) Uani d . 1 1
H H15 0.1671 0.6693 0.1285 0.047 Uiso calc R 1 1
C C16 0.54084(11) 0.71985(10) 0.15828(6) 0.0339(3) Uani d . 1 1
H H16A 0.5928 0.7887 0.1609 0.041 Uiso calc R 1 1
H H16B 0.5745 0.6675 0.1938 0.041 Uiso calc R 1 1
H H16C 0.4570 0.7423 0.1613 0.041 Uiso calc R 1 1
H H1O 0.4958(12) 0.7058(13) 0.0054(7) 0.059(5) Uiso d . 1 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
C1 O1 H1O 107.6(9)
C8 N1 C9 122.99(10)
C8 N1 C1 113.62(9)
C9 N1 C1 122.48(9)
O1 C1 N1 110.67(9)
O1 C1 C2 113.42(9)
N1 C1 C2 100.65(8)
O1 C1 C16 106.91(9)
N1 C1 C16 111.22(9)
C2 C1 C16 113.96(9)
C3 C2 C7 120.32(10)
C3 C2 C1 129.45(10)
C7 C2 C1 110.23(9)
C2 C3 C4 117.82(10)
C2 C3 H3 121.1
C4 C3 H3 121.1
C3 C4 C5 121.78(10)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 C4 120.23(11)
C6 C5 H5 119.9
C4 C5 H5 119.9
C7 C6 C5 117.57(10)
C7 C6 H6 121.2
C5 C6 H6 121.2
C6 C7 C2 122.26(10)
C6 C7 C8 129.28(10)
C2 C7 C8 108.44(9)
O2 C8 N1 125.37(11)
O2 C8 C7 127.62(10)
N1 C8 C7 106.98(9)
N1 C9 C10 115.80(10)
N1 C9 H9A 108.3
C10 C9 H9A 108.3
N1 C9 H9B 108.3
C10 C9 H9B 108.3
H9A C9 H9B 107.4
C11 C10 C15 118.60(11)
C11 C10 C9 122.08(11)
C15 C10 C9 119.16(11)
C10 C11 C12 120.40(12)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 120.42(13)
C13 C12 H12 119.8
C11 C12 H12 119.8
C14 C13 C12 119.65(13)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C15 120.15(13)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C10 120.77(13)
C14 C15 H15 119.6
C10 C15 H15 119.6
C1 C16 H16A 109.5
C1 C16 H16B 109.5
H16A C16 H16B 109.5
C1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4102(13)
O1 H1O 0.960(15)
O2 C8 1.2377(13)
N1 C8 1.3538(14)
N1 C9 1.4573(16)
N1 C1 1.4871(14)
C1 C2 1.5151(16)
C1 C16 1.5196(15)
C2 C3 1.3831(15)
C2 C7 1.3870(15)
C3 C4 1.3918(16)
C3 H3 0.9500
C4 C5 1.3925(17)
C4 H4 0.9500
C5 C6 1.3900(16)
C5 H5 0.9500
C6 C7 1.3864(15)
C6 H6 0.9500
C7 C8 1.4757(16)
C9 C10 1.5103(16)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.3880(17)
C10 C15 1.3894(17)
C11 C12 1.3888(18)
C11 H11 0.9500
C12 C13 1.380(2)
C12 H12 0.9500
C13 C14 1.376(2)
C13 H13 0.9500
C14 C15 1.3879(18)
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
O1 H1O O2 5_665 0.960(15) 1.836(15) 2.7938(14) 175.3(12)
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
C8 N1 C1 O1 119.71(10)
C9 N1 C1 O1 -49.64(13)
C8 N1 C1 C2 -0.51(11)
C9 N1 C1 C2 -169.86(9)
C8 N1 C1 C16 -121.59(10)
C9 N1 C1 C16 69.06(12)
O1 C1 C2 C3 60.18(15)
N1 C1 C2 C3 178.40(11)
C16 C1 C2 C3 -62.48(15)
O1 C1 C2 C7 -119.60(10)
N1 C1 C2 C7 -1.37(11)
C16 C1 C2 C7 117.75(11)
C7 C2 C3 C4 -0.60(16)
C1 C2 C3 C4 179.64(10)
C2 C3 C4 C5 -0.64(17)
C3 C4 C5 C6 1.07(17)
C4 C5 C6 C7 -0.23(16)
C5 C6 C7 C2 -1.03(16)
C5 C6 C7 C8 177.31(10)
C3 C2 C7 C6 1.47(16)
C1 C2 C7 C6 -178.73(9)
C3 C2 C7 C8 -177.17(9)
C1 C2 C7 C8 2.63(12)
C9 N1 C8 O2 -7.00(17)
C1 N1 C8 O2 -176.29(10)
C9 N1 C8 C7 171.34(9)
C1 N1 C8 C7 2.05(12)
C6 C7 C8 O2 -3.10(19)
C2 C7 C8 O2 175.41(11)
C6 C7 C8 N1 178.60(10)
C2 C7 C8 N1 -2.89(12)
C8 N1 C9 C10 99.09(13)
C1 N1 C9 C10 -92.55(12)
N1 C9 C10 C11 -51.07(15)
N1 C9 C10 C15 133.51(12)
C15 C10 C11 C12 1.30(18)
C9 C10 C11 C12 -174.15(11)
C10 C11 C12 C13 -0.1(2)
C11 C12 C13 C14 -1.0(2)
C12 C13 C14 C15 0.9(2)
C13 C14 C15 C10 0.3(2)
C11 C10 C15 C14 -1.39(19)
C9 C10 C15 C14 174.19(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 565492
